Structure

Physi-Chem Properties

Molecular Weight:  330.18
Volume:  344.865
LogP:  1.723
LogD:  1.11
LogS:  -4.574
# Rotatable Bonds:  1
TPSA:  66.76
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.726
Synthetic Accessibility Score:  5.303
Fsp3:  0.65
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:  -4.96
MDCK Permeability:  3.0204426366253756e-05
Pgp-inhibitor:  0.987
Pgp-substrate:  0.027
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.603
30% Bioavailability (F30%):  0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.984
Plasma Protein Binding (PPB):  90.68566131591797%
Volume Distribution (VD):  1.064
Pgp-substrate:  9.205591201782227%

ADMET: Metabolism

CYP1A2-inhibitor:  0.057
CYP1A2-substrate:  0.898
CYP2C19-inhibitor:  0.164
CYP2C19-substrate:  0.804
CYP2C9-inhibitor:  0.17
CYP2C9-substrate:  0.055
CYP2D6-inhibitor:  0.286
CYP2D6-substrate:  0.034
CYP3A4-inhibitor:  0.87
CYP3A4-substrate:  0.902

ADMET: Excretion

Clearance (CL):  2.886
Half-life (T1/2):  0.606

ADMET: Toxicity

hERG Blockers:  0.065
Human Hepatotoxicity (H-HT):  0.399
Drug-inuced Liver Injury (DILI):  0.04
AMES Toxicity:  0.647
Rat Oral Acute Toxicity:  0.958
Maximum Recommended Daily Dose:  0.957
Skin Sensitization:  0.353
Carcinogencity:  0.941
Eye Corrosion:  0.003
Eye Irritation:  0.029
Respiratory Toxicity:  0.957

Download Data

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

  Natural Product: NPC20192

Natural Product ID:  NPC20192
Common Name*:   Libertellenone F
IUPAC Name:   n.a.
Synonyms:   Libertellenone F
Standard InCHIKey:  ZVMOVDFPTOHIGA-CNVPOBLBSA-N
Standard InCHI:  InChI=1S/C20H26O4/c1-5-17(2)8-9-20(23)12(10-17)14(22)15-16-18(3,11-24-15)7-6-13(21)19(16,20)4/h5,10,13,21,23H,1,6-9,11H2,2-4H3/t13-,17+,18+,19+,20-/m1/s1
SMILES:  C=C[C@@]1(C)CC[C@]2(C(=C1)C(=O)C1=C3[C@]2(C)[C@H](O)CC[C@]3(CO1)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1812032
PubChem CID:   53388301
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001634] Naphthofurans

*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
NPO19108 Arthrinium sacchari Species Apiosporaceae Eukaryota n.a. n.a. n.a. PMID[21718054]
NPO19108 Arthrinium sacchari Species Apiosporaceae 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
NPT737 Cell Line HUVEC Homo sapiens IC50 = 64100.0 nM PMID[530550]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 97800.0 nM PMID[530550]

☑ 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 NPC20192 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
0.9524 High Similarity NPC261330
0.93 High Similarity NPC470184
0.8649 High Similarity NPC477116
0.8649 High Similarity NPC27999
0.8496 Intermediate Similarity NPC268958
0.8304 Intermediate Similarity NPC247069
0.8261 Intermediate Similarity NPC478051
0.8224 Intermediate Similarity NPC131366
0.8214 Intermediate Similarity NPC472926
0.82 Intermediate Similarity NPC58271
0.8174 Intermediate Similarity NPC472933
0.8087 Intermediate Similarity NPC21326
0.8073 Intermediate Similarity NPC472645
0.8067 Intermediate Similarity NPC225049
0.8056 Intermediate Similarity NPC230918
0.802 Intermediate Similarity NPC53454
0.8018 Intermediate Similarity NPC87335
0.8018 Intermediate Similarity NPC220705
0.8 Intermediate Similarity NPC472925
0.8 Intermediate Similarity NPC472927
0.7965 Intermediate Similarity NPC90769
0.7961 Intermediate Similarity NPC73457
0.7944 Intermediate Similarity NPC472972
0.7931 Intermediate Similarity NPC251310
0.7925 Intermediate Similarity NPC273269
0.7925 Intermediate Similarity NPC471916
0.7909 Intermediate Similarity NPC85529
0.7909 Intermediate Similarity NPC32006
0.7905 Intermediate Similarity NPC272617
0.7895 Intermediate Similarity NPC25909
0.7895 Intermediate Similarity NPC198539
0.7895 Intermediate Similarity NPC321496
0.789 Intermediate Similarity NPC320154
0.7876 Intermediate Similarity NPC207689
0.7876 Intermediate Similarity NPC171888
0.7876 Intermediate Similarity NPC146945
0.787 Intermediate Similarity NPC112613
0.787 Intermediate Similarity NPC207885
0.7864 Intermediate Similarity NPC230332
0.7863 Intermediate Similarity NPC470777
0.7857 Intermediate Similarity NPC470615
0.7845 Intermediate Similarity NPC472934
0.7833 Intermediate Similarity NPC24651
0.7833 Intermediate Similarity NPC470922
0.7826 Intermediate Similarity NPC238667
0.7818 Intermediate Similarity NPC40170
0.781 Intermediate Similarity NPC212812
0.7807 Intermediate Similarity NPC277769
0.7807 Intermediate Similarity NPC269530
0.7807 Intermediate Similarity NPC472002
0.7807 Intermediate Similarity NPC90952
0.78 Intermediate Similarity NPC40687
0.7797 Intermediate Similarity NPC112038
0.7788 Intermediate Similarity NPC472978
0.7788 Intermediate Similarity NPC478209
0.7788 Intermediate Similarity NPC5103
0.7778 Intermediate Similarity NPC306856
0.7778 Intermediate Similarity NPC240509
0.7778 Intermediate Similarity NPC46761
0.7768 Intermediate Similarity NPC322903
0.7768 Intermediate Similarity NPC65941
0.7759 Intermediate Similarity NPC179626
0.775 Intermediate Similarity NPC120724
0.7745 Intermediate Similarity NPC220930
0.7745 Intermediate Similarity NPC272039
0.7739 Intermediate Similarity NPC208998
0.7739 Intermediate Similarity NPC7921
0.7739 Intermediate Similarity NPC474271
0.7739 Intermediate Similarity NPC159333
0.7736 Intermediate Similarity NPC476245
0.7731 Intermediate Similarity NPC472001
0.7731 Intermediate Similarity NPC46570
0.7727 Intermediate Similarity NPC247957
0.7727 Intermediate Similarity NPC159442
0.7727 Intermediate Similarity NPC320294
0.7727 Intermediate Similarity NPC249187
0.7727 Intermediate Similarity NPC95899
0.7727 Intermediate Similarity NPC111323
0.7724 Intermediate Similarity NPC221414
0.7719 Intermediate Similarity NPC472928
0.7719 Intermediate Similarity NPC324683
0.7712 Intermediate Similarity NPC469488
0.7706 Intermediate Similarity NPC472643
0.7699 Intermediate Similarity NPC286174
0.7699 Intermediate Similarity NPC77947
0.7692 Intermediate Similarity NPC287343
0.7692 Intermediate Similarity NPC97908
0.7692 Intermediate Similarity NPC470854
0.7692 Intermediate Similarity NPC122033
0.7692 Intermediate Similarity NPC474518
0.7692 Intermediate Similarity NPC176513
0.7692 Intermediate Similarity NPC134321
0.7692 Intermediate Similarity NPC474654
0.7692 Intermediate Similarity NPC469684
0.7692 Intermediate Similarity NPC470775
0.7686 Intermediate Similarity NPC476729
0.7685 Intermediate Similarity NPC300584
0.7679 Intermediate Similarity NPC44063
0.7679 Intermediate Similarity NPC473165
0.7672 Intermediate Similarity NPC470953
0.7672 Intermediate Similarity NPC80650
0.767 Intermediate Similarity NPC185059
0.767 Intermediate Similarity NPC475001
0.7667 Intermediate Similarity NPC312833
0.7667 Intermediate Similarity NPC107493
0.7664 Intermediate Similarity NPC94337
0.7664 Intermediate Similarity NPC249954
0.7661 Intermediate Similarity NPC476863
0.7661 Intermediate Similarity NPC476862
0.7658 Intermediate Similarity NPC96268
0.7658 Intermediate Similarity NPC118911
0.7652 Intermediate Similarity NPC4573
0.7647 Intermediate Similarity NPC472974
0.7642 Intermediate Similarity NPC196227
0.7642 Intermediate Similarity NPC476859
0.7642 Intermediate Similarity NPC472976
0.7642 Intermediate Similarity NPC478089
0.7642 Intermediate Similarity NPC472977
0.7636 Intermediate Similarity NPC119601
0.7636 Intermediate Similarity NPC162973
0.7636 Intermediate Similarity NPC308726
0.7636 Intermediate Similarity NPC295791
0.7632 Intermediate Similarity NPC235077
0.7632 Intermediate Similarity NPC473036
0.7632 Intermediate Similarity NPC272898
0.7632 Intermediate Similarity NPC129689
0.7632 Intermediate Similarity NPC153036
0.7627 Intermediate Similarity NPC470776
0.7627 Intermediate Similarity NPC204552
0.7627 Intermediate Similarity NPC188667
0.7627 Intermediate Similarity NPC297179
0.7627 Intermediate Similarity NPC17772
0.7623 Intermediate Similarity NPC477745
0.7619 Intermediate Similarity NPC478072
0.7619 Intermediate Similarity NPC248913
0.7619 Intermediate Similarity NPC99380
0.7615 Intermediate Similarity NPC476299
0.7615 Intermediate Similarity NPC144956
0.7615 Intermediate Similarity NPC472644
0.7615 Intermediate Similarity NPC104861
0.7615 Intermediate Similarity NPC474012
0.7615 Intermediate Similarity NPC54705
0.7611 Intermediate Similarity NPC102843
0.7611 Intermediate Similarity NPC264819
0.7607 Intermediate Similarity NPC478216
0.7607 Intermediate Similarity NPC207217
0.7607 Intermediate Similarity NPC270478
0.7603 Intermediate Similarity NPC91693
0.7603 Intermediate Similarity NPC265557
0.7603 Intermediate Similarity NPC67251
0.7603 Intermediate Similarity NPC18945
0.7603 Intermediate Similarity NPC469789
0.7603 Intermediate Similarity NPC105926
0.76 Intermediate Similarity NPC102316
0.76 Intermediate Similarity NPC476193
0.7596 Intermediate Similarity NPC472973
0.7596 Intermediate Similarity NPC474918
0.7593 Intermediate Similarity NPC20078
0.7593 Intermediate Similarity NPC38530
0.7593 Intermediate Similarity NPC473574
0.7593 Intermediate Similarity NPC84335
0.7589 Intermediate Similarity NPC128828
0.7589 Intermediate Similarity NPC478052
0.7589 Intermediate Similarity NPC166607
0.7589 Intermediate Similarity NPC257353
0.7589 Intermediate Similarity NPC1679
0.7589 Intermediate Similarity NPC478208
0.7586 Intermediate Similarity NPC73300
0.7586 Intermediate Similarity NPC469496
0.7586 Intermediate Similarity NPC478212
0.7586 Intermediate Similarity NPC108721
0.7586 Intermediate Similarity NPC472929
0.7586 Intermediate Similarity NPC469463
0.7586 Intermediate Similarity NPC51978
0.7586 Intermediate Similarity NPC326264
0.7586 Intermediate Similarity NPC469454
0.7586 Intermediate Similarity NPC477266
0.7583 Intermediate Similarity NPC472401
0.7573 Intermediate Similarity NPC298904
0.757 Intermediate Similarity NPC259286
0.757 Intermediate Similarity NPC477437
0.757 Intermediate Similarity NPC134067
0.757 Intermediate Similarity NPC316215
0.757 Intermediate Similarity NPC477438
0.757 Intermediate Similarity NPC91408
0.7568 Intermediate Similarity NPC311612
0.7568 Intermediate Similarity NPC159533
0.7568 Intermediate Similarity NPC478057
0.7565 Intermediate Similarity NPC317107
0.7565 Intermediate Similarity NPC158523
0.7565 Intermediate Similarity NPC179798
0.7565 Intermediate Similarity NPC304180
0.7565 Intermediate Similarity NPC475937
0.7565 Intermediate Similarity NPC188738
0.7565 Intermediate Similarity NPC474229
0.7565 Intermediate Similarity NPC115303
0.7561 Intermediate Similarity NPC476008
0.7561 Intermediate Similarity NPC470882
0.7561 Intermediate Similarity NPC152091
0.7561 Intermediate Similarity NPC473253

  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 NPC20192 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
0.7798 Intermediate Similarity NPD5211 Phase 2
0.7679 Intermediate Similarity NPD5697 Approved
0.7658 Intermediate Similarity NPD5141 Approved
0.7647 Intermediate Similarity NPD6054 Approved
0.7647 Intermediate Similarity NPD6319 Approved
0.7632 Intermediate Similarity NPD4634 Approved
0.7615 Intermediate Similarity NPD5285 Approved
0.7615 Intermediate Similarity NPD5286 Approved
0.7615 Intermediate Similarity NPD4696 Approved
0.7611 Intermediate Similarity NPD6881 Approved
0.7611 Intermediate Similarity NPD6899 Approved
0.7583 Intermediate Similarity NPD6015 Approved
0.7583 Intermediate Similarity NPD6016 Approved
0.7544 Intermediate Similarity NPD6012 Approved
0.7544 Intermediate Similarity NPD6013 Approved
0.7544 Intermediate Similarity NPD6014 Approved
0.7521 Intermediate Similarity NPD6370 Approved
0.7521 Intermediate Similarity NPD5988 Approved
0.7478 Intermediate Similarity NPD7102 Approved
0.7478 Intermediate Similarity NPD6883 Approved
0.7478 Intermediate Similarity NPD7290 Approved
0.7477 Intermediate Similarity NPD5225 Approved
0.7477 Intermediate Similarity NPD5224 Approved
0.7477 Intermediate Similarity NPD5282 Discontinued
0.7477 Intermediate Similarity NPD5226 Approved
0.7477 Intermediate Similarity NPD4633 Approved
0.7456 Intermediate Similarity NPD6011 Approved
0.7434 Intermediate Similarity NPD6402 Approved
0.7434 Intermediate Similarity NPD5739 Approved
0.7434 Intermediate Similarity NPD6675 Approved
0.7434 Intermediate Similarity NPD7128 Approved
0.7431 Intermediate Similarity NPD4755 Approved
0.7414 Intermediate Similarity NPD6650 Approved
0.7414 Intermediate Similarity NPD8130 Phase 1
0.7414 Intermediate Similarity NPD6649 Approved
0.7414 Intermediate Similarity NPD6847 Approved
0.7414 Intermediate Similarity NPD6869 Approved
0.7414 Intermediate Similarity NPD6617 Approved
0.7411 Intermediate Similarity NPD5175 Approved
0.7411 Intermediate Similarity NPD5174 Approved
0.7398 Intermediate Similarity NPD7492 Approved
0.7387 Intermediate Similarity NPD5223 Approved
0.7368 Intermediate Similarity NPD5701 Approved
0.7355 Intermediate Similarity NPD6059 Approved
0.735 Intermediate Similarity NPD6882 Approved
0.735 Intermediate Similarity NPD8297 Approved
0.7339 Intermediate Similarity NPD5221 Approved
0.7339 Intermediate Similarity NPD5222 Approved
0.7339 Intermediate Similarity NPD6616 Approved
0.7339 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7304 Intermediate Similarity NPD7320 Approved
0.7297 Intermediate Similarity NPD4700 Approved
0.7288 Intermediate Similarity NPD4632 Approved
0.728 Intermediate Similarity NPD7078 Approved
0.7273 Intermediate Similarity NPD5173 Approved
0.725 Intermediate Similarity NPD6009 Approved
0.7241 Intermediate Similarity NPD6373 Approved
0.7241 Intermediate Similarity NPD6372 Approved
0.7222 Intermediate Similarity NPD7736 Approved
0.7222 Intermediate Similarity NPD5778 Approved
0.7222 Intermediate Similarity NPD5779 Approved
0.7155 Intermediate Similarity NPD4729 Approved
0.7155 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7155 Intermediate Similarity NPD4730 Approved
0.7154 Intermediate Similarity NPD5983 Phase 2
0.713 Intermediate Similarity NPD6079 Approved
0.7107 Intermediate Similarity NPD7115 Discovery
0.7094 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.704 Intermediate Similarity NPD7604 Phase 2
0.7034 Intermediate Similarity NPD5251 Approved
0.7034 Intermediate Similarity NPD5250 Approved
0.7034 Intermediate Similarity NPD5247 Approved
0.7034 Intermediate Similarity NPD5248 Approved
0.7034 Intermediate Similarity NPD5249 Phase 3
0.7027 Intermediate Similarity NPD4697 Phase 3
0.7025 Intermediate Similarity NPD6274 Approved
0.7009 Intermediate Similarity NPD5128 Approved
0.7008 Intermediate Similarity NPD8293 Discontinued
0.6992 Remote Similarity NPD7100 Approved
0.6992 Remote Similarity NPD7101 Approved
0.6983 Remote Similarity NPD4767 Approved
0.6983 Remote Similarity NPD4768 Approved
0.6975 Remote Similarity NPD5215 Approved
0.6975 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6975 Remote Similarity NPD5216 Approved
0.6975 Remote Similarity NPD5217 Approved
0.6972 Remote Similarity NPD6411 Approved
0.6967 Remote Similarity NPD6317 Approved
0.6957 Remote Similarity NPD4754 Approved
0.6944 Remote Similarity NPD5328 Approved
0.6937 Remote Similarity NPD5695 Phase 3
0.6929 Remote Similarity NPD6336 Discontinued
0.6911 Remote Similarity NPD6314 Approved
0.6911 Remote Similarity NPD6335 Approved
0.6911 Remote Similarity NPD6313 Approved
0.6905 Remote Similarity NPD8328 Phase 3
0.6903 Remote Similarity NPD4225 Approved
0.6893 Remote Similarity NPD4695 Discontinued
0.6891 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6891 Remote Similarity NPD5169 Approved
0.6891 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6891 Remote Similarity NPD5135 Approved
0.6887 Remote Similarity NPD1696 Phase 3
0.6842 Remote Similarity NPD7640 Approved
0.6842 Remote Similarity NPD7639 Approved
0.6838 Remote Similarity NPD6008 Approved
0.6833 Remote Similarity NPD5127 Approved
0.6822 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6822 Remote Similarity NPD6033 Approved
0.6822 Remote Similarity NPD5279 Phase 3
0.6822 Remote Similarity NPD3618 Phase 1
0.6814 Remote Similarity NPD6084 Phase 2
0.6814 Remote Similarity NPD6083 Phase 2
0.6789 Remote Similarity NPD4753 Phase 2
0.6789 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6789 Remote Similarity NPD6101 Approved
0.6786 Remote Similarity NPD4629 Approved
0.6786 Remote Similarity NPD5210 Approved
0.6777 Remote Similarity NPD6053 Discontinued
0.6757 Remote Similarity NPD4202 Approved
0.6754 Remote Similarity NPD7638 Approved
0.6748 Remote Similarity NPD6868 Approved
0.6723 Remote Similarity NPD6686 Approved
0.6723 Remote Similarity NPD5168 Approved
0.6694 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5690 Phase 2
0.6667 Remote Similarity NPD5167 Approved
0.6641 Remote Similarity NPD7319 Approved
0.6639 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6637 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6618 Remote Similarity NPD6334 Approved
0.6618 Remote Similarity NPD6333 Approved
0.6614 Remote Similarity NPD6909 Approved
0.6614 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6614 Remote Similarity NPD6908 Approved
0.6609 Remote Similarity NPD5696 Approved
0.6606 Remote Similarity NPD3573 Approved
0.6604 Remote Similarity NPD3667 Approved
0.6571 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6549 Remote Similarity NPD7748 Approved
0.6541 Remote Similarity NPD7260 Phase 2
0.6538 Remote Similarity NPD7507 Approved
0.6522 Remote Similarity NPD7902 Approved
0.6518 Remote Similarity NPD7515 Phase 2
0.6514 Remote Similarity NPD4623 Approved
0.6514 Remote Similarity NPD4519 Discontinued
0.65 Remote Similarity NPD6412 Phase 2
0.6496 Remote Similarity NPD5344 Discontinued
0.6484 Remote Similarity NPD6921 Approved
0.6481 Remote Similarity NPD4786 Approved
0.6481 Remote Similarity NPD3133 Approved
0.6481 Remote Similarity NPD3666 Approved
0.6481 Remote Similarity NPD3665 Phase 1
0.6475 Remote Similarity NPD6371 Approved
0.6466 Remote Similarity NPD5956 Approved
0.646 Remote Similarity NPD6399 Phase 3
0.6457 Remote Similarity NPD4522 Approved
0.6441 Remote Similarity NPD7632 Discontinued
0.6422 Remote Similarity NPD1694 Approved
0.6396 Remote Similarity NPD5737 Approved
0.6396 Remote Similarity NPD6672 Approved
0.6389 Remote Similarity NPD6110 Phase 1
0.6381 Remote Similarity NPD3617 Approved
0.6372 Remote Similarity NPD7983 Approved
0.6372 Remote Similarity NPD7637 Suspended
0.6372 Remote Similarity NPD5694 Approved
0.6364 Remote Similarity NPD5280 Approved
0.6364 Remote Similarity NPD4694 Approved
0.6357 Remote Similarity NPD8517 Approved
0.6357 Remote Similarity NPD8513 Phase 3
0.6357 Remote Similarity NPD8516 Approved
0.6357 Remote Similarity NPD8515 Approved
0.6339 Remote Similarity NPD7285 Clinical (unspecified phase)
0.633 Remote Similarity NPD4197 Approved
0.6296 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6283 Remote Similarity NPD5692 Phase 3
0.6283 Remote Similarity NPD5785 Approved
0.6273 Remote Similarity NPD5329 Approved
0.6271 Remote Similarity NPD6648 Approved
0.6261 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6261 Remote Similarity NPD7900 Approved
0.626 Remote Similarity NPD8132 Clinical (unspecified phase)
0.625 Remote Similarity NPD6845 Suspended
0.6231 Remote Similarity NPD7503 Approved
0.623 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6228 Remote Similarity NPD5693 Phase 1
0.6228 Remote Similarity NPD6050 Approved
0.6228 Remote Similarity NPD5284 Approved
0.6228 Remote Similarity NPD5281 Approved
0.6222 Remote Similarity NPD6914 Discontinued
0.6195 Remote Similarity NPD6673 Approved
0.6195 Remote Similarity NPD6080 Approved
0.6195 Remote Similarity NPD6904 Approved
0.6182 Remote Similarity NPD3668 Phase 3
0.6182 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6147 Remote Similarity NPD4223 Phase 3
0.6147 Remote Similarity NPD4221 Approved
0.6132 Remote Similarity NPD4756 Discovery
0.6126 Remote Similarity NPD5363 Approved
0.6124 Remote Similarity NPD7327 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