Structure

Physi-Chem Properties

Molecular Weight:  318.22
Volume:  347.268
LogP:  3.339
LogD:  3.559
LogS:  -4.678
# Rotatable Bonds:  2
TPSA:  54.37
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.626
Synthetic Accessibility Score:  4.807
Fsp3:  0.8
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.846
MDCK Permeability:  2.2955515305511653e-05
Pgp-inhibitor:  0.357
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.162
Plasma Protein Binding (PPB):  92.64655303955078%
Volume Distribution (VD):  0.526
Pgp-substrate:  7.977788925170898%

ADMET: Metabolism

CYP1A2-inhibitor:  0.089
CYP1A2-substrate:  0.633
CYP2C19-inhibitor:  0.192
CYP2C19-substrate:  0.882
CYP2C9-inhibitor:  0.228
CYP2C9-substrate:  0.107
CYP2D6-inhibitor:  0.038
CYP2D6-substrate:  0.131
CYP3A4-inhibitor:  0.905
CYP3A4-substrate:  0.591

ADMET: Excretion

Clearance (CL):  3.729
Half-life (T1/2):  0.207

ADMET: Toxicity

hERG Blockers:  0.042
Human Hepatotoxicity (H-HT):  0.176
Drug-inuced Liver Injury (DILI):  0.099
AMES Toxicity:  0.026
Rat Oral Acute Toxicity:  0.108
Maximum Recommended Daily Dose:  0.048
Skin Sensitization:  0.882
Carcinogencity:  0.091
Eye Corrosion:  0.417
Eye Irritation:  0.68
Respiratory Toxicity:  0.475

Download Data

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

  Natural Product: NPC94666

Natural Product ID:  NPC94666
Common Name*:   3Beta,19-Dihydroxy-1(10),15-Rosadien-2-One
IUPAC Name:   (1S,2R,4bR,7R,8aR,10aR)-7-ethenyl-2-hydroxy-1-(hydroxymethyl)-1,4b,7-trimethyl-2,5,6,8,8a,9,10,10a-octahydrophenanthren-3-one
Synonyms:  
Standard InCHIKey:  MTAGALXGQXZRRV-JSTLVUAASA-N
Standard InCHI:  InChI=1S/C20H30O3/c1-5-18(2)8-9-19(3)13(11-18)6-7-14-15(19)10-16(22)17(23)20(14,4)12-21/h5,10,13-14,17,21,23H,1,6-9,11-12H2,2-4H3/t13-,14-,17+,18-,19-,20-/m1/s1
SMILES:  C=C[C@]1(C)CC[C@]2(C)[C@H](CC[C@@H]3C2=CC(=O)[C@@H]([C@]3(C)CO)O)C1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3234209
PubChem CID:   90670332
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0001194] 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
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota roots n.a. n.a. PMID[24660966]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota Roots n.a. n.a. PMID[29148766]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[31184480]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae 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
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 1020.0 nM PMID[533361]

☑ 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 NPC94666 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
0.9012 High Similarity NPC2482
0.8941 High Similarity NPC58063
0.8902 High Similarity NPC14151
0.8902 High Similarity NPC121984
0.8824 High Similarity NPC474732
0.8824 High Similarity NPC31564
0.8824 High Similarity NPC51014
0.8824 High Similarity NPC474733
0.8824 High Similarity NPC474778
0.8824 High Similarity NPC327115
0.8824 High Similarity NPC145879
0.8824 High Similarity NPC20688
0.881 High Similarity NPC237712
0.8795 High Similarity NPC151519
0.8795 High Similarity NPC48362
0.8736 High Similarity NPC119416
0.8736 High Similarity NPC1015
0.8736 High Similarity NPC31985
0.8721 High Similarity NPC475740
0.8659 High Similarity NPC474113
0.8621 High Similarity NPC472802
0.8605 High Similarity NPC222613
0.8605 High Similarity NPC118648
0.8605 High Similarity NPC475022
0.8588 High Similarity NPC59453
0.8588 High Similarity NPC85774
0.8588 High Similarity NPC58841
0.8588 High Similarity NPC180834
0.8588 High Similarity NPC161423
0.8588 High Similarity NPC227064
0.8588 High Similarity NPC214043
0.8588 High Similarity NPC221758
0.8588 High Similarity NPC321187
0.8588 High Similarity NPC329043
0.8571 High Similarity NPC103486
0.8571 High Similarity NPC212083
0.8556 High Similarity NPC23170
0.8556 High Similarity NPC245972
0.8556 High Similarity NPC196485
0.8554 High Similarity NPC476809
0.8554 High Similarity NPC108955
0.8539 High Similarity NPC131872
0.8539 High Similarity NPC185936
0.8539 High Similarity NPC168027
0.8523 High Similarity NPC186688
0.8523 High Similarity NPC310010
0.8523 High Similarity NPC76879
0.8523 High Similarity NPC474245
0.8523 High Similarity NPC26959
0.8523 High Similarity NPC326627
0.8523 High Similarity NPC268406
0.8506 High Similarity NPC73064
0.8506 High Similarity NPC136548
0.8488 Intermediate Similarity NPC469948
0.8488 Intermediate Similarity NPC470574
0.8488 Intermediate Similarity NPC476426
0.8488 Intermediate Similarity NPC6185
0.8488 Intermediate Similarity NPC241512
0.8471 Intermediate Similarity NPC64600
0.8462 Intermediate Similarity NPC280725
0.8452 Intermediate Similarity NPC55869
0.8452 Intermediate Similarity NPC225515
0.8444 Intermediate Similarity NPC12722
0.8444 Intermediate Similarity NPC134826
0.8444 Intermediate Similarity NPC233118
0.8427 Intermediate Similarity NPC48010
0.8421 Intermediate Similarity NPC247957
0.8421 Intermediate Similarity NPC249187
0.8415 Intermediate Similarity NPC197659
0.8409 Intermediate Similarity NPC471722
0.8409 Intermediate Similarity NPC206060
0.8409 Intermediate Similarity NPC230387
0.8409 Intermediate Similarity NPC310752
0.8409 Intermediate Similarity NPC292491
0.8409 Intermediate Similarity NPC474677
0.8409 Intermediate Similarity NPC158778
0.8409 Intermediate Similarity NPC328539
0.8391 Intermediate Similarity NPC475862
0.8391 Intermediate Similarity NPC472985
0.8391 Intermediate Similarity NPC158393
0.8391 Intermediate Similarity NPC74363
0.8391 Intermediate Similarity NPC213412
0.8391 Intermediate Similarity NPC472986
0.8391 Intermediate Similarity NPC472974
0.8372 Intermediate Similarity NPC33913
0.8372 Intermediate Similarity NPC473246
0.8372 Intermediate Similarity NPC472265
0.837 Intermediate Similarity NPC192428
0.8353 Intermediate Similarity NPC73882
0.8353 Intermediate Similarity NPC310989
0.8352 Intermediate Similarity NPC474328
0.8333 Intermediate Similarity NPC99380
0.8333 Intermediate Similarity NPC172013
0.8333 Intermediate Similarity NPC272746
0.8333 Intermediate Similarity NPC472478
0.8333 Intermediate Similarity NPC469637
0.8333 Intermediate Similarity NPC475806
0.8316 Intermediate Similarity NPC87351
0.8315 Intermediate Similarity NPC477943
0.8315 Intermediate Similarity NPC477973
0.8315 Intermediate Similarity NPC309603
0.8315 Intermediate Similarity NPC473999
0.8313 Intermediate Similarity NPC476808
0.8313 Intermediate Similarity NPC178852
0.8298 Intermediate Similarity NPC144956
0.8295 Intermediate Similarity NPC93778
0.8295 Intermediate Similarity NPC298904
0.8295 Intermediate Similarity NPC141292
0.8293 Intermediate Similarity NPC263582
0.8293 Intermediate Similarity NPC92080
0.8293 Intermediate Similarity NPC470525
0.828 Intermediate Similarity NPC18509
0.8276 Intermediate Similarity NPC132228
0.8276 Intermediate Similarity NPC474218
0.8276 Intermediate Similarity NPC8518
0.8276 Intermediate Similarity NPC474680
0.8276 Intermediate Similarity NPC32037
0.8276 Intermediate Similarity NPC133954
0.8276 Intermediate Similarity NPC263997
0.8276 Intermediate Similarity NPC469993
0.8272 Intermediate Similarity NPC471797
0.8261 Intermediate Similarity NPC272617
0.8261 Intermediate Similarity NPC473170
0.8261 Intermediate Similarity NPC474602
0.8261 Intermediate Similarity NPC476245
0.8256 Intermediate Similarity NPC105803
0.8256 Intermediate Similarity NPC53733
0.8247 Intermediate Similarity NPC257353
0.8242 Intermediate Similarity NPC109305
0.8242 Intermediate Similarity NPC474736
0.8242 Intermediate Similarity NPC211230
0.8235 Intermediate Similarity NPC3915
0.8235 Intermediate Similarity NPC116797
0.8235 Intermediate Similarity NPC328264
0.8235 Intermediate Similarity NPC473420
0.8235 Intermediate Similarity NPC136150
0.8229 Intermediate Similarity NPC311612
0.8222 Intermediate Similarity NPC85173
0.8222 Intermediate Similarity NPC46441
0.8222 Intermediate Similarity NPC129913
0.8222 Intermediate Similarity NPC474209
0.8222 Intermediate Similarity NPC475823
0.8214 Intermediate Similarity NPC476177
0.8214 Intermediate Similarity NPC308038
0.8202 Intermediate Similarity NPC328313
0.8202 Intermediate Similarity NPC473229
0.8193 Intermediate Similarity NPC165711
0.8182 Intermediate Similarity NPC194417
0.8182 Intermediate Similarity NPC72133
0.8182 Intermediate Similarity NPC82979
0.8182 Intermediate Similarity NPC155011
0.8182 Intermediate Similarity NPC470955
0.8172 Intermediate Similarity NPC167193
0.8172 Intermediate Similarity NPC473158
0.8172 Intermediate Similarity NPC157113
0.8172 Intermediate Similarity NPC62516
0.8172 Intermediate Similarity NPC472806
0.8171 Intermediate Similarity NPC114236
0.8163 Intermediate Similarity NPC185
0.8161 Intermediate Similarity NPC476412
0.8161 Intermediate Similarity NPC144258
0.8161 Intermediate Similarity NPC82902
0.8152 Intermediate Similarity NPC8993
0.8152 Intermediate Similarity NPC473172
0.8152 Intermediate Similarity NPC474690
0.8152 Intermediate Similarity NPC471207
0.8152 Intermediate Similarity NPC474882
0.8148 Intermediate Similarity NPC471799
0.8144 Intermediate Similarity NPC72255
0.814 Intermediate Similarity NPC93590
0.8132 Intermediate Similarity NPC472978
0.8132 Intermediate Similarity NPC65120
0.8132 Intermediate Similarity NPC158030
0.8132 Intermediate Similarity NPC145067
0.8132 Intermediate Similarity NPC155304
0.8132 Intermediate Similarity NPC26865
0.8132 Intermediate Similarity NPC4036
0.8132 Intermediate Similarity NPC474525
0.8132 Intermediate Similarity NPC473998
0.8132 Intermediate Similarity NPC233455
0.8132 Intermediate Similarity NPC19114
0.8111 Intermediate Similarity NPC472973
0.8111 Intermediate Similarity NPC32830
0.8111 Intermediate Similarity NPC472475
0.8111 Intermediate Similarity NPC275740
0.8111 Intermediate Similarity NPC86319
0.8111 Intermediate Similarity NPC472477
0.8095 Intermediate Similarity NPC471409
0.8095 Intermediate Similarity NPC62336
0.8095 Intermediate Similarity NPC321180
0.8095 Intermediate Similarity NPC475994
0.8095 Intermediate Similarity NPC275494
0.8095 Intermediate Similarity NPC30321
0.809 Intermediate Similarity NPC71507
0.809 Intermediate Similarity NPC220930
0.809 Intermediate Similarity NPC272039
0.809 Intermediate Similarity NPC472484
0.809 Intermediate Similarity NPC472482
0.809 Intermediate Similarity NPC470523
0.809 Intermediate Similarity NPC230016

  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 NPC94666 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
0.8824 High Similarity NPD3618 Phase 1
0.8795 High Similarity NPD3667 Approved
0.8588 High Similarity NPD3133 Approved
0.8588 High Similarity NPD4786 Approved
0.8588 High Similarity NPD3666 Approved
0.8588 High Similarity NPD3665 Phase 1
0.8554 High Similarity NPD4695 Discontinued
0.8523 High Similarity NPD4753 Phase 2
0.8462 Intermediate Similarity NPD5210 Approved
0.8462 Intermediate Similarity NPD4629 Approved
0.8391 Intermediate Similarity NPD5279 Phase 3
0.837 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.837 Intermediate Similarity NPD5222 Approved
0.837 Intermediate Similarity NPD4697 Phase 3
0.837 Intermediate Similarity NPD5221 Approved
0.8333 Intermediate Similarity NPD6079 Approved
0.8315 Intermediate Similarity NPD5328 Approved
0.8298 Intermediate Similarity NPD5286 Approved
0.8298 Intermediate Similarity NPD4696 Approved
0.8298 Intermediate Similarity NPD5285 Approved
0.828 Intermediate Similarity NPD5173 Approved
0.828 Intermediate Similarity NPD4755 Approved
0.8161 Intermediate Similarity NPD4197 Approved
0.8132 Intermediate Similarity NPD7515 Phase 2
0.8125 Intermediate Similarity NPD5211 Phase 2
0.8125 Intermediate Similarity NPD4633 Approved
0.8125 Intermediate Similarity NPD5224 Approved
0.8125 Intermediate Similarity NPD5226 Approved
0.8125 Intermediate Similarity NPD5225 Approved
0.8105 Intermediate Similarity NPD4700 Approved
0.8095 Intermediate Similarity NPD3617 Approved
0.8068 Intermediate Similarity NPD5329 Approved
0.8043 Intermediate Similarity NPD4202 Approved
0.8041 Intermediate Similarity NPD5174 Approved
0.8041 Intermediate Similarity NPD5175 Approved
0.8021 Intermediate Similarity NPD5223 Approved
0.7978 Intermediate Similarity NPD5690 Phase 2
0.7959 Intermediate Similarity NPD5141 Approved
0.7955 Intermediate Similarity NPD3668 Phase 3
0.7931 Intermediate Similarity NPD4221 Approved
0.7931 Intermediate Similarity NPD4223 Phase 3
0.7895 Intermediate Similarity NPD6084 Phase 2
0.7895 Intermediate Similarity NPD6083 Phase 2
0.7849 Intermediate Similarity NPD6399 Phase 3
0.7812 Intermediate Similarity NPD5696 Approved
0.78 Intermediate Similarity NPD5697 Approved
0.7778 Intermediate Similarity NPD5280 Approved
0.7778 Intermediate Similarity NPD4519 Discontinued
0.7778 Intermediate Similarity NPD4623 Approved
0.7778 Intermediate Similarity NPD4694 Approved
0.7766 Intermediate Similarity NPD7748 Approved
0.7723 Intermediate Similarity NPD6881 Approved
0.7723 Intermediate Similarity NPD4729 Approved
0.7723 Intermediate Similarity NPD6899 Approved
0.7723 Intermediate Similarity NPD4730 Approved
0.7717 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.7708 Intermediate Similarity NPD7902 Approved
0.7701 Intermediate Similarity NPD8259 Clinical (unspecified phase)
0.77 Intermediate Similarity NPD5739 Approved
0.77 Intermediate Similarity NPD7128 Approved
0.77 Intermediate Similarity NPD6675 Approved
0.77 Intermediate Similarity NPD6402 Approved
0.77 Intermediate Similarity NPD4768 Approved
0.77 Intermediate Similarity NPD4767 Approved
0.7684 Intermediate Similarity NPD5695 Phase 3
0.7677 Intermediate Similarity NPD4754 Approved
0.767 Intermediate Similarity NPD6650 Approved
0.767 Intermediate Similarity NPD6649 Approved
0.7647 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD6014 Approved
0.7647 Intermediate Similarity NPD6373 Approved
0.7647 Intermediate Similarity NPD6372 Approved
0.7647 Intermediate Similarity NPD6012 Approved
0.7647 Intermediate Similarity NPD6013 Approved
0.7624 Intermediate Similarity NPD5701 Approved
0.7609 Intermediate Similarity NPD5737 Approved
0.7609 Intermediate Similarity NPD6672 Approved
0.7582 Intermediate Similarity NPD6409 Approved
0.7582 Intermediate Similarity NPD4689 Approved
0.7582 Intermediate Similarity NPD5205 Approved
0.7582 Intermediate Similarity NPD7521 Approved
0.7582 Intermediate Similarity NPD7334 Approved
0.7582 Intermediate Similarity NPD4690 Approved
0.7582 Intermediate Similarity NPD5330 Approved
0.7582 Intermediate Similarity NPD4138 Approved
0.7582 Intermediate Similarity NPD7146 Approved
0.7582 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7582 Intermediate Similarity NPD6684 Approved
0.7582 Intermediate Similarity NPD4688 Approved
0.7582 Intermediate Similarity NPD4693 Phase 3
0.7573 Intermediate Similarity NPD5249 Phase 3
0.7573 Intermediate Similarity NPD5248 Approved
0.7573 Intermediate Similarity NPD7290 Approved
0.7573 Intermediate Similarity NPD5250 Approved
0.7573 Intermediate Similarity NPD5251 Approved
0.7573 Intermediate Similarity NPD4634 Approved
0.7573 Intermediate Similarity NPD6883 Approved
0.7573 Intermediate Similarity NPD7102 Approved
0.7573 Intermediate Similarity NPD5247 Approved
0.7549 Intermediate Similarity NPD5128 Approved
0.7549 Intermediate Similarity NPD7320 Approved
0.7549 Intermediate Similarity NPD6011 Approved
0.7549 Intermediate Similarity NPD5168 Approved
0.7529 Intermediate Similarity NPD6942 Approved
0.7529 Intermediate Similarity NPD7339 Approved
0.75 Intermediate Similarity NPD8130 Phase 1
0.75 Intermediate Similarity NPD5215 Approved
0.75 Intermediate Similarity NPD6847 Approved
0.75 Intermediate Similarity NPD6869 Approved
0.75 Intermediate Similarity NPD6617 Approved
0.75 Intermediate Similarity NPD5217 Approved
0.75 Intermediate Similarity NPD5216 Approved
0.7429 Intermediate Similarity NPD6882 Approved
0.7429 Intermediate Similarity NPD8297 Approved
0.7419 Intermediate Similarity NPD6903 Approved
0.7419 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7404 Intermediate Similarity NPD5135 Approved
0.7404 Intermediate Similarity NPD5134 Clinical (unspecified phase)
0.7404 Intermediate Similarity NPD5169 Approved
0.7396 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD7900 Approved
0.7386 Intermediate Similarity NPD4195 Approved
0.7386 Intermediate Similarity NPD7645 Phase 2
0.7368 Intermediate Similarity NPD5284 Approved
0.7368 Intermediate Similarity NPD5281 Approved
0.7349 Intermediate Similarity NPD4137 Phase 3
0.7333 Intermediate Similarity NPD5127 Approved
0.7312 Intermediate Similarity NPD3573 Approved
0.7262 Intermediate Similarity NPD4691 Approved
0.7262 Intermediate Similarity NPD4747 Approved
0.7253 Intermediate Similarity NPD4788 Approved
0.7228 Intermediate Similarity NPD5091 Approved
0.7216 Intermediate Similarity NPD5282 Discontinued
0.7209 Intermediate Similarity NPD4058 Approved
0.7196 Intermediate Similarity NPD4632 Approved
0.7188 Intermediate Similarity NPD6411 Approved
0.717 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD6673 Approved
0.7158 Intermediate Similarity NPD6080 Approved
0.7158 Intermediate Similarity NPD6904 Approved
0.7156 Intermediate Similarity NPD7115 Discovery
0.713 Intermediate Similarity NPD5167 Approved
0.7115 Intermediate Similarity NPD6412 Phase 2
0.7113 Intermediate Similarity NPD5133 Approved
0.7097 Intermediate Similarity NPD1696 Phase 3
0.7097 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7064 Intermediate Similarity NPD6274 Approved
0.7064 Intermediate Similarity NPD6868 Approved
0.7053 Intermediate Similarity NPD4518 Approved
0.7027 Intermediate Similarity NPD7100 Approved
0.7027 Intermediate Similarity NPD7101 Approved
0.7021 Intermediate Similarity NPD6098 Approved
0.7011 Intermediate Similarity NPD4687 Approved
0.701 Intermediate Similarity NPD5694 Approved
0.701 Intermediate Similarity NPD5693 Phase 1
0.7 Intermediate Similarity NPD6009 Approved
0.7 Intermediate Similarity NPD6317 Approved
0.6979 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6979 Remote Similarity NPD6101 Approved
0.6964 Remote Similarity NPD6319 Approved
0.6964 Remote Similarity NPD6054 Approved
0.6941 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6941 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6937 Remote Similarity NPD6313 Approved
0.6937 Remote Similarity NPD6314 Approved
0.6937 Remote Similarity NPD6335 Approved
0.6931 Remote Similarity NPD4225 Approved
0.6931 Remote Similarity NPD7638 Approved
0.6931 Remote Similarity NPD5290 Discontinued
0.6923 Remote Similarity NPD7525 Registered
0.6915 Remote Similarity NPD1694 Approved
0.6907 Remote Similarity NPD5692 Phase 3
0.6907 Remote Similarity NPD4096 Approved
0.6907 Remote Similarity NPD5207 Approved
0.6903 Remote Similarity NPD6015 Approved
0.6903 Remote Similarity NPD6016 Approved
0.6903 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6875 Remote Similarity NPD5208 Approved
0.6875 Remote Similarity NPD4522 Approved
0.6863 Remote Similarity NPD7640 Approved
0.6863 Remote Similarity NPD7639 Approved
0.686 Remote Similarity NPD4789 Approved
0.6857 Remote Similarity NPD6008 Approved
0.6848 Remote Similarity NPD4692 Approved
0.6848 Remote Similarity NPD4139 Approved
0.6842 Remote Similarity NPD5988 Approved
0.6842 Remote Similarity NPD6370 Approved
0.6837 Remote Similarity NPD6050 Approved
0.6824 Remote Similarity NPD3621 Clinical (unspecified phase)
0.6818 Remote Similarity NPD4784 Approved
0.6818 Remote Similarity NPD6926 Approved
0.6818 Remote Similarity NPD5733 Approved
0.6818 Remote Similarity NPD4785 Approved
0.6818 Remote Similarity NPD6924 Approved
0.6814 Remote Similarity NPD6059 Approved
0.68 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6786 Remote Similarity NPD7331 Phase 2
0.6783 Remote Similarity NPD8328 Phase 3
0.6782 Remote Similarity NPD7152 Approved
0.6782 Remote Similarity NPD4809 Clinical (unspecified phase)

  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