Structure

Physi-Chem Properties

Molecular Weight:  348.12
Volume:  339.928
LogP:  0.454
LogD:  0.64
LogS:  -2.868
# Rotatable Bonds:  4
TPSA:  130.61
# H-Bond Aceptor:  7
# H-Bond Donor:  6
# Rings:  3
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.462
Synthetic Accessibility Score:  3.886
Fsp3:  0.333
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.873
MDCK Permeability:  4.514490228757495e-06
Pgp-inhibitor:  0.005
Pgp-substrate:  0.399
Human Intestinal Absorption (HIA):  0.752
20% Bioavailability (F20%):  0.931
30% Bioavailability (F30%):  0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.036
Plasma Protein Binding (PPB):  72.5104751586914%
Volume Distribution (VD):  0.589
Pgp-substrate:  25.266033172607422%

ADMET: Metabolism

CYP1A2-inhibitor:  0.101
CYP1A2-substrate:  0.082
CYP2C19-inhibitor:  0.019
CYP2C19-substrate:  0.057
CYP2C9-inhibitor:  0.111
CYP2C9-substrate:  0.318
CYP2D6-inhibitor:  0.059
CYP2D6-substrate:  0.251
CYP3A4-inhibitor:  0.141
CYP3A4-substrate:  0.246

ADMET: Excretion

Clearance (CL):  17.518
Half-life (T1/2):  0.89

ADMET: Toxicity

hERG Blockers:  0.065
Human Hepatotoxicity (H-HT):  0.186
Drug-inuced Liver Injury (DILI):  0.31
AMES Toxicity:  0.525
Rat Oral Acute Toxicity:  0.318
Maximum Recommended Daily Dose:  0.023
Skin Sensitization:  0.954
Carcinogencity:  0.264
Eye Corrosion:  0.004
Eye Irritation:  0.936
Respiratory Toxicity:  0.069

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

  Natural Product: NPC473451

Natural Product ID:  NPC473451
Common Name*:   (+)-3,3'-Bisdemethyltanegool
IUPAC Name:   4-[(2S,3S,4R)-4-[(S)-(3,4-dihydroxyphenyl)-hydroxymethyl]-3-(hydroxymethyl)oxolan-2-yl]benzene-1,2-diol
Synonyms:   (+)-3,3'-Bisdemethyltanegool
Standard InCHIKey:  XRDXBFUYROIFCX-FVEFGIFQSA-N
Standard InCHI:  InChI=1S/C18H20O7/c19-7-11-12(17(24)9-1-3-13(20)15(22)5-9)8-25-18(11)10-2-4-14(21)16(23)6-10/h1-6,11-12,17-24H,7-8H2/t11-,12+,17-,18-/m1/s1
SMILES:  C1C(C(C(O1)C2=CC(=C(C=C2)O)O)CO)C(C3=CC(=C(C=C3)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL436990
PubChem CID:   44423052
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds
      • [CHEMONTID:0003686] Furanoid lignans
        • [CHEMONTID:0001604] Tetrahydrofuran lignans
          • [CHEMONTID:0003422] 7,9'-epoxylignans

*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
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. leaf n.a. PMID[11348221]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota fruit n.a. n.a. PMID[15844957]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota fruits n.a. n.a. PMID[16378361]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota fruits Tahiti n.a. PMID[17378609]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota Fruits n.a. n.a. PMID[17480098]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota roots n.a. n.a. PMID[18076142]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[24224843]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[27196335]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota Fruits n.a. n.a. PMID[32083868]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4323 Morinda citrifolia Species Rubiaceae 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
NPT570 Individual Protein Arachidonate 5-lipoxygenase Homo sapiens IC50 = 9200.0 nM PMID[515527]
NPT257 Individual Protein Arachidonate 15-lipoxygenase Oryctolagus cuniculus IC50 = 760.0 nM PMID[515527]
NPT31 Individual Protein Cyclooxygenase-2 Homo sapiens IC50 = 73900.0 nM PMID[515527]

☑ 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 NPC473451 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
0.9746 High Similarity NPC257682
0.9746 High Similarity NPC146355
0.9746 High Similarity NPC131747
0.9431 High Similarity NPC187998
0.9431 High Similarity NPC64201
0.9431 High Similarity NPC257582
0.9431 High Similarity NPC77040
0.9431 High Similarity NPC174495
0.9431 High Similarity NPC153739
0.9431 High Similarity NPC42300
0.9431 High Similarity NPC241522
0.9431 High Similarity NPC92164
0.9431 High Similarity NPC145305
0.9431 High Similarity NPC242807
0.9355 High Similarity NPC277804
0.935 High Similarity NPC475875
0.9268 High Similarity NPC128208
0.9268 High Similarity NPC184733
0.9268 High Similarity NPC11258
0.9268 High Similarity NPC282703
0.9268 High Similarity NPC21867
0.9268 High Similarity NPC129570
0.9268 High Similarity NPC470084
0.9268 High Similarity NPC45774
0.9231 High Similarity NPC476266
0.92 High Similarity NPC161557
0.92 High Similarity NPC27843
0.92 High Similarity NPC40432
0.92 High Similarity NPC7171
0.92 High Similarity NPC115207
0.92 High Similarity NPC158079
0.92 High Similarity NPC228346
0.9187 High Similarity NPC165045
0.9187 High Similarity NPC118533
0.9138 High Similarity NPC120280
0.9134 High Similarity NPC287745
0.9127 High Similarity NPC181049
0.9127 High Similarity NPC207400
0.9106 High Similarity NPC206882
0.9083 High Similarity NPC470414
0.9055 High Similarity NPC158331
0.9032 High Similarity NPC5428
0.9024 High Similarity NPC148627
0.8992 High Similarity NPC177160
0.8992 High Similarity NPC10737
0.8992 High Similarity NPC263367
0.8992 High Similarity NPC29799
0.8992 High Similarity NPC209985
0.8992 High Similarity NPC54743
0.8992 High Similarity NPC477939
0.8992 High Similarity NPC156502
0.8984 High Similarity NPC67247
0.8984 High Similarity NPC244983
0.8984 High Similarity NPC326095
0.8976 High Similarity NPC4940
0.8976 High Similarity NPC204215
0.8976 High Similarity NPC175067
0.896 High Similarity NPC245826
0.896 High Similarity NPC252307
0.896 High Similarity NPC474178
0.8915 High Similarity NPC184938
0.8915 High Similarity NPC101624
0.8915 High Similarity NPC126409
0.8915 High Similarity NPC99572
0.8898 High Similarity NPC474017
0.8889 High Similarity NPC123175
0.8889 High Similarity NPC176730
0.888 High Similarity NPC292056
0.888 High Similarity NPC41706
0.888 High Similarity NPC118787
0.888 High Similarity NPC183181
0.888 High Similarity NPC163332
0.888 High Similarity NPC147821
0.888 High Similarity NPC319625
0.888 High Similarity NPC111247
0.8879 High Similarity NPC187583
0.8879 High Similarity NPC257430
0.8879 High Similarity NPC179002
0.8862 High Similarity NPC31344
0.8862 High Similarity NPC280704
0.8862 High Similarity NPC471693
0.8862 High Similarity NPC317769
0.8846 High Similarity NPC77861
0.8846 High Similarity NPC471988
0.8837 High Similarity NPC193026
0.8837 High Similarity NPC187616
0.8837 High Similarity NPC471942
0.8837 High Similarity NPC49603
0.8828 High Similarity NPC106739
0.8828 High Similarity NPC471505
0.8824 High Similarity NPC301651
0.8824 High Similarity NPC473556
0.881 High Similarity NPC72529
0.88 High Similarity NPC191037
0.88 High Similarity NPC58607
0.88 High Similarity NPC178284
0.8793 High Similarity NPC120982
0.8793 High Similarity NPC147634
0.8793 High Similarity NPC79793
0.8793 High Similarity NPC174096
0.8793 High Similarity NPC226401
0.8788 High Similarity NPC55793
0.878 High Similarity NPC85488
0.8779 High Similarity NPC281780
0.8779 High Similarity NPC308976
0.8769 High Similarity NPC135777
0.8769 High Similarity NPC34103
0.8769 High Similarity NPC24490
0.8769 High Similarity NPC142547
0.8769 High Similarity NPC165155
0.8769 High Similarity NPC141765
0.876 High Similarity NPC26394
0.874 High Similarity NPC476968
0.874 High Similarity NPC170844
0.874 High Similarity NPC86030
0.874 High Similarity NPC5851
0.8729 High Similarity NPC471485
0.8722 High Similarity NPC263261
0.8722 High Similarity NPC472711
0.8722 High Similarity NPC471414
0.8722 High Similarity NPC87725
0.872 High Similarity NPC194519
0.8712 High Similarity NPC88640
0.8712 High Similarity NPC123526
0.8712 High Similarity NPC193666
0.8707 High Similarity NPC62258
0.8707 High Similarity NPC55617
0.8699 High Similarity NPC312713
0.8699 High Similarity NPC113865
0.8699 High Similarity NPC184651
0.8699 High Similarity NPC54872
0.8699 High Similarity NPC216929
0.8699 High Similarity NPC126935
0.8699 High Similarity NPC476343
0.8699 High Similarity NPC57268
0.8699 High Similarity NPC262156
0.8699 High Similarity NPC470804
0.8699 High Similarity NPC470212
0.8699 High Similarity NPC312675
0.8699 High Similarity NPC473853
0.8699 High Similarity NPC172676
0.8699 High Similarity NPC65933
0.8699 High Similarity NPC343720
0.8699 High Similarity NPC324571
0.8692 High Similarity NPC478085
0.8682 High Similarity NPC230219
0.8682 High Similarity NPC201587
0.8682 High Similarity NPC470752
0.8682 High Similarity NPC253105
0.8682 High Similarity NPC254275
0.8672 High Similarity NPC143483
0.8672 High Similarity NPC173308
0.8672 High Similarity NPC181079
0.8661 High Similarity NPC206615
0.8661 High Similarity NPC186843
0.8661 High Similarity NPC470213
0.8661 High Similarity NPC98631
0.8657 High Similarity NPC253878
0.8657 High Similarity NPC476356
0.8647 High Similarity NPC184797
0.8647 High Similarity NPC309124
0.8647 High Similarity NPC254759
0.8647 High Similarity NPC160283
0.8644 High Similarity NPC290353
0.8644 High Similarity NPC42911
0.8644 High Similarity NPC153795
0.864 High Similarity NPC293701
0.864 High Similarity NPC109822
0.864 High Similarity NPC121783
0.864 High Similarity NPC48990
0.864 High Similarity NPC18449
0.864 High Similarity NPC114901
0.864 High Similarity NPC34902
0.864 High Similarity NPC94276
0.8636 High Similarity NPC474039
0.8626 High Similarity NPC93783
0.8626 High Similarity NPC18576
0.8618 High Similarity NPC207613
0.8607 High Similarity NPC109371
0.8607 High Similarity NPC470214
0.8607 High Similarity NPC470215
0.8605 High Similarity NPC309787
0.8605 High Similarity NPC470096
0.8605 High Similarity NPC472597
0.8605 High Similarity NPC470095
0.8593 High Similarity NPC477616
0.8593 High Similarity NPC185307
0.8593 High Similarity NPC470950
0.8593 High Similarity NPC477898
0.8583 High Similarity NPC231607
0.8583 High Similarity NPC127587
0.8583 High Similarity NPC264900
0.8583 High Similarity NPC79715
0.8583 High Similarity NPC108659
0.8582 High Similarity NPC311530
0.8582 High Similarity NPC470372
0.8582 High Similarity NPC100675
0.8571 High Similarity NPC292882
0.8571 High Similarity NPC473739
0.8571 High Similarity NPC90318

  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 NPC473451 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
0.874 High Similarity NPD3027 Phase 3
0.8547 High Similarity NPD3021 Approved
0.8547 High Similarity NPD3022 Approved
0.8397 Intermediate Similarity NPD1613 Approved
0.8397 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8154 Intermediate Similarity NPD2861 Phase 2
0.8092 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.8029 Intermediate Similarity NPD7266 Discontinued
0.8029 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.8015 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7967 Intermediate Similarity NPD5283 Phase 1
0.7863 Intermediate Similarity NPD3094 Phase 2
0.7852 Intermediate Similarity NPD3620 Phase 2
0.7852 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7805 Intermediate Similarity NPD228 Approved
0.7778 Intermediate Similarity NPD3020 Approved
0.7692 Intermediate Similarity NPD3705 Approved
0.7692 Intermediate Similarity NPD3092 Approved
0.7692 Intermediate Similarity NPD1610 Phase 2
0.7687 Intermediate Similarity NPD4908 Phase 1
0.7676 Intermediate Similarity NPD6190 Approved
0.7639 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7591 Intermediate Similarity NPD3061 Approved
0.7591 Intermediate Similarity NPD3062 Approved
0.7591 Intermediate Similarity NPD3059 Approved
0.7576 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7574 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7538 Intermediate Similarity NPD9381 Approved
0.7538 Intermediate Similarity NPD9384 Approved
0.7538 Intermediate Similarity NPD5125 Phase 3
0.7538 Intermediate Similarity NPD5126 Approved
0.7535 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7521 Intermediate Similarity NPD2860 Approved
0.7521 Intermediate Similarity NPD2859 Approved
0.7519 Intermediate Similarity NPD3091 Approved
0.75 Intermediate Similarity NPD5588 Approved
0.75 Intermediate Similarity NPD6234 Discontinued
0.7482 Intermediate Similarity NPD5314 Approved
0.7464 Intermediate Similarity NPD4060 Phase 1
0.7462 Intermediate Similarity NPD1357 Approved
0.7444 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD2934 Approved
0.7436 Intermediate Similarity NPD2933 Approved
0.7422 Intermediate Similarity NPD7157 Approved
0.7419 Intermediate Similarity NPD2684 Approved
0.7417 Intermediate Similarity NPD1242 Phase 1
0.7413 Intermediate Similarity NPD4236 Phase 3
0.7413 Intermediate Similarity NPD4237 Approved
0.741 Intermediate Similarity NPD5735 Approved
0.74 Intermediate Similarity NPD37 Approved
0.7385 Intermediate Similarity NPD1548 Phase 1
0.7368 Intermediate Similarity NPD4966 Approved
0.7368 Intermediate Similarity NPD4965 Approved
0.7368 Intermediate Similarity NPD4967 Phase 2
0.7351 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7338 Intermediate Similarity NPD1558 Phase 1
0.7338 Intermediate Similarity NPD2238 Phase 2
0.7323 Intermediate Similarity NPD7843 Approved
0.7313 Intermediate Similarity NPD2983 Phase 2
0.7313 Intermediate Similarity NPD2982 Phase 2
0.7313 Intermediate Similarity NPD9622 Approved
0.7305 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD4536 Approved
0.7305 Intermediate Similarity NPD4538 Approved
0.7302 Intermediate Similarity NPD9280 Clinical (unspecified phase)
0.7293 Intermediate Similarity NPD1091 Approved
0.7292 Intermediate Similarity NPD3060 Approved
0.7292 Intermediate Similarity NPD6674 Discontinued
0.7286 Intermediate Similarity NPD230 Phase 1
0.7285 Intermediate Similarity NPD1934 Approved
0.7278 Intermediate Similarity NPD7228 Approved
0.7273 Intermediate Similarity NPD3095 Discontinued
0.726 Intermediate Similarity NPD5058 Phase 3
0.7258 Intermediate Similarity NPD968 Approved
0.7254 Intermediate Similarity NPD5960 Phase 3
0.7252 Intermediate Similarity NPD7741 Discontinued
0.7241 Intermediate Similarity NPD8166 Discontinued
0.7239 Intermediate Similarity NPD2231 Phase 2
0.7239 Intermediate Similarity NPD2981 Phase 2
0.7239 Intermediate Similarity NPD2235 Phase 2
0.7237 Intermediate Similarity NPD2977 Approved
0.7237 Intermediate Similarity NPD2978 Approved
0.7226 Intermediate Similarity NPD3018 Phase 2
0.7222 Intermediate Similarity NPD4750 Phase 3
0.7211 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7194 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7194 Intermediate Similarity NPD3764 Approved
0.7185 Intermediate Similarity NPD4749 Approved
0.717 Intermediate Similarity NPD3818 Discontinued
0.7163 Intermediate Similarity NPD6355 Discontinued
0.7154 Intermediate Similarity NPD6671 Approved
0.7153 Intermediate Similarity NPD5762 Approved
0.7153 Intermediate Similarity NPD9619 Approved
0.7153 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7153 Intermediate Similarity NPD9620 Approved
0.7153 Intermediate Similarity NPD9621 Approved
0.7153 Intermediate Similarity NPD6584 Phase 3
0.7153 Intermediate Similarity NPD5763 Approved
0.7143 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD3882 Suspended
0.7143 Intermediate Similarity NPD5238 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD1432 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD5846 Approved
0.7143 Intermediate Similarity NPD6516 Phase 2
0.7133 Intermediate Similarity NPD1653 Approved
0.7132 Intermediate Similarity NPD8651 Approved
0.7123 Intermediate Similarity NPD6331 Phase 2
0.7123 Intermediate Similarity NPD4110 Phase 3
0.7123 Intermediate Similarity NPD4628 Phase 3
0.7123 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7122 Intermediate Similarity NPD4625 Phase 3
0.7113 Intermediate Similarity NPD823 Approved
0.7113 Intermediate Similarity NPD6653 Approved
0.7113 Intermediate Similarity NPD817 Approved
0.7101 Intermediate Similarity NPD5736 Approved
0.7095 Intermediate Similarity NPD1511 Approved
0.7092 Intermediate Similarity NPD4140 Approved
0.708 Intermediate Similarity NPD4339 Clinical (unspecified phase)
0.7075 Intermediate Similarity NPD2677 Approved
0.7075 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD940 Approved
0.7073 Intermediate Similarity NPD846 Approved
0.7071 Intermediate Similarity NPD597 Approved
0.7071 Intermediate Similarity NPD598 Approved
0.7071 Intermediate Similarity NPD601 Approved
0.7071 Intermediate Similarity NPD2028 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD7199 Phase 2
0.7063 Intermediate Similarity NPD290 Approved
0.7059 Intermediate Similarity NPD5327 Phase 3
0.7055 Intermediate Similarity NPD5177 Phase 3
0.7054 Intermediate Similarity NPD9377 Approved
0.7054 Intermediate Similarity NPD9379 Approved
0.7054 Intermediate Similarity NPD7635 Approved
0.7047 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD5536 Phase 2
0.7044 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD6166 Phase 2
0.7034 Intermediate Similarity NPD1375 Discontinued
0.7025 Intermediate Similarity NPD288 Approved
0.7021 Intermediate Similarity NPD1136 Approved
0.7021 Intermediate Similarity NPD6407 Approved
0.7021 Intermediate Similarity NPD1130 Approved
0.7021 Intermediate Similarity NPD1132 Approved
0.7021 Intermediate Similarity NPD6405 Approved
0.7013 Intermediate Similarity NPD2801 Approved
0.7007 Intermediate Similarity NPD3892 Phase 2
0.7007 Intermediate Similarity NPD5311 Approved
0.7007 Intermediate Similarity NPD5310 Approved
0.7007 Intermediate Similarity NPD6696 Suspended
0.7 Intermediate Similarity NPD7095 Approved
0.7 Intermediate Similarity NPD1512 Approved
0.6992 Remote Similarity NPD1182 Approved
0.6992 Remote Similarity NPD289 Clinical (unspecified phase)
0.6986 Remote Similarity NPD7037 Approved
0.6985 Remote Similarity NPD1608 Approved
0.6985 Remote Similarity NPD2233 Approved
0.6985 Remote Similarity NPD2230 Approved
0.6985 Remote Similarity NPD1840 Phase 2
0.6985 Remote Similarity NPD2232 Approved
0.6972 Remote Similarity NPD943 Approved
0.6968 Remote Similarity NPD2563 Approved
0.6968 Remote Similarity NPD6374 Clinical (unspecified phase)
0.6968 Remote Similarity NPD2560 Approved
0.6966 Remote Similarity NPD2161 Phase 2
0.6957 Remote Similarity NPD3055 Approved
0.6957 Remote Similarity NPD3053 Approved
0.695 Remote Similarity NPD5109 Approved
0.695 Remote Similarity NPD5111 Phase 2
0.695 Remote Similarity NPD5110 Phase 2
0.6944 Remote Similarity NPD4978 Clinical (unspecified phase)
0.6942 Remote Similarity NPD844 Approved
0.6939 Remote Similarity NPD4162 Approved
0.6937 Remote Similarity NPD27 Approved
0.6937 Remote Similarity NPD2489 Approved
0.6934 Remote Similarity NPD6583 Phase 3
0.6934 Remote Similarity NPD4659 Approved
0.6934 Remote Similarity NPD6582 Phase 2
0.6933 Remote Similarity NPD4123 Phase 3
0.6928 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6928 Remote Similarity NPD4380 Phase 2
0.6923 Remote Similarity NPD3657 Discovery
0.6918 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6918 Remote Similarity NPD6002 Phase 3
0.6918 Remote Similarity NPD6004 Phase 3
0.6918 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6918 Remote Similarity NPD6005 Phase 3
0.6912 Remote Similarity NPD5350 Clinical (unspecified phase)
0.6912 Remote Similarity NPD5351 Clinical (unspecified phase)
0.6906 Remote Similarity NPD4624 Approved
0.6906 Remote Similarity NPD558 Phase 2
0.6903 Remote Similarity NPD5773 Approved
0.6903 Remote Similarity NPD5772 Approved
0.6901 Remote Similarity NPD2674 Phase 3
0.6901 Remote Similarity NPD6663 Approved
0.6901 Remote Similarity NPD6233 Phase 2
0.6897 Remote Similarity NPD7033 Discontinued
0.689 Remote Similarity NPD7685 Pre-registration
0.6889 Remote Similarity NPD2668 Approved
0.6889 Remote Similarity NPD2667 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