Structure

Physi-Chem Properties

Molecular Weight:  1030.26
Volume:  959.775
LogP:  2.393
LogD:  1.354
LogS:  -5.191
# Rotatable Bonds:  26
TPSA:  330.13
# H-Bond Aceptor:  26
# H-Bond Donor:  0
# Rings:  5
# Heavy Atoms:  26

MedChem Properties

QED Drug-Likeness Score:  0.113
Synthetic Accessibility Score:  5.637
Fsp3:  0.468
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.15
MDCK Permeability:  0.00030147007782943547
Pgp-inhibitor:  0.999
Pgp-substrate:  0.684
Human Intestinal Absorption (HIA):  0.953
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.92

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.098
Plasma Protein Binding (PPB):  52.02408981323242%
Volume Distribution (VD):  0.517
Pgp-substrate:  16.74860191345215%

ADMET: Metabolism

CYP1A2-inhibitor:  0.008
CYP1A2-substrate:  0.001
CYP2C19-inhibitor:  0.011
CYP2C19-substrate:  0.044
CYP2C9-inhibitor:  0.042
CYP2C9-substrate:  0.024
CYP2D6-inhibitor:  0.962
CYP2D6-substrate:  0.043
CYP3A4-inhibitor:  0.182
CYP3A4-substrate:  0.132

ADMET: Excretion

Clearance (CL):  1.23
Half-life (T1/2):  0.813

ADMET: Toxicity

hERG Blockers:  0.002
Human Hepatotoxicity (H-HT):  0.999
Drug-inuced Liver Injury (DILI):  0.989
AMES Toxicity:  0.186
Rat Oral Acute Toxicity:  0.493
Maximum Recommended Daily Dose:  0.022
Skin Sensitization:  0.932
Carcinogencity:  0.015
Eye Corrosion:  0.003
Eye Irritation:  0.022
Respiratory Toxicity:  0.014

Download Data

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

  Natural Product: NPC476180

Natural Product ID:  NPC476180
Common Name*:   Rutin Decaacetate
IUPAC Name:   [(2S,3S,4R,5R,6R)-4,5-diacetyloxy-2-methyl-6-[[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[5,7-diacetyloxy-2-(3,4-diacetyloxyphenyl)-4-oxochromen-3-yl]oxyoxan-2-yl]methoxy]oxan-3-yl] acetate
Synonyms:   Rutin Decaacetate
Standard InCHIKey:  SYDKOLLYPJCLPT-HXSSPYSRSA-N
Standard InCHI:  InChI=1S/C47H50O26/c1-18-38(65-23(6)52)42(67-25(8)54)44(69-27(10)56)46(60-18)59-17-35-40(66-24(7)53)43(68-26(9)55)45(70-28(11)57)47(72-35)73-41-37(58)36-33(64-22(5)51)15-30(61-19(2)48)16-34(36)71-39(41)29-12-13-31(62-20(3)49)32(14-29)63-21(4)50/h12-16,18,35,38,40,42-47H,17H2,1-11H3/t18-,35+,38-,40+,42+,43-,44+,45+,46+,47-/m0/s1
SMILES:  CC(=O)Oc1cc(OC(=O)C)c2c(c1)oc(c(c2=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)OC(=O)C)[C@H]([C@@H]([C@H]1OC(=O)C)OC(=O)C)OC(=O)C)c1ccc(c(c1)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL55153
PubChem CID:   13034804
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
NPO33118 Rhamnus Genus Rhamnaceae Eukaryota n.a. n.a. n.a. PMID[8350094]

☑ 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
NPT20967 CELL-LINE Platelet n.a. Activity = 72.4 % PMID[476656]
NPT20967 CELL-LINE Platelet n.a. Activity = 25.9 % PMID[476656]
NPT20967 CELL-LINE Platelet n.a. Activity = 27.3 % PMID[476656]
NPT20967 CELL-LINE Platelet n.a. Activity = 88.7 % PMID[476656]

☑ 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 NPC476180 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
0.9937 High Similarity NPC475434
0.9873 High Similarity NPC475214
0.9684 High Similarity NPC414831
0.9627 High Similarity NPC477165
0.9557 High Similarity NPC321478
0.9497 High Similarity NPC473516
0.9455 High Similarity NPC473862
0.943 High Similarity NPC117478
0.9398 High Similarity NPC173837
0.9337 High Similarity NPC471669
0.9337 High Similarity NPC89127
0.9337 High Similarity NPC48984
0.929 High Similarity NPC21359
0.929 High Similarity NPC470451
0.929 High Similarity NPC470713
0.929 High Similarity NPC25946
0.929 High Similarity NPC460984
0.929 High Similarity NPC470455
0.929 High Similarity NPC470717
0.929 High Similarity NPC470720
0.9281 High Similarity NPC89052
0.9281 High Similarity NPC251417
0.9277 High Similarity NPC16194
0.9277 High Similarity NPC19108
0.9277 High Similarity NPC220173
0.9277 High Similarity NPC473327
0.9277 High Similarity NPC294815
0.9277 High Similarity NPC476472
0.9235 High Similarity NPC295625
0.9235 High Similarity NPC470719
0.9235 High Similarity NPC473554
0.9231 High Similarity NPC470445
0.9231 High Similarity NPC470446
0.9231 High Similarity NPC162394
0.9231 High Similarity NPC470449
0.9231 High Similarity NPC241781
0.9231 High Similarity NPC156785
0.9231 High Similarity NPC470718
0.9231 High Similarity NPC470447
0.9226 High Similarity NPC192539
0.9222 High Similarity NPC292019
0.9222 High Similarity NPC122467
0.9222 High Similarity NPC219043
0.9222 High Similarity NPC14187
0.9222 High Similarity NPC202908
0.9202 High Similarity NPC475366
0.9202 High Similarity NPC15358
0.9202 High Similarity NPC284277
0.9202 High Similarity NPC475497
0.9193 High Similarity NPC477164
0.9182 High Similarity NPC471746
0.9176 High Similarity NPC249560
0.9176 High Similarity NPC223860
0.9176 High Similarity NPC275977
0.9167 High Similarity NPC120952
0.9167 High Similarity NPC477895
0.9162 High Similarity NPC253685
0.9157 High Similarity NPC153755
0.9157 High Similarity NPC60735
0.9157 High Similarity NPC176740
0.9157 High Similarity NPC471725
0.9157 High Similarity NPC26230
0.9157 High Similarity NPC134532
0.9157 High Similarity NPC33054
0.9157 High Similarity NPC471748
0.9157 High Similarity NPC155877
0.9157 High Similarity NPC203259
0.9123 High Similarity NPC104910
0.9123 High Similarity NPC33083
0.9123 High Similarity NPC474093
0.9114 High Similarity NPC474388
0.9114 High Similarity NPC472535
0.9114 High Similarity NPC474170
0.9112 High Similarity NPC241423
0.9112 High Similarity NPC110941
0.9112 High Similarity NPC470443
0.9112 High Similarity NPC126784
0.9112 High Similarity NPC473682
0.9112 High Similarity NPC470444
0.9112 High Similarity NPC473571
0.9102 High Similarity NPC4390
0.9096 High Similarity NPC136042
0.9096 High Similarity NPC156869
0.9096 High Similarity NPC95866
0.9096 High Similarity NPC67326
0.9096 High Similarity NPC285197
0.9096 High Similarity NPC244776
0.9096 High Similarity NPC254855
0.9096 High Similarity NPC255157
0.9096 High Similarity NPC116864
0.9096 High Similarity NPC29958
0.9096 High Similarity NPC67105
0.9096 High Similarity NPC259896
0.907 High Similarity NPC475179
0.907 High Similarity NPC97817
0.907 High Similarity NPC72554
0.907 High Similarity NPC30011
0.9053 High Similarity NPC217520
0.9053 High Similarity NPC139571
0.9051 High Similarity NPC177839
0.9048 High Similarity NPC198199
0.9048 High Similarity NPC264735
0.9042 High Similarity NPC190003
0.9042 High Similarity NPC175107
0.9042 High Similarity NPC180918
0.9036 High Similarity NPC195257
0.9036 High Similarity NPC225434
0.9036 High Similarity NPC227508
0.9036 High Similarity NPC86008
0.9036 High Similarity NPC120099
0.9036 High Similarity NPC219904
0.9036 High Similarity NPC203050
0.9036 High Similarity NPC223747
0.9036 High Similarity NPC209296
0.903 High Similarity NPC64425
0.9018 High Similarity NPC182045
0.9006 High Similarity NPC473072
0.9006 High Similarity NPC257277
0.8994 High Similarity NPC472384
0.8994 High Similarity NPC472382
0.8994 High Similarity NPC198324
0.8994 High Similarity NPC65563
0.8994 High Similarity NPC470949
0.8994 High Similarity NPC169733
0.8994 High Similarity NPC472385
0.8994 High Similarity NPC8573
0.8994 High Similarity NPC472380
0.8982 High Similarity NPC235260
0.8982 High Similarity NPC209550
0.8982 High Similarity NPC206123
0.8982 High Similarity NPC155763
0.8982 High Similarity NPC277532
0.8982 High Similarity NPC20505
0.8982 High Similarity NPC175429
0.8982 High Similarity NPC138990
0.8976 High Similarity NPC173637
0.8976 High Similarity NPC127546
0.8976 High Similarity NPC325555
0.8976 High Similarity NPC52550
0.8976 High Similarity NPC223424
0.8976 High Similarity NPC275454
0.8976 High Similarity NPC226304
0.8976 High Similarity NPC265530
0.8976 High Similarity NPC317489
0.8976 High Similarity NPC84362
0.8963 High Similarity NPC244875
0.8957 High Similarity NPC110349
0.8953 High Similarity NPC470416
0.8953 High Similarity NPC148710
0.8947 High Similarity NPC473073
0.8947 High Similarity NPC473071
0.8944 High Similarity NPC284353
0.8944 High Similarity NPC34725
0.8944 High Similarity NPC241774
0.8944 High Similarity NPC276059
0.8944 High Similarity NPC122623
0.8941 High Similarity NPC267680
0.8941 High Similarity NPC196127
0.8941 High Similarity NPC253521
0.8941 High Similarity NPC217387
0.8941 High Similarity NPC293626
0.8941 High Similarity NPC35167
0.8941 High Similarity NPC475261
0.8941 High Similarity NPC258044
0.8941 High Similarity NPC37668
0.8941 High Similarity NPC113836
0.8935 High Similarity NPC477848
0.8935 High Similarity NPC34267
0.8935 High Similarity NPC294629
0.8935 High Similarity NPC81042
0.8935 High Similarity NPC115760
0.8935 High Similarity NPC214621
0.8935 High Similarity NPC43211
0.8935 High Similarity NPC135277
0.8935 High Similarity NPC49344
0.8935 High Similarity NPC210094
0.8935 High Similarity NPC101191
0.8935 High Similarity NPC223426
0.8935 High Similarity NPC237435
0.8929 High Similarity NPC475155
0.8929 High Similarity NPC474522
0.8922 High Similarity NPC61791
0.8922 High Similarity NPC52382
0.8922 High Similarity NPC293629
0.8922 High Similarity NPC270578
0.8922 High Similarity NPC138927
0.8916 High Similarity NPC189564
0.8916 High Similarity NPC274618
0.8916 High Similarity NPC186816
0.8916 High Similarity NPC203145
0.8916 High Similarity NPC113968
0.8916 High Similarity NPC145038
0.8916 High Similarity NPC277174
0.8916 High Similarity NPC12013
0.8916 High Similarity NPC256188
0.8916 High Similarity NPC276222
0.8916 High Similarity NPC11432
0.8916 High Similarity NPC281131
0.8916 High Similarity NPC118284
0.8916 High Similarity NPC221342

  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 NPC476180 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
0.9394 High Similarity NPD7808 Phase 3
0.9217 High Similarity NPD7251 Discontinued
0.9157 High Similarity NPD6797 Phase 2
0.9096 High Similarity NPD7472 Approved
0.9036 High Similarity NPD7054 Approved
0.8944 High Similarity NPD3817 Phase 2
0.8935 High Similarity NPD4338 Clinical (unspecified phase)
0.8869 High Similarity NPD7074 Phase 3
0.881 High Similarity NPD7804 Clinical (unspecified phase)
0.8521 High Similarity NPD6166 Phase 2
0.8521 High Similarity NPD6168 Clinical (unspecified phase)
0.8521 High Similarity NPD6167 Clinical (unspecified phase)
0.8421 Intermediate Similarity NPD3818 Discontinued
0.8383 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8313 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8284 Intermediate Similarity NPD5494 Approved
0.8274 Intermediate Similarity NPD7075 Discontinued
0.8253 Intermediate Similarity NPD1934 Approved
0.8225 Intermediate Similarity NPD919 Approved
0.821 Intermediate Similarity NPD6799 Approved
0.8171 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.8171 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8155 Intermediate Similarity NPD5402 Approved
0.8144 Intermediate Similarity NPD6801 Discontinued
0.8107 Intermediate Similarity NPD3882 Suspended
0.8095 Intermediate Similarity NPD2801 Approved
0.8095 Intermediate Similarity NPD7819 Suspended
0.8095 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8061 Intermediate Similarity NPD5403 Approved
0.8049 Intermediate Similarity NPD5401 Approved
0.8 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD2796 Approved
0.8 Intermediate Similarity NPD1512 Approved
0.7923 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7917 Intermediate Similarity NPD6599 Discontinued
0.7879 Intermediate Similarity NPD1511 Approved
0.7862 Intermediate Similarity NPD1933 Approved
0.7853 Intermediate Similarity NPD5844 Phase 1
0.7831 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7829 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7821 Intermediate Similarity NPD6559 Discontinued
0.7816 Intermediate Similarity NPD1247 Approved
0.7811 Intermediate Similarity NPD4380 Phase 2
0.7765 Intermediate Similarity NPD7411 Suspended
0.774 Intermediate Similarity NPD7473 Discontinued
0.7735 Intermediate Similarity NPD8312 Approved
0.7735 Intermediate Similarity NPD8313 Approved
0.7733 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD3926 Phase 2
0.7692 Intermediate Similarity NPD1653 Approved
0.7684 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7674 Intermediate Similarity NPD8455 Phase 2
0.7674 Intermediate Similarity NPD1465 Phase 2
0.767 Intermediate Similarity NPD6232 Discontinued
0.767 Intermediate Similarity NPD3787 Discontinued
0.7624 Intermediate Similarity NPD7685 Pre-registration
0.7622 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7614 Intermediate Similarity NPD6959 Discontinued
0.7614 Intermediate Similarity NPD7199 Phase 2
0.7598 Intermediate Similarity NPD3751 Discontinued
0.7598 Intermediate Similarity NPD7228 Approved
0.7584 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7576 Intermediate Similarity NPD1549 Phase 2
0.7554 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7547 Intermediate Similarity NPD6832 Phase 2
0.7529 Intermediate Similarity NPD920 Approved
0.7527 Intermediate Similarity NPD7240 Approved
0.75 Intermediate Similarity NPD8151 Discontinued
0.75 Intermediate Similarity NPD3748 Approved
0.7456 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7425 Intermediate Similarity NPD1243 Approved
0.7423 Intermediate Similarity NPD7435 Discontinued
0.7414 Intermediate Similarity NPD37 Approved
0.7412 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7412 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD1510 Phase 2
0.7386 Intermediate Similarity NPD4966 Approved
0.7386 Intermediate Similarity NPD7768 Phase 2
0.7386 Intermediate Similarity NPD4965 Approved
0.7386 Intermediate Similarity NPD4967 Phase 2
0.7365 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD7783 Phase 2
0.7333 Intermediate Similarity NPD7697 Approved
0.7333 Intermediate Similarity NPD7698 Approved
0.7333 Intermediate Similarity NPD7696 Phase 3
0.733 Intermediate Similarity NPD5353 Approved
0.7317 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD447 Suspended
0.7305 Intermediate Similarity NPD7266 Discontinued
0.7303 Intermediate Similarity NPD6234 Discontinued
0.7292 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7286 Intermediate Similarity NPD7874 Approved
0.7286 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD3750 Approved
0.7247 Intermediate Similarity NPD3749 Approved
0.7208 Intermediate Similarity NPD7870 Phase 2
0.7208 Intermediate Similarity NPD7871 Phase 2
0.7208 Intermediate Similarity NPD8320 Phase 1
0.7208 Intermediate Similarity NPD8319 Approved
0.7186 Intermediate Similarity NPD7701 Phase 2
0.7179 Intermediate Similarity NPD6782 Approved
0.7179 Intermediate Similarity NPD6779 Approved
0.7179 Intermediate Similarity NPD6777 Approved
0.7179 Intermediate Similarity NPD6778 Approved
0.7179 Intermediate Similarity NPD6781 Approved
0.7179 Intermediate Similarity NPD6776 Approved
0.7179 Intermediate Similarity NPD6780 Approved
0.7159 Intermediate Similarity NPD6385 Approved
0.7159 Intermediate Similarity NPD6386 Approved
0.7152 Intermediate Similarity NPD1240 Approved
0.7143 Intermediate Similarity NPD8434 Phase 2
0.7143 Intermediate Similarity NPD1551 Phase 2
0.7143 Intermediate Similarity NPD7458 Discontinued
0.7143 Intermediate Similarity NPD5242 Approved
0.7136 Intermediate Similarity NPD7584 Approved
0.7135 Intermediate Similarity NPD6190 Approved
0.7118 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD5005 Approved
0.7107 Intermediate Similarity NPD5006 Approved
0.7077 Intermediate Similarity NPD7699 Phase 2
0.7077 Intermediate Similarity NPD7700 Phase 2
0.7076 Intermediate Similarity NPD4628 Phase 3
0.7066 Intermediate Similarity NPD1607 Approved
0.7053 Intermediate Similarity NPD8150 Discontinued
0.705 Intermediate Similarity NPD7583 Approved
0.7045 Intermediate Similarity NPD3226 Approved
0.7041 Intermediate Similarity NPD2935 Discontinued
0.7041 Intermediate Similarity NPD8285 Discontinued
0.7035 Intermediate Similarity NPD3887 Approved
0.7033 Intermediate Similarity NPD8127 Discontinued
0.703 Intermediate Similarity NPD6798 Discontinued
0.7015 Intermediate Similarity NPD7585 Approved
0.7011 Intermediate Similarity NPD2532 Approved
0.7011 Intermediate Similarity NPD2534 Approved
0.7011 Intermediate Similarity NPD3688 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD2533 Approved
0.7011 Intermediate Similarity NPD3146 Approved
0.7006 Intermediate Similarity NPD230 Phase 1
0.7006 Intermediate Similarity NPD6355 Discontinued
0.7 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.6995 Remote Similarity NPD7801 Approved
0.699 Remote Similarity NPD4420 Approved
0.6988 Remote Similarity NPD6233 Phase 2
0.6946 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6946 Remote Similarity NPD1613 Approved
0.6938 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6933 Remote Similarity NPD3266 Approved
0.6933 Remote Similarity NPD3267 Approved
0.6928 Remote Similarity NPD2313 Discontinued
0.6923 Remote Similarity NPD6535 Approved
0.6923 Remote Similarity NPD6534 Approved
0.6919 Remote Similarity NPD2403 Approved
0.6919 Remote Similarity NPD1652 Phase 2
0.6919 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6915 Remote Similarity NPD5953 Discontinued
0.6914 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6901 Remote Similarity NPD2346 Discontinued
0.69 Remote Similarity NPD7680 Approved
0.6898 Remote Similarity NPD7286 Phase 2
0.689 Remote Similarity NPD1019 Discontinued
0.689 Remote Similarity NPD2798 Approved
0.6882 Remote Similarity NPD2799 Discontinued
0.6882 Remote Similarity NPD7033 Discontinued
0.6869 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6854 Remote Similarity NPD8158 Clinical (unspecified phase)
0.685 Remote Similarity NPD6823 Phase 2
0.6845 Remote Similarity NPD943 Approved
0.6845 Remote Similarity NPD4307 Phase 2
0.6842 Remote Similarity NPD7549 Discontinued
0.6833 Remote Similarity NPD6844 Discontinued
0.6831 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6829 Remote Similarity NPD1203 Approved
0.6826 Remote Similarity NPD3268 Approved
0.6826 Remote Similarity NPD1296 Phase 2
0.6824 Remote Similarity NPD7097 Phase 1
0.6821 Remote Similarity NPD6674 Discontinued
0.6807 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6805 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6805 Remote Similarity NPD5124 Phase 1
0.6802 Remote Similarity NPD2353 Approved
0.6802 Remote Similarity NPD2355 Clinical (unspecified phase)
0.6792 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6782 Remote Similarity NPD6398 Clinical (unspecified phase)
0.678 Remote Similarity NPD1940 Clinical (unspecified phase)
0.6778 Remote Similarity NPD5889 Approved
0.6778 Remote Similarity NPD5890 Approved
0.6778 Remote Similarity NPD7615 Clinical (unspecified phase)
0.677 Remote Similarity NPD17 Approved
0.6768 Remote Similarity NPD3225 Approved
0.6766 Remote Similarity NPD3027 Phase 3
0.6755 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6748 Remote Similarity NPD9717 Approved
0.6747 Remote Similarity NPD3018 Phase 2
0.6747 Remote Similarity NPD1530 Clinical (unspecified phase)

  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