Structure

Physi-Chem Properties

Molecular Weight:  726.2
Volume:  656.612
LogP:  -0.293
LogD:  -0.326
LogS:  -3.073
# Rotatable Bonds:  8
TPSA:  308.12
# H-Bond Aceptor:  19
# H-Bond Donor:  11
# Rings:  6
# Heavy Atoms:  19

MedChem Properties

QED Drug-Likeness Score:  0.111
Synthetic Accessibility Score:  5.27
Fsp3:  0.531
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:  -6.451
MDCK Permeability:  3.600470881792717e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.999
Human Intestinal Absorption (HIA):  0.918
20% Bioavailability (F20%):  0.036
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.125
Plasma Protein Binding (PPB):  78.65316009521484%
Volume Distribution (VD):  0.524
Pgp-substrate:  21.481487274169922%

ADMET: Metabolism

CYP1A2-inhibitor:  0.05
CYP1A2-substrate:  0.021
CYP2C19-inhibitor:  0.037
CYP2C19-substrate:  0.051
CYP2C9-inhibitor:  0.004
CYP2C9-substrate:  0.065
CYP2D6-inhibitor:  0.017
CYP2D6-substrate:  0.091
CYP3A4-inhibitor:  0.039
CYP3A4-substrate:  0.002

ADMET: Excretion

Clearance (CL):  0.84
Half-life (T1/2):  0.65

ADMET: Toxicity

hERG Blockers:  0.393
Human Hepatotoxicity (H-HT):  0.052
Drug-inuced Liver Injury (DILI):  0.981
AMES Toxicity:  0.81
Rat Oral Acute Toxicity:  0.061
Maximum Recommended Daily Dose:  0.002
Skin Sensitization:  0.922
Carcinogencity:  0.075
Eye Corrosion:  0.003
Eye Irritation:  0.078
Respiratory Toxicity:  0.015

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

  Natural Product: NPC476470

Natural Product ID:  NPC476470
Common Name*:   3-[(2S,3R,4S,5R,6R)-4,5-Dihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-Trihydroxy-6-Methyloxan-2-Yl]Oxymethyl]-3-[(2R,3S,4R,5S)-3,4,5-Trihydroxyoxan-2-Yl]Oxyoxan-2-Yl]Oxy-5,7-Dihydroxy-2-(4-Hydroxyphenyl)Chromen-4-One
IUPAC Name:   3-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]-3-[(2R,3S,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
Synonyms:  
Standard InCHIKey:  LLPRITPJQPQXIR-PELFOGQRSA-N
Standard InCHI:  InChI=1S/C32H38O19/c1-10-19(37)23(41)26(44)30(47-10)46-9-17-21(39)24(42)29(51-31-25(43)20(38)15(36)8-45-31)32(49-17)50-28-22(40)18-14(35)6-13(34)7-16(18)48-27(28)11-2-4-12(33)5-3-11/h2-7,10,15,17,19-21,23-26,29-39,41-44H,8-9H2,1H3/t10-,15-,17+,19-,20+,21-,23+,24-,25-,26+,29+,30+,31+,32-/m0/s1
SMILES:  Oc1ccc(cc1)c1oc2cc(O)cc(c2c(=O)c1O[C@@H]1O[C@H](CO[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)[C@@H]([C@@H]([C@H]1O[C@H]1OC[C@@H]([C@H]([C@@H]1O)O)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL81853
PubChem CID:   44460439
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
NPO33513 hydrangeae dulcis folium Species n.a. n.a. n.a. n.a. n.a. PMID[11549443]
NPO33513 hydrangeae dulcis folium Species n.a. n.a. n.a. n.a. n.a. PMID[9871657]

☑ 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
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Activity = 58.9 ng ml-1 PMID[482970]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Activity = 68.7 ng ml-1 PMID[482970]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Activity = 54.2 ng ml-1 PMID[482970]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Activity = 37.6 ng ml-1 PMID[482970]

☑ 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 NPC476470 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 NPC186816
1.0 High Similarity NPC477613
1.0 High Similarity NPC11432
1.0 High Similarity NPC32641
1.0 High Similarity NPC12013
1.0 High Similarity NPC256188
1.0 High Similarity NPC221342
1.0 High Similarity NPC203145
1.0 High Similarity NPC142142
1.0 High Similarity NPC189564
0.9936 High Similarity NPC292929
0.9936 High Similarity NPC135358
0.9936 High Similarity NPC287889
0.9936 High Similarity NPC76831
0.9936 High Similarity NPC289667
0.9808 High Similarity NPC244875
0.9808 High Similarity NPC475382
0.9808 High Similarity NPC240306
0.9747 High Similarity NPC64425
0.9745 High Similarity NPC473644
0.9745 High Similarity NPC311850
0.9744 High Similarity NPC265885
0.9744 High Similarity NPC116458
0.9744 High Similarity NPC170052
0.9744 High Similarity NPC163242
0.9744 High Similarity NPC246943
0.9744 High Similarity NPC476215
0.9744 High Similarity NPC215710
0.9744 High Similarity NPC139320
0.9744 High Similarity NPC473438
0.9744 High Similarity NPC253788
0.9744 High Similarity NPC173582
0.9744 High Similarity NPC64305
0.9744 High Similarity NPC276377
0.9744 High Similarity NPC135846
0.9744 High Similarity NPC249281
0.9744 High Similarity NPC297987
0.9744 High Similarity NPC181465
0.9688 High Similarity NPC209550
0.9688 High Similarity NPC175429
0.9688 High Similarity NPC277532
0.9688 High Similarity NPC138990
0.9679 High Similarity NPC304741
0.9679 High Similarity NPC136761
0.9679 High Similarity NPC471079
0.9679 High Similarity NPC187379
0.9679 High Similarity NPC470405
0.9627 High Similarity NPC470715
0.9627 High Similarity NPC470714
0.9627 High Similarity NPC474522
0.9627 High Similarity NPC470716
0.9625 High Similarity NPC5319
0.9623 High Similarity NPC262222
0.9623 High Similarity NPC68592
0.9623 High Similarity NPC298666
0.9615 High Similarity NPC41121
0.9615 High Similarity NPC138811
0.9615 High Similarity NPC473634
0.9615 High Similarity NPC320283
0.9615 High Similarity NPC22062
0.9615 High Similarity NPC472459
0.9615 High Similarity NPC111929
0.9571 High Similarity NPC292019
0.9571 High Similarity NPC202908
0.9571 High Similarity NPC122467
0.9571 High Similarity NPC231787
0.9571 High Similarity NPC48984
0.9571 High Similarity NPC14187
0.9565 High Similarity NPC164704
0.9565 High Similarity NPC470712
0.9557 High Similarity NPC298171
0.9554 High Similarity NPC271270
0.9554 High Similarity NPC153342
0.9554 High Similarity NPC473623
0.9554 High Similarity NPC142860
0.9554 High Similarity NPC97285
0.9554 High Similarity NPC246469
0.9551 High Similarity NPC108831
0.9551 High Similarity NPC129827
0.9551 High Similarity NPC65003
0.9551 High Similarity NPC78263
0.9551 High Similarity NPC133671
0.9551 High Similarity NPC135391
0.9551 High Similarity NPC197304
0.9551 High Similarity NPC77672
0.9551 High Similarity NPC54802
0.9551 High Similarity NPC182634
0.9551 High Similarity NPC44931
0.9551 High Similarity NPC473512
0.9512 High Similarity NPC251417
0.9512 High Similarity NPC89052
0.9494 High Similarity NPC224530
0.9494 High Similarity NPC48093
0.9494 High Similarity NPC216496
0.9494 High Similarity NPC159579
0.9494 High Similarity NPC101636
0.9494 High Similarity NPC259957
0.9494 High Similarity NPC129217
0.9494 High Similarity NPC470125
0.9494 High Similarity NPC85707
0.9487 High Similarity NPC307938
0.9487 High Similarity NPC295613
0.9487 High Similarity NPC323593
0.9487 High Similarity NPC203500
0.9487 High Similarity NPC473657
0.9455 High Similarity NPC192539
0.9451 High Similarity NPC219043
0.9434 High Similarity NPC150164
0.9434 High Similarity NPC190450
0.9434 High Similarity NPC27942
0.9423 High Similarity NPC27408
0.9423 High Similarity NPC95090
0.939 High Similarity NPC16194
0.939 High Similarity NPC220173
0.939 High Similarity NPC294815
0.939 High Similarity NPC19108
0.939 High Similarity NPC476472
0.939 High Similarity NPC473327
0.9387 High Similarity NPC217822
0.9387 High Similarity NPC155877
0.9387 High Similarity NPC203259
0.9387 High Similarity NPC471725
0.9387 High Similarity NPC471748
0.9387 High Similarity NPC11847
0.9387 High Similarity NPC101399
0.9387 High Similarity NPC221288
0.9387 High Similarity NPC176740
0.9387 High Similarity NPC134532
0.9387 High Similarity NPC33054
0.9375 High Similarity NPC124155
0.9375 High Similarity NPC66087
0.9375 High Similarity NPC121703
0.9375 High Similarity NPC179198
0.9375 High Similarity NPC257566
0.9375 High Similarity NPC278419
0.9371 High Similarity NPC303913
0.9371 High Similarity NPC282169
0.9371 High Similarity NPC473516
0.9367 High Similarity NPC104677
0.9363 High Similarity NPC206378
0.9359 High Similarity NPC83283
0.9359 High Similarity NPC143851
0.9359 High Similarity NPC210003
0.9359 High Similarity NPC39360
0.9359 High Similarity NPC29763
0.9333 High Similarity NPC471669
0.9333 High Similarity NPC89127
0.9333 High Similarity NPC473862
0.9325 High Similarity NPC218161
0.9325 High Similarity NPC469344
0.9325 High Similarity NPC136042
0.9325 High Similarity NPC280642
0.9325 High Similarity NPC67326
0.9325 High Similarity NPC92815
0.9325 High Similarity NPC67105
0.9325 High Similarity NPC156869
0.9325 High Similarity NPC29958
0.9325 High Similarity NPC259896
0.9325 High Similarity NPC96605
0.9325 High Similarity NPC188815
0.9325 High Similarity NPC254855
0.9325 High Similarity NPC95866
0.9325 High Similarity NPC255157
0.9317 High Similarity NPC85751
0.9317 High Similarity NPC129264
0.9317 High Similarity NPC72016
0.9317 High Similarity NPC19240
0.9317 High Similarity NPC205824
0.9317 High Similarity NPC139060
0.9313 High Similarity NPC44947
0.9313 High Similarity NPC259834
0.9313 High Similarity NPC131745
0.9308 High Similarity NPC321478
0.9304 High Similarity NPC288084
0.9304 High Similarity NPC6985
0.9304 High Similarity NPC60966
0.9299 High Similarity NPC169248
0.9299 High Similarity NPC97052
0.9299 High Similarity NPC26195
0.9299 High Similarity NPC39351
0.9299 High Similarity NPC72649
0.9286 High Similarity NPC249560
0.9286 High Similarity NPC223860
0.9286 High Similarity NPC275977
0.9277 High Similarity NPC173837
0.9273 High Similarity NPC198199
0.9268 High Similarity NPC288152
0.9268 High Similarity NPC9002
0.9268 High Similarity NPC180918
0.9268 High Similarity NPC60735
0.9268 High Similarity NPC137871
0.9268 High Similarity NPC26230
0.9268 High Similarity NPC257011
0.9264 High Similarity NPC227508
0.9259 High Similarity NPC70441
0.9255 High Similarity NPC80068
0.9255 High Similarity NPC183672
0.925 High Similarity NPC47923
0.9245 High Similarity NPC73511
0.9241 High Similarity NPC170475

  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 NPC476470 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
0.9625 High Similarity NPD7804 Clinical (unspecified phase)
0.9509 High Similarity NPD7808 Phase 3
0.9448 High Similarity NPD7251 Discontinued
0.9387 High Similarity NPD6797 Phase 2
0.9207 High Similarity NPD7472 Approved
0.9182 High Similarity NPD4381 Clinical (unspecified phase)
0.9146 High Similarity NPD7054 Approved
0.9091 High Similarity NPD7074 Phase 3
0.8817 High Similarity NPD4338 Clinical (unspecified phase)
0.8712 High Similarity NPD7075 Discontinued
0.8623 High Similarity NPD6168 Clinical (unspecified phase)
0.8623 High Similarity NPD6167 Clinical (unspecified phase)
0.8623 High Similarity NPD6166 Phase 2
0.858 High Similarity NPD6801 Discontinued
0.8571 High Similarity NPD4380 Phase 2
0.8528 High Similarity NPD7096 Clinical (unspecified phase)
0.8521 High Similarity NPD3818 Discontinued
0.85 High Similarity NPD5403 Approved
0.8428 Intermediate Similarity NPD6799 Approved
0.8375 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8375 Intermediate Similarity NPD5401 Approved
0.8364 Intermediate Similarity NPD3817 Phase 2
0.828 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.828 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8253 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8253 Intermediate Similarity NPD5402 Approved
0.8242 Intermediate Similarity NPD1934 Approved
0.8228 Intermediate Similarity NPD1549 Phase 2
0.8218 Intermediate Similarity NPD6559 Discontinued
0.8212 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8193 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8161 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8121 Intermediate Similarity NPD6599 Discontinued
0.8098 Intermediate Similarity NPD1512 Approved
0.8095 Intermediate Similarity NPD3882 Suspended
0.8084 Intermediate Similarity NPD2801 Approved
0.8072 Intermediate Similarity NPD7411 Suspended
0.8037 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8023 Intermediate Similarity NPD8313 Approved
0.8023 Intermediate Similarity NPD8312 Approved
0.7987 Intermediate Similarity NPD2796 Approved
0.7976 Intermediate Similarity NPD7819 Suspended
0.7976 Intermediate Similarity NPD8455 Phase 2
0.7975 Intermediate Similarity NPD1511 Approved
0.7925 Intermediate Similarity NPD1510 Phase 2
0.7907 Intermediate Similarity NPD6959 Discontinued
0.7886 Intermediate Similarity NPD3751 Discontinued
0.7882 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7874 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7861 Intermediate Similarity NPD3787 Discontinued
0.7838 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7785 Intermediate Similarity NPD1240 Approved
0.7749 Intermediate Similarity NPD7584 Approved
0.7688 Intermediate Similarity NPD1607 Approved
0.7684 Intermediate Similarity NPD7435 Discontinued
0.7684 Intermediate Similarity NPD7697 Approved
0.7684 Intermediate Similarity NPD7696 Phase 3
0.7684 Intermediate Similarity NPD7698 Approved
0.7683 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7674 Intermediate Similarity NPD7768 Phase 2
0.7668 Intermediate Similarity NPD8151 Discontinued
0.7658 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7644 Intermediate Similarity NPD5494 Approved
0.7619 Intermediate Similarity NPD6776 Approved
0.7619 Intermediate Similarity NPD6777 Approved
0.7619 Intermediate Similarity NPD6781 Approved
0.7619 Intermediate Similarity NPD6779 Approved
0.7619 Intermediate Similarity NPD6780 Approved
0.7619 Intermediate Similarity NPD6782 Approved
0.7619 Intermediate Similarity NPD6778 Approved
0.7617 Intermediate Similarity NPD7701 Phase 2
0.759 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.759 Intermediate Similarity NPD7783 Phase 2
0.7576 Intermediate Similarity NPD3750 Approved
0.7571 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7552 Intermediate Similarity NPD7871 Phase 2
0.7552 Intermediate Similarity NPD8320 Phase 1
0.7552 Intermediate Similarity NPD7870 Phase 2
0.7552 Intermediate Similarity NPD8319 Approved
0.7538 Intermediate Similarity NPD7874 Approved
0.7538 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD7685 Pre-registration
0.7513 Intermediate Similarity NPD7699 Phase 2
0.7513 Intermediate Similarity NPD7700 Phase 2
0.7486 Intermediate Similarity NPD7228 Approved
0.7471 Intermediate Similarity NPD1653 Approved
0.747 Intermediate Similarity NPD4628 Phase 3
0.7455 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7444 Intermediate Similarity NPD5844 Phase 1
0.7439 Intermediate Similarity NPD1551 Phase 2
0.743 Intermediate Similarity NPD7473 Discontinued
0.7429 Intermediate Similarity NPD3749 Approved
0.7416 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7411 Intermediate Similarity NPD7801 Approved
0.741 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.736 Intermediate Similarity NPD6232 Discontinued
0.7356 Intermediate Similarity NPD1465 Phase 2
0.7354 Intermediate Similarity NPD6535 Approved
0.7354 Intermediate Similarity NPD6534 Approved
0.7351 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7347 Intermediate Similarity NPD7585 Approved
0.7329 Intermediate Similarity NPD6798 Discontinued
0.7326 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7326 Intermediate Similarity NPD7458 Discontinued
0.7312 Intermediate Similarity NPD6832 Phase 2
0.7312 Intermediate Similarity NPD8434 Phase 2
0.731 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD1091 Approved
0.7303 Intermediate Similarity NPD7199 Phase 2
0.7301 Intermediate Similarity NPD1933 Approved
0.7296 Intermediate Similarity NPD7583 Approved
0.7289 Intermediate Similarity NPD7266 Discontinued
0.7288 Intermediate Similarity NPD919 Approved
0.7284 Intermediate Similarity NPD6233 Phase 2
0.7273 Intermediate Similarity NPD7033 Discontinued
0.7273 Intermediate Similarity NPD3748 Approved
0.7268 Intermediate Similarity NPD6823 Phase 2
0.7256 Intermediate Similarity NPD6651 Approved
0.7253 Intermediate Similarity NPD7286 Phase 2
0.7228 Intermediate Similarity NPD7240 Approved
0.7219 Intermediate Similarity NPD8150 Discontinued
0.7209 Intermediate Similarity NPD920 Approved
0.7207 Intermediate Similarity NPD1247 Approved
0.7202 Intermediate Similarity NPD2800 Approved
0.7202 Intermediate Similarity NPD1652 Phase 2
0.7195 Intermediate Similarity NPD6355 Discontinued
0.7189 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7174 Intermediate Similarity NPD5953 Discontinued
0.7173 Intermediate Similarity NPD4363 Phase 3
0.7173 Intermediate Similarity NPD4360 Phase 2
0.7171 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD1613 Approved
0.7134 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7127 Intermediate Similarity NPD3926 Phase 2
0.7126 Intermediate Similarity NPD2935 Discontinued
0.7125 Intermediate Similarity NPD1203 Approved
0.7118 Intermediate Similarity NPD6190 Approved
0.7102 Intermediate Similarity NPD37 Approved
0.7101 Intermediate Similarity NPD1243 Approved
0.7099 Intermediate Similarity NPD4908 Phase 1
0.7095 Intermediate Similarity NPD6234 Discontinued
0.7093 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7093 Intermediate Similarity NPD2533 Approved
0.7093 Intermediate Similarity NPD2532 Approved
0.7093 Intermediate Similarity NPD2534 Approved
0.7091 Intermediate Similarity NPD5124 Phase 1
0.7091 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD2798 Approved
0.7079 Intermediate Similarity NPD4967 Phase 2
0.7079 Intermediate Similarity NPD4966 Approved
0.7079 Intermediate Similarity NPD4965 Approved
0.7076 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7051 Intermediate Similarity NPD1548 Phase 1
0.7045 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7024 Intermediate Similarity NPD6100 Approved
0.7024 Intermediate Similarity NPD6099 Approved
0.7012 Intermediate Similarity NPD3268 Approved
0.7012 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7012 Intermediate Similarity NPD2313 Discontinued
0.7006 Intermediate Similarity NPD7097 Phase 1
0.7006 Intermediate Similarity NPD6844 Discontinued
0.6994 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6982 Remote Similarity NPD2344 Approved
0.6981 Remote Similarity NPD422 Phase 1
0.697 Remote Similarity NPD4062 Phase 3
0.6964 Remote Similarity NPD2799 Discontinued
0.6957 Remote Similarity NPD3225 Approved
0.6943 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6943 Remote Similarity NPD6212 Phase 3
0.6943 Remote Similarity NPD6213 Phase 3
0.6937 Remote Similarity NPD9717 Approved
0.6936 Remote Similarity NPD7390 Discontinued
0.6932 Remote Similarity NPD3226 Approved
0.6928 Remote Similarity NPD943 Approved
0.6919 Remote Similarity NPD3887 Approved
0.6919 Remote Similarity NPD2354 Approved
0.6914 Remote Similarity NPD2797 Approved
0.689 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6886 Remote Similarity NPD230 Phase 1
0.6886 Remote Similarity NPD4340 Discontinued
0.6878 Remote Similarity NPD7930 Approved
0.6875 Remote Similarity NPD1610 Phase 2
0.686 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6848 Remote Similarity NPD3027 Phase 3
0.6829 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6821 Remote Similarity NPD2309 Approved
0.6818 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6816 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6811 Remote Similarity NPD2403 Approved
0.6802 Remote Similarity NPD2654 Approved
0.68 Remote Similarity NPD7680 Approved
0.68 Remote Similarity NPD4662 Approved
0.68 Remote Similarity NPD4661 Approved
0.6786 Remote Similarity NPD4362 Clinical (unspecified phase)
0.6786 Remote Similarity NPD447 Suspended
0.6786 Remote Similarity NPD4361 Phase 2
0.6786 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6784 Remote Similarity NPD2346 Discontinued

  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