Structure

Physi-Chem Properties

Molecular Weight:  906.27
Volume:  922.582
LogP:  8.596
LogD:  4.936
LogS:  -3.848
# Rotatable Bonds:  8
TPSA:  209.76
# H-Bond Aceptor:  12
# H-Bond Donor:  9
# Rings:  11
# Heavy Atoms:  12

MedChem Properties

QED Drug-Likeness Score:  0.065
Synthetic Accessibility Score:  4.998
Fsp3:  0.107
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.418
MDCK Permeability:  5.886277449462796e-06
Pgp-inhibitor:  0.587
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.981
20% Bioavailability (F20%):  0.978
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.001
Plasma Protein Binding (PPB):  98.5830078125%
Volume Distribution (VD):  0.577
Pgp-substrate:  3.6162567138671875%

ADMET: Metabolism

CYP1A2-inhibitor:  0.074
CYP1A2-substrate:  0.44
CYP2C19-inhibitor:  0.954
CYP2C19-substrate:  0.042
CYP2C9-inhibitor:  0.854
CYP2C9-substrate:  0.999
CYP2D6-inhibitor:  0.043
CYP2D6-substrate:  0.922
CYP3A4-inhibitor:  0.54
CYP3A4-substrate:  0.254

ADMET: Excretion

Clearance (CL):  9.267
Half-life (T1/2):  0.38

ADMET: Toxicity

hERG Blockers:  0.114
Human Hepatotoxicity (H-HT):  0.755
Drug-inuced Liver Injury (DILI):  0.839
AMES Toxicity:  0.229
Rat Oral Acute Toxicity:  0.891
Maximum Recommended Daily Dose:  0.989
Skin Sensitization:  0.952
Carcinogencity:  0.035
Eye Corrosion:  0.003
Eye Irritation:  0.897
Respiratory Toxicity:  0.024

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

  Natural Product: NPC149633

Natural Product ID:  NPC149633
Common Name*:   Miyabenol A
IUPAC Name:   5-[(2R,3R)-6-hydroxy-4-[(2S,3S)-6-hydroxy-4-[(2R,3R)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol
Synonyms:  
Standard InCHIKey:  UCGUBQISONYIPQ-JEORVNINSA-N
Standard InCHI:  InChI=1S/C56H42O12/c57-34-11-2-28(3-12-34)1-4-32-19-40(63)25-45-48(32)52(55(66-45)30-7-15-36(59)16-8-30)44-24-42(65)27-47-51(44)53(56(68-47)31-9-17-37(60)18-10-31)43-23-41(64)26-46-50(43)49(33-20-38(61)22-39(62)21-33)54(67-46)29-5-13-35(58)14-6-29/h1-27,49,52-65H/b4-1+/t49-,52-,53+,54+,55+,56-/m1/s1
SMILES:  C(=Cc1cc(cc2c1[C@@H](c1cc(cc3c1[C@H](c1cc(cc4c1[C@@H](c1cc(cc(c1)O)O)[C@H](c1ccc(cc1)O)O4)O)[C@@H](c1ccc(cc1)O)O3)O)[C@H](c1ccc(cc1)O)O2)O)/c1ccc(cc1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL499861
PubChem CID:   16129868
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO1276 Thonningia sanguinea Species Balanophoraceae Eukaryota n.a. n.a. n.a. PMID[10843586]
NPO5239 Hyrtios erecta Species Thorectidae Eukaryota n.a. Okinawan n.a. PMID[11076554]
NPO11304 Vitis thunbergii Species Vitaceae Eukaryota Roots n.a. n.a. PMID[15730246]
NPO5239 Hyrtios erecta Species Thorectidae Eukaryota n.a. red sea n.a. PMID[16180827]
NPO5239 Hyrtios erecta Species Thorectidae Eukaryota n.a. Red Sea n.a. PMID[17190441]
NPO1276 Thonningia sanguinea Species Balanophoraceae Eukaryota Subaerial Parts n.a. n.a. PMID[30207720]
NPO5239 Hyrtios erecta Species Thorectidae Eukaryota n.a. n.a. n.a. PMID[3572416]
NPO5239 Hyrtios erecta Species Thorectidae Eukaryota n.a. n.a. n.a. PMID[8778242]
NPO5239 Hyrtios erecta Species Thorectidae Eukaryota n.a. n.a. n.a. PMID[9461648]
NPO16596 Dysoxylum schiffneri Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5239 Hyrtios erecta Species Thorectidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20597 Phascolion strombus Species Phascolionidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO222 Phebalium drummondii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8519 Garcinia andamanica Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11304 Vitis thunbergii Species Vitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5899 Ainsliaea uniflora Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6028 Laurencia pinnatifida Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10086 Scrophularia scorodonia Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9038 Aconitum burnatii Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4980 Lycopodium erythraeum Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12049 Lecania gerlachei Species Ramalinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1276 Thonningia sanguinea Species Balanophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10313 Plantago arborescens Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11941 Helleborus serbicus Species Ranunculaceae 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
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 7500.0 nM PMID[454182]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. EC50 = 6600.0 nM PMID[454182]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 9000.0 nM PMID[454182]

☑ 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 NPC149633 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
0.9856 High Similarity NPC6702
0.9856 High Similarity NPC133209
0.9856 High Similarity NPC112819
0.9784 High Similarity NPC71686
0.9784 High Similarity NPC176804
0.9574 High Similarity NPC224921
0.9574 High Similarity NPC111134
0.9574 High Similarity NPC231712
0.9574 High Similarity NPC237546
0.9574 High Similarity NPC242774
0.951 High Similarity NPC218801
0.9444 High Similarity NPC105073
0.9444 High Similarity NPC224528
0.9444 High Similarity NPC233886
0.9444 High Similarity NPC157081
0.9366 High Similarity NPC14468
0.9343 High Similarity NPC11727
0.9343 High Similarity NPC15109
0.932 High Similarity NPC202104
0.9306 High Similarity NPC180605
0.9306 High Similarity NPC122980
0.9306 High Similarity NPC148516
0.9306 High Similarity NPC177172
0.9306 High Similarity NPC107862
0.9247 High Similarity NPC473018
0.9247 High Similarity NPC120633
0.9122 High Similarity NPC157333
0.9078 High Similarity NPC213607
0.9078 High Similarity NPC174787
0.9078 High Similarity NPC182509
0.9065 High Similarity NPC125579
0.9 High Similarity NPC141717
0.8958 High Similarity NPC15659
0.8958 High Similarity NPC304894
0.8936 High Similarity NPC470307
0.8936 High Similarity NPC470308
0.8913 High Similarity NPC473309
0.8889 High Similarity NPC173203
0.8889 High Similarity NPC90822
0.8889 High Similarity NPC163508
0.8865 High Similarity NPC471522
0.8859 High Similarity NPC233467
0.8859 High Similarity NPC476391
0.8857 High Similarity NPC476617
0.8857 High Similarity NPC476616
0.8857 High Similarity NPC476615
0.8792 High Similarity NPC329343
0.8792 High Similarity NPC321972
0.8792 High Similarity NPC324517
0.8768 High Similarity NPC471519
0.8768 High Similarity NPC471518
0.8766 High Similarity NPC48880
0.8681 High Similarity NPC273623
0.8658 High Similarity NPC470826
0.8658 High Similarity NPC473266
0.8658 High Similarity NPC470098
0.8652 High Similarity NPC469610
0.8649 High Similarity NPC320671
0.8649 High Similarity NPC328567
0.8649 High Similarity NPC320970
0.8649 High Similarity NPC327412
0.8643 High Similarity NPC471517
0.8643 High Similarity NPC8899
0.8609 High Similarity NPC59692
0.8592 High Similarity NPC473107
0.8591 High Similarity NPC227516
0.8591 High Similarity NPC329836
0.8591 High Similarity NPC20757
0.8582 High Similarity NPC469611
0.8581 High Similarity NPC317053
0.8581 High Similarity NPC324492
0.8571 High Similarity NPC254000
0.8542 High Similarity NPC71465
0.8542 High Similarity NPC472646
0.8533 High Similarity NPC476969
0.8533 High Similarity NPC321657
0.8533 High Similarity NPC318373
0.8531 High Similarity NPC258780
0.8531 High Similarity NPC37410
0.8511 High Similarity NPC238168
0.8511 High Similarity NPC237424
0.8493 Intermediate Similarity NPC277331
0.8493 Intermediate Similarity NPC100482
0.8487 Intermediate Similarity NPC226809
0.8487 Intermediate Similarity NPC279406
0.8478 Intermediate Similarity NPC113495
0.8477 Intermediate Similarity NPC477612
0.8472 Intermediate Similarity NPC133463
0.8472 Intermediate Similarity NPC472647
0.8472 Intermediate Similarity NPC206525
0.8472 Intermediate Similarity NPC170328
0.8472 Intermediate Similarity NPC472648
0.8472 Intermediate Similarity NPC191462
0.8472 Intermediate Similarity NPC472649
0.8446 Intermediate Similarity NPC471415
0.8446 Intermediate Similarity NPC475492
0.8446 Intermediate Similarity NPC114119
0.8446 Intermediate Similarity NPC470097
0.8431 Intermediate Similarity NPC224161
0.8429 Intermediate Similarity NPC39064
0.8429 Intermediate Similarity NPC47283
0.8425 Intermediate Similarity NPC472091
0.8425 Intermediate Similarity NPC472090
0.8425 Intermediate Similarity NPC472092
0.8417 Intermediate Similarity NPC471215
0.8417 Intermediate Similarity NPC262573
0.84 Intermediate Similarity NPC294558
0.84 Intermediate Similarity NPC236202
0.84 Intermediate Similarity NPC58190
0.84 Intermediate Similarity NPC202742
0.84 Intermediate Similarity NPC262911
0.84 Intermediate Similarity NPC18185
0.84 Intermediate Similarity NPC70409
0.84 Intermediate Similarity NPC204770
0.84 Intermediate Similarity NPC153182
0.84 Intermediate Similarity NPC108811
0.84 Intermediate Similarity NPC174251
0.84 Intermediate Similarity NPC263940
0.84 Intermediate Similarity NPC170103
0.84 Intermediate Similarity NPC82917
0.8389 Intermediate Similarity NPC181615
0.8387 Intermediate Similarity NPC55463
0.8387 Intermediate Similarity NPC166116
0.838 Intermediate Similarity NPC268917
0.838 Intermediate Similarity NPC472590
0.838 Intermediate Similarity NPC129106
0.838 Intermediate Similarity NPC150011
0.838 Intermediate Similarity NPC118114
0.838 Intermediate Similarity NPC207892
0.838 Intermediate Similarity NPC476166
0.838 Intermediate Similarity NPC12875
0.838 Intermediate Similarity NPC271945
0.838 Intermediate Similarity NPC300875
0.838 Intermediate Similarity NPC196765
0.838 Intermediate Similarity NPC280653
0.838 Intermediate Similarity NPC17343
0.838 Intermediate Similarity NPC228369
0.838 Intermediate Similarity NPC129784
0.838 Intermediate Similarity NPC236014
0.838 Intermediate Similarity NPC181497
0.838 Intermediate Similarity NPC206224
0.838 Intermediate Similarity NPC282508
0.838 Intermediate Similarity NPC164574
0.8377 Intermediate Similarity NPC46335
0.8367 Intermediate Similarity NPC178054
0.8354 Intermediate Similarity NPC261896
0.8344 Intermediate Similarity NPC281549
0.8333 Intermediate Similarity NPC225696
0.8333 Intermediate Similarity NPC296915
0.8333 Intermediate Similarity NPC96576
0.8333 Intermediate Similarity NPC260397
0.8333 Intermediate Similarity NPC215678
0.8333 Intermediate Similarity NPC198154
0.8333 Intermediate Similarity NPC223008
0.8333 Intermediate Similarity NPC274454
0.8333 Intermediate Similarity NPC97834
0.8333 Intermediate Similarity NPC115335
0.8322 Intermediate Similarity NPC171932
0.8322 Intermediate Similarity NPC28440
0.8322 Intermediate Similarity NPC13005
0.8311 Intermediate Similarity NPC472088
0.8311 Intermediate Similarity NPC472087
0.831 Intermediate Similarity NPC27187
0.831 Intermediate Similarity NPC470225
0.8301 Intermediate Similarity NPC471403
0.8299 Intermediate Similarity NPC22317
0.8299 Intermediate Similarity NPC262189
0.8289 Intermediate Similarity NPC470208
0.8289 Intermediate Similarity NPC295573
0.8289 Intermediate Similarity NPC211561
0.8288 Intermediate Similarity NPC474687
0.8286 Intermediate Similarity NPC230479
0.8286 Intermediate Similarity NPC283049
0.8286 Intermediate Similarity NPC50315
0.8286 Intermediate Similarity NPC26879
0.8278 Intermediate Similarity NPC262297
0.8252 Intermediate Similarity NPC162801
0.8243 Intermediate Similarity NPC470372
0.8243 Intermediate Similarity NPC472089
0.8239 Intermediate Similarity NPC93962
0.8235 Intermediate Similarity NPC118000
0.8235 Intermediate Similarity NPC205501
0.8235 Intermediate Similarity NPC162976
0.8231 Intermediate Similarity NPC55947
0.8231 Intermediate Similarity NPC260842
0.8228 Intermediate Similarity NPC100936
0.8228 Intermediate Similarity NPC1253
0.8219 Intermediate Similarity NPC234952
0.8219 Intermediate Similarity NPC3049
0.8217 Intermediate Similarity NPC73517
0.8217 Intermediate Similarity NPC4809
0.8217 Intermediate Similarity NPC147743
0.8217 Intermediate Similarity NPC125495
0.8217 Intermediate Similarity NPC470827
0.8212 Intermediate Similarity NPC248053
0.8212 Intermediate Similarity NPC102280
0.8212 Intermediate Similarity NPC155564
0.8207 Intermediate Similarity NPC66840
0.8207 Intermediate Similarity NPC256307
0.8201 Intermediate Similarity NPC76465

  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 NPC149633 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
0.8561 High Similarity NPD4908 Phase 1
0.844 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.8188 Intermediate Similarity NPD1610 Phase 2
0.7972 Intermediate Similarity NPD2861 Phase 2
0.7899 Intermediate Similarity NPD1548 Phase 1
0.7862 Intermediate Similarity NPD4625 Phase 3
0.7823 Intermediate Similarity NPD1613 Approved
0.7823 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD4749 Approved
0.7687 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7671 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.764 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7628 Intermediate Similarity NPD7447 Phase 1
0.7622 Intermediate Similarity NPD6959 Discontinued
0.7603 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7564 Intermediate Similarity NPD7213 Phase 3
0.7564 Intermediate Similarity NPD7212 Phase 2
0.7515 Intermediate Similarity NPD7199 Phase 2
0.75 Intermediate Similarity NPD3027 Phase 3
0.75 Intermediate Similarity NPD7228 Approved
0.75 Intermediate Similarity NPD6234 Discontinued
0.7485 Intermediate Similarity NPD4965 Approved
0.7485 Intermediate Similarity NPD4966 Approved
0.7485 Intermediate Similarity NPD4967 Phase 2
0.7485 Intermediate Similarity NPD7768 Phase 2
0.7484 Intermediate Similarity NPD3892 Phase 2
0.7484 Intermediate Similarity NPD7466 Approved
0.7468 Intermediate Similarity NPD7037 Approved
0.7425 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7417 Intermediate Similarity NPD5735 Approved
0.7415 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7405 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7372 Intermediate Similarity NPD3750 Approved
0.7365 Intermediate Similarity NPD7229 Phase 3
0.7362 Intermediate Similarity NPD7819 Suspended
0.7351 Intermediate Similarity NPD4060 Phase 1
0.7338 Intermediate Similarity NPD6100 Approved
0.7338 Intermediate Similarity NPD6099 Approved
0.7333 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD5327 Phase 3
0.7329 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7301 Intermediate Similarity NPD37 Approved
0.7278 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7256 Intermediate Similarity NPD8455 Phase 2
0.7255 Intermediate Similarity NPD6353 Approved
0.7233 Intermediate Similarity NPD7040 Clinical (unspecified phase)
0.7233 Intermediate Similarity NPD7041 Phase 2
0.7229 Intermediate Similarity NPD3749 Approved
0.72 Intermediate Similarity NPD8054 Approved
0.72 Intermediate Similarity NPD8053 Approved
0.719 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.719 Intermediate Similarity NPD5124 Phase 1
0.7181 Intermediate Similarity NPD6584 Phase 3
0.7179 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD6166 Phase 2
0.7168 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7162 Intermediate Similarity NPD6696 Suspended
0.7143 Intermediate Similarity NPD8313 Approved
0.7143 Intermediate Similarity NPD8312 Approved
0.7134 Intermediate Similarity NPD1549 Phase 2
0.7126 Intermediate Similarity NPD7240 Approved
0.7124 Intermediate Similarity NPD4140 Approved
0.7089 Intermediate Similarity NPD6674 Discontinued
0.7081 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7075 Intermediate Similarity NPD422 Phase 1
0.707 Intermediate Similarity NPD5762 Approved
0.707 Intermediate Similarity NPD5763 Approved
0.7063 Intermediate Similarity NPD6671 Approved
0.7052 Intermediate Similarity NPD5844 Phase 1
0.7052 Intermediate Similarity NPD8156 Discontinued
0.7051 Intermediate Similarity NPD3748 Approved
0.7048 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7047 Intermediate Similarity NPD8651 Approved
0.7044 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7043 Intermediate Similarity NPD7680 Approved
0.7032 Intermediate Similarity NPD4097 Suspended
0.703 Intermediate Similarity NPD7411 Suspended
0.702 Intermediate Similarity NPD3018 Phase 2
0.7012 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7012 Intermediate Similarity NPD8158 Clinical (unspecified phase)
0.6994 Remote Similarity NPD8251 Approved
0.6994 Remote Similarity NPD8252 Approved
0.6994 Remote Similarity NPD8099 Discontinued
0.6993 Remote Similarity NPD6812 Clinical (unspecified phase)
0.6989 Remote Similarity NPD8453 Clinical (unspecified phase)
0.6988 Remote Similarity NPD1934 Approved
0.6987 Remote Similarity NPD7097 Phase 1
0.6987 Remote Similarity NPD7119 Phase 2
0.698 Remote Similarity NPD6582 Phase 2
0.698 Remote Similarity NPD6583 Phase 3
0.6975 Remote Similarity NPD7446 Clinical (unspecified phase)
0.6975 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6972 Remote Similarity NPD7843 Approved
0.697 Remote Similarity NPD4380 Phase 2
0.6968 Remote Similarity NPD6355 Discontinued
0.6959 Remote Similarity NPD3787 Discontinued
0.6944 Remote Similarity NPD7157 Approved
0.6943 Remote Similarity NPD1510 Phase 2
0.6936 Remote Similarity NPD7473 Discontinued
0.6928 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6923 Remote Similarity NPD7075 Discontinued
0.6923 Remote Similarity NPD2157 Approved
0.6923 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6918 Remote Similarity NPD970 Clinical (unspecified phase)
0.6914 Remote Similarity NPD7390 Discontinued
0.6914 Remote Similarity NPD7074 Phase 3
0.6903 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6903 Remote Similarity NPD2238 Phase 2
0.6903 Remote Similarity NPD3620 Phase 2
0.6899 Remote Similarity NPD2796 Approved
0.6897 Remote Similarity NPD3818 Discontinued
0.6883 Remote Similarity NPD6798 Discontinued
0.6879 Remote Similarity NPD4750 Phase 3
0.6871 Remote Similarity NPD4160 Clinical (unspecified phase)
0.6867 Remote Similarity NPD2983 Phase 2
0.6867 Remote Similarity NPD2982 Phase 2
0.6864 Remote Similarity NPD3882 Suspended
0.686 Remote Similarity NPD6232 Discontinued
0.6857 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6857 Remote Similarity NPD7054 Approved
0.6848 Remote Similarity NPD1653 Approved
0.6846 Remote Similarity NPD1091 Approved
0.6842 Remote Similarity NPD5494 Approved
0.6842 Remote Similarity NPD4624 Approved
0.6836 Remote Similarity NPD6559 Discontinued
0.6835 Remote Similarity NPD7033 Discontinued
0.6835 Remote Similarity NPD5588 Approved
0.6832 Remote Similarity NPD7003 Approved
0.6829 Remote Similarity NPD6273 Approved
0.6824 Remote Similarity NPD5846 Approved
0.6824 Remote Similarity NPD6516 Phase 2
0.6818 Remote Similarity NPD7472 Approved
0.6818 Remote Similarity NPD7095 Approved
0.681 Remote Similarity NPD1511 Approved
0.6806 Remote Similarity NPD5283 Phase 1
0.6803 Remote Similarity NPD3091 Approved
0.6803 Remote Similarity NPD7741 Discontinued
0.6802 Remote Similarity NPD8127 Discontinued
0.68 Remote Similarity NPD1840 Phase 2
0.68 Remote Similarity NPD2981 Phase 2
0.6798 Remote Similarity NPD7808 Phase 3
0.6798 Remote Similarity NPD7549 Discontinued
0.6797 Remote Similarity NPD1712 Approved
0.6796 Remote Similarity NPD7906 Approved
0.6788 Remote Similarity NPD1242 Phase 1
0.6786 Remote Similarity NPD968 Approved
0.6778 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6776 Remote Similarity NPD3094 Phase 2
0.6776 Remote Similarity NPD2797 Approved
0.6774 Remote Similarity NPD3764 Approved
0.677 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6768 Remote Similarity NPD2533 Approved
0.6768 Remote Similarity NPD7019 Approved
0.6768 Remote Similarity NPD2532 Approved
0.6768 Remote Similarity NPD7020 Approved
0.6768 Remote Similarity NPD2534 Approved
0.6758 Remote Similarity NPD8397 Clinical (unspecified phase)
0.675 Remote Similarity NPD6002 Phase 3
0.675 Remote Similarity NPD6005 Phase 3
0.675 Remote Similarity NPD6003 Clinical (unspecified phase)
0.675 Remote Similarity NPD6006 Clinical (unspecified phase)
0.675 Remote Similarity NPD2029 Clinical (unspecified phase)
0.675 Remote Similarity NPD6004 Phase 3
0.6746 Remote Similarity NPD7046 Clinical (unspecified phase)
0.6746 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6746 Remote Similarity NPD2801 Approved
0.6746 Remote Similarity NPD1465 Phase 2
0.6742 Remote Similarity NPD7251 Discontinued
0.6739 Remote Similarity NPD940 Approved
0.6739 Remote Similarity NPD846 Approved
0.6738 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6736 Remote Similarity NPD5535 Approved
0.6733 Remote Similarity NPD3705 Approved
0.6733 Remote Similarity NPD3092 Approved
0.6731 Remote Similarity NPD8032 Phase 2
0.6727 Remote Similarity NPD1512 Approved
0.6725 Remote Similarity NPD7832 Clinical (unspecified phase)
0.6725 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6725 Remote Similarity NPD7831 Phase 2
0.6725 Remote Similarity NPD7833 Phase 2
0.6724 Remote Similarity NPD8051 Clinical (unspecified phase)
0.6722 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6711 Remote Similarity NPD4626 Approved
0.6711 Remote Similarity NPD3225 Approved
0.6707 Remote Similarity NPD6055 Clinical (unspecified phase)
0.6707 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6706 Remote Similarity NPD6374 Clinical (unspecified phase)
0.6706 Remote Similarity NPD5402 Approved
0.6705 Remote Similarity NPD3751 Discontinued
0.669 Remote Similarity NPD2684 Approved
0.6689 Remote Similarity NPD2231 Phase 2
0.6689 Remote Similarity NPD1608 Approved
0.6689 Remote Similarity NPD2235 Phase 2
0.6688 Remote Similarity NPD5837 Clinical (unspecified phase)
0.6688 Remote Similarity NPD5736 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