Structure

Physi-Chem Properties

Molecular Weight:  350.21
Volume:  358.929
LogP:  2.672
LogD:  2.19
LogS:  -3.794
# Rotatable Bonds:  2
TPSA:  75.99
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.589
Synthetic Accessibility Score:  6.283
Fsp3:  0.85
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.503
MDCK Permeability:  2.122254591085948e-05
Pgp-inhibitor:  0.044
Pgp-substrate:  0.247
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.006
30% Bioavailability (F30%):  0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.777
Plasma Protein Binding (PPB):  68.30945587158203%
Volume Distribution (VD):  0.721
Pgp-substrate:  29.339262008666992%

ADMET: Metabolism

CYP1A2-inhibitor:  0.011
CYP1A2-substrate:  0.94
CYP2C19-inhibitor:  0.016
CYP2C19-substrate:  0.866
CYP2C9-inhibitor:  0.057
CYP2C9-substrate:  0.093
CYP2D6-inhibitor:  0.007
CYP2D6-substrate:  0.112
CYP3A4-inhibitor:  0.296
CYP3A4-substrate:  0.387

ADMET: Excretion

Clearance (CL):  4.338
Half-life (T1/2):  0.531

ADMET: Toxicity

hERG Blockers:  0.034
Human Hepatotoxicity (H-HT):  0.27
Drug-inuced Liver Injury (DILI):  0.134
AMES Toxicity:  0.057
Rat Oral Acute Toxicity:  0.965
Maximum Recommended Daily Dose:  0.944
Skin Sensitization:  0.439
Carcinogencity:  0.945
Eye Corrosion:  0.679
Eye Irritation:  0.361
Respiratory Toxicity:  0.985

Download Data

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

  Natural Product: NPC472851

Natural Product ID:  NPC472851
Common Name*:   NVIRVAAOVXZOTN-LUGRNRNJSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  NVIRVAAOVXZOTN-LUGRNRNJSA-N
Standard InCHI:  InChI=1S/C20H30O5/c1-12(2)19-8-9-20(25-24-19)13(11-19)14(21)10-15-17(3,16(22)23)6-5-7-18(15,20)4/h11-12,14-15,21H,5-10H2,1-4H3,(H,22,23)/t14-,15+,17-,18+,19-,20+/m0/s1
SMILES:  O[C@H]1C[C@@H]2[C@](C)(CCC[C@]2([C@]23C1=C[C@](CC2)(OO3)C(C)C)C)C(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3590334
PubChem CID:   n.a.
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000368] Dioxanes
        • [CHEMONTID:0001312] 1,2-dioxanes

*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
NPO13153 Callicarpa macrophylla Species Lamiaceae Eukaryota Leaves n.a. n.a. PMID[26110519]
NPO13153 Callicarpa macrophylla Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13153 Callicarpa macrophylla Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13153 Callicarpa macrophylla Species Lamiaceae 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
NPT681 Cell Line PC-12 Rattus norvegicus EC50 = 10600.0 nM PMID[567799]

☑ 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 NPC472851 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
0.9348 High Similarity NPC266899
0.9111 High Similarity NPC475101
0.9111 High Similarity NPC476427
0.9111 High Similarity NPC124927
0.8889 High Similarity NPC470415
0.8632 High Similarity NPC470958
0.8632 High Similarity NPC470957
0.8557 High Similarity NPC189880
0.8542 High Similarity NPC272617
0.8454 Intermediate Similarity NPC476327
0.8454 Intermediate Similarity NPC476318
0.8431 Intermediate Similarity NPC64844
0.8431 Intermediate Similarity NPC42847
0.8416 Intermediate Similarity NPC474281
0.8351 Intermediate Similarity NPC473240
0.8298 Intermediate Similarity NPC104560
0.828 Intermediate Similarity NPC473226
0.8269 Intermediate Similarity NPC143706
0.8269 Intermediate Similarity NPC472534
0.8265 Intermediate Similarity NPC116457
0.8247 Intermediate Similarity NPC159365
0.8235 Intermediate Similarity NPC201763
0.8229 Intermediate Similarity NPC475708
0.8229 Intermediate Similarity NPC472978
0.8172 Intermediate Similarity NPC471344
0.8163 Intermediate Similarity NPC290481
0.8163 Intermediate Similarity NPC53565
0.8163 Intermediate Similarity NPC134067
0.8148 Intermediate Similarity NPC474734
0.8137 Intermediate Similarity NPC478057
0.8137 Intermediate Similarity NPC90177
0.8125 Intermediate Similarity NPC130278
0.8125 Intermediate Similarity NPC232202
0.8119 Intermediate Similarity NPC118964
0.8119 Intermediate Similarity NPC256247
0.81 Intermediate Similarity NPC174663
0.81 Intermediate Similarity NPC260149
0.81 Intermediate Similarity NPC58942
0.8085 Intermediate Similarity NPC476104
0.8085 Intermediate Similarity NPC82979
0.8085 Intermediate Similarity NPC472985
0.8085 Intermediate Similarity NPC472986
0.8085 Intermediate Similarity NPC73038
0.8081 Intermediate Similarity NPC19376
0.8081 Intermediate Similarity NPC307282
0.8081 Intermediate Similarity NPC305464
0.8081 Intermediate Similarity NPC134072
0.8081 Intermediate Similarity NPC25848
0.8081 Intermediate Similarity NPC234993
0.8073 Intermediate Similarity NPC470775
0.8073 Intermediate Similarity NPC176513
0.8061 Intermediate Similarity NPC114159
0.8061 Intermediate Similarity NPC6818
0.8061 Intermediate Similarity NPC103527
0.8061 Intermediate Similarity NPC191412
0.8058 Intermediate Similarity NPC475036
0.8041 Intermediate Similarity NPC476417
0.8039 Intermediate Similarity NPC476081
0.8037 Intermediate Similarity NPC90952
0.8037 Intermediate Similarity NPC302146
0.8021 Intermediate Similarity NPC270768
0.8021 Intermediate Similarity NPC130520
0.8021 Intermediate Similarity NPC290972
0.8021 Intermediate Similarity NPC61543
0.8021 Intermediate Similarity NPC225585
0.8021 Intermediate Similarity NPC293048
0.8021 Intermediate Similarity NPC64872
0.8021 Intermediate Similarity NPC25906
0.8021 Intermediate Similarity NPC472973
0.8021 Intermediate Similarity NPC127689
0.8021 Intermediate Similarity NPC59263
0.8021 Intermediate Similarity NPC121798
0.8021 Intermediate Similarity NPC263393
0.8021 Intermediate Similarity NPC234346
0.802 Intermediate Similarity NPC470074
0.8 Intermediate Similarity NPC476879
0.8 Intermediate Similarity NPC470776
0.8 Intermediate Similarity NPC251310
0.8 Intermediate Similarity NPC254496
0.8 Intermediate Similarity NPC231599
0.8 Intermediate Similarity NPC163216
0.8 Intermediate Similarity NPC170131
0.8 Intermediate Similarity NPC472219
0.8 Intermediate Similarity NPC472218
0.8 Intermediate Similarity NPC472217
0.8 Intermediate Similarity NPC476878
0.7982 Intermediate Similarity NPC474046
0.7982 Intermediate Similarity NPC470628
0.7982 Intermediate Similarity NPC259306
0.798 Intermediate Similarity NPC139570
0.7963 Intermediate Similarity NPC25909
0.7961 Intermediate Similarity NPC222153
0.7959 Intermediate Similarity NPC202728
0.7959 Intermediate Similarity NPC477855
0.7959 Intermediate Similarity NPC158059
0.7959 Intermediate Similarity NPC118490
0.7959 Intermediate Similarity NPC229281
0.7959 Intermediate Similarity NPC118519
0.7944 Intermediate Similarity NPC469655
0.7944 Intermediate Similarity NPC469656
0.7944 Intermediate Similarity NPC474846
0.7944 Intermediate Similarity NPC146945
0.7944 Intermediate Similarity NPC171888
0.7941 Intermediate Similarity NPC471412
0.7941 Intermediate Similarity NPC81530
0.7938 Intermediate Similarity NPC111110
0.7938 Intermediate Similarity NPC290614
0.7938 Intermediate Similarity NPC210037
0.7938 Intermediate Similarity NPC126369
0.7938 Intermediate Similarity NPC134321
0.7938 Intermediate Similarity NPC120968
0.7938 Intermediate Similarity NPC470589
0.7938 Intermediate Similarity NPC273621
0.7938 Intermediate Similarity NPC227467
0.7938 Intermediate Similarity NPC128672
0.7938 Intermediate Similarity NPC18872
0.7938 Intermediate Similarity NPC477872
0.7938 Intermediate Similarity NPC7260
0.7925 Intermediate Similarity NPC285298
0.7925 Intermediate Similarity NPC257082
0.7921 Intermediate Similarity NPC119036
0.7917 Intermediate Similarity NPC182797
0.7917 Intermediate Similarity NPC52169
0.7909 Intermediate Similarity NPC473590
0.7905 Intermediate Similarity NPC67321
0.7905 Intermediate Similarity NPC263729
0.7905 Intermediate Similarity NPC187435
0.7905 Intermediate Similarity NPC230541
0.79 Intermediate Similarity NPC477853
0.79 Intermediate Similarity NPC235053
0.79 Intermediate Similarity NPC132824
0.79 Intermediate Similarity NPC202833
0.7895 Intermediate Similarity NPC322159
0.7895 Intermediate Similarity NPC262085
0.789 Intermediate Similarity NPC117712
0.789 Intermediate Similarity NPC472274
0.789 Intermediate Similarity NPC470919
0.789 Intermediate Similarity NPC469877
0.7889 Intermediate Similarity NPC474433
0.7885 Intermediate Similarity NPC239162
0.7879 Intermediate Similarity NPC91010
0.7879 Intermediate Similarity NPC472977
0.7879 Intermediate Similarity NPC196227
0.7879 Intermediate Similarity NPC469982
0.7879 Intermediate Similarity NPC88116
0.7879 Intermediate Similarity NPC20235
0.7879 Intermediate Similarity NPC474529
0.7879 Intermediate Similarity NPC263548
0.7879 Intermediate Similarity NPC282395
0.7879 Intermediate Similarity NPC472976
0.7879 Intermediate Similarity NPC231063
0.7879 Intermediate Similarity NPC145667
0.7879 Intermediate Similarity NPC32407
0.7879 Intermediate Similarity NPC299996
0.7872 Intermediate Similarity NPC102048
0.787 Intermediate Similarity NPC277769
0.787 Intermediate Similarity NPC472002
0.787 Intermediate Similarity NPC4573
0.787 Intermediate Similarity NPC174836
0.7864 Intermediate Similarity NPC271980
0.7864 Intermediate Similarity NPC162973
0.7864 Intermediate Similarity NPC136289
0.7864 Intermediate Similarity NPC193934
0.7857 Intermediate Similarity NPC228784
0.7857 Intermediate Similarity NPC155120
0.7857 Intermediate Similarity NPC288833
0.7857 Intermediate Similarity NPC966
0.7857 Intermediate Similarity NPC105189
0.7857 Intermediate Similarity NPC187722
0.7857 Intermediate Similarity NPC282616
0.7857 Intermediate Similarity NPC324341
0.785 Intermediate Similarity NPC478209
0.7843 Intermediate Similarity NPC471041
0.7843 Intermediate Similarity NPC474718
0.7843 Intermediate Similarity NPC472972
0.7843 Intermediate Similarity NPC471727
0.7843 Intermediate Similarity NPC471413
0.7835 Intermediate Similarity NPC194642
0.7835 Intermediate Similarity NPC314727
0.7835 Intermediate Similarity NPC474704
0.7835 Intermediate Similarity NPC281524
0.7835 Intermediate Similarity NPC475921
0.7835 Intermediate Similarity NPC198664
0.7835 Intermediate Similarity NPC471342
0.7835 Intermediate Similarity NPC143232
0.7835 Intermediate Similarity NPC101886
0.7835 Intermediate Similarity NPC469866
0.7835 Intermediate Similarity NPC274330
0.783 Intermediate Similarity NPC293850
0.783 Intermediate Similarity NPC189075
0.783 Intermediate Similarity NPC275539
0.7822 Intermediate Similarity NPC9613
0.7822 Intermediate Similarity NPC43686
0.7822 Intermediate Similarity NPC247139
0.7822 Intermediate Similarity NPC285513
0.7818 Intermediate Similarity NPC179626
0.7812 Intermediate Similarity NPC242468
0.7812 Intermediate Similarity NPC298904
0.7812 Intermediate Similarity NPC88716
0.7812 Intermediate Similarity NPC51700

  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 NPC472851 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
0.7677 Intermediate Similarity NPD7515 Phase 2
0.7524 Intermediate Similarity NPD5211 Phase 2
0.75 Intermediate Similarity NPD7640 Approved
0.75 Intermediate Similarity NPD7639 Approved
0.7477 Intermediate Similarity NPD5739 Approved
0.7477 Intermediate Similarity NPD6675 Approved
0.7477 Intermediate Similarity NPD7128 Approved
0.7477 Intermediate Similarity NPD6402 Approved
0.7476 Intermediate Similarity NPD4755 Approved
0.7426 Intermediate Similarity NPD5778 Approved
0.7426 Intermediate Similarity NPD5779 Approved
0.7407 Intermediate Similarity NPD5701 Approved
0.7407 Intermediate Similarity NPD5697 Approved
0.7404 Intermediate Similarity NPD7638 Approved
0.7383 Intermediate Similarity NPD5141 Approved
0.7353 Intermediate Similarity NPD7748 Approved
0.7339 Intermediate Similarity NPD6881 Approved
0.7339 Intermediate Similarity NPD6899 Approved
0.7339 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7339 Intermediate Similarity NPD7320 Approved
0.7333 Intermediate Similarity NPD5285 Approved
0.7333 Intermediate Similarity NPD5286 Approved
0.7333 Intermediate Similarity NPD4700 Approved
0.7333 Intermediate Similarity NPD4696 Approved
0.7327 Intermediate Similarity NPD6411 Approved
0.7308 Intermediate Similarity NPD7902 Approved
0.73 Intermediate Similarity NPD5328 Approved
0.7273 Intermediate Similarity NPD6012 Approved
0.7273 Intermediate Similarity NPD3573 Approved
0.7273 Intermediate Similarity NPD6014 Approved
0.7273 Intermediate Similarity NPD6013 Approved
0.7273 Intermediate Similarity NPD6373 Approved
0.7273 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD6372 Approved
0.7245 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7227 Intermediate Similarity NPD7507 Approved
0.7207 Intermediate Similarity NPD7290 Approved
0.7207 Intermediate Similarity NPD6883 Approved
0.7207 Intermediate Similarity NPD7102 Approved
0.7196 Intermediate Similarity NPD4633 Approved
0.7196 Intermediate Similarity NPD5224 Approved
0.7196 Intermediate Similarity NPD5225 Approved
0.7196 Intermediate Similarity NPD5226 Approved
0.719 Intermediate Similarity NPD7319 Approved
0.7182 Intermediate Similarity NPD6686 Approved
0.7182 Intermediate Similarity NPD6011 Approved
0.7172 Intermediate Similarity NPD3618 Phase 1
0.7168 Intermediate Similarity NPD4632 Approved
0.7157 Intermediate Similarity NPD6079 Approved
0.7143 Intermediate Similarity NPD8130 Phase 1
0.7143 Intermediate Similarity NPD6869 Approved
0.7143 Intermediate Similarity NPD6617 Approved
0.7143 Intermediate Similarity NPD6847 Approved
0.7143 Intermediate Similarity NPD6649 Approved
0.7143 Intermediate Similarity NPD6650 Approved
0.713 Intermediate Similarity NPD7115 Discovery
0.713 Intermediate Similarity NPD5174 Approved
0.713 Intermediate Similarity NPD5175 Approved
0.7129 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.7129 Intermediate Similarity NPD6101 Approved
0.7113 Intermediate Similarity NPD3667 Approved
0.7103 Intermediate Similarity NPD5223 Approved
0.7087 Intermediate Similarity NPD6399 Phase 3
0.7087 Intermediate Similarity NPD4202 Approved
0.708 Intermediate Similarity NPD8297 Approved
0.708 Intermediate Similarity NPD6882 Approved
0.7075 Intermediate Similarity NPD4225 Approved
0.7054 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7054 Intermediate Similarity NPD4634 Approved
0.7048 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD5222 Approved
0.7048 Intermediate Similarity NPD5221 Approved
0.7048 Intermediate Similarity NPD4697 Phase 3
0.7019 Intermediate Similarity NPD7900 Approved
0.7019 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD4767 Approved
0.7 Intermediate Similarity NPD4768 Approved
0.7 Intermediate Similarity NPD6008 Approved
0.6991 Remote Similarity NPD6401 Clinical (unspecified phase)
0.699 Remote Similarity NPD8034 Phase 2
0.699 Remote Similarity NPD8035 Phase 2
0.699 Remote Similarity NPD7637 Suspended
0.6983 Remote Similarity NPD6009 Approved
0.6981 Remote Similarity NPD5173 Approved
0.6972 Remote Similarity NPD4754 Approved
0.697 Remote Similarity NPD4786 Approved
0.6964 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6949 Remote Similarity NPD6319 Approved
0.6917 Remote Similarity NPD8328 Phase 3
0.6907 Remote Similarity NPD7525 Registered
0.6897 Remote Similarity NPD6274 Approved
0.6881 Remote Similarity NPD7632 Discontinued
0.6875 Remote Similarity NPD4729 Approved
0.6875 Remote Similarity NPD4730 Approved
0.6875 Remote Similarity NPD5128 Approved
0.6838 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6822 Remote Similarity NPD6083 Phase 2
0.6822 Remote Similarity NPD6084 Phase 2
0.6804 Remote Similarity NPD7645 Phase 2
0.68 Remote Similarity NPD7338 Clinical (unspecified phase)
0.68 Remote Similarity NPD3666 Approved
0.68 Remote Similarity NPD3133 Approved
0.68 Remote Similarity NPD3665 Phase 1
0.6796 Remote Similarity NPD4753 Phase 2
0.6786 Remote Similarity NPD6412 Phase 2
0.6786 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6783 Remote Similarity NPD6053 Discontinued
0.678 Remote Similarity NPD7328 Approved
0.678 Remote Similarity NPD7327 Approved
0.6768 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6754 Remote Similarity NPD5249 Phase 3
0.6754 Remote Similarity NPD5247 Approved
0.6754 Remote Similarity NPD5250 Approved
0.6754 Remote Similarity NPD5251 Approved
0.6754 Remote Similarity NPD5248 Approved
0.675 Remote Similarity NPD5983 Phase 2
0.675 Remote Similarity NPD8513 Phase 3
0.6735 Remote Similarity NPD6930 Phase 2
0.6735 Remote Similarity NPD6931 Approved
0.6724 Remote Similarity NPD8133 Approved
0.6723 Remote Similarity NPD7516 Approved
0.6723 Remote Similarity NPD7100 Approved
0.6723 Remote Similarity NPD7101 Approved
0.6721 Remote Similarity NPD7492 Approved
0.6701 Remote Similarity NPD6118 Approved
0.6701 Remote Similarity NPD6114 Approved
0.6701 Remote Similarity NPD6115 Approved
0.6701 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6701 Remote Similarity NPD6697 Approved
0.67 Remote Similarity NPD6695 Phase 3
0.6696 Remote Similarity NPD5217 Approved
0.6696 Remote Similarity NPD5215 Approved
0.6696 Remote Similarity NPD5216 Approved
0.6695 Remote Similarity NPD6317 Approved
0.6694 Remote Similarity NPD7736 Approved
0.6667 Remote Similarity NPD6616 Approved
0.6667 Remote Similarity NPD6054 Approved
0.6667 Remote Similarity NPD4623 Approved
0.6667 Remote Similarity NPD7983 Approved
0.6667 Remote Similarity NPD6059 Approved
0.6667 Remote Similarity NPD4519 Discontinued
0.6639 Remote Similarity NPD6314 Approved
0.6639 Remote Similarity NPD7604 Phase 2
0.6639 Remote Similarity NPD6335 Approved
0.6639 Remote Similarity NPD6313 Approved
0.6636 Remote Similarity NPD5344 Discontinued
0.6636 Remote Similarity NPD5695 Phase 3
0.6634 Remote Similarity NPD3668 Phase 3
0.6633 Remote Similarity NPD6929 Approved
0.6613 Remote Similarity NPD7078 Approved
0.6613 Remote Similarity NPD8293 Discontinued
0.6612 Remote Similarity NPD6015 Approved
0.6612 Remote Similarity NPD6016 Approved
0.6612 Remote Similarity NPD6921 Approved
0.6612 Remote Similarity NPD8517 Approved
0.6612 Remote Similarity NPD6909 Approved
0.6612 Remote Similarity NPD8378 Approved
0.6612 Remote Similarity NPD8515 Approved
0.6612 Remote Similarity NPD8296 Approved
0.6612 Remote Similarity NPD8516 Approved
0.6612 Remote Similarity NPD8379 Approved
0.6612 Remote Similarity NPD6908 Approved
0.6612 Remote Similarity NPD8380 Approved
0.6612 Remote Similarity NPD8335 Approved
0.6609 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6609 Remote Similarity NPD5169 Approved
0.6609 Remote Similarity NPD5135 Approved
0.6606 Remote Similarity NPD5696 Approved
0.6602 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6598 Remote Similarity NPD6116 Phase 1
0.6574 Remote Similarity NPD7839 Suspended
0.6571 Remote Similarity NPD46 Approved
0.6571 Remote Similarity NPD6698 Approved
0.6566 Remote Similarity NPD4821 Approved
0.6566 Remote Similarity NPD4695 Discontinued
0.6566 Remote Similarity NPD7514 Phase 3
0.6566 Remote Similarity NPD4822 Approved
0.6566 Remote Similarity NPD7332 Phase 2
0.6566 Remote Similarity NPD4819 Approved
0.6566 Remote Similarity NPD4820 Approved
0.6566 Remote Similarity NPD5368 Approved
0.6562 Remote Similarity NPD3703 Phase 2
0.6557 Remote Similarity NPD5988 Approved
0.6557 Remote Similarity NPD6370 Approved
0.6552 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6552 Remote Similarity NPD5127 Approved
0.6538 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6532 Remote Similarity NPD6336 Discontinued
0.6529 Remote Similarity NPD8377 Approved
0.6529 Remote Similarity NPD8294 Approved
0.6509 Remote Similarity NPD5284 Approved
0.6509 Remote Similarity NPD5281 Approved
0.6505 Remote Similarity NPD7334 Approved
0.6505 Remote Similarity NPD5279 Phase 3
0.6505 Remote Similarity NPD7521 Approved
0.6505 Remote Similarity NPD5330 Approved
0.6505 Remote Similarity NPD7146 Approved
0.6505 Remote Similarity NPD6684 Approved
0.6505 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6505 Remote Similarity NPD6409 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