Structure

Physi-Chem Properties

Molecular Weight:  734.13
Volume:  702.329
LogP:  4.4
LogD:  2.116
LogS:  -3.514
# Rotatable Bonds:  7
TPSA:  261.7
# H-Bond Aceptor:  15
# H-Bond Donor:  8
# Rings:  7
# Heavy Atoms:  15

MedChem Properties

QED Drug-Likeness Score:  0.095
Synthetic Accessibility Score:  4.652
Fsp3:  0.051
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.567
MDCK Permeability:  1.195035110868048e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.306
Human Intestinal Absorption (HIA):  0.327
20% Bioavailability (F20%):  0.997
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.001
Plasma Protein Binding (PPB):  97.04155731201172%
Volume Distribution (VD):  0.355
Pgp-substrate:  5.390861988067627%

ADMET: Metabolism

CYP1A2-inhibitor:  0.234
CYP1A2-substrate:  0.516
CYP2C19-inhibitor:  0.044
CYP2C19-substrate:  0.028
CYP2C9-inhibitor:  0.644
CYP2C9-substrate:  0.925
CYP2D6-inhibitor:  0.005
CYP2D6-substrate:  0.867
CYP3A4-inhibitor:  0.168
CYP3A4-substrate:  0.124

ADMET: Excretion

Clearance (CL):  7.621
Half-life (T1/2):  0.643

ADMET: Toxicity

hERG Blockers:  0.239
Human Hepatotoxicity (H-HT):  0.622
Drug-inuced Liver Injury (DILI):  0.989
AMES Toxicity:  0.011
Rat Oral Acute Toxicity:  0.758
Maximum Recommended Daily Dose:  0.896
Skin Sensitization:  0.954
Carcinogencity:  0.035
Eye Corrosion:  0.003
Eye Irritation:  0.874
Respiratory Toxicity:  0.009

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

  Natural Product: NPC270268

Natural Product ID:  NPC270268
Common Name*:   Phellinstatin
IUPAC Name:   (2S,3S)-2-(3,4-dihydroxyphenyl)-6-[(E)-2-[2-[6-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-4-hydroxy-2-oxopyran-3-yl]-4,5-dihydroxyphenyl]ethenyl]-3-(4-hydroxy-6-oxopyran-2-yl)-2,3-dihydrofuro[3,2-c]pyran-4-one
Synonyms:   Phellinstatin
Standard InCHIKey:  KAEWYNFUJFCGQA-UPSVAIHWSA-N
Standard InCHI:  InChI=1S/C39H26O15/c40-20-12-31(53-33(48)13-20)35-36-32(54-37(35)19-4-8-25(42)27(44)11-19)15-22(52-39(36)50)6-3-18-10-28(45)29(46)16-23(18)34-30(47)14-21(51-38(34)49)5-1-17-2-7-24(41)26(43)9-17/h1-16,35,37,40-47H/b5-1+,6-3+/t35-,37+/m0/s1
SMILES:  C(=Cc1cc(c(c2cc(c(cc2/C=C/c2cc3c([C@H](c4cc(cc(=O)o4)O)[C@@H](c4ccc(c(c4)O)O)O3)c(=O)o2)O)O)c(=O)o1)O)/c1ccc(c(c1)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1682259
PubChem CID:   54728876
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000134] Phenols
        • [CHEMONTID:0001286] Benzenediols
          • [CHEMONTID:0000135] Catechols

*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
NPO25991 Commiphora mukul Species Burseraceae Eukaryota n.a. latex n.a. PMID[21800858]
NPO17752 Mentha X piperita Strain Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO17752 Mentha X piperita Strain Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO17752 Mentha X piperita Strain Lamiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO17752 Mentha X piperita Strain Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO17752 Mentha X piperita Strain Lamiaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO9049 Tanacetum parthenium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25991 Commiphora mukul Species Burseraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17752 Mentha X piperita Strain Lamiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO17752 Mentha X piperita Strain Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9049 Tanacetum parthenium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25991 Commiphora mukul Species Burseraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9049 Tanacetum parthenium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17752 Mentha X piperita Strain Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5654 Pleocarphus revolutus n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO25991 Commiphora mukul Species Burseraceae 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
NPT5154 Individual Protein Enoyl-[acyl-carrier-protein] reductase Staphylococcus aureus subsp. aureus MRSA252 IC50 = 6000.0 nM PMID[495161]
NPT1101 Organism Staphylococcus aureus subsp. aureus RN4220 Staphylococcus aureus subsp. aureus RN4220 MIC = 128.0 ug.mL-1 PMID[495161]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 128.0 ug.mL-1 PMID[495161]

☑ 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 NPC270268 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
0.9236 High Similarity NPC9218
0.9189 High Similarity NPC155910
0.9189 High Similarity NPC17042
0.9178 High Similarity NPC470130
0.8904 High Similarity NPC191280
0.8797 High Similarity NPC322982
0.8792 High Similarity NPC183824
0.8784 High Similarity NPC91546
0.8725 High Similarity NPC285550
0.8716 High Similarity NPC290664
0.8701 High Similarity NPC267091
0.8654 High Similarity NPC203757
0.8636 High Similarity NPC243891
0.8608 High Similarity NPC471750
0.8562 High Similarity NPC144557
0.8528 High Similarity NPC216403
0.8528 High Similarity NPC186100
0.8528 High Similarity NPC41494
0.8526 High Similarity NPC475162
0.8526 High Similarity NPC475216
0.8526 High Similarity NPC266084
0.8526 High Similarity NPC475595
0.8526 High Similarity NPC475145
0.8526 High Similarity NPC83663
0.8526 High Similarity NPC473544
0.8509 High Similarity NPC134047
0.8509 High Similarity NPC223006
0.8509 High Similarity NPC272750
0.8509 High Similarity NPC173729
0.8487 Intermediate Similarity NPC477333
0.8462 Intermediate Similarity NPC476434
0.8442 Intermediate Similarity NPC1580
0.8428 Intermediate Similarity NPC187205
0.8424 Intermediate Similarity NPC47386
0.8395 Intermediate Similarity NPC45943
0.8389 Intermediate Similarity NPC308976
0.8365 Intermediate Similarity NPC123208
0.8356 Intermediate Similarity NPC318799
0.8354 Intermediate Similarity NPC469888
0.8344 Intermediate Similarity NPC38473
0.8333 Intermediate Similarity NPC145847
0.8333 Intermediate Similarity NPC32197
0.8323 Intermediate Similarity NPC142528
0.8322 Intermediate Similarity NPC156307
0.8313 Intermediate Similarity NPC38779
0.8313 Intermediate Similarity NPC160512
0.8313 Intermediate Similarity NPC114179
0.8313 Intermediate Similarity NPC289322
0.8313 Intermediate Similarity NPC156818
0.8313 Intermediate Similarity NPC68324
0.8311 Intermediate Similarity NPC106406
0.8311 Intermediate Similarity NPC248150
0.8303 Intermediate Similarity NPC202428
0.8303 Intermediate Similarity NPC266545
0.8293 Intermediate Similarity NPC175793
0.8289 Intermediate Similarity NPC67467
0.8289 Intermediate Similarity NPC35702
0.8289 Intermediate Similarity NPC206095
0.8289 Intermediate Similarity NPC477335
0.8289 Intermediate Similarity NPC13818
0.8289 Intermediate Similarity NPC471027
0.8289 Intermediate Similarity NPC224389
0.8289 Intermediate Similarity NPC297517
0.8288 Intermediate Similarity NPC285361
0.8284 Intermediate Similarity NPC198902
0.8282 Intermediate Similarity NPC109990
0.828 Intermediate Similarity NPC477334
0.8276 Intermediate Similarity NPC167463
0.8272 Intermediate Similarity NPC139540
0.8272 Intermediate Similarity NPC177100
0.8272 Intermediate Similarity NPC266365
0.8272 Intermediate Similarity NPC469889
0.8272 Intermediate Similarity NPC216916
0.8258 Intermediate Similarity NPC246229
0.8258 Intermediate Similarity NPC229264
0.8258 Intermediate Similarity NPC191899
0.8258 Intermediate Similarity NPC474991
0.825 Intermediate Similarity NPC473275
0.825 Intermediate Similarity NPC318432
0.825 Intermediate Similarity NPC291948
0.825 Intermediate Similarity NPC104983
0.825 Intermediate Similarity NPC88803
0.825 Intermediate Similarity NPC470896
0.825 Intermediate Similarity NPC300845
0.825 Intermediate Similarity NPC250436
0.8242 Intermediate Similarity NPC177362
0.8242 Intermediate Similarity NPC217781
0.8242 Intermediate Similarity NPC261411
0.8242 Intermediate Similarity NPC43918
0.8242 Intermediate Similarity NPC190204
0.8242 Intermediate Similarity NPC311389
0.8242 Intermediate Similarity NPC470271
0.8239 Intermediate Similarity NPC281703
0.8239 Intermediate Similarity NPC125487
0.8239 Intermediate Similarity NPC473365
0.8235 Intermediate Similarity NPC472016
0.8235 Intermediate Similarity NPC284948
0.8235 Intermediate Similarity NPC258469
0.8235 Intermediate Similarity NPC220664
0.8235 Intermediate Similarity NPC192831
0.8235 Intermediate Similarity NPC303090
0.8235 Intermediate Similarity NPC319628
0.8235 Intermediate Similarity NPC37331
0.8235 Intermediate Similarity NPC277315
0.8235 Intermediate Similarity NPC43158
0.8232 Intermediate Similarity NPC162169
0.8232 Intermediate Similarity NPC166851
0.8224 Intermediate Similarity NPC100675
0.8221 Intermediate Similarity NPC473445
0.8221 Intermediate Similarity NPC291957
0.8221 Intermediate Similarity NPC14030
0.8219 Intermediate Similarity NPC64111
0.8219 Intermediate Similarity NPC208536
0.821 Intermediate Similarity NPC24164
0.821 Intermediate Similarity NPC24627
0.821 Intermediate Similarity NPC53889
0.8205 Intermediate Similarity NPC471076
0.8205 Intermediate Similarity NPC476463
0.8205 Intermediate Similarity NPC472969
0.8205 Intermediate Similarity NPC192568
0.8199 Intermediate Similarity NPC143328
0.8194 Intermediate Similarity NPC84786
0.8182 Intermediate Similarity NPC121573
0.8182 Intermediate Similarity NPC22176
0.8182 Intermediate Similarity NPC26536
0.8182 Intermediate Similarity NPC142707
0.8182 Intermediate Similarity NPC49983
0.8182 Intermediate Similarity NPC200726
0.8182 Intermediate Similarity NPC226738
0.8182 Intermediate Similarity NPC190587
0.8182 Intermediate Similarity NPC317671
0.8176 Intermediate Similarity NPC295646
0.8176 Intermediate Similarity NPC65591
0.8176 Intermediate Similarity NPC178574
0.8171 Intermediate Similarity NPC291977
0.8171 Intermediate Similarity NPC470898
0.8165 Intermediate Similarity NPC252979
0.8165 Intermediate Similarity NPC119252
0.8158 Intermediate Similarity NPC134969
0.8155 Intermediate Similarity NPC316539
0.8155 Intermediate Similarity NPC98583
0.8153 Intermediate Similarity NPC42464
0.8153 Intermediate Similarity NPC98809
0.8153 Intermediate Similarity NPC476394
0.8151 Intermediate Similarity NPC46192
0.8148 Intermediate Similarity NPC87317
0.8148 Intermediate Similarity NPC7543
0.8148 Intermediate Similarity NPC94220
0.8148 Intermediate Similarity NPC24339
0.8148 Intermediate Similarity NPC166456
0.8148 Intermediate Similarity NPC98083
0.8144 Intermediate Similarity NPC180768
0.8144 Intermediate Similarity NPC472803
0.8144 Intermediate Similarity NPC47521
0.8144 Intermediate Similarity NPC470272
0.8137 Intermediate Similarity NPC239019
0.8137 Intermediate Similarity NPC165483
0.8137 Intermediate Similarity NPC247629
0.8137 Intermediate Similarity NPC134925
0.8133 Intermediate Similarity NPC31034
0.8129 Intermediate Similarity NPC228940
0.8129 Intermediate Similarity NPC223185
0.8129 Intermediate Similarity NPC53520
0.8129 Intermediate Similarity NPC257025
0.8125 Intermediate Similarity NPC288945
0.8125 Intermediate Similarity NPC477299
0.8125 Intermediate Similarity NPC85565
0.8121 Intermediate Similarity NPC471749
0.8121 Intermediate Similarity NPC142614
0.811 Intermediate Similarity NPC42797
0.8107 Intermediate Similarity NPC171706
0.8105 Intermediate Similarity NPC29599
0.8105 Intermediate Similarity NPC477279
0.8101 Intermediate Similarity NPC221091
0.8101 Intermediate Similarity NPC306343
0.8101 Intermediate Similarity NPC259576
0.8101 Intermediate Similarity NPC327962
0.8098 Intermediate Similarity NPC476373
0.8095 Intermediate Similarity NPC65333
0.8095 Intermediate Similarity NPC94810
0.8095 Intermediate Similarity NPC100251
0.8092 Intermediate Similarity NPC219428
0.8092 Intermediate Similarity NPC37250
0.8092 Intermediate Similarity NPC257173
0.8092 Intermediate Similarity NPC278068
0.8092 Intermediate Similarity NPC152942
0.8092 Intermediate Similarity NPC142703
0.8092 Intermediate Similarity NPC302857
0.8089 Intermediate Similarity NPC252402
0.8089 Intermediate Similarity NPC127046
0.8089 Intermediate Similarity NPC43123
0.8089 Intermediate Similarity NPC473138
0.8089 Intermediate Similarity NPC28776
0.8089 Intermediate Similarity NPC102934
0.8089 Intermediate Similarity NPC81835
0.8086 Intermediate Similarity NPC238419
0.8086 Intermediate Similarity NPC167098
0.8086 Intermediate Similarity NPC133984
0.8086 Intermediate Similarity NPC296044
0.8086 Intermediate Similarity NPC172419

  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 NPC270268 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
0.825 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8235 Intermediate Similarity NPD6190 Approved
0.8013 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7965 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7935 Intermediate Similarity NPD8166 Discontinued
0.7927 Intermediate Similarity NPD6234 Discontinued
0.7919 Intermediate Similarity NPD3764 Approved
0.7882 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7836 Intermediate Similarity NPD7685 Pre-registration
0.7811 Intermediate Similarity NPD7228 Approved
0.7784 Intermediate Similarity NPD6232 Discontinued
0.7763 Intermediate Similarity NPD230 Phase 1
0.7751 Intermediate Similarity NPD7473 Discontinued
0.773 Intermediate Similarity NPD37 Approved
0.7727 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7697 Intermediate Similarity NPD4966 Approved
0.7697 Intermediate Similarity NPD4965 Approved
0.7697 Intermediate Similarity NPD4967 Phase 2
0.7692 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD6166 Phase 2
0.7692 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7683 Intermediate Similarity NPD1465 Phase 2
0.7661 Intermediate Similarity NPD5844 Phase 1
0.7628 Intermediate Similarity NPD7266 Discontinued
0.7625 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7619 Intermediate Similarity NPD7199 Phase 2
0.7602 Intermediate Similarity NPD3818 Discontinued
0.7576 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD1934 Approved
0.7486 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD4628 Phase 3
0.747 Intermediate Similarity NPD2801 Approved
0.7457 Intermediate Similarity NPD7054 Approved
0.7453 Intermediate Similarity NPD1511 Approved
0.7443 Intermediate Similarity NPD8313 Approved
0.7443 Intermediate Similarity NPD8312 Approved
0.7425 Intermediate Similarity NPD3817 Phase 2
0.7423 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7416 Intermediate Similarity NPD8150 Discontinued
0.7414 Intermediate Similarity NPD7074 Phase 3
0.7414 Intermediate Similarity NPD7472 Approved
0.7412 Intermediate Similarity NPD8127 Discontinued
0.7394 Intermediate Similarity NPD4380 Phase 2
0.7375 Intermediate Similarity NPD3750 Approved
0.7371 Intermediate Similarity NPD6797 Phase 2
0.7365 Intermediate Similarity NPD8455 Phase 2
0.7365 Intermediate Similarity NPD7819 Suspended
0.7362 Intermediate Similarity NPD1512 Approved
0.7358 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.733 Intermediate Similarity NPD7251 Discontinued
0.733 Intermediate Similarity NPD7240 Approved
0.7321 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7312 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD6959 Discontinued
0.7288 Intermediate Similarity NPD7808 Phase 3
0.7278 Intermediate Similarity NPD3882 Suspended
0.7267 Intermediate Similarity NPD1608 Approved
0.7256 Intermediate Similarity NPD6273 Approved
0.7253 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7235 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7235 Intermediate Similarity NPD3749 Approved
0.7229 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD5402 Approved
0.7195 Intermediate Similarity NPD2534 Approved
0.7195 Intermediate Similarity NPD2533 Approved
0.7195 Intermediate Similarity NPD2532 Approved
0.7184 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD6233 Phase 2
0.7179 Intermediate Similarity NPD6663 Approved
0.7168 Intermediate Similarity NPD7229 Phase 3
0.7162 Intermediate Similarity NPD9545 Approved
0.7161 Intermediate Similarity NPD3027 Phase 3
0.716 Intermediate Similarity NPD7003 Approved
0.7152 Intermediate Similarity NPD9269 Phase 2
0.7151 Intermediate Similarity NPD5494 Approved
0.7143 Intermediate Similarity NPD7680 Approved
0.7143 Intermediate Similarity NPD5736 Approved
0.7143 Intermediate Similarity NPD7411 Suspended
0.7135 Intermediate Similarity NPD7075 Discontinued
0.7134 Intermediate Similarity NPD943 Approved
0.7126 Intermediate Similarity NPD3226 Approved
0.7125 Intermediate Similarity NPD5405 Approved
0.7125 Intermediate Similarity NPD2438 Suspended
0.7125 Intermediate Similarity NPD5406 Approved
0.7125 Intermediate Similarity NPD5408 Approved
0.7125 Intermediate Similarity NPD5404 Approved
0.7115 Intermediate Similarity NPD6798 Discontinued
0.7102 Intermediate Similarity NPD3751 Discontinued
0.7089 Intermediate Similarity NPD6355 Discontinued
0.7076 Intermediate Similarity NPD7768 Phase 2
0.7069 Intermediate Similarity NPD3787 Discontinued
0.7067 Intermediate Similarity NPD17 Approved
0.7063 Intermediate Similarity NPD7033 Discontinued
0.7063 Intermediate Similarity NPD1510 Phase 2
0.7063 Intermediate Similarity NPD3748 Approved
0.7062 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD1283 Approved
0.7055 Intermediate Similarity NPD4110 Phase 3
0.7055 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7033 Intermediate Similarity NPD8434 Phase 2
0.7032 Intermediate Similarity NPD9494 Approved
0.703 Intermediate Similarity NPD7390 Discontinued
0.7025 Intermediate Similarity NPD2979 Phase 3
0.7025 Intermediate Similarity NPD1613 Approved
0.7025 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD4060 Phase 1
0.7024 Intermediate Similarity NPD3455 Phase 2
0.7024 Intermediate Similarity NPD7458 Discontinued
0.7021 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD2935 Discontinued
0.7017 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7013 Intermediate Similarity NPD2797 Approved
0.7006 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD5403 Approved
0.7006 Intermediate Similarity NPD3268 Approved
0.7 Intermediate Similarity NPD6801 Discontinued
0.6993 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6988 Remote Similarity NPD4160 Clinical (unspecified phase)
0.6988 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6988 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6975 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6975 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6975 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6964 Remote Similarity NPD1653 Approved
0.6959 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6957 Remote Similarity NPD651 Clinical (unspecified phase)
0.6948 Remote Similarity NPD3225 Approved
0.6941 Remote Similarity NPD6385 Approved
0.6941 Remote Similarity NPD6386 Approved
0.6933 Remote Similarity NPD1549 Phase 2
0.6923 Remote Similarity NPD2861 Phase 2
0.6918 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6918 Remote Similarity NPD3620 Phase 2
0.6897 Remote Similarity NPD3021 Approved
0.6897 Remote Similarity NPD3022 Approved
0.6894 Remote Similarity NPD7097 Phase 1
0.6887 Remote Similarity NPD9268 Approved
0.6886 Remote Similarity NPD5401 Approved
0.6879 Remote Similarity NPD4908 Phase 1
0.6879 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6872 Remote Similarity NPD8151 Discontinued
0.6863 Remote Similarity NPD1281 Approved
0.6855 Remote Similarity NPD8032 Phase 2
0.6851 Remote Similarity NPD6559 Discontinued
0.6842 Remote Similarity NPD3019 Approved
0.6839 Remote Similarity NPD8319 Approved
0.6839 Remote Similarity NPD8320 Phase 1
0.6836 Remote Similarity NPD5242 Approved
0.6835 Remote Similarity NPD7095 Approved
0.6826 Remote Similarity NPD6799 Approved
0.6816 Remote Similarity NPD7177 Discontinued
0.6815 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6813 Remote Similarity NPD4140 Approved
0.681 Remote Similarity NPD2796 Approved
0.6802 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6802 Remote Similarity NPD7783 Phase 2
0.6795 Remote Similarity NPD3094 Phase 2
0.6795 Remote Similarity NPD1470 Approved
0.6792 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6788 Remote Similarity NPD7435 Discontinued
0.6784 Remote Similarity NPD6599 Discontinued
0.6772 Remote Similarity NPD7667 Clinical (unspecified phase)
0.6768 Remote Similarity NPD2346 Discontinued
0.6758 Remote Similarity NPD7038 Approved
0.6758 Remote Similarity NPD7039 Approved
0.6753 Remote Similarity NPD1201 Approved
0.6752 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6748 Remote Similarity NPD2799 Discontinued
0.6748 Remote Similarity NPD1509 Clinical (unspecified phase)
0.6747 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6743 Remote Similarity NPD6971 Discontinued
0.6732 Remote Similarity NPD2932 Approved
0.673 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6728 Remote Similarity NPD6653 Approved
0.6727 Remote Similarity NPD5958 Discontinued
0.6724 Remote Similarity NPD5353 Approved
0.6721 Remote Similarity NPD7549 Discontinued
0.672 Remote Similarity NPD6534 Approved
0.672 Remote Similarity NPD6535 Approved
0.6719 Remote Similarity NPD6779 Approved
0.6719 Remote Similarity NPD6776 Approved
0.6719 Remote Similarity NPD6780 Approved
0.6719 Remote Similarity NPD6781 Approved
0.6719 Remote Similarity NPD6782 Approved
0.6719 Remote Similarity NPD6777 Approved
0.6719 Remote Similarity NPD6778 Approved
0.671 Remote Similarity NPD1481 Phase 2
0.6708 Remote Similarity NPD1240 Approved
0.6708 Remote Similarity NPD826 Approved
0.6708 Remote Similarity NPD825 Approved
0.6707 Remote Similarity NPD6100 Approved
0.6707 Remote Similarity NPD6099 Approved
0.6707 Remote Similarity NPD2531 Phase 2
0.6706 Remote Similarity NPD7427 Discontinued
0.6702 Remote Similarity NPD7700 Phase 2
0.6702 Remote Similarity NPD7699 Phase 2
0.6688 Remote Similarity NPD3266 Approved
0.6688 Remote Similarity NPD3267 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