Structure

Physi-Chem Properties

Molecular Weight:  344.24
Volume:  373.304
LogP:  4.021
LogD:  3.459
LogS:  -5.073
# Rotatable Bonds:  2
TPSA:  46.53
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.566
Synthetic Accessibility Score:  5.983
Fsp3:  0.773
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.829
MDCK Permeability:  2.46551262534922e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.848
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.933
30% Bioavailability (F30%):  0.413

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.211
Plasma Protein Binding (PPB):  81.52488708496094%
Volume Distribution (VD):  1.728
Pgp-substrate:  22.32970428466797%

ADMET: Metabolism

CYP1A2-inhibitor:  0.017
CYP1A2-substrate:  0.237
CYP2C19-inhibitor:  0.131
CYP2C19-substrate:  0.77
CYP2C9-inhibitor:  0.297
CYP2C9-substrate:  0.159
CYP2D6-inhibitor:  0.019
CYP2D6-substrate:  0.11
CYP3A4-inhibitor:  0.867
CYP3A4-substrate:  0.3

ADMET: Excretion

Clearance (CL):  3.632
Half-life (T1/2):  0.165

ADMET: Toxicity

hERG Blockers:  0.006
Human Hepatotoxicity (H-HT):  0.376
Drug-inuced Liver Injury (DILI):  0.154
AMES Toxicity:  0.072
Rat Oral Acute Toxicity:  0.579
Maximum Recommended Daily Dose:  0.923
Skin Sensitization:  0.123
Carcinogencity:  0.582
Eye Corrosion:  0.084
Eye Irritation:  0.373
Respiratory Toxicity:  0.964

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

  Natural Product: NPC473647

Natural Product ID:  NPC473647
Common Name*:   MGAQBUXQYBWJAX-DQEBDXAXSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  MGAQBUXQYBWJAX-DQEBDXAXSA-N
Standard InCHI:  InChI=1S/C22H32O3/c1-13-15-7-8-17-21(5)10-6-9-20(3,4)18(21)16(24)12-22(17,11-15)19(13)25-14(2)23/h8,15-16,18-19,24H,1,6-7,9-12H2,2-5H3/t15-,16+,18-,19-,21+,22+/m1/s1
SMILES:  CC(=O)OC1C(=C)C2CC=C3C1(C2)CC(C4C3(CCCC4(C)C)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL448113
PubChem CID:   44587444
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] Diterpenoids
          • [CHEMONTID:0003782] Kaurane diterpenoids

*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
NPO33117 jungermannia atrobrunnea Species Jungermanniaceae Eukaryota n.a. n.a. n.a. PMID[18665642]

☑ 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
NPT20 Organism Candida albicans Candida albicans MIC = 128.0 ug.mL-1 PMID[513089]

☑ 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 NPC473647 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
0.9405 High Similarity NPC286153
0.8953 High Similarity NPC474970
0.875 High Similarity NPC471952
0.8696 High Similarity NPC253115
0.8696 High Similarity NPC88009
0.8696 High Similarity NPC304899
0.8667 High Similarity NPC234335
0.8617 High Similarity NPC473510
0.8602 High Similarity NPC475033
0.8602 High Similarity NPC210337
0.8602 High Similarity NPC475032
0.8588 High Similarity NPC142163
0.8571 High Similarity NPC100906
0.8526 High Similarity NPC475617
0.8488 Intermediate Similarity NPC470049
0.8478 Intermediate Similarity NPC3359
0.8469 Intermediate Similarity NPC475781
0.8462 Intermediate Similarity NPC177641
0.8462 Intermediate Similarity NPC130840
0.8438 Intermediate Similarity NPC476471
0.8438 Intermediate Similarity NPC475344
0.8421 Intermediate Similarity NPC208358
0.8421 Intermediate Similarity NPC230546
0.8391 Intermediate Similarity NPC52108
0.8391 Intermediate Similarity NPC474789
0.8372 Intermediate Similarity NPC474752
0.8372 Intermediate Similarity NPC7505
0.8372 Intermediate Similarity NPC82986
0.8372 Intermediate Similarity NPC474731
0.8372 Intermediate Similarity NPC474759
0.8372 Intermediate Similarity NPC474683
0.837 Intermediate Similarity NPC470375
0.837 Intermediate Similarity NPC470376
0.8367 Intermediate Similarity NPC119855
0.8367 Intermediate Similarity NPC220217
0.8353 Intermediate Similarity NPC242767
0.8353 Intermediate Similarity NPC153987
0.8353 Intermediate Similarity NPC44083
0.8353 Intermediate Similarity NPC1319
0.8352 Intermediate Similarity NPC78973
0.8352 Intermediate Similarity NPC221111
0.8352 Intermediate Similarity NPC280149
0.8351 Intermediate Similarity NPC474124
0.8351 Intermediate Similarity NPC160583
0.8333 Intermediate Similarity NPC222875
0.8333 Intermediate Similarity NPC160304
0.8333 Intermediate Similarity NPC268829
0.8333 Intermediate Similarity NPC295110
0.8333 Intermediate Similarity NPC247701
0.8333 Intermediate Similarity NPC155974
0.8333 Intermediate Similarity NPC474327
0.8333 Intermediate Similarity NPC25177
0.8316 Intermediate Similarity NPC176845
0.8315 Intermediate Similarity NPC137306
0.8315 Intermediate Similarity NPC84121
0.8298 Intermediate Similarity NPC276103
0.8298 Intermediate Similarity NPC54248
0.8295 Intermediate Similarity NPC470077
0.8295 Intermediate Similarity NPC124172
0.828 Intermediate Similarity NPC474922
0.8265 Intermediate Similarity NPC473543
0.8261 Intermediate Similarity NPC154101
0.8242 Intermediate Similarity NPC472240
0.8242 Intermediate Similarity NPC262858
0.8242 Intermediate Similarity NPC146554
0.8235 Intermediate Similarity NPC477522
0.8235 Intermediate Similarity NPC477514
0.8229 Intermediate Similarity NPC477972
0.8229 Intermediate Similarity NPC161527
0.8229 Intermediate Similarity NPC219285
0.8229 Intermediate Similarity NPC228251
0.8229 Intermediate Similarity NPC477971
0.8229 Intermediate Similarity NPC20113
0.8229 Intermediate Similarity NPC477968
0.8222 Intermediate Similarity NPC142361
0.8222 Intermediate Similarity NPC474684
0.8222 Intermediate Similarity NPC166857
0.8211 Intermediate Similarity NPC231751
0.8202 Intermediate Similarity NPC157257
0.8202 Intermediate Similarity NPC474349
0.8202 Intermediate Similarity NPC274448
0.8202 Intermediate Similarity NPC474189
0.8202 Intermediate Similarity NPC266511
0.8202 Intermediate Similarity NPC191965
0.8202 Intermediate Similarity NPC35933
0.8191 Intermediate Similarity NPC184848
0.8191 Intermediate Similarity NPC469599
0.8191 Intermediate Similarity NPC69548
0.8191 Intermediate Similarity NPC276110
0.8172 Intermediate Similarity NPC473678
0.8172 Intermediate Similarity NPC53555
0.8172 Intermediate Similarity NPC470224
0.8172 Intermediate Similarity NPC38232
0.8172 Intermediate Similarity NPC26046
0.8163 Intermediate Similarity NPC473523
0.8163 Intermediate Similarity NPC36688
0.8163 Intermediate Similarity NPC189588
0.8163 Intermediate Similarity NPC97487
0.8163 Intermediate Similarity NPC10232
0.8163 Intermediate Similarity NPC187302
0.8163 Intermediate Similarity NPC196471
0.8163 Intermediate Similarity NPC472821
0.8152 Intermediate Similarity NPC123252
0.8152 Intermediate Similarity NPC219937
0.8152 Intermediate Similarity NPC471896
0.8152 Intermediate Similarity NPC194485
0.8152 Intermediate Similarity NPC53890
0.8132 Intermediate Similarity NPC473879
0.8132 Intermediate Similarity NPC470613
0.8132 Intermediate Similarity NPC470612
0.8125 Intermediate Similarity NPC477813
0.8119 Intermediate Similarity NPC75389
0.8118 Intermediate Similarity NPC283619
0.8111 Intermediate Similarity NPC24277
0.8111 Intermediate Similarity NPC155011
0.8111 Intermediate Similarity NPC329692
0.8111 Intermediate Similarity NPC472505
0.8111 Intermediate Similarity NPC131813
0.8111 Intermediate Similarity NPC325594
0.809 Intermediate Similarity NPC209802
0.8085 Intermediate Similarity NPC201725
0.8085 Intermediate Similarity NPC119562
0.8085 Intermediate Similarity NPC279410
0.8085 Intermediate Similarity NPC105490
0.8068 Intermediate Similarity NPC201852
0.8068 Intermediate Similarity NPC472504
0.8068 Intermediate Similarity NPC470614
0.8068 Intermediate Similarity NPC1272
0.8065 Intermediate Similarity NPC26888
0.8065 Intermediate Similarity NPC23434
0.8065 Intermediate Similarity NPC329842
0.8065 Intermediate Similarity NPC477574
0.8065 Intermediate Similarity NPC233345
0.8065 Intermediate Similarity NPC186363
0.8061 Intermediate Similarity NPC136289
0.8046 Intermediate Similarity NPC206735
0.8046 Intermediate Similarity NPC26117
0.8043 Intermediate Similarity NPC246028
0.8043 Intermediate Similarity NPC261320
0.8043 Intermediate Similarity NPC177141
0.8043 Intermediate Similarity NPC474704
0.8043 Intermediate Similarity NPC16265
0.8043 Intermediate Similarity NPC475921
0.8041 Intermediate Similarity NPC251680
0.8041 Intermediate Similarity NPC474190
0.8041 Intermediate Similarity NPC201406
0.8023 Intermediate Similarity NPC473943
0.8023 Intermediate Similarity NPC474216
0.8023 Intermediate Similarity NPC244385
0.8023 Intermediate Similarity NPC6978
0.8023 Intermediate Similarity NPC167037
0.8023 Intermediate Similarity NPC275910
0.8023 Intermediate Similarity NPC138621
0.8022 Intermediate Similarity NPC159046
0.8022 Intermediate Similarity NPC233836
0.8022 Intermediate Similarity NPC187376
0.8022 Intermediate Similarity NPC149224
0.8022 Intermediate Similarity NPC478104
0.8021 Intermediate Similarity NPC57416
0.8021 Intermediate Similarity NPC107243
0.8021 Intermediate Similarity NPC274793
0.8021 Intermediate Similarity NPC141401
0.8021 Intermediate Similarity NPC475894
0.802 Intermediate Similarity NPC275060
0.8 Intermediate Similarity NPC295843
0.8 Intermediate Similarity NPC107059
0.8 Intermediate Similarity NPC45324
0.8 Intermediate Similarity NPC231530
0.8 Intermediate Similarity NPC240604
0.8 Intermediate Similarity NPC474013
0.8 Intermediate Similarity NPC278628
0.8 Intermediate Similarity NPC162001
0.8 Intermediate Similarity NPC189883
0.8 Intermediate Similarity NPC321016
0.8 Intermediate Similarity NPC300324
0.8 Intermediate Similarity NPC96319
0.8 Intermediate Similarity NPC321381
0.8 Intermediate Similarity NPC8774
0.8 Intermediate Similarity NPC186668
0.8 Intermediate Similarity NPC222845
0.8 Intermediate Similarity NPC318390
0.8 Intermediate Similarity NPC471795
0.798 Intermediate Similarity NPC140723
0.798 Intermediate Similarity NPC171014
0.798 Intermediate Similarity NPC297617
0.7979 Intermediate Similarity NPC7349
0.7978 Intermediate Similarity NPC5280
0.7978 Intermediate Similarity NPC110778
0.7978 Intermediate Similarity NPC477818
0.7978 Intermediate Similarity NPC472473
0.7978 Intermediate Similarity NPC23748
0.7978 Intermediate Similarity NPC139206
0.7978 Intermediate Similarity NPC477667
0.7978 Intermediate Similarity NPC470558
0.7978 Intermediate Similarity NPC42476
0.7978 Intermediate Similarity NPC311070
0.7959 Intermediate Similarity NPC81530
0.7959 Intermediate Similarity NPC176406
0.7957 Intermediate Similarity NPC310479
0.7957 Intermediate Similarity NPC111585

  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 NPC473647 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
0.8242 Intermediate Similarity NPD6051 Approved
0.8125 Intermediate Similarity NPD7638 Approved
0.8041 Intermediate Similarity NPD7640 Approved
0.8041 Intermediate Similarity NPD7639 Approved
0.8 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7979 Intermediate Similarity NPD6399 Phase 3
0.7882 Intermediate Similarity NPD7339 Approved
0.7882 Intermediate Similarity NPD6942 Approved
0.7841 Intermediate Similarity NPD7525 Registered
0.7822 Intermediate Similarity NPD6675 Approved
0.7822 Intermediate Similarity NPD6402 Approved
0.7822 Intermediate Similarity NPD7128 Approved
0.7822 Intermediate Similarity NPD5739 Approved
0.7717 Intermediate Similarity NPD7521 Approved
0.7717 Intermediate Similarity NPD7334 Approved
0.7717 Intermediate Similarity NPD7146 Approved
0.7717 Intermediate Similarity NPD6409 Approved
0.7717 Intermediate Similarity NPD6684 Approved
0.7717 Intermediate Similarity NPD5330 Approved
0.7692 Intermediate Similarity NPD4786 Approved
0.767 Intermediate Similarity NPD6881 Approved
0.767 Intermediate Similarity NPD6899 Approved
0.767 Intermediate Similarity NPD7320 Approved
0.7653 Intermediate Similarity NPD6084 Phase 2
0.7653 Intermediate Similarity NPD6083 Phase 2
0.7604 Intermediate Similarity NPD4202 Approved
0.7596 Intermediate Similarity NPD6373 Approved
0.7596 Intermediate Similarity NPD6372 Approved
0.7573 Intermediate Similarity NPD5701 Approved
0.7573 Intermediate Similarity NPD5697 Approved
0.7558 Intermediate Similarity NPD4785 Approved
0.7558 Intermediate Similarity NPD4784 Approved
0.7553 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7553 Intermediate Similarity NPD6903 Approved
0.7529 Intermediate Similarity NPD4243 Approved
0.7528 Intermediate Similarity NPD7645 Phase 2
0.7524 Intermediate Similarity NPD7102 Approved
0.7524 Intermediate Similarity NPD7290 Approved
0.7524 Intermediate Similarity NPD6883 Approved
0.75 Intermediate Similarity NPD6011 Approved
0.75 Intermediate Similarity NPD3665 Phase 1
0.75 Intermediate Similarity NPD3133 Approved
0.75 Intermediate Similarity NPD3666 Approved
0.7474 Intermediate Similarity NPD5328 Approved
0.7473 Intermediate Similarity NPD3667 Approved
0.7453 Intermediate Similarity NPD8130 Phase 1
0.7453 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD6617 Approved
0.7453 Intermediate Similarity NPD6650 Approved
0.7453 Intermediate Similarity NPD6869 Approved
0.7453 Intermediate Similarity NPD6649 Approved
0.7453 Intermediate Similarity NPD6847 Approved
0.7447 Intermediate Similarity NPD4751 Clinical (unspecified phase)
0.7429 Intermediate Similarity NPD6012 Approved
0.7429 Intermediate Similarity NPD6014 Approved
0.7429 Intermediate Similarity NPD6013 Approved
0.7419 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.74 Intermediate Similarity NPD4225 Approved
0.7383 Intermediate Similarity NPD6882 Approved
0.7383 Intermediate Similarity NPD8297 Approved
0.7364 Intermediate Similarity NPD7327 Approved
0.7364 Intermediate Similarity NPD7328 Approved
0.7356 Intermediate Similarity NPD6926 Approved
0.7356 Intermediate Similarity NPD6924 Approved
0.7353 Intermediate Similarity NPD7632 Discontinued
0.7347 Intermediate Similarity NPD7748 Approved
0.734 Intermediate Similarity NPD3618 Phase 1
0.734 Intermediate Similarity NPD6098 Approved
0.7333 Intermediate Similarity NPD4195 Approved
0.7321 Intermediate Similarity NPD7503 Approved
0.7321 Intermediate Similarity NPD8033 Approved
0.732 Intermediate Similarity NPD8035 Phase 2
0.732 Intermediate Similarity NPD5693 Phase 1
0.732 Intermediate Similarity NPD7515 Phase 2
0.732 Intermediate Similarity NPD6079 Approved
0.732 Intermediate Similarity NPD8034 Phase 2
0.7312 Intermediate Similarity NPD7338 Clinical (unspecified phase)
0.73 Intermediate Similarity NPD7902 Approved
0.73 Intermediate Similarity NPD4755 Approved
0.7297 Intermediate Similarity NPD7516 Approved
0.7273 Intermediate Similarity NPD7115 Discovery
0.7273 Intermediate Similarity NPD5695 Phase 3
0.7273 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7253 Intermediate Similarity NPD4748 Discontinued
0.7234 Intermediate Similarity NPD6082 Clinical (unspecified phase)
0.7232 Intermediate Similarity NPD8377 Approved
0.7232 Intermediate Similarity NPD8294 Approved
0.7228 Intermediate Similarity NPD5696 Approved
0.7204 Intermediate Similarity NPD6695 Phase 3
0.7191 Intermediate Similarity NPD6933 Approved
0.7188 Intermediate Similarity NPD5737 Approved
0.7188 Intermediate Similarity NPD6672 Approved
0.7184 Intermediate Similarity NPD5211 Phase 2
0.7168 Intermediate Similarity NPD8296 Approved
0.7168 Intermediate Similarity NPD8335 Approved
0.7168 Intermediate Similarity NPD8380 Approved
0.7168 Intermediate Similarity NPD8379 Approved
0.7168 Intermediate Similarity NPD8378 Approved
0.7157 Intermediate Similarity NPD5285 Approved
0.7157 Intermediate Similarity NPD5286 Approved
0.7157 Intermediate Similarity NPD4700 Approved
0.7157 Intermediate Similarity NPD4696 Approved
0.7143 Intermediate Similarity NPD7637 Suspended
0.7143 Intermediate Similarity NPD6929 Approved
0.7143 Intermediate Similarity NPD6008 Approved
0.7113 Intermediate Similarity NPD6673 Approved
0.7113 Intermediate Similarity NPD6080 Approved
0.7113 Intermediate Similarity NPD6904 Approved
0.7113 Intermediate Similarity NPD4753 Phase 2
0.7097 Intermediate Similarity NPD4221 Approved
0.7097 Intermediate Similarity NPD4223 Phase 3
0.7093 Intermediate Similarity NPD6922 Approved
0.7093 Intermediate Similarity NPD6923 Approved
0.7087 Intermediate Similarity NPD5223 Approved
0.7079 Intermediate Similarity NPD4190 Phase 3
0.7079 Intermediate Similarity NPD5275 Approved
0.7065 Intermediate Similarity NPD6931 Approved
0.7065 Intermediate Similarity NPD6930 Phase 2
0.7065 Intermediate Similarity NPD7509 Discontinued
0.7064 Intermediate Similarity NPD6053 Discontinued
0.7054 Intermediate Similarity NPD6335 Approved
0.7053 Intermediate Similarity NPD5329 Approved
0.7048 Intermediate Similarity NPD5141 Approved
0.7027 Intermediate Similarity NPD6274 Approved
0.7019 Intermediate Similarity NPD5225 Approved
0.7019 Intermediate Similarity NPD5226 Approved
0.7019 Intermediate Similarity NPD4633 Approved
0.7019 Intermediate Similarity NPD5224 Approved
0.7011 Intermediate Similarity NPD7144 Approved
0.7011 Intermediate Similarity NPD7143 Approved
0.701 Intermediate Similarity NPD5208 Approved
0.7 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6001 Approved
0.7 Intermediate Similarity NPD7900 Approved
0.7 Intermediate Similarity NPD4632 Approved
0.6991 Remote Similarity NPD7100 Approved
0.6991 Remote Similarity NPD7101 Approved
0.697 Remote Similarity NPD6411 Approved
0.697 Remote Similarity NPD5281 Approved
0.697 Remote Similarity NPD5284 Approved
0.6964 Remote Similarity NPD6317 Approved
0.6952 Remote Similarity NPD5174 Approved
0.6952 Remote Similarity NPD5175 Approved
0.6952 Remote Similarity NPD4754 Approved
0.6947 Remote Similarity NPD4197 Approved
0.6947 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6932 Remote Similarity NPD7150 Approved
0.6932 Remote Similarity NPD7151 Approved
0.6932 Remote Similarity NPD7152 Approved
0.6923 Remote Similarity NPD7507 Approved
0.6923 Remote Similarity NPD5776 Phase 2
0.6923 Remote Similarity NPD6925 Approved
0.6923 Remote Similarity NPD4159 Approved
0.6916 Remote Similarity NPD6412 Phase 2
0.6915 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6907 Remote Similarity NPD7750 Discontinued
0.6907 Remote Similarity NPD7524 Approved
0.6903 Remote Similarity NPD6314 Approved
0.6903 Remote Similarity NPD6313 Approved
0.6882 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6875 Remote Similarity NPD1694 Approved
0.687 Remote Similarity NPD6908 Approved
0.687 Remote Similarity NPD6909 Approved
0.6863 Remote Similarity NPD5221 Approved
0.6863 Remote Similarity NPD4697 Phase 3
0.6863 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6863 Remote Similarity NPD5222 Approved
0.6852 Remote Similarity NPD6686 Approved
0.6848 Remote Similarity NPD7145 Approved
0.6842 Remote Similarity NPD5362 Discontinued
0.6842 Remote Similarity NPD4788 Approved
0.6832 Remote Similarity NPD5707 Approved
0.6822 Remote Similarity NPD4767 Approved
0.6822 Remote Similarity NPD4768 Approved
0.6814 Remote Similarity NPD6009 Approved
0.6804 Remote Similarity NPD4138 Approved
0.6804 Remote Similarity NPD5205 Approved
0.6804 Remote Similarity NPD4688 Approved
0.6804 Remote Similarity NPD5279 Phase 3
0.6804 Remote Similarity NPD4690 Approved
0.6804 Remote Similarity NPD4693 Phase 3
0.6804 Remote Similarity NPD4689 Approved
0.68 Remote Similarity NPD6050 Approved
0.6796 Remote Similarity NPD5173 Approved
0.6789 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6783 Remote Similarity NPD6319 Approved
0.6771 Remote Similarity NPD3668 Phase 3
0.6768 Remote Similarity NPD6101 Approved
0.6768 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6765 Remote Similarity NPD4629 Approved
0.6765 Remote Similarity NPD5210 Approved
0.6752 Remote Similarity NPD7604 Phase 2
0.675 Remote Similarity NPD7319 Approved
0.6739 Remote Similarity NPD6116 Phase 1
0.6739 Remote Similarity NPD6932 Approved
0.6726 Remote Similarity NPD6868 Approved
0.6724 Remote Similarity NPD5983 Phase 2
0.6724 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6703 Remote Similarity NPD8264 Approved
0.6702 Remote Similarity NPD4821 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