Structure

Physi-Chem Properties

Molecular Weight:  802.22
Volume:  717.575
LogP:  -1.714
LogD:  -0.864
LogS:  -2.497
# Rotatable Bonds:  11
TPSA:  368.81
# H-Bond Aceptor:  22
# H-Bond Donor:  14
# Rings:  6
# Heavy Atoms:  22

MedChem Properties

QED Drug-Likeness Score:  0.086
Synthetic Accessibility Score:  5.492
Fsp3:  0.559
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.632
MDCK Permeability:  9.671888983575627e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.994
Human Intestinal Absorption (HIA):  0.99
20% Bioavailability (F20%):  0.007
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.411
Plasma Protein Binding (PPB):  66.6873550415039%
Volume Distribution (VD):  0.546
Pgp-substrate:  18.78571128845215%

ADMET: Metabolism

CYP1A2-inhibitor:  0.026
CYP1A2-substrate:  0.007
CYP2C19-inhibitor:  0.004
CYP2C19-substrate:  0.05
CYP2C9-inhibitor:  0.0
CYP2C9-substrate:  0.034
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.088
CYP3A4-inhibitor:  0.004
CYP3A4-substrate:  0.001

ADMET: Excretion

Clearance (CL):  0.988
Half-life (T1/2):  0.907

ADMET: Toxicity

hERG Blockers:  0.452
Human Hepatotoxicity (H-HT):  0.201
Drug-inuced Liver Injury (DILI):  0.978
AMES Toxicity:  0.341
Rat Oral Acute Toxicity:  0.003
Maximum Recommended Daily Dose:  0.0
Skin Sensitization:  0.072
Carcinogencity:  0.049
Eye Corrosion:  0.003
Eye Irritation:  0.017
Respiratory Toxicity:  0.003

Download Data

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

  Natural Product: NPC180918

Natural Product ID:  NPC180918
Common Name*:   Pedunculosumoside E
IUPAC Name:   7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-3-(hydroxymethyl)-2-[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one
Synonyms:   Pedunculosumoside E
Standard InCHIKey:  MGXHVYURWVASGT-JGKQFCEOSA-N
Standard InCHI:  InChI=1S/C34H42O22/c35-6-12-21(41)20-14(40)4-11(50-34-31(27(47)24(44)19(9-38)55-34)56-33-29(49)26(46)23(43)18(8-37)54-33)5-16(20)51-30(12)10-1-2-15(13(39)3-10)52-32-28(48)25(45)22(42)17(7-36)53-32/h1-5,17-19,22-29,31-40,42-49H,6-9H2/t17-,18-,19-,22-,23-,24-,25+,26+,27+,28-,29-,31-,32-,33+,34-/m1/s1
SMILES:  OC[C@H]1O[C@@H](Oc2cc(O)c3c(c2)oc(c(c3=O)CO)c2ccc(c(c2)O)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1773498
PubChem CID:   52951747
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001111] Flavonoid glycosides
          • [CHEMONTID:0001583] Flavonoid O-glycosides
            • [CHEMONTID:0003533] Flavonoid-7-O-glycosides

*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
NPO31176 Ophioglossum pedunculosum Species Ophioglossaceae Eukaryota n.a. whole plant n.a. PMID[21401115]

☑ 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
NPT27 Others Unspecified CC50 > 100000.0 nM PMID[453197]

☑ 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 NPC180918 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
0.9877 High Similarity NPC198199
0.9875 High Similarity NPC86008
0.9816 High Similarity NPC219043
0.9756 High Similarity NPC251417
0.9756 High Similarity NPC89052
0.9756 High Similarity NPC120952
0.9752 High Similarity NPC105283
0.9752 High Similarity NPC209296
0.9752 High Similarity NPC195257
0.975 High Similarity NPC8856
0.9697 High Similarity NPC192539
0.9695 High Similarity NPC202908
0.9695 High Similarity NPC14187
0.9695 High Similarity NPC122467
0.9695 High Similarity NPC255799
0.9695 High Similarity NPC292019
0.9695 High Similarity NPC48984
0.9691 High Similarity NPC285197
0.9691 High Similarity NPC105095
0.9691 High Similarity NPC44328
0.9691 High Similarity NPC79056
0.9691 High Similarity NPC177731
0.9634 High Similarity NPC294815
0.9634 High Similarity NPC16194
0.9634 High Similarity NPC476472
0.9634 High Similarity NPC19108
0.9634 High Similarity NPC473327
0.9634 High Similarity NPC220173
0.9632 High Similarity NPC60735
0.9632 High Similarity NPC3583
0.9632 High Similarity NPC26230
0.9632 High Similarity NPC259152
0.963 High Similarity NPC43587
0.963 High Similarity NPC293629
0.9627 High Similarity NPC210073
0.9627 High Similarity NPC115674
0.9625 High Similarity NPC270335
0.9625 High Similarity NPC191306
0.9573 High Similarity NPC204693
0.9573 High Similarity NPC208668
0.9573 High Similarity NPC25724
0.9571 High Similarity NPC29958
0.9571 High Similarity NPC259896
0.9571 High Similarity NPC51326
0.9571 High Similarity NPC218488
0.9571 High Similarity NPC136042
0.9571 High Similarity NPC67326
0.9571 High Similarity NPC255157
0.9571 High Similarity NPC67105
0.9571 High Similarity NPC156869
0.9571 High Similarity NPC231194
0.9571 High Similarity NPC254855
0.9568 High Similarity NPC275454
0.9565 High Similarity NPC475497
0.9565 High Similarity NPC311830
0.9565 High Similarity NPC15358
0.9565 High Similarity NPC284277
0.9565 High Similarity NPC22832
0.9565 High Similarity NPC475366
0.9563 High Similarity NPC189142
0.9563 High Similarity NPC77660
0.9518 High Similarity NPC173837
0.9515 High Similarity NPC102028
0.9515 High Similarity NPC142996
0.9512 High Similarity NPC155877
0.9512 High Similarity NPC134532
0.9512 High Similarity NPC33054
0.9512 High Similarity NPC203259
0.9512 High Similarity NPC256760
0.9512 High Similarity NPC471748
0.9512 High Similarity NPC176740
0.9512 High Similarity NPC471725
0.9509 High Similarity NPC227508
0.9506 High Similarity NPC21100
0.9506 High Similarity NPC236934
0.9506 High Similarity NPC5778
0.9506 High Similarity NPC197285
0.9503 High Similarity NPC243930
0.9503 High Similarity NPC222936
0.9503 High Similarity NPC284960
0.9503 High Similarity NPC168822
0.9503 High Similarity NPC88023
0.9503 High Similarity NPC309025
0.9503 High Similarity NPC29830
0.9503 High Similarity NPC19709
0.9467 High Similarity NPC295625
0.9467 High Similarity NPC470719
0.9467 High Similarity NPC473554
0.9464 High Similarity NPC470718
0.9461 High Similarity NPC473682
0.9461 High Similarity NPC126784
0.9461 High Similarity NPC470443
0.9461 High Similarity NPC470444
0.9461 High Similarity NPC110941
0.9461 High Similarity NPC241423
0.9461 High Similarity NPC473571
0.9458 High Similarity NPC471669
0.9458 High Similarity NPC89127
0.9458 High Similarity NPC473862
0.9458 High Similarity NPC8573
0.9458 High Similarity NPC169733
0.9455 High Similarity NPC51774
0.9455 High Similarity NPC239549
0.9455 High Similarity NPC236191
0.9451 High Similarity NPC150767
0.9451 High Similarity NPC78734
0.9451 High Similarity NPC95866
0.9448 High Similarity NPC45618
0.9448 High Similarity NPC229729
0.9448 High Similarity NPC58716
0.9448 High Similarity NPC45400
0.9448 High Similarity NPC146792
0.9444 High Similarity NPC277205
0.9441 High Similarity NPC475382
0.9441 High Similarity NPC473043
0.9408 High Similarity NPC25946
0.9408 High Similarity NPC460984
0.9408 High Similarity NPC470720
0.9408 High Similarity NPC470717
0.9408 High Similarity NPC470451
0.9408 High Similarity NPC470455
0.9408 High Similarity NPC21359
0.9408 High Similarity NPC275977
0.9408 High Similarity NPC470713
0.9408 High Similarity NPC223860
0.9408 High Similarity NPC249560
0.9401 High Similarity NPC241196
0.9401 High Similarity NPC475261
0.9398 High Similarity NPC253685
0.9394 High Similarity NPC301683
0.9394 High Similarity NPC267254
0.9394 High Similarity NPC156977
0.9394 High Similarity NPC261254
0.939 High Similarity NPC105025
0.939 High Similarity NPC93337
0.939 High Similarity NPC45638
0.939 High Similarity NPC223747
0.939 High Similarity NPC471457
0.939 High Similarity NPC219904
0.939 High Similarity NPC469931
0.939 High Similarity NPC475942
0.939 High Similarity NPC61791
0.939 High Similarity NPC225434
0.939 High Similarity NPC58053
0.939 High Similarity NPC203050
0.939 High Similarity NPC120099
0.939 High Similarity NPC229687
0.939 High Similarity NPC201292
0.939 High Similarity NPC226294
0.939 High Similarity NPC186807
0.939 High Similarity NPC170675
0.939 High Similarity NPC112755
0.9387 High Similarity NPC274618
0.9387 High Similarity NPC56077
0.9387 High Similarity NPC118284
0.9387 High Similarity NPC281131
0.9387 High Similarity NPC308404
0.9387 High Similarity NPC88789
0.9387 High Similarity NPC145038
0.9387 High Similarity NPC179950
0.9387 High Similarity NPC276222
0.9387 High Similarity NPC253662
0.9383 High Similarity NPC311850
0.9383 High Similarity NPC473644
0.9383 High Similarity NPC88043
0.9379 High Similarity NPC182045
0.9353 High Similarity NPC33083
0.9349 High Similarity NPC470446
0.9349 High Similarity NPC241781
0.9349 High Similarity NPC470449
0.9349 High Similarity NPC162394
0.9349 High Similarity NPC473072
0.9349 High Similarity NPC199172
0.9349 High Similarity NPC156785
0.9349 High Similarity NPC470445
0.9349 High Similarity NPC470447
0.9349 High Similarity NPC35924
0.9345 High Similarity NPC471030
0.9345 High Similarity NPC473895
0.9341 High Similarity NPC470949
0.9341 High Similarity NPC65563
0.9337 High Similarity NPC472993
0.9333 High Similarity NPC194483
0.9333 High Similarity NPC52353
0.9333 High Similarity NPC21190
0.9333 High Similarity NPC293004
0.9333 High Similarity NPC245014
0.9333 High Similarity NPC84265
0.9333 High Similarity NPC282987
0.9333 High Similarity NPC471416
0.9333 High Similarity NPC183357
0.9333 High Similarity NPC34287
0.9333 High Similarity NPC206123
0.9333 High Similarity NPC22195
0.9329 High Similarity NPC92565
0.9329 High Similarity NPC226304
0.9329 High Similarity NPC84362
0.9329 High Similarity NPC160156
0.9329 High Similarity NPC325555
0.9329 High Similarity NPC223424

  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 NPC180918 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
0.9814 High Similarity NPD7472 Approved
0.9752 High Similarity NPD7054 Approved
0.9691 High Similarity NPD7074 Phase 3
0.9634 High Similarity NPD7808 Phase 3
0.9573 High Similarity NPD7251 Discontinued
0.9512 High Similarity NPD6797 Phase 2
0.9212 High Similarity NPD3818 Discontinued
0.9167 High Similarity NPD4338 Clinical (unspecified phase)
0.9074 High Similarity NPD4381 Clinical (unspecified phase)
0.9042 High Similarity NPD7804 Clinical (unspecified phase)
0.8976 High Similarity NPD6166 Phase 2
0.8976 High Similarity NPD6167 Clinical (unspecified phase)
0.8976 High Similarity NPD6168 Clinical (unspecified phase)
0.8827 High Similarity NPD1934 Approved
0.8659 High Similarity NPD2393 Clinical (unspecified phase)
0.8659 High Similarity NPD2801 Approved
0.8562 High Similarity NPD1511 Approved
0.8497 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8494 Intermediate Similarity NPD3817 Phase 2
0.8476 Intermediate Similarity NPD4380 Phase 2
0.8457 Intermediate Similarity NPD1512 Approved
0.8443 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD3882 Suspended
0.8239 Intermediate Similarity NPD6559 Discontinued
0.8176 Intermediate Similarity NPD7075 Discontinued
0.8146 Intermediate Similarity NPD8312 Approved
0.8146 Intermediate Similarity NPD8313 Approved
0.8133 Intermediate Similarity NPD1653 Approved
0.8081 Intermediate Similarity NPD5494 Approved
0.8075 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8075 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8059 Intermediate Similarity NPD5402 Approved
0.8059 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8034 Intermediate Similarity NPD7685 Pre-registration
0.8025 Intermediate Similarity NPD1549 Phase 2
0.8011 Intermediate Similarity NPD7228 Approved
0.8 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD7819 Suspended
0.8 Intermediate Similarity NPD1465 Phase 2
0.7964 Intermediate Similarity NPD5403 Approved
0.7952 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7941 Intermediate Similarity NPD6801 Discontinued
0.7935 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7931 Intermediate Similarity NPD6959 Discontinued
0.7895 Intermediate Similarity NPD8455 Phase 2
0.7865 Intermediate Similarity NPD5844 Phase 1
0.7853 Intermediate Similarity NPD7473 Discontinued
0.7844 Intermediate Similarity NPD5401 Approved
0.784 Intermediate Similarity NPD1510 Phase 2
0.7826 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7809 Intermediate Similarity NPD3751 Discontinued
0.7791 Intermediate Similarity NPD2796 Approved
0.7784 Intermediate Similarity NPD6232 Discontinued
0.7784 Intermediate Similarity NPD8151 Discontinued
0.7784 Intermediate Similarity NPD3787 Discontinued
0.7784 Intermediate Similarity NPD6799 Approved
0.7778 Intermediate Similarity NPD7411 Suspended
0.7751 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7744 Intermediate Similarity NPD7266 Discontinued
0.7738 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD7199 Phase 2
0.7702 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7702 Intermediate Similarity NPD1613 Approved
0.7697 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7663 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7637 Intermediate Similarity NPD7240 Approved
0.7614 Intermediate Similarity NPD7783 Phase 2
0.7614 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7614 Intermediate Similarity NPD6234 Discontinued
0.759 Intermediate Similarity NPD7584 Approved
0.7542 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD37 Approved
0.7526 Intermediate Similarity NPD7696 Phase 3
0.7526 Intermediate Similarity NPD7697 Approved
0.7526 Intermediate Similarity NPD7698 Approved
0.7514 Intermediate Similarity NPD6599 Discontinued
0.75 Intermediate Similarity NPD3750 Approved
0.75 Intermediate Similarity NPD4966 Approved
0.75 Intermediate Similarity NPD4965 Approved
0.75 Intermediate Similarity NPD4967 Phase 2
0.75 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7768 Phase 2
0.7485 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD1240 Approved
0.7485 Intermediate Similarity NPD943 Approved
0.7471 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7462 Intermediate Similarity NPD7701 Phase 2
0.7461 Intermediate Similarity NPD6781 Approved
0.7461 Intermediate Similarity NPD6779 Approved
0.7461 Intermediate Similarity NPD6777 Approved
0.7461 Intermediate Similarity NPD6776 Approved
0.7461 Intermediate Similarity NPD6780 Approved
0.7461 Intermediate Similarity NPD6778 Approved
0.7461 Intermediate Similarity NPD6782 Approved
0.7453 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7439 Intermediate Similarity NPD1933 Approved
0.7436 Intermediate Similarity NPD7435 Discontinued
0.7416 Intermediate Similarity NPD919 Approved
0.7407 Intermediate Similarity NPD3027 Phase 3
0.7398 Intermediate Similarity NPD7870 Phase 2
0.7398 Intermediate Similarity NPD7871 Phase 2
0.7394 Intermediate Similarity NPD1607 Approved
0.7391 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD1551 Phase 2
0.7362 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.736 Intermediate Similarity NPD3749 Approved
0.7358 Intermediate Similarity NPD7700 Phase 2
0.7358 Intermediate Similarity NPD7699 Phase 2
0.7353 Intermediate Similarity NPD6190 Approved
0.7348 Intermediate Similarity NPD3926 Phase 2
0.7333 Intermediate Similarity NPD1247 Approved
0.7333 Intermediate Similarity NPD230 Phase 1
0.731 Intermediate Similarity NPD8320 Phase 1
0.731 Intermediate Similarity NPD8319 Approved
0.7306 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.73 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.73 Intermediate Similarity NPD7874 Approved
0.7296 Intermediate Similarity NPD6823 Phase 2
0.7294 Intermediate Similarity NPD4628 Phase 3
0.7264 Intermediate Similarity NPD7801 Approved
0.7259 Intermediate Similarity NPD7680 Approved
0.7231 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7229 Intermediate Similarity NPD447 Suspended
0.7202 Intermediate Similarity NPD3748 Approved
0.7202 Intermediate Similarity NPD6534 Approved
0.7202 Intermediate Similarity NPD6535 Approved
0.72 Intermediate Similarity NPD7585 Approved
0.7194 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD2935 Discontinued
0.7159 Intermediate Similarity NPD7458 Discontinued
0.7158 Intermediate Similarity NPD8150 Discontinued
0.7158 Intermediate Similarity NPD8434 Phase 2
0.715 Intermediate Similarity NPD7583 Approved
0.7135 Intermediate Similarity NPD6674 Discontinued
0.7135 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD2532 Approved
0.7126 Intermediate Similarity NPD2534 Approved
0.7126 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD2533 Approved
0.7125 Intermediate Similarity NPD1091 Approved
0.7101 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD6100 Approved
0.7059 Intermediate Similarity NPD6099 Approved
0.7045 Intermediate Similarity NPD920 Approved
0.7039 Intermediate Similarity NPD6844 Discontinued
0.7037 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD2800 Approved
0.703 Intermediate Similarity NPD6832 Phase 2
0.7029 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7026 Intermediate Similarity NPD4360 Phase 2
0.7026 Intermediate Similarity NPD4363 Phase 3
0.7021 Intermediate Similarity NPD5953 Discontinued
0.7011 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7005 Intermediate Similarity NPD7286 Phase 2
0.7 Intermediate Similarity NPD7033 Discontinued
0.6982 Remote Similarity NPD6651 Approved
0.6974 Remote Similarity NPD6213 Phase 3
0.6974 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6974 Remote Similarity NPD6212 Phase 3
0.6971 Remote Similarity NPD7390 Discontinued
0.697 Remote Similarity NPD9494 Approved
0.6966 Remote Similarity NPD3226 Approved
0.6961 Remote Similarity NPD5353 Approved
0.6957 Remote Similarity NPD8127 Discontinued
0.6952 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6951 Remote Similarity NPD1203 Approved
0.6946 Remote Similarity NPD2313 Discontinued
0.6936 Remote Similarity NPD1243 Approved
0.6936 Remote Similarity NPD1652 Phase 2
0.6933 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6928 Remote Similarity NPD4908 Phase 1
0.6914 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6909 Remote Similarity NPD2798 Approved
0.6908 Remote Similarity NPD7930 Approved
0.6897 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6887 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6875 Remote Similarity NPD1548 Phase 1
0.6872 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6856 Remote Similarity NPD6843 Phase 3
0.6856 Remote Similarity NPD6841 Approved
0.6856 Remote Similarity NPD6842 Approved
0.6845 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6824 Remote Similarity NPD5124 Phase 1
0.6824 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6824 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6821 Remote Similarity NPD2344 Approved
0.6821 Remote Similarity NPD2346 Discontinued
0.681 Remote Similarity NPD1610 Phase 2
0.6802 Remote Similarity NPD2799 Discontinued
0.6796 Remote Similarity NPD6386 Approved
0.6796 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6796 Remote Similarity NPD6385 Approved
0.6791 Remote Similarity NPD8058 Clinical (unspecified phase)
0.6791 Remote Similarity NPD8059 Phase 3
0.6791 Remote Similarity NPD5242 Approved
0.6788 Remote Similarity NPD3225 Approved
0.6788 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6782 Remote Similarity NPD5005 Approved
0.6782 Remote Similarity NPD5006 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