Structure

Physi-Chem Properties

Molecular Weight:  344.2
Volume:  368.081
LogP:  3.749
LogD:  3.006
LogS:  -3.945
# Rotatable Bonds:  2
TPSA:  74.6
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.568
Synthetic Accessibility Score:  4.407
Fsp3:  0.619
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.064
MDCK Permeability:  2.4711956939427182e-05
Pgp-inhibitor:  0.978
Pgp-substrate:  0.029
Human Intestinal Absorption (HIA):  0.015
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.094
Plasma Protein Binding (PPB):  95.61634063720703%
Volume Distribution (VD):  0.568
Pgp-substrate:  4.287018775939941%

ADMET: Metabolism

CYP1A2-inhibitor:  0.399
CYP1A2-substrate:  0.522
CYP2C19-inhibitor:  0.307
CYP2C19-substrate:  0.525
CYP2C9-inhibitor:  0.465
CYP2C9-substrate:  0.558
CYP2D6-inhibitor:  0.649
CYP2D6-substrate:  0.13
CYP3A4-inhibitor:  0.637
CYP3A4-substrate:  0.187

ADMET: Excretion

Clearance (CL):  1.011
Half-life (T1/2):  0.204

ADMET: Toxicity

hERG Blockers:  0.011
Human Hepatotoxicity (H-HT):  0.864
Drug-inuced Liver Injury (DILI):  0.163
AMES Toxicity:  0.017
Rat Oral Acute Toxicity:  0.945
Maximum Recommended Daily Dose:  0.345
Skin Sensitization:  0.926
Carcinogencity:  0.833
Eye Corrosion:  0.07
Eye Irritation:  0.054
Respiratory Toxicity:  0.972

Download Data

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

  Natural Product: NPC55869

Natural Product ID:  NPC55869
Common Name*:   3'6'-Dihydroxyavarone
IUPAC Name:   3-[[(1R,2S,4aS,8aS)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]methyl]-2,5-dihydroxycyclohexa-2,5-diene-1,4-dione
Synonyms:   3'6'-Dihydroxyavarone
Standard InCHIKey:  VANVRUQTXGDQDJ-NUATZEMDSA-N
Standard InCHI:  InChI=1S/C21H28O4/c1-12-6-5-7-17-20(12,3)9-8-13(2)21(17,4)11-14-18(24)15(22)10-16(23)19(14)25/h6,10,13,17,22,25H,5,7-9,11H2,1-4H3/t13-,17+,20+,21+/m0/s1
SMILES:  O=C1C(=CC(=O)C(=C1C[C@]1(C)[C@@H](C)CC[C@]2([C@H]1CCC=C2C)C)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL517455
PubChem CID:   44567043
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001534] Quinone and hydroquinone lipids
          • [CHEMONTID:0002802] Prenylquinones

*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
NPO33143 Dysidea cinerea Species n.a. n.a. n.a. n.a. n.a. PMID[1710654]
NPO33143 Dysidea cinerea Species n.a. n.a. n.a. n.a. n.a. PMID[31532203]

☑ 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
NPT168 Cell Line P388 Mus musculus IC50 = 1.2 ug.mL-1 PMID[506407]
NPT20 Organism Candida albicans Candida albicans MIC = 50.0 ug.mL-1 PMID[506407]

☑ 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 NPC55869 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
0.9867 High Similarity NPC108955
0.9494 High Similarity NPC263997
0.9494 High Similarity NPC132228
0.9494 High Similarity NPC8518
0.9359 High Similarity NPC103486
0.9342 High Similarity NPC30321
0.9333 High Similarity NPC92080
0.925 High Similarity NPC241512
0.925 High Similarity NPC6185
0.9241 High Similarity NPC105803
0.9231 High Similarity NPC225515
0.9221 High Similarity NPC27817
0.9091 High Similarity NPC189485
0.9079 High Similarity NPC1254
0.9012 High Similarity NPC474680
0.9 High Similarity NPC53733
0.8987 High Similarity NPC474085
0.8846 High Similarity NPC74410
0.8831 High Similarity NPC110725
0.878 High Similarity NPC33663
0.875 High Similarity NPC116797
0.875 High Similarity NPC99308
0.875 High Similarity NPC278459
0.8734 High Similarity NPC192329
0.8701 High Similarity NPC175079
0.8625 High Similarity NPC476809
0.8625 High Similarity NPC2482
0.8621 High Similarity NPC23170
0.8608 High Similarity NPC476808
0.859 High Similarity NPC470525
0.859 High Similarity NPC180886
0.8588 High Similarity NPC65615
0.8588 High Similarity NPC112454
0.8588 High Similarity NPC68148
0.8554 High Similarity NPC32037
0.8554 High Similarity NPC133652
0.8554 High Similarity NPC469993
0.8537 High Similarity NPC49019
0.8523 High Similarity NPC147232
0.8519 High Similarity NPC44963
0.8519 High Similarity NPC121984
0.8519 High Similarity NPC472684
0.8506 High Similarity NPC263780
0.8488 Intermediate Similarity NPC474209
0.8488 Intermediate Similarity NPC475823
0.8481 Intermediate Similarity NPC165711
0.8452 Intermediate Similarity NPC94666
0.8434 Intermediate Similarity NPC237712
0.8434 Intermediate Similarity NPC144258
0.8395 Intermediate Similarity NPC18955
0.8391 Intermediate Similarity NPC174167
0.8391 Intermediate Similarity NPC470036
0.8391 Intermediate Similarity NPC99380
0.8375 Intermediate Similarity NPC471409
0.8375 Intermediate Similarity NPC275494
0.8372 Intermediate Similarity NPC474918
0.8354 Intermediate Similarity NPC26504
0.8353 Intermediate Similarity NPC220930
0.8353 Intermediate Similarity NPC470523
0.8353 Intermediate Similarity NPC272039
0.8333 Intermediate Similarity NPC474537
0.8313 Intermediate Similarity NPC168188
0.8313 Intermediate Similarity NPC470015
0.8295 Intermediate Similarity NPC211230
0.8293 Intermediate Similarity NPC470034
0.8293 Intermediate Similarity NPC189237
0.8293 Intermediate Similarity NPC473217
0.8293 Intermediate Similarity NPC471898
0.8293 Intermediate Similarity NPC475863
0.8276 Intermediate Similarity NPC129913
0.8272 Intermediate Similarity NPC472490
0.8256 Intermediate Similarity NPC72397
0.8256 Intermediate Similarity NPC307298
0.8256 Intermediate Similarity NPC58271
0.8256 Intermediate Similarity NPC470524
0.825 Intermediate Similarity NPC266193
0.825 Intermediate Similarity NPC476811
0.825 Intermediate Similarity NPC257666
0.825 Intermediate Similarity NPC97377
0.8235 Intermediate Similarity NPC327115
0.8235 Intermediate Similarity NPC472974
0.8214 Intermediate Similarity NPC473246
0.8214 Intermediate Similarity NPC96095
0.8202 Intermediate Similarity NPC474882
0.8202 Intermediate Similarity NPC474328
0.8193 Intermediate Similarity NPC260956
0.8193 Intermediate Similarity NPC238991
0.8193 Intermediate Similarity NPC302661
0.8193 Intermediate Similarity NPC193347
0.8171 Intermediate Similarity NPC26139
0.8171 Intermediate Similarity NPC472478
0.8171 Intermediate Similarity NPC469637
0.8171 Intermediate Similarity NPC287063
0.8161 Intermediate Similarity NPC326627
0.8161 Intermediate Similarity NPC310010
0.8161 Intermediate Similarity NPC477973
0.8158 Intermediate Similarity NPC260474
0.8158 Intermediate Similarity NPC188292
0.8148 Intermediate Similarity NPC62336
0.8148 Intermediate Similarity NPC207772
0.8125 Intermediate Similarity NPC186554
0.8125 Intermediate Similarity NPC76966
0.8125 Intermediate Similarity NPC309399
0.8125 Intermediate Similarity NPC69143
0.8125 Intermediate Similarity NPC263582
0.8118 Intermediate Similarity NPC311702
0.8118 Intermediate Similarity NPC255174
0.8118 Intermediate Similarity NPC469948
0.8118 Intermediate Similarity NPC123319
0.8118 Intermediate Similarity NPC29447
0.8118 Intermediate Similarity NPC94531
0.8111 Intermediate Similarity NPC777
0.8101 Intermediate Similarity NPC147438
0.8095 Intermediate Similarity NPC102197
0.8072 Intermediate Similarity NPC475833
0.8072 Intermediate Similarity NPC477372
0.8072 Intermediate Similarity NPC226068
0.8072 Intermediate Similarity NPC201912
0.8072 Intermediate Similarity NPC90055
0.8072 Intermediate Similarity NPC38350
0.8068 Intermediate Similarity NPC223093
0.8068 Intermediate Similarity NPC113393
0.8052 Intermediate Similarity NPC474060
0.8049 Intermediate Similarity NPC170394
0.8049 Intermediate Similarity NPC475681
0.8049 Intermediate Similarity NPC199595
0.8049 Intermediate Similarity NPC476177
0.8046 Intermediate Similarity NPC53454
0.8046 Intermediate Similarity NPC48107
0.8046 Intermediate Similarity NPC471722
0.8043 Intermediate Similarity NPC147954
0.8025 Intermediate Similarity NPC472300
0.8025 Intermediate Similarity NPC197659
0.8023 Intermediate Similarity NPC31564
0.8023 Intermediate Similarity NPC51014
0.8023 Intermediate Similarity NPC475022
0.8023 Intermediate Similarity NPC474778
0.8023 Intermediate Similarity NPC222613
0.8023 Intermediate Similarity NPC145879
0.8023 Intermediate Similarity NPC474733
0.8023 Intermediate Similarity NPC474732
0.8023 Intermediate Similarity NPC20688
0.8023 Intermediate Similarity NPC118648
0.8 Intermediate Similarity NPC279666
0.8 Intermediate Similarity NPC192540
0.8 Intermediate Similarity NPC85774
0.8 Intermediate Similarity NPC160413
0.8 Intermediate Similarity NPC196485
0.8 Intermediate Similarity NPC245972
0.8 Intermediate Similarity NPC227064
0.8 Intermediate Similarity NPC476795
0.8 Intermediate Similarity NPC58841
0.8 Intermediate Similarity NPC321187
0.8 Intermediate Similarity NPC329043
0.8 Intermediate Similarity NPC53385
0.8 Intermediate Similarity NPC214043
0.8 Intermediate Similarity NPC476412
0.8 Intermediate Similarity NPC161423
0.7978 Intermediate Similarity NPC185936
0.7978 Intermediate Similarity NPC168027
0.7978 Intermediate Similarity NPC204341
0.7978 Intermediate Similarity NPC26865
0.7976 Intermediate Similarity NPC212083
0.7976 Intermediate Similarity NPC69101
0.7976 Intermediate Similarity NPC48362
0.7976 Intermediate Similarity NPC310989
0.7976 Intermediate Similarity NPC320514
0.7976 Intermediate Similarity NPC251779
0.7976 Intermediate Similarity NPC151519
0.7957 Intermediate Similarity NPC474720
0.7955 Intermediate Similarity NPC184663
0.7955 Intermediate Similarity NPC474245
0.7955 Intermediate Similarity NPC31985
0.7955 Intermediate Similarity NPC1015
0.7955 Intermediate Similarity NPC262043
0.7955 Intermediate Similarity NPC119416
0.7952 Intermediate Similarity NPC37038
0.7931 Intermediate Similarity NPC93778
0.7931 Intermediate Similarity NPC476409
0.7931 Intermediate Similarity NPC58063
0.7931 Intermediate Similarity NPC475740
0.7931 Intermediate Similarity NPC136548
0.7931 Intermediate Similarity NPC136948
0.7927 Intermediate Similarity NPC198240
0.7927 Intermediate Similarity NPC280654
0.7927 Intermediate Similarity NPC110094
0.7927 Intermediate Similarity NPC260385
0.7927 Intermediate Similarity NPC475994
0.7927 Intermediate Similarity NPC321514
0.7922 Intermediate Similarity NPC310992
0.7922 Intermediate Similarity NPC87141
0.7912 Intermediate Similarity NPC280725
0.7912 Intermediate Similarity NPC295347
0.7907 Intermediate Similarity NPC79573
0.7907 Intermediate Similarity NPC476426
0.7907 Intermediate Similarity NPC33881
0.7901 Intermediate Similarity NPC472305
0.7895 Intermediate Similarity NPC111323
0.7889 Intermediate Similarity NPC134826
0.7889 Intermediate Similarity NPC271652

  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 NPC55869 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
0.9605 High Similarity NPD4695 Discontinued
0.8675 High Similarity NPD5690 Phase 2
0.8608 High Similarity NPD3617 Approved
0.8588 High Similarity NPD7285 Clinical (unspecified phase)
0.8452 Intermediate Similarity NPD4694 Approved
0.8452 Intermediate Similarity NPD5280 Approved
0.8434 Intermediate Similarity NPD4197 Approved
0.8333 Intermediate Similarity NPD5329 Approved
0.8235 Intermediate Similarity NPD5279 Phase 3
0.8193 Intermediate Similarity NPD4223 Phase 3
0.8193 Intermediate Similarity NPD4221 Approved
0.8161 Intermediate Similarity NPD4753 Phase 2
0.8023 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD3665 Phase 1
0.8 Intermediate Similarity NPD3666 Approved
0.8 Intermediate Similarity NPD3133 Approved
0.7976 Intermediate Similarity NPD3667 Approved
0.7912 Intermediate Similarity NPD5695 Phase 3
0.7912 Intermediate Similarity NPD5210 Approved
0.7912 Intermediate Similarity NPD4629 Approved
0.7826 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7826 Intermediate Similarity NPD5221 Approved
0.7826 Intermediate Similarity NPD5222 Approved
0.7816 Intermediate Similarity NPD4690 Approved
0.7816 Intermediate Similarity NPD3618 Phase 1
0.7816 Intermediate Similarity NPD4688 Approved
0.7816 Intermediate Similarity NPD4693 Phase 3
0.7816 Intermediate Similarity NPD4138 Approved
0.7816 Intermediate Similarity NPD4519 Discontinued
0.7816 Intermediate Similarity NPD4689 Approved
0.7816 Intermediate Similarity NPD4623 Approved
0.7816 Intermediate Similarity NPD5205 Approved
0.7791 Intermediate Similarity NPD4786 Approved
0.7778 Intermediate Similarity NPD5281 Approved
0.7778 Intermediate Similarity NPD5284 Approved
0.7742 Intermediate Similarity NPD5173 Approved
0.7733 Intermediate Similarity NPD2664 Clinical (unspecified phase)
0.7722 Intermediate Similarity NPD4691 Approved
0.7692 Intermediate Similarity NPD5133 Approved
0.7667 Intermediate Similarity NPD5692 Phase 3
0.764 Intermediate Similarity NPD5737 Approved
0.764 Intermediate Similarity NPD6672 Approved
0.7634 Intermediate Similarity NPD4697 Phase 3
0.7619 Intermediate Similarity NPD4195 Approved
0.7595 Intermediate Similarity NPD4137 Phase 3
0.7586 Intermediate Similarity NPD3668 Phase 3
0.7582 Intermediate Similarity NPD7515 Phase 2
0.7582 Intermediate Similarity NPD6079 Approved
0.7582 Intermediate Similarity NPD6050 Approved
0.7582 Intermediate Similarity NPD5694 Approved
0.7579 Intermediate Similarity NPD5285 Approved
0.7579 Intermediate Similarity NPD5286 Approved
0.7579 Intermediate Similarity NPD4696 Approved
0.7556 Intermediate Similarity NPD5328 Approved
0.7556 Intermediate Similarity NPD6904 Approved
0.7556 Intermediate Similarity NPD6673 Approved
0.7556 Intermediate Similarity NPD6080 Approved
0.7553 Intermediate Similarity NPD6083 Phase 2
0.7553 Intermediate Similarity NPD6084 Phase 2
0.7553 Intermediate Similarity NPD4755 Approved
0.75 Intermediate Similarity NPD5223 Approved
0.75 Intermediate Similarity NPD4747 Approved
0.7474 Intermediate Similarity NPD5696 Approved
0.7473 Intermediate Similarity NPD4096 Approved
0.7447 Intermediate Similarity NPD7614 Phase 1
0.7444 Intermediate Similarity NPD4518 Approved
0.7442 Intermediate Similarity NPD4692 Approved
0.7442 Intermediate Similarity NPD4139 Approved
0.7439 Intermediate Similarity NPD4058 Approved
0.7439 Intermediate Similarity NPD5733 Approved
0.7439 Intermediate Similarity NPD4687 Approved
0.7423 Intermediate Similarity NPD5211 Phase 2
0.7423 Intermediate Similarity NPD5091 Approved
0.7423 Intermediate Similarity NPD4633 Approved
0.7423 Intermediate Similarity NPD5225 Approved
0.7423 Intermediate Similarity NPD5224 Approved
0.7423 Intermediate Similarity NPD5226 Approved
0.7419 Intermediate Similarity NPD7748 Approved
0.7407 Intermediate Similarity NPD5276 Approved
0.7396 Intermediate Similarity NPD4700 Approved
0.7391 Intermediate Similarity NPD5693 Phase 1
0.7347 Intermediate Similarity NPD5175 Approved
0.7347 Intermediate Similarity NPD5174 Approved
0.7333 Intermediate Similarity NPD3573 Approved
0.7326 Intermediate Similarity NPD8259 Clinical (unspecified phase)
0.7312 Intermediate Similarity NPD6399 Phase 3
0.7312 Intermediate Similarity NPD4202 Approved
0.7273 Intermediate Similarity NPD4788 Approved
0.7273 Intermediate Similarity NPD5141 Approved
0.7222 Intermediate Similarity NPD5330 Approved
0.7222 Intermediate Similarity NPD7334 Approved
0.7222 Intermediate Similarity NPD7521 Approved
0.7222 Intermediate Similarity NPD6098 Approved
0.7222 Intermediate Similarity NPD6684 Approved
0.7222 Intermediate Similarity NPD7146 Approved
0.7222 Intermediate Similarity NPD6409 Approved
0.7215 Intermediate Similarity NPD7331 Phase 2
0.7188 Intermediate Similarity NPD7902 Approved
0.7172 Intermediate Similarity NPD4754 Approved
0.7158 Intermediate Similarity NPD5654 Approved
0.7129 Intermediate Similarity NPD5697 Approved
0.7097 Intermediate Similarity NPD5207 Approved
0.7089 Intermediate Similarity NPD7341 Phase 2
0.7065 Intermediate Similarity NPD6903 Approved
0.7065 Intermediate Similarity NPD5208 Approved
0.7065 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD6899 Approved
0.7059 Intermediate Similarity NPD6881 Approved
0.7059 Intermediate Similarity NPD4729 Approved
0.7059 Intermediate Similarity NPD4730 Approved
0.7059 Intermediate Similarity NPD5128 Approved
0.7059 Intermediate Similarity NPD6011 Approved
0.7059 Intermediate Similarity NPD5168 Approved
0.7037 Intermediate Similarity NPD3621 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD6402 Approved
0.703 Intermediate Similarity NPD5739 Approved
0.703 Intermediate Similarity NPD4767 Approved
0.703 Intermediate Similarity NPD4768 Approved
0.703 Intermediate Similarity NPD6675 Approved
0.703 Intermediate Similarity NPD7128 Approved
0.701 Intermediate Similarity NPD5959 Approved
0.699 Remote Similarity NPD6012 Approved
0.699 Remote Similarity NPD6014 Approved
0.699 Remote Similarity NPD6013 Approved
0.6966 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6961 Remote Similarity NPD5701 Approved
0.6923 Remote Similarity NPD4634 Approved
0.6923 Remote Similarity NPD5248 Approved
0.6923 Remote Similarity NPD7102 Approved
0.6923 Remote Similarity NPD6883 Approved
0.6923 Remote Similarity NPD5247 Approved
0.6923 Remote Similarity NPD5135 Approved
0.6923 Remote Similarity NPD5249 Phase 3
0.6923 Remote Similarity NPD7290 Approved
0.6923 Remote Similarity NPD5169 Approved
0.6923 Remote Similarity NPD1696 Phase 3
0.6923 Remote Similarity NPD5250 Approved
0.6923 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6923 Remote Similarity NPD5251 Approved
0.6907 Remote Similarity NPD7732 Phase 3
0.6893 Remote Similarity NPD7320 Approved
0.6889 Remote Similarity NPD3527 Clinical (unspecified phase)
0.6875 Remote Similarity NPD7900 Approved
0.6875 Remote Similarity NPD5282 Discontinued
0.6875 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6869 Remote Similarity NPD6404 Discontinued
0.686 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6857 Remote Similarity NPD5127 Approved
0.6857 Remote Similarity NPD5215 Approved
0.6857 Remote Similarity NPD8130 Phase 1
0.6857 Remote Similarity NPD5217 Approved
0.6857 Remote Similarity NPD6650 Approved
0.6857 Remote Similarity NPD6617 Approved
0.6857 Remote Similarity NPD6869 Approved
0.6857 Remote Similarity NPD6649 Approved
0.6857 Remote Similarity NPD6847 Approved
0.6857 Remote Similarity NPD5216 Approved
0.6854 Remote Similarity NPD8028 Phase 2
0.6842 Remote Similarity NPD6411 Approved
0.6827 Remote Similarity NPD6373 Approved
0.6827 Remote Similarity NPD6372 Approved
0.6824 Remote Similarity NPD4785 Approved
0.6824 Remote Similarity NPD4784 Approved
0.6804 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6792 Remote Similarity NPD6882 Approved
0.6792 Remote Similarity NPD8297 Approved
0.679 Remote Similarity NPD6108 Clinical (unspecified phase)
0.679 Remote Similarity NPD3704 Approved
0.6786 Remote Similarity NPD4243 Approved
0.6782 Remote Similarity NPD4756 Discovery
0.6753 Remote Similarity NPD287 Approved
0.6744 Remote Similarity NPD7339 Approved
0.6744 Remote Similarity NPD6942 Approved
0.6729 Remote Similarity NPD4632 Approved
0.6701 Remote Similarity NPD6001 Approved
0.6698 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5167 Approved
0.6635 Remote Similarity NPD6614 Approved
0.6635 Remote Similarity NPD6412 Phase 2
0.6632 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6632 Remote Similarity NPD6101 Approved
0.6606 Remote Similarity NPD6274 Approved
0.6606 Remote Similarity NPD6868 Approved
0.6559 Remote Similarity NPD1694 Approved
0.6552 Remote Similarity NPD4190 Phase 3
0.6552 Remote Similarity NPD5275 Approved
0.6545 Remote Similarity NPD6009 Approved
0.6545 Remote Similarity NPD6317 Approved
0.6486 Remote Similarity NPD6313 Approved
0.6486 Remote Similarity NPD6314 Approved
0.6486 Remote Similarity NPD6335 Approved
0.6471 Remote Similarity NPD4789 Approved
0.6444 Remote Similarity NPD7645 Phase 2
0.6436 Remote Similarity NPD7638 Approved
0.6429 Remote Similarity NPD4522 Approved
0.6429 Remote Similarity NPD7101 Approved
0.6429 Remote Similarity NPD7100 Approved
0.6413 Remote Similarity NPD4800 Clinical (unspecified phase)
0.6396 Remote Similarity NPD7115 Discovery
0.6386 Remote Similarity NPD4224 Phase 2

  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