Structure

Physi-Chem Properties

Molecular Weight:  708.19
Volume:  651.105
LogP:  0.748
LogD:  0.454
LogS:  -4.022
# Rotatable Bonds:  11
TPSA:  270.57
# H-Bond Aceptor:  18
# H-Bond Donor:  7
# Rings:  5
# Heavy Atoms:  18

MedChem Properties

QED Drug-Likeness Score:  0.141
Synthetic Accessibility Score:  4.967
Fsp3:  0.469
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.431
MDCK Permeability:  5.7361405197298154e-05
Pgp-inhibitor:  0.087
Pgp-substrate:  0.986
Human Intestinal Absorption (HIA):  0.819
20% Bioavailability (F20%):  0.001
30% Bioavailability (F30%):  0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.058
Plasma Protein Binding (PPB):  80.7018814086914%
Volume Distribution (VD):  0.509
Pgp-substrate:  22.886981964111328%

ADMET: Metabolism

CYP1A2-inhibitor:  0.029
CYP1A2-substrate:  0.068
CYP2C19-inhibitor:  0.015
CYP2C19-substrate:  0.055
CYP2C9-inhibitor:  0.017
CYP2C9-substrate:  0.1
CYP2D6-inhibitor:  0.052
CYP2D6-substrate:  0.103
CYP3A4-inhibitor:  0.098
CYP3A4-substrate:  0.027

ADMET: Excretion

Clearance (CL):  1.268
Half-life (T1/2):  0.896

ADMET: Toxicity

hERG Blockers:  0.294
Human Hepatotoxicity (H-HT):  0.947
Drug-inuced Liver Injury (DILI):  0.989
AMES Toxicity:  0.667
Rat Oral Acute Toxicity:  0.028
Maximum Recommended Daily Dose:  0.002
Skin Sensitization:  0.104
Carcinogencity:  0.062
Eye Corrosion:  0.003
Eye Irritation:  0.029
Respiratory Toxicity:  0.021

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

  Natural Product: NPC470455

Natural Product ID:  NPC470455
Common Name*:   6-Methoxykaempferol-3-O-(2,3-Di-O-Acetyl)-Alpha-L-Rhamnopyranosyl-(1->6)-Beta-D-Glucopyranoside
IUPAC Name:   [(2R,3R,4R,5S,6S)-3-acetyloxy-2-[[(2R,3S,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-6-methoxy-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-5-hydroxy-6-methyloxan-4-yl] acetate
Synonyms:  
Standard InCHIKey:  GRFWNAVOCWDWDU-CEQRJNGLSA-N
Standard InCHI:  InChI=1S/C32H36O18/c1-11-20(37)28(46-12(2)33)30(47-13(3)34)32(45-11)44-10-18-21(38)24(41)25(42)31(49-18)50-29-23(40)19-17(9-16(36)27(43-4)22(19)39)48-26(29)14-5-7-15(35)8-6-14/h5-9,11,18,20-21,24-25,28,30-32,35-39,41-42H,10H2,1-4H3/t11-,18+,20-,21+,24-,25+,28+,30+,31-,32+/m0/s1
SMILES:  COc1c(O)cc2c(c1O)c(=O)c(c(o2)c1ccc(cc1)O)O[C@@H]1O[C@H](CO[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2OC(=O)C)OC(=O)C)O)[C@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2037058
PubChem CID:   57408401
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001111] Flavonoid glycosides
          • [CHEMONTID:0001583] Flavonoid O-glycosides
            • [CHEMONTID:0003531] Flavonoid-3-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
NPO33486 paepalanthus geniculatus Species Eriocaulaceae Eukaryota Flowers Santana do Riacho, State Minas Gerais, Brazil n.a. PMID[22506638]

☑ 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. Activity = 1.397 mM PMID[489012]

☑ 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 NPC470455 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
1.0 High Similarity NPC470451
0.994 High Similarity NPC470445
0.994 High Similarity NPC470449
0.994 High Similarity NPC470447
0.994 High Similarity NPC470446
0.9821 High Similarity NPC473571
0.9821 High Similarity NPC470443
0.9821 High Similarity NPC470444
0.9821 High Similarity NPC126784
0.9821 High Similarity NPC110941
0.9821 High Similarity NPC473682
0.9821 High Similarity NPC241423
0.9762 High Similarity NPC173837
0.9706 High Similarity NPC473072
0.9702 High Similarity NPC169733
0.9702 High Similarity NPC198324
0.9702 High Similarity NPC89127
0.9702 High Similarity NPC65563
0.9702 High Similarity NPC8573
0.9702 High Similarity NPC472385
0.9702 High Similarity NPC471669
0.9702 High Similarity NPC470949
0.9702 High Similarity NPC473862
0.9649 High Similarity NPC21359
0.9649 High Similarity NPC460984
0.9649 High Similarity NPC470416
0.9649 High Similarity NPC25946
0.9649 High Similarity NPC470720
0.9649 High Similarity NPC470717
0.9649 High Similarity NPC148710
0.9649 High Similarity NPC470713
0.9647 High Similarity NPC473071
0.9647 High Similarity NPC473073
0.9645 High Similarity NPC89052
0.9645 High Similarity NPC251417
0.9643 High Similarity NPC16194
0.9643 High Similarity NPC237435
0.9643 High Similarity NPC253685
0.9643 High Similarity NPC101191
0.9643 High Similarity NPC135277
0.9643 High Similarity NPC476472
0.9643 High Similarity NPC473327
0.9643 High Similarity NPC220173
0.9643 High Similarity NPC19108
0.9643 High Similarity NPC115760
0.9643 High Similarity NPC294815
0.9643 High Similarity NPC43211
0.9643 High Similarity NPC264735
0.9643 High Similarity NPC210094
0.9643 High Similarity NPC49344
0.9643 High Similarity NPC477848
0.9593 High Similarity NPC295625
0.9593 High Similarity NPC470719
0.9593 High Similarity NPC473554
0.9591 High Similarity NPC156785
0.9591 High Similarity NPC470718
0.9591 High Similarity NPC36138
0.9591 High Similarity NPC241781
0.9591 High Similarity NPC162394
0.9588 High Similarity NPC192539
0.9586 High Similarity NPC219043
0.9586 High Similarity NPC472384
0.9586 High Similarity NPC14187
0.9586 High Similarity NPC211532
0.9586 High Similarity NPC292019
0.9586 High Similarity NPC472382
0.9586 High Similarity NPC202908
0.9586 High Similarity NPC122467
0.9586 High Similarity NPC472380
0.9586 High Similarity NPC48984
0.9586 High Similarity NPC268533
0.9586 High Similarity NPC233994
0.9583 High Similarity NPC21666
0.9583 High Similarity NPC169977
0.9583 High Similarity NPC204693
0.9583 High Similarity NPC42773
0.9583 High Similarity NPC4390
0.9583 High Similarity NPC101026
0.9583 High Similarity NPC24043
0.9583 High Similarity NPC45522
0.9535 High Similarity NPC275977
0.9535 High Similarity NPC223860
0.9535 High Similarity NPC249560
0.9529 High Similarity NPC120952
0.9524 High Similarity NPC203259
0.9524 High Similarity NPC33054
0.9524 High Similarity NPC259152
0.9524 High Similarity NPC117260
0.9524 High Similarity NPC471748
0.9524 High Similarity NPC175107
0.9524 High Similarity NPC176740
0.9524 High Similarity NPC254540
0.9524 High Similarity NPC26230
0.9524 High Similarity NPC476405
0.9524 High Similarity NPC153755
0.9524 High Similarity NPC172807
0.9524 High Similarity NPC155877
0.9524 High Similarity NPC211594
0.9524 High Similarity NPC190003
0.9524 High Similarity NPC3583
0.9524 High Similarity NPC471725
0.9524 High Similarity NPC60735
0.9524 High Similarity NPC134532
0.948 High Similarity NPC33083
0.948 High Similarity NPC474093
0.948 High Similarity NPC104910
0.9477 High Similarity NPC107987
0.9464 High Similarity NPC20505
0.9464 High Similarity NPC245014
0.9464 High Similarity NPC155763
0.9464 High Similarity NPC67326
0.9464 High Similarity NPC255157
0.9464 High Similarity NPC235260
0.9464 High Similarity NPC67105
0.9464 High Similarity NPC282987
0.9464 High Similarity NPC156869
0.9464 High Similarity NPC244776
0.9464 High Similarity NPC254855
0.9464 High Similarity NPC84265
0.9464 High Similarity NPC29958
0.9464 High Similarity NPC116864
0.9464 High Similarity NPC136042
0.9464 High Similarity NPC95866
0.9464 High Similarity NPC259896
0.9464 High Similarity NPC285197
0.9425 High Similarity NPC97817
0.9425 High Similarity NPC475179
0.9425 High Similarity NPC72554
0.9425 High Similarity NPC30011
0.9419 High Similarity NPC222674
0.9415 High Similarity NPC258044
0.9415 High Similarity NPC217520
0.9415 High Similarity NPC113836
0.9415 High Similarity NPC139571
0.9415 High Similarity NPC35167
0.9415 High Similarity NPC293626
0.9415 High Similarity NPC267680
0.9415 High Similarity NPC168584
0.9415 High Similarity NPC477895
0.9415 High Similarity NPC253521
0.9415 High Similarity NPC217387
0.9415 High Similarity NPC196127
0.9415 High Similarity NPC37668
0.9412 High Similarity NPC102028
0.9412 High Similarity NPC142996
0.9412 High Similarity NPC198199
0.9408 High Similarity NPC472386
0.9408 High Similarity NPC180918
0.9405 High Similarity NPC225434
0.9405 High Similarity NPC209296
0.9405 High Similarity NPC203050
0.9405 High Similarity NPC138927
0.9405 High Similarity NPC226294
0.9405 High Similarity NPC219904
0.9405 High Similarity NPC186807
0.9405 High Similarity NPC475942
0.9405 High Similarity NPC469931
0.9405 High Similarity NPC223747
0.9405 High Similarity NPC105025
0.9405 High Similarity NPC227508
0.9405 High Similarity NPC58053
0.9405 High Similarity NPC86008
0.9405 High Similarity NPC45638
0.9405 High Similarity NPC120099
0.9405 High Similarity NPC201292
0.9405 High Similarity NPC93337
0.9405 High Similarity NPC195257
0.9364 High Similarity NPC297503
0.9364 High Similarity NPC135831
0.9364 High Similarity NPC97119
0.9357 High Similarity NPC472992
0.9357 High Similarity NPC144097
0.9357 High Similarity NPC472991
0.9357 High Similarity NPC61904
0.9353 High Similarity NPC163165
0.9353 High Similarity NPC51774
0.9353 High Similarity NPC236191
0.9353 High Similarity NPC239549
0.9349 High Similarity NPC22195
0.9349 High Similarity NPC183357
0.9349 High Similarity NPC206123
0.9349 High Similarity NPC21190
0.9345 High Similarity NPC84362
0.9345 High Similarity NPC226304
0.9345 High Similarity NPC325555
0.9345 High Similarity NPC223424
0.9345 High Similarity NPC265530
0.9345 High Similarity NPC58716
0.9345 High Similarity NPC173637
0.9345 High Similarity NPC127546
0.9345 High Similarity NPC275454
0.9345 High Similarity NPC317489
0.9345 High Similarity NPC52550
0.9345 High Similarity NPC45618
0.9345 High Similarity NPC146792
0.9333 High Similarity NPC470450
0.9302 High Similarity NPC475261
0.9302 High Similarity NPC476622
0.9302 High Similarity NPC476621
0.9302 High Similarity NPC476618

  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 NPC470455 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
0.9643 High Similarity NPD7808 Phase 3
0.9643 High Similarity NPD4338 Clinical (unspecified phase)
0.9583 High Similarity NPD7251 Discontinued
0.9524 High Similarity NPD6797 Phase 2
0.9464 High Similarity NPD7472 Approved
0.9405 High Similarity NPD7054 Approved
0.9235 High Similarity NPD7074 Phase 3
0.9064 High Similarity NPD7804 Clinical (unspecified phase)
0.8895 High Similarity NPD3818 Discontinued
0.8889 High Similarity NPD6167 Clinical (unspecified phase)
0.8889 High Similarity NPD6166 Phase 2
0.8889 High Similarity NPD6168 Clinical (unspecified phase)
0.875 High Similarity NPD3817 Phase 2
0.869 High Similarity NPD2801 Approved
0.8647 High Similarity NPD4381 Clinical (unspecified phase)
0.8636 High Similarity NPD7993 Clinical (unspecified phase)
0.8529 High Similarity NPD5402 Approved
0.8521 High Similarity NPD1934 Approved
0.848 Intermediate Similarity NPD3882 Suspended
0.847 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.843 Intermediate Similarity NPD7075 Discontinued
0.8372 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8363 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8274 Intermediate Similarity NPD1512 Approved
0.8256 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8198 Intermediate Similarity NPD6801 Discontinued
0.8176 Intermediate Similarity NPD1653 Approved
0.8155 Intermediate Similarity NPD1511 Approved
0.8125 Intermediate Similarity NPD5494 Approved
0.8118 Intermediate Similarity NPD5403 Approved
0.8087 Intermediate Similarity NPD8313 Approved
0.8087 Intermediate Similarity NPD8312 Approved
0.8081 Intermediate Similarity NPD4380 Phase 2
0.8077 Intermediate Similarity NPD7685 Pre-registration
0.8077 Intermediate Similarity NPD6559 Discontinued
0.8065 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.8056 Intermediate Similarity NPD7228 Approved
0.8047 Intermediate Similarity NPD6799 Approved
0.8011 Intermediate Similarity NPD5844 Phase 1
0.8 Intermediate Similarity NPD5401 Approved
0.8 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7956 Intermediate Similarity NPD3751 Discontinued
0.7943 Intermediate Similarity NPD7819 Suspended
0.7943 Intermediate Similarity NPD1465 Phase 2
0.7938 Intermediate Similarity NPD7435 Discontinued
0.7933 Intermediate Similarity NPD3787 Discontinued
0.7901 Intermediate Similarity NPD7473 Discontinued
0.7895 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7833 Intermediate Similarity NPD6232 Discontinued
0.7828 Intermediate Similarity NPD8151 Discontinued
0.7797 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.779 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7789 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7789 Intermediate Similarity NPD7874 Approved
0.7771 Intermediate Similarity NPD6599 Discontinued
0.7755 Intermediate Similarity NPD7697 Approved
0.7755 Intermediate Similarity NPD7698 Approved
0.7755 Intermediate Similarity NPD7696 Phase 3
0.775 Intermediate Similarity NPD7783 Phase 2
0.775 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.774 Intermediate Similarity NPD8455 Phase 2
0.7727 Intermediate Similarity NPD7411 Suspended
0.7719 Intermediate Similarity NPD6190 Approved
0.7701 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD6779 Approved
0.7692 Intermediate Similarity NPD6778 Approved
0.7692 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD6780 Approved
0.7692 Intermediate Similarity NPD6777 Approved
0.7692 Intermediate Similarity NPD6776 Approved
0.7692 Intermediate Similarity NPD6782 Approved
0.7692 Intermediate Similarity NPD7266 Discontinued
0.7692 Intermediate Similarity NPD6781 Approved
0.7688 Intermediate Similarity NPD7240 Approved
0.7688 Intermediate Similarity NPD7701 Phase 2
0.768 Intermediate Similarity NPD6959 Discontinued
0.768 Intermediate Similarity NPD1247 Approved
0.768 Intermediate Similarity NPD7199 Phase 2
0.7667 Intermediate Similarity NPD919 Approved
0.7667 Intermediate Similarity NPD6234 Discontinued
0.765 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD1549 Phase 2
0.7626 Intermediate Similarity NPD7871 Phase 2
0.7626 Intermediate Similarity NPD7870 Phase 2
0.759 Intermediate Similarity NPD7699 Phase 2
0.759 Intermediate Similarity NPD7700 Phase 2
0.7584 Intermediate Similarity NPD37 Approved
0.7558 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7556 Intermediate Similarity NPD4967 Phase 2
0.7556 Intermediate Similarity NPD4966 Approved
0.7556 Intermediate Similarity NPD4965 Approved
0.7538 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7538 Intermediate Similarity NPD8320 Phase 1
0.7538 Intermediate Similarity NPD8319 Approved
0.7529 Intermediate Similarity NPD2796 Approved
0.7488 Intermediate Similarity NPD7801 Approved
0.7487 Intermediate Similarity NPD8434 Phase 2
0.7487 Intermediate Similarity NPD8150 Discontinued
0.7486 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD1510 Phase 2
0.7459 Intermediate Similarity NPD7768 Phase 2
0.7442 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD6535 Approved
0.7436 Intermediate Similarity NPD6534 Approved
0.7429 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7416 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7405 Intermediate Similarity NPD3926 Phase 2
0.7396 Intermediate Similarity NPD230 Phase 1
0.7396 Intermediate Similarity NPD1933 Approved
0.7376 Intermediate Similarity NPD7584 Approved
0.7356 Intermediate Similarity NPD3750 Approved
0.735 Intermediate Similarity NPD6823 Phase 2
0.7337 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD1613 Approved
0.7326 Intermediate Similarity NPD2935 Discontinued
0.7322 Intermediate Similarity NPD3749 Approved
0.7321 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7313 Intermediate Similarity NPD7680 Approved
0.7294 Intermediate Similarity NPD447 Suspended
0.7286 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD4628 Phase 3
0.7235 Intermediate Similarity NPD1240 Approved
0.7235 Intermediate Similarity NPD943 Approved
0.7225 Intermediate Similarity NPD1551 Phase 2
0.7191 Intermediate Similarity NPD2533 Approved
0.7191 Intermediate Similarity NPD2532 Approved
0.7191 Intermediate Similarity NPD2534 Approved
0.7183 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD6233 Phase 2
0.7171 Intermediate Similarity NPD7585 Approved
0.716 Intermediate Similarity NPD3027 Phase 3
0.7151 Intermediate Similarity NPD1607 Approved
0.7127 Intermediate Similarity NPD7458 Discontinued
0.7122 Intermediate Similarity NPD7583 Approved
0.7111 Intermediate Similarity NPD920 Approved
0.7104 Intermediate Similarity NPD6844 Discontinued
0.7102 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD5953 Discontinued
0.7079 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7069 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7069 Intermediate Similarity NPD3748 Approved
0.7068 Intermediate Similarity NPD7286 Phase 2
0.7041 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD6213 Phase 3
0.7035 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD6212 Phase 3
0.7033 Intermediate Similarity NPD3226 Approved
0.7027 Intermediate Similarity NPD5353 Approved
0.7018 Intermediate Similarity NPD6798 Discontinued
0.7 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6832 Phase 2
0.6994 Remote Similarity NPD6355 Discontinued
0.6971 Remote Similarity NPD7033 Discontinued
0.6931 Remote Similarity NPD8127 Discontinued
0.6923 Remote Similarity NPD7549 Discontinued
0.6919 Remote Similarity NPD2313 Discontinued
0.691 Remote Similarity NPD2800 Approved
0.691 Remote Similarity NPD1243 Approved
0.691 Remote Similarity NPD6674 Discontinued
0.691 Remote Similarity NPD1652 Phase 2
0.6908 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6893 Remote Similarity NPD2346 Discontinued
0.6889 Remote Similarity NPD643 Clinical (unspecified phase)
0.6887 Remote Similarity NPD7930 Approved
0.6875 Remote Similarity NPD2799 Discontinued
0.6872 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6865 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6865 Remote Similarity NPD6386 Approved
0.6865 Remote Similarity NPD6385 Approved
0.6859 Remote Similarity NPD5242 Approved
0.6853 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6852 Remote Similarity NPD7907 Approved
0.6849 Remote Similarity NPD8058 Clinical (unspecified phase)
0.6849 Remote Similarity NPD8059 Phase 3
0.6845 Remote Similarity NPD5006 Approved
0.6845 Remote Similarity NPD5005 Approved
0.6842 Remote Similarity NPD9494 Approved
0.6837 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6836 Remote Similarity NPD6100 Approved
0.6836 Remote Similarity NPD6099 Approved
0.6833 Remote Similarity NPD8067 Phase 3
0.6832 Remote Similarity NPD4363 Phase 3
0.6832 Remote Similarity NPD4360 Phase 2
0.6824 Remote Similarity NPD1203 Approved
0.6818 Remote Similarity NPD7097 Phase 1
0.6806 Remote Similarity NPD5710 Approved
0.6806 Remote Similarity NPD5711 Approved
0.68 Remote Similarity NPD5124 Phase 1
0.68 Remote Similarity NPD5123 Clinical (unspecified phase)
0.68 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6786 Remote Similarity NPD1091 Approved
0.6786 Remote Similarity NPD8368 Discontinued
0.6761 Remote Similarity NPD6651 Approved
0.6758 Remote Similarity NPD7390 Discontinued
0.6757 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6746 Remote Similarity NPD9269 Phase 2

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data