Structure

Physi-Chem Properties

Molecular Weight:  724.18
Volume:  707.368
LogP:  4.795
LogD:  2.97
LogS:  -4.272
# Rotatable Bonds:  11
TPSA:  222.65
# H-Bond Aceptor:  14
# H-Bond Donor:  6
# Rings:  6
# Heavy Atoms:  14

MedChem Properties

QED Drug-Likeness Score:  0.089
Synthetic Accessibility Score:  4.502
Fsp3:  0.154
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:  -5.538
MDCK Permeability:  2.7890513592865318e-05
Pgp-inhibitor:  0.04
Pgp-substrate:  0.071
Human Intestinal Absorption (HIA):  0.098
20% Bioavailability (F20%):  0.904
30% Bioavailability (F30%):  0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.011
Plasma Protein Binding (PPB):  101.29537200927734%
Volume Distribution (VD):  0.521
Pgp-substrate:  0.9377084970474243%

ADMET: Metabolism

CYP1A2-inhibitor:  0.616
CYP1A2-substrate:  0.022
CYP2C19-inhibitor:  0.895
CYP2C19-substrate:  0.041
CYP2C9-inhibitor:  0.574
CYP2C9-substrate:  0.973
CYP2D6-inhibitor:  0.915
CYP2D6-substrate:  0.415
CYP3A4-inhibitor:  0.664
CYP3A4-substrate:  0.09

ADMET: Excretion

Clearance (CL):  6.264
Half-life (T1/2):  0.896

ADMET: Toxicity

hERG Blockers:  0.358
Human Hepatotoxicity (H-HT):  0.882
Drug-inuced Liver Injury (DILI):  0.982
AMES Toxicity:  0.664
Rat Oral Acute Toxicity:  0.047
Maximum Recommended Daily Dose:  0.33
Skin Sensitization:  0.952
Carcinogencity:  0.103
Eye Corrosion:  0.003
Eye Irritation:  0.272
Respiratory Toxicity:  0.02

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Structure MOL file  
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Similar NPs/Drugs  

  Natural Product: NPC11847

Natural Product ID:  NPC11847
Common Name*:   Kaempferol 3-O-Alpha-L-(2''-Z-P-Coumaroyl-3''-E-P-Coumaroyl)Rhamnoside
IUPAC Name:   [(2S,3R,4R,5S,6S)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-5-hydroxy-3-[(Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-6-methyloxan-4-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:  
Standard InCHIKey:  HKZIBACORRUGAC-SYXHEPFYSA-N
Standard InCHI:  InChI=1S/C39H32O14/c1-20-33(47)36(51-30(45)16-6-21-2-10-24(40)11-3-21)38(52-31(46)17-7-22-4-12-25(41)13-5-22)39(49-20)53-37-34(48)32-28(44)18-27(43)19-29(32)50-35(37)23-8-14-26(42)15-9-23/h2-20,33,36,38-44,47H,1H3/b16-6+,17-7-/t20-,33-,36+,38+,39-/m0/s1
SMILES:  C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)Oc1c(=O)c2c(cc(cc2oc1c1ccc(cc1)O)O)O)OC(=O)/C=Cc1ccc(cc1)O)OC(=O)/C=C/c1ccc(cc1)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1080027
PubChem CID:   44612902
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
NPO19205 Buxus sempervirens Species Buxaceae Eukaryota roots n.a. n.a. PMID[10346940]
NPO28097 Platanus occidentalis Species Platanaceae Eukaryota whole?plant USA n.a. PMID[16124770]
NPO28097 Platanus occidentalis Species Platanaceae Eukaryota n.a. n.a. n.a. PMID[19904995]
NPO19205 Buxus sempervirens Species Buxaceae Eukaryota n.a. n.a. n.a. PMID[26722868]
NPO19205 Buxus sempervirens Species Buxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19205 Buxus sempervirens Species Buxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19205 Buxus sempervirens Species Buxaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19205 Buxus sempervirens Species Buxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28097 Platanus occidentalis Species Platanaceae 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
NPT165 Cell Line HeLa Homo sapiens IC50 = 9300.0 nM PMID[556059]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus IC50 = 0.7 ug.mL-1 PMID[556058]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 1.3 ug.mL-1 PMID[556058]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus IC50 = 1.4 ug.mL-1 PMID[556058]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 3.8 ug.mL-1 PMID[556058]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 500.0 nM PMID[556059]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 4100.0 nM PMID[556059]
NPT2 Others Unspecified Ratio IC50 = 8.2 n.a. PMID[556059]
NPT27 Others Unspecified Ratio IC50 = 19.0 n.a. PMID[556059]
NPT27 Others Unspecified Ratio IC50 = 2.3 n.a. PMID[556059]

☑ 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 NPC11847 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 NPC217822
1.0 High Similarity NPC101399
1.0 High Similarity NPC221288
0.9938 High Similarity NPC280642
0.9938 High Similarity NPC218161
0.9938 High Similarity NPC188815
0.9938 High Similarity NPC469344
0.9938 High Similarity NPC96605
0.9816 High Similarity NPC231787
0.9814 High Similarity NPC92815
0.9753 High Similarity NPC474522
0.975 High Similarity NPC260504
0.975 High Similarity NPC473278
0.975 High Similarity NPC89809
0.9691 High Similarity NPC470712
0.9691 High Similarity NPC164704
0.9688 High Similarity NPC129264
0.9688 High Similarity NPC19240
0.9688 High Similarity NPC205824
0.9688 High Similarity NPC85751
0.9688 High Similarity NPC139060
0.9632 High Similarity NPC470716
0.9632 High Similarity NPC470714
0.9632 High Similarity NPC470715
0.9625 High Similarity NPC80068
0.9506 High Similarity NPC64425
0.95 High Similarity NPC159579
0.95 High Similarity NPC48093
0.95 High Similarity NPC210961
0.95 High Similarity NPC259957
0.95 High Similarity NPC477628
0.95 High Similarity NPC472994
0.95 High Similarity NPC129217
0.95 High Similarity NPC270675
0.95 High Similarity NPC470125
0.95 High Similarity NPC477629
0.95 High Similarity NPC224530
0.95 High Similarity NPC195685
0.95 High Similarity NPC85707
0.95 High Similarity NPC216496
0.9467 High Similarity NPC474093
0.9467 High Similarity NPC104910
0.9451 High Similarity NPC209550
0.9451 High Similarity NPC175429
0.9451 High Similarity NPC277532
0.9451 High Similarity NPC76047
0.9451 High Similarity NPC138990
0.9441 High Similarity NPC27942
0.9441 High Similarity NPC240306
0.9412 High Similarity NPC30011
0.9412 High Similarity NPC97817
0.9412 High Similarity NPC475179
0.9412 High Similarity NPC72554
0.9408 High Similarity NPC75574
0.9401 High Similarity NPC477895
0.9387 High Similarity NPC12013
0.9387 High Similarity NPC32641
0.9387 High Similarity NPC11432
0.9387 High Similarity NPC203145
0.9387 High Similarity NPC189564
0.9387 High Similarity NPC221342
0.9387 High Similarity NPC476470
0.9387 High Similarity NPC142142
0.9387 High Similarity NPC477613
0.9387 High Similarity NPC186816
0.9387 High Similarity NPC256188
0.9383 High Similarity NPC121703
0.9379 High Similarity NPC101636
0.9379 High Similarity NPC249281
0.9379 High Similarity NPC473438
0.9379 High Similarity NPC476215
0.9379 High Similarity NPC246943
0.9379 High Similarity NPC265885
0.9379 High Similarity NPC139320
0.9379 High Similarity NPC253788
0.9379 High Similarity NPC282169
0.9379 High Similarity NPC181465
0.9379 High Similarity NPC163242
0.9379 High Similarity NPC215710
0.9379 High Similarity NPC276377
0.9379 High Similarity NPC173582
0.9379 High Similarity NPC116458
0.9375 High Similarity NPC320283
0.9375 High Similarity NPC472459
0.9375 High Similarity NPC104677
0.9375 High Similarity NPC111929
0.9375 High Similarity NPC41121
0.9349 High Similarity NPC135831
0.9349 High Similarity NPC241781
0.9349 High Similarity NPC297503
0.9349 High Similarity NPC97119
0.9349 High Similarity NPC156785
0.9349 High Similarity NPC162394
0.9345 High Similarity NPC471030
0.9325 High Similarity NPC72016
0.9325 High Similarity NPC292929
0.9325 High Similarity NPC287889
0.9325 High Similarity NPC76831
0.9325 High Similarity NPC135358
0.9325 High Similarity NPC289667
0.9321 High Similarity NPC298171
0.9321 High Similarity NPC472876
0.9317 High Similarity NPC304741
0.9317 High Similarity NPC187379
0.9317 High Similarity NPC471079
0.9317 High Similarity NPC470405
0.9313 High Similarity NPC182634
0.9313 High Similarity NPC108831
0.9313 High Similarity NPC77672
0.9313 High Similarity NPC197304
0.9313 High Similarity NPC54802
0.9313 High Similarity NPC78263
0.9313 High Similarity NPC133671
0.9313 High Similarity NPC135391
0.9294 High Similarity NPC470717
0.9294 High Similarity NPC223860
0.9294 High Similarity NPC460984
0.9294 High Similarity NPC21359
0.9294 High Similarity NPC25946
0.9294 High Similarity NPC470720
0.9294 High Similarity NPC470713
0.9294 High Similarity NPC249560
0.9294 High Similarity NPC275977
0.9286 High Similarity NPC217520
0.9286 High Similarity NPC139571
0.9286 High Similarity NPC35167
0.9281 High Similarity NPC34267
0.9281 High Similarity NPC223426
0.9281 High Similarity NPC81042
0.9281 High Similarity NPC214621
0.9273 High Similarity NPC5319
0.9268 High Similarity NPC298666
0.9268 High Similarity NPC262222
0.9268 High Similarity NPC68592
0.9259 High Similarity NPC135846
0.9259 High Similarity NPC297987
0.9259 High Similarity NPC170052
0.9259 High Similarity NPC64305
0.9255 High Similarity NPC138811
0.9255 High Similarity NPC473634
0.9255 High Similarity NPC22062
0.925 High Similarity NPC307938
0.925 High Similarity NPC323593
0.925 High Similarity NPC203500
0.924 High Similarity NPC295625
0.924 High Similarity NPC33083
0.924 High Similarity NPC473554
0.924 High Similarity NPC470719
0.9235 High Similarity NPC470718
0.9226 High Similarity NPC144097
0.9226 High Similarity NPC61904
0.9202 High Similarity NPC150164
0.9202 High Similarity NPC244875
0.9202 High Similarity NPC475382
0.9198 High Similarity NPC136761
0.9198 High Similarity NPC473623
0.9198 High Similarity NPC153342
0.9193 High Similarity NPC129827
0.9193 High Similarity NPC44931
0.9193 High Similarity NPC65003
0.9193 High Similarity NPC473512
0.9193 High Similarity NPC43638
0.9187 High Similarity NPC95090
0.9187 High Similarity NPC27408
0.9181 High Similarity NPC470416
0.9172 High Similarity NPC293626
0.9172 High Similarity NPC217387
0.9172 High Similarity NPC37668
0.9172 High Similarity NPC113836
0.9172 High Similarity NPC267680
0.9172 High Similarity NPC258044
0.9172 High Similarity NPC253521
0.9172 High Similarity NPC196127
0.9146 High Similarity NPC473644
0.9146 High Similarity NPC66087
0.9146 High Similarity NPC278419
0.9146 High Similarity NPC311850
0.9146 High Similarity NPC179198
0.9141 High Similarity NPC303913
0.9136 High Similarity NPC43761
0.9136 High Similarity NPC73511
0.913 High Similarity NPC127406
0.913 High Similarity NPC473657
0.913 High Similarity NPC295613
0.9125 High Similarity NPC210003
0.9125 High Similarity NPC83283
0.9125 High Similarity NPC29763
0.9125 High Similarity NPC143851
0.9125 High Similarity NPC39360
0.9123 High Similarity NPC36138
0.9118 High Similarity NPC179862
0.9112 High Similarity NPC89127
0.9112 High Similarity NPC471669
0.9112 High Similarity NPC473862
0.9107 High Similarity NPC472993
0.9102 High Similarity NPC116864
0.9102 High Similarity NPC244776
0.9085 High Similarity NPC131745
0.908 High Similarity NPC142860
0.908 High Similarity NPC97285

  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 NPC11847 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
0.9273 High Similarity NPD7804 Clinical (unspecified phase)
0.9074 High Similarity NPD4381 Clinical (unspecified phase)
0.9053 High Similarity NPD7808 Phase 3
0.8994 High Similarity NPD7251 Discontinued
0.8935 High Similarity NPD6797 Phase 2
0.8841 High Similarity NPD7075 Discontinued
0.883 High Similarity NPD4338 Clinical (unspecified phase)
0.8817 High Similarity NPD7054 Approved
0.8765 High Similarity NPD7472 Approved
0.8712 High Similarity NPD6801 Discontinued
0.8659 High Similarity NPD7096 Clinical (unspecified phase)
0.8655 High Similarity NPD7074 Phase 3
0.8634 High Similarity NPD5403 Approved
0.8562 High Similarity NPD6799 Approved
0.8539 High Similarity NPD7879 Clinical (unspecified phase)
0.8529 High Similarity NPD6166 Phase 2
0.8529 High Similarity NPD6168 Clinical (unspecified phase)
0.8529 High Similarity NPD6167 Clinical (unspecified phase)
0.8509 High Similarity NPD5401 Approved
0.8497 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8476 Intermediate Similarity NPD4380 Phase 2
0.843 Intermediate Similarity NPD3818 Discontinued
0.8424 Intermediate Similarity NPD7411 Suspended
0.8421 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8383 Intermediate Similarity NPD3817 Phase 2
0.8383 Intermediate Similarity NPD5402 Approved
0.8352 Intermediate Similarity NPD8313 Approved
0.8352 Intermediate Similarity NPD8312 Approved
0.8343 Intermediate Similarity NPD6559 Discontinued
0.8274 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8253 Intermediate Similarity NPD6599 Discontinued
0.8225 Intermediate Similarity NPD7768 Phase 2
0.8225 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8214 Intermediate Similarity NPD8455 Phase 2
0.8171 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8171 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8152 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.8137 Intermediate Similarity NPD1549 Phase 2
0.8107 Intermediate Similarity NPD7819 Suspended
0.8075 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8075 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8047 Intermediate Similarity NPD1934 Approved
0.8035 Intermediate Similarity NPD6959 Discontinued
0.8012 Intermediate Similarity NPD3882 Suspended
0.8 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7989 Intermediate Similarity NPD7435 Discontinued
0.791 Intermediate Similarity NPD3751 Discontinued
0.7904 Intermediate Similarity NPD1512 Approved
0.7901 Intermediate Similarity NPD2796 Approved
0.7895 Intermediate Similarity NPD2801 Approved
0.7886 Intermediate Similarity NPD3787 Discontinued
0.7876 Intermediate Similarity NPD8151 Discontinued
0.7861 Intermediate Similarity NPD3749 Approved
0.784 Intermediate Similarity NPD1510 Phase 2
0.7835 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7835 Intermediate Similarity NPD7874 Approved
0.7826 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7818 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7784 Intermediate Similarity NPD1511 Approved
0.7765 Intermediate Similarity NPD5844 Phase 1
0.776 Intermediate Similarity NPD7871 Phase 2
0.776 Intermediate Similarity NPD7870 Phase 2
0.7758 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7737 Intermediate Similarity NPD6776 Approved
0.7737 Intermediate Similarity NPD6777 Approved
0.7737 Intermediate Similarity NPD6778 Approved
0.7737 Intermediate Similarity NPD6779 Approved
0.7737 Intermediate Similarity NPD6782 Approved
0.7737 Intermediate Similarity NPD6780 Approved
0.7737 Intermediate Similarity NPD6781 Approved
0.7711 Intermediate Similarity NPD3750 Approved
0.7708 Intermediate Similarity NPD7697 Approved
0.7708 Intermediate Similarity NPD7696 Phase 3
0.7708 Intermediate Similarity NPD7698 Approved
0.7702 Intermediate Similarity NPD1240 Approved
0.7697 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.768 Intermediate Similarity NPD7584 Approved
0.7668 Intermediate Similarity NPD8319 Approved
0.7668 Intermediate Similarity NPD8320 Phase 1
0.7661 Intermediate Similarity NPD7458 Discontinued
0.7654 Intermediate Similarity NPD7473 Discontinued
0.7647 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7641 Intermediate Similarity NPD7701 Phase 2
0.764 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7637 Intermediate Similarity NPD7685 Pre-registration
0.7614 Intermediate Similarity NPD7783 Phase 2
0.7614 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7607 Intermediate Similarity NPD1607 Approved
0.7605 Intermediate Similarity NPD4628 Phase 3
0.7602 Intermediate Similarity NPD1653 Approved
0.7584 Intermediate Similarity NPD6232 Discontinued
0.7578 Intermediate Similarity NPD6798 Discontinued
0.7576 Intermediate Similarity NPD1551 Phase 2
0.7568 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7539 Intermediate Similarity NPD7700 Phase 2
0.7539 Intermediate Similarity NPD7699 Phase 2
0.7537 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7531 Intermediate Similarity NPD6233 Phase 2
0.7528 Intermediate Similarity NPD7199 Phase 2
0.7525 Intermediate Similarity NPD7801 Approved
0.7514 Intermediate Similarity NPD7228 Approved
0.7485 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7474 Intermediate Similarity NPD6535 Approved
0.7474 Intermediate Similarity NPD6534 Approved
0.7472 Intermediate Similarity NPD5494 Approved
0.7462 Intermediate Similarity NPD7585 Approved
0.7453 Intermediate Similarity NPD6832 Phase 2
0.7439 Intermediate Similarity NPD1933 Approved
0.7433 Intermediate Similarity NPD8150 Discontinued
0.7416 Intermediate Similarity NPD919 Approved
0.7411 Intermediate Similarity NPD7583 Approved
0.741 Intermediate Similarity NPD3748 Approved
0.7386 Intermediate Similarity NPD1465 Phase 2
0.7385 Intermediate Similarity NPD6823 Phase 2
0.7377 Intermediate Similarity NPD7286 Phase 2
0.7353 Intermediate Similarity NPD6190 Approved
0.7341 Intermediate Similarity NPD920 Approved
0.734 Intermediate Similarity NPD8434 Phase 2
0.7321 Intermediate Similarity NPD7266 Discontinued
0.7305 Intermediate Similarity NPD7033 Discontinued
0.7297 Intermediate Similarity NPD5953 Discontinued
0.7267 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD1203 Approved
0.7262 Intermediate Similarity NPD2935 Discontinued
0.7246 Intermediate Similarity NPD7097 Phase 1
0.7235 Intermediate Similarity NPD1243 Approved
0.7235 Intermediate Similarity NPD1652 Phase 2
0.7232 Intermediate Similarity NPD37 Approved
0.7229 Intermediate Similarity NPD6355 Discontinued
0.7225 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7225 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD6234 Discontinued
0.7209 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7207 Intermediate Similarity NPD4965 Approved
0.7207 Intermediate Similarity NPD4966 Approved
0.7207 Intermediate Similarity NPD4967 Phase 2
0.7168 Intermediate Similarity NPD7390 Discontinued
0.7166 Intermediate Similarity NPD7240 Approved
0.7159 Intermediate Similarity NPD3226 Approved
0.7158 Intermediate Similarity NPD3926 Phase 2
0.7152 Intermediate Similarity NPD2313 Discontinued
0.7143 Intermediate Similarity NPD1247 Approved
0.7134 Intermediate Similarity NPD4908 Phase 1
0.7126 Intermediate Similarity NPD2532 Approved
0.7126 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD2534 Approved
0.7126 Intermediate Similarity NPD2533 Approved
0.7126 Intermediate Similarity NPD5124 Phase 1
0.7125 Intermediate Similarity NPD1091 Approved
0.7101 Intermediate Similarity NPD2799 Discontinued
0.7083 Intermediate Similarity NPD6651 Approved
0.7081 Intermediate Similarity NPD9717 Approved
0.7079 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD6213 Phase 3
0.7062 Intermediate Similarity NPD6212 Phase 3
0.7052 Intermediate Similarity NPD2354 Approved
0.7052 Intermediate Similarity NPD3887 Approved
0.7048 Intermediate Similarity NPD3268 Approved
0.7048 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD2800 Approved
0.7026 Intermediate Similarity NPD4360 Phase 2
0.7026 Intermediate Similarity NPD4363 Phase 3
0.7024 Intermediate Similarity NPD230 Phase 1
0.7019 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD422 Phase 1
0.7018 Intermediate Similarity NPD2344 Approved
0.7012 Intermediate Similarity NPD2798 Approved
0.7006 Intermediate Similarity NPD4062 Phase 3
0.6995 Remote Similarity NPD4287 Approved
0.6994 Remote Similarity NPD3225 Approved
0.6994 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6964 Remote Similarity NPD1613 Approved
0.6964 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6952 Remote Similarity NPD7799 Discontinued
0.6951 Remote Similarity NPD2797 Approved
0.6944 Remote Similarity NPD6844 Discontinued
0.6931 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6923 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6923 Remote Similarity NPD447 Suspended
0.6923 Remote Similarity NPD4340 Discontinued
0.6919 Remote Similarity NPD2346 Discontinued
0.6915 Remote Similarity NPD7680 Approved
0.6914 Remote Similarity NPD7440 Discontinued
0.6908 Remote Similarity NPD7930 Approved
0.6901 Remote Similarity NPD4308 Phase 3
0.6897 Remote Similarity NPD7003 Approved
0.6893 Remote Similarity NPD5049 Phase 3
0.6875 Remote Similarity NPD9545 Approved
0.6875 Remote Similarity NPD1548 Phase 1
0.6872 Remote Similarity NPD8158 Clinical (unspecified phase)
0.6869 Remote Similarity NPD8058 Clinical (unspecified phase)
0.6869 Remote Similarity NPD8059 Phase 3
0.6868 Remote Similarity NPD4288 Approved
0.6865 Remote Similarity NPD8127 Discontinued
0.6864 Remote Similarity NPD943 Approved
0.686 Remote Similarity NPD6100 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