Structure

Physi-Chem Properties

Molecular Weight:  348.19
Volume:  362.212
LogP:  1.202
LogD:  0.62
LogS:  -3.917
# Rotatable Bonds:  2
TPSA:  94.83
# H-Bond Aceptor:  5
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.52
Synthetic Accessibility Score:  5.168
Fsp3:  0.7
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
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:  -4.853
MDCK Permeability:  2.5201496100635268e-05
Pgp-inhibitor:  0.103
Pgp-substrate:  0.027
Human Intestinal Absorption (HIA):  0.019
20% Bioavailability (F20%):  0.021
30% Bioavailability (F30%):  0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.885
Plasma Protein Binding (PPB):  77.70685577392578%
Volume Distribution (VD):  0.414
Pgp-substrate:  17.050769805908203%

ADMET: Metabolism

CYP1A2-inhibitor:  0.012
CYP1A2-substrate:  0.954
CYP2C19-inhibitor:  0.022
CYP2C19-substrate:  0.718
CYP2C9-inhibitor:  0.04
CYP2C9-substrate:  0.045
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.04
CYP3A4-inhibitor:  0.819
CYP3A4-substrate:  0.573

ADMET: Excretion

Clearance (CL):  3.251
Half-life (T1/2):  0.459

ADMET: Toxicity

hERG Blockers:  0.029
Human Hepatotoxicity (H-HT):  0.473
Drug-inuced Liver Injury (DILI):  0.044
AMES Toxicity:  0.606
Rat Oral Acute Toxicity:  0.944
Maximum Recommended Daily Dose:  0.954
Skin Sensitization:  0.442
Carcinogencity:  0.804
Eye Corrosion:  0.004
Eye Irritation:  0.074
Respiratory Toxicity:  0.978

Download Data

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

  Natural Product: NPC470184

Natural Product ID:  NPC470184
Common Name*:   Libertellenone C
IUPAC Name:   (1S,4R,4aR,4bS,7R)-7-ethenyl-4,4b,10-trihydroxy-1-(hydroxymethyl)-1,4a,7-trimethyl-3,4,5,6-tetrahydro-2H-phenanthren-9-one
Synonyms:   Libertellenone C
Standard InCHIKey:  YFSWTQQLSUEQBY-FZIGORSYSA-N
Standard InCHI:  InChI=1S/C20H28O5/c1-5-17(2)8-9-20(25)12(10-17)14(23)15(24)16-18(3,11-21)7-6-13(22)19(16,20)4/h5,10,13,21-22,24-25H,1,6-9,11H2,2-4H3/t13-,17+,18-,19+,20-/m1/s1
SMILES:  CC1(CCC2(C(=C1)C(=O)C(=C3C2(C(CCC3(C)CO)O)C)O)O)C=C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1812034
PubChem CID:   56662710
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000025] Phenanthrenes and derivatives
        • [CHEMONTID:0000223] Hydrophenanthrenes

*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 = 29700.0 nM PMID[508244]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 68700.0 nM PMID[508244]

☑ 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 NPC470184 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
0.93 High Similarity NPC20192
0.8857 High Similarity NPC261330
0.8817 High Similarity NPC58271
0.8614 High Similarity NPC230918
0.8542 High Similarity NPC73457
0.8485 Intermediate Similarity NPC273269
0.8469 Intermediate Similarity NPC272617
0.8387 Intermediate Similarity NPC40687
0.8365 Intermediate Similarity NPC472925
0.8351 Intermediate Similarity NPC472978
0.8349 Intermediate Similarity NPC27999
0.8349 Intermediate Similarity NPC477116
0.8316 Intermediate Similarity NPC220930
0.8316 Intermediate Similarity NPC272039
0.8283 Intermediate Similarity NPC476245
0.8252 Intermediate Similarity NPC131366
0.8247 Intermediate Similarity NPC230332
0.8247 Intermediate Similarity NPC134321
0.8211 Intermediate Similarity NPC472974
0.8198 Intermediate Similarity NPC268958
0.8182 Intermediate Similarity NPC472976
0.8182 Intermediate Similarity NPC196227
0.8182 Intermediate Similarity NPC478089
0.8182 Intermediate Similarity NPC472977
0.8163 Intermediate Similarity NPC99380
0.8144 Intermediate Similarity NPC472973
0.8144 Intermediate Similarity NPC474918
0.8125 Intermediate Similarity NPC298904
0.8113 Intermediate Similarity NPC65941
0.8095 Intermediate Similarity NPC85529
0.8095 Intermediate Similarity NPC32006
0.8077 Intermediate Similarity NPC111323
0.8077 Intermediate Similarity NPC247957
0.8077 Intermediate Similarity NPC249187
0.8061 Intermediate Similarity NPC128672
0.8056 Intermediate Similarity NPC472928
0.8041 Intermediate Similarity NPC53454
0.8041 Intermediate Similarity NPC471793
0.8041 Intermediate Similarity NPC471791
0.8037 Intermediate Similarity NPC87335
0.8021 Intermediate Similarity NPC472985
0.8021 Intermediate Similarity NPC472986
0.802 Intermediate Similarity NPC249954
0.8 Intermediate Similarity NPC247069
0.8 Intermediate Similarity NPC103527
0.798 Intermediate Similarity NPC172101
0.798 Intermediate Similarity NPC116726
0.7963 Intermediate Similarity NPC235077
0.7961 Intermediate Similarity NPC198880
0.7961 Intermediate Similarity NPC144956
0.7961 Intermediate Similarity NPC46761
0.7946 Intermediate Similarity NPC251310
0.7941 Intermediate Similarity NPC471916
0.7925 Intermediate Similarity NPC166607
0.7925 Intermediate Similarity NPC257353
0.7921 Intermediate Similarity NPC266899
0.7921 Intermediate Similarity NPC474602
0.7921 Intermediate Similarity NPC259286
0.7917 Intermediate Similarity NPC255174
0.7909 Intermediate Similarity NPC472926
0.7909 Intermediate Similarity NPC73300
0.7909 Intermediate Similarity NPC108721
0.7905 Intermediate Similarity NPC311612
0.79 Intermediate Similarity NPC131840
0.789 Intermediate Similarity NPC171888
0.789 Intermediate Similarity NPC146945
0.7885 Intermediate Similarity NPC112613
0.7885 Intermediate Similarity NPC302537
0.7885 Intermediate Similarity NPC472924
0.7885 Intermediate Similarity NPC163372
0.7885 Intermediate Similarity NPC207885
0.7876 Intermediate Similarity NPC472933
0.787 Intermediate Similarity NPC214644
0.787 Intermediate Similarity NPC220705
0.7857 Intermediate Similarity NPC307298
0.785 Intermediate Similarity NPC185
0.785 Intermediate Similarity NPC58370
0.785 Intermediate Similarity NPC43285
0.783 Intermediate Similarity NPC160843
0.783 Intermediate Similarity NPC72255
0.783 Intermediate Similarity NPC118911
0.783 Intermediate Similarity NPC474281
0.7822 Intermediate Similarity NPC23170
0.7822 Intermediate Similarity NPC212812
0.7818 Intermediate Similarity NPC90769
0.7818 Intermediate Similarity NPC90952
0.7818 Intermediate Similarity NPC277769
0.781 Intermediate Similarity NPC119601
0.781 Intermediate Similarity NPC308726
0.781 Intermediate Similarity NPC87351
0.781 Intermediate Similarity NPC473424
0.7807 Intermediate Similarity NPC478051
0.78 Intermediate Similarity NPC472975
0.7789 Intermediate Similarity NPC103486
0.7788 Intermediate Similarity NPC472972
0.7788 Intermediate Similarity NPC474720
0.7788 Intermediate Similarity NPC327431
0.7778 Intermediate Similarity NPC217201
0.7778 Intermediate Similarity NPC225049
0.7778 Intermediate Similarity NPC473100
0.7778 Intermediate Similarity NPC472983
0.7767 Intermediate Similarity NPC18509
0.7757 Intermediate Similarity NPC128828
0.7757 Intermediate Similarity NPC1679
0.7757 Intermediate Similarity NPC472645
0.7757 Intermediate Similarity NPC323834
0.7755 Intermediate Similarity NPC472324
0.7748 Intermediate Similarity NPC198539
0.7748 Intermediate Similarity NPC208998
0.7748 Intermediate Similarity NPC7921
0.7748 Intermediate Similarity NPC25909
0.7745 Intermediate Similarity NPC134067
0.7745 Intermediate Similarity NPC280725
0.7736 Intermediate Similarity NPC251017
0.7736 Intermediate Similarity NPC320294
0.7736 Intermediate Similarity NPC95899
0.7732 Intermediate Similarity NPC476426
0.7732 Intermediate Similarity NPC32037
0.7732 Intermediate Similarity NPC79573
0.7723 Intermediate Similarity NPC477436
0.7723 Intermediate Similarity NPC472930
0.7723 Intermediate Similarity NPC477435
0.7723 Intermediate Similarity NPC69454
0.7714 Intermediate Similarity NPC472637
0.7714 Intermediate Similarity NPC115862
0.7708 Intermediate Similarity NPC64600
0.7708 Intermediate Similarity NPC251475
0.7708 Intermediate Similarity NPC169941
0.7706 Intermediate Similarity NPC11710
0.7706 Intermediate Similarity NPC470257
0.7706 Intermediate Similarity NPC163004
0.7706 Intermediate Similarity NPC300026
0.7706 Intermediate Similarity NPC470615
0.77 Intermediate Similarity NPC473099
0.77 Intermediate Similarity NPC113393
0.7699 Intermediate Similarity NPC472934
0.7699 Intermediate Similarity NPC472927
0.7692 Intermediate Similarity NPC114274
0.7692 Intermediate Similarity NPC316598
0.7685 Intermediate Similarity NPC220229
0.7685 Intermediate Similarity NPC473165
0.7685 Intermediate Similarity NPC475060
0.7685 Intermediate Similarity NPC83744
0.7679 Intermediate Similarity NPC238667
0.7677 Intermediate Similarity NPC158778
0.7677 Intermediate Similarity NPC475001
0.7677 Intermediate Similarity NPC185059
0.767 Intermediate Similarity NPC94337
0.767 Intermediate Similarity NPC117133
0.767 Intermediate Similarity NPC471463
0.7664 Intermediate Similarity NPC40170
0.7664 Intermediate Similarity NPC213366
0.7658 Intermediate Similarity NPC269530
0.7658 Intermediate Similarity NPC472002
0.7658 Intermediate Similarity NPC4573
0.7653 Intermediate Similarity NPC470955
0.7653 Intermediate Similarity NPC94666
0.7653 Intermediate Similarity NPC194417
0.7652 Intermediate Similarity NPC112038
0.7647 Intermediate Similarity NPC470957
0.7647 Intermediate Similarity NPC196485
0.7647 Intermediate Similarity NPC470958
0.7647 Intermediate Similarity NPC78159
0.7647 Intermediate Similarity NPC474328
0.7647 Intermediate Similarity NPC245972
0.7647 Intermediate Similarity NPC181393
0.7647 Intermediate Similarity NPC258674
0.7647 Intermediate Similarity NPC471207
0.7647 Intermediate Similarity NPC474882
0.7647 Intermediate Similarity NPC217624
0.7642 Intermediate Similarity NPC80781
0.7636 Intermediate Similarity NPC473036
0.7636 Intermediate Similarity NPC272898
0.7636 Intermediate Similarity NPC5103
0.7632 Intermediate Similarity NPC21326
0.7629 Intermediate Similarity NPC476412
0.7624 Intermediate Similarity NPC233116
0.7624 Intermediate Similarity NPC185936
0.7624 Intermediate Similarity NPC248913
0.7624 Intermediate Similarity NPC26865
0.7624 Intermediate Similarity NPC63748
0.7624 Intermediate Similarity NPC168027
0.7619 Intermediate Similarity NPC306856
0.7619 Intermediate Similarity NPC154072
0.7615 Intermediate Similarity NPC329417
0.7615 Intermediate Similarity NPC168883
0.7615 Intermediate Similarity NPC264819
0.7615 Intermediate Similarity NPC295244
0.7615 Intermediate Similarity NPC102843
0.7615 Intermediate Similarity NPC322903
0.7611 Intermediate Similarity NPC179626
0.7604 Intermediate Similarity NPC158411
0.7604 Intermediate Similarity NPC38796
0.76 Intermediate Similarity NPC472688
0.76 Intermediate Similarity NPC472489
0.76 Intermediate Similarity NPC472676
0.7596 Intermediate Similarity NPC161147
0.7596 Intermediate Similarity NPC472851
0.7596 Intermediate Similarity NPC254496
0.7596 Intermediate Similarity NPC320306

  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 NPC470184 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
0.8155 Intermediate Similarity NPD5211 Phase 2
0.8 Intermediate Similarity NPD5141 Approved
0.7963 Intermediate Similarity NPD4634 Approved
0.7961 Intermediate Similarity NPD4696 Approved
0.7961 Intermediate Similarity NPD5286 Approved
0.7961 Intermediate Similarity NPD5285 Approved
0.781 Intermediate Similarity NPD4633 Approved
0.781 Intermediate Similarity NPD5226 Approved
0.781 Intermediate Similarity NPD5224 Approved
0.781 Intermediate Similarity NPD5225 Approved
0.7767 Intermediate Similarity NPD4755 Approved
0.7736 Intermediate Similarity NPD5175 Approved
0.7736 Intermediate Similarity NPD5174 Approved
0.7714 Intermediate Similarity NPD5223 Approved
0.767 Intermediate Similarity NPD5221 Approved
0.767 Intermediate Similarity NPD5222 Approved
0.767 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7619 Intermediate Similarity NPD4700 Approved
0.7596 Intermediate Similarity NPD5173 Approved
0.7523 Intermediate Similarity NPD5697 Approved
0.7455 Intermediate Similarity NPD6899 Approved
0.7455 Intermediate Similarity NPD4730 Approved
0.7455 Intermediate Similarity NPD4729 Approved
0.7455 Intermediate Similarity NPD6881 Approved
0.7451 Intermediate Similarity NPD6079 Approved
0.7396 Intermediate Similarity NPD4695 Discontinued
0.7387 Intermediate Similarity NPD6012 Approved
0.7387 Intermediate Similarity NPD6014 Approved
0.7387 Intermediate Similarity NPD6013 Approved
0.7379 Intermediate Similarity NPD5779 Approved
0.7379 Intermediate Similarity NPD5778 Approved
0.735 Intermediate Similarity NPD6319 Approved
0.735 Intermediate Similarity NPD6054 Approved
0.7333 Intermediate Similarity NPD4697 Phase 3
0.7321 Intermediate Similarity NPD6883 Approved
0.7321 Intermediate Similarity NPD5251 Approved
0.7321 Intermediate Similarity NPD7102 Approved
0.7321 Intermediate Similarity NPD5247 Approved
0.7321 Intermediate Similarity NPD5250 Approved
0.7321 Intermediate Similarity NPD7290 Approved
0.7321 Intermediate Similarity NPD5248 Approved
0.7321 Intermediate Similarity NPD5249 Phase 3
0.7297 Intermediate Similarity NPD6011 Approved
0.7297 Intermediate Similarity NPD5128 Approved
0.7288 Intermediate Similarity NPD6015 Approved
0.7288 Intermediate Similarity NPD6016 Approved
0.7281 Intermediate Similarity NPD4632 Approved
0.7273 Intermediate Similarity NPD5739 Approved
0.7273 Intermediate Similarity NPD7128 Approved
0.7273 Intermediate Similarity NPD4768 Approved
0.7273 Intermediate Similarity NPD6675 Approved
0.7273 Intermediate Similarity NPD4767 Approved
0.7273 Intermediate Similarity NPD6402 Approved
0.7257 Intermediate Similarity NPD6650 Approved
0.7257 Intermediate Similarity NPD5216 Approved
0.7257 Intermediate Similarity NPD8130 Phase 1
0.7257 Intermediate Similarity NPD5215 Approved
0.7257 Intermediate Similarity NPD6617 Approved
0.7257 Intermediate Similarity NPD5217 Approved
0.7257 Intermediate Similarity NPD6649 Approved
0.7257 Intermediate Similarity NPD6869 Approved
0.7257 Intermediate Similarity NPD6847 Approved
0.7255 Intermediate Similarity NPD5328 Approved
0.7248 Intermediate Similarity NPD4754 Approved
0.7227 Intermediate Similarity NPD5988 Approved
0.7227 Intermediate Similarity NPD6370 Approved
0.7207 Intermediate Similarity NPD5701 Approved
0.72 Intermediate Similarity NPD1696 Phase 3
0.7193 Intermediate Similarity NPD6882 Approved
0.7193 Intermediate Similarity NPD8297 Approved
0.7168 Intermediate Similarity NPD5169 Approved
0.7168 Intermediate Similarity NPD5134 Clinical (unspecified phase)
0.7168 Intermediate Similarity NPD5135 Approved
0.7143 Intermediate Similarity NPD5282 Discontinued
0.7143 Intermediate Similarity NPD7320 Approved
0.7143 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7129 Intermediate Similarity NPD3618 Phase 1
0.7129 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7129 Intermediate Similarity NPD5279 Phase 3
0.7115 Intermediate Similarity NPD6411 Approved
0.7107 Intermediate Similarity NPD7492 Approved
0.7105 Intermediate Similarity NPD5127 Approved
0.7094 Intermediate Similarity NPD6009 Approved
0.7094 Intermediate Similarity NPD7115 Discovery
0.7087 Intermediate Similarity NPD4753 Phase 2
0.708 Intermediate Similarity NPD6373 Approved
0.708 Intermediate Similarity NPD6372 Approved
0.7075 Intermediate Similarity NPD4629 Approved
0.7075 Intermediate Similarity NPD5210 Approved
0.7059 Intermediate Similarity NPD6059 Approved
0.7049 Intermediate Similarity NPD6616 Approved
0.7048 Intermediate Similarity NPD4202 Approved
0.7041 Intermediate Similarity NPD8259 Clinical (unspecified phase)
0.6992 Remote Similarity NPD7078 Approved
0.6991 Remote Similarity NPD5168 Approved
0.6961 Remote Similarity NPD5690 Phase 2
0.6952 Remote Similarity NPD7515 Phase 2
0.6935 Remote Similarity NPD7736 Approved
0.6923 Remote Similarity NPD6101 Approved
0.6923 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6923 Remote Similarity NPD5167 Approved
0.69 Remote Similarity NPD3667 Approved
0.6881 Remote Similarity NPD4225 Approved
0.6864 Remote Similarity NPD6274 Approved
0.686 Remote Similarity NPD5983 Phase 2
0.6833 Remote Similarity NPD7101 Approved
0.6833 Remote Similarity NPD7100 Approved
0.681 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6807 Remote Similarity NPD6317 Approved
0.6796 Remote Similarity NPD4519 Discontinued
0.6796 Remote Similarity NPD4623 Approved
0.6783 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6765 Remote Similarity NPD3666 Approved
0.6765 Remote Similarity NPD4786 Approved
0.6765 Remote Similarity NPD3665 Phase 1
0.6765 Remote Similarity NPD3133 Approved
0.6762 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6759 Remote Similarity NPD5695 Phase 3
0.675 Remote Similarity NPD6314 Approved
0.675 Remote Similarity NPD6313 Approved
0.675 Remote Similarity NPD6335 Approved
0.6748 Remote Similarity NPD7604 Phase 2
0.6748 Remote Similarity NPD8328 Phase 3
0.6731 Remote Similarity NPD3573 Approved
0.672 Remote Similarity NPD8293 Discontinued
0.6694 Remote Similarity NPD4522 Approved
0.6667 Remote Similarity NPD6008 Approved
0.6667 Remote Similarity NPD7639 Approved
0.6667 Remote Similarity NPD3617 Approved
0.6667 Remote Similarity NPD7748 Approved
0.6667 Remote Similarity NPD7640 Approved
0.664 Remote Similarity NPD6336 Discontinued
0.6636 Remote Similarity NPD6083 Phase 2
0.6636 Remote Similarity NPD7902 Approved
0.6636 Remote Similarity NPD6084 Phase 2
0.6635 Remote Similarity NPD4694 Approved
0.6635 Remote Similarity NPD5280 Approved
0.6606 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6602 Remote Similarity NPD4197 Approved
0.6585 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6583 Remote Similarity NPD6868 Approved
0.6581 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6577 Remote Similarity NPD7638 Approved
0.6538 Remote Similarity NPD5329 Approved
0.6535 Remote Similarity NPD6033 Approved
0.6529 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6481 Remote Similarity NPD5281 Approved
0.6481 Remote Similarity NPD5284 Approved
0.6471 Remote Similarity NPD6053 Discontinued
0.646 Remote Similarity NPD5344 Discontinued
0.6452 Remote Similarity NPD6908 Approved
0.6452 Remote Similarity NPD6921 Approved
0.6452 Remote Similarity NPD6909 Approved
0.6442 Remote Similarity NPD3668 Phase 3
0.6429 Remote Similarity NPD5696 Approved
0.6422 Remote Similarity NPD6399 Phase 3
0.641 Remote Similarity NPD6686 Approved
0.6408 Remote Similarity NPD4221 Approved
0.6408 Remote Similarity NPD4223 Phase 3
0.6389 Remote Similarity NPD5785 Approved
0.6385 Remote Similarity NPD7260 Phase 2
0.6381 Remote Similarity NPD1694 Approved
0.6381 Remote Similarity NPD5363 Approved
0.6364 Remote Similarity NPD8264 Approved
0.6364 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6364 Remote Similarity NPD7900 Approved
0.6357 Remote Similarity NPD7319 Approved
0.633 Remote Similarity NPD7983 Approved
0.633 Remote Similarity NPD7637 Suspended
0.6325 Remote Similarity NPD6412 Phase 2
0.6325 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6303 Remote Similarity NPD6371 Approved
0.6273 Remote Similarity NPD5133 Approved
0.6262 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6261 Remote Similarity NPD7632 Discontinued
0.625 Remote Similarity NPD7507 Approved
0.625 Remote Similarity NPD4800 Clinical (unspecified phase)
0.6237 Remote Similarity NPD2664 Clinical (unspecified phase)
0.6228 Remote Similarity NPD6648 Approved
0.6222 Remote Similarity NPD6334 Approved
0.6222 Remote Similarity NPD6333 Approved
0.6218 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6214 Remote Similarity NPD7525 Registered
0.6211 Remote Similarity NPD7331 Phase 2
0.6204 Remote Similarity NPD4518 Approved
0.6204 Remote Similarity NPD6672 Approved
0.6204 Remote Similarity NPD5737 Approved
0.62 Remote Similarity NPD3703 Phase 2
0.619 Remote Similarity NPD6110 Phase 1
0.619 Remote Similarity NPD8516 Approved
0.619 Remote Similarity NPD4788 Approved
0.619 Remote Similarity NPD8515 Approved
0.619 Remote Similarity NPD8517 Approved
0.619 Remote Similarity NPD8513 Phase 3
0.6183 Remote Similarity NPD5956 Approved
0.6182 Remote Similarity NPD5694 Approved
0.6168 Remote Similarity NPD5205 Approved
0.6168 Remote Similarity NPD4689 Approved
0.6168 Remote Similarity NPD4688 Approved
0.6168 Remote Similarity NPD4138 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