Structure

Physi-Chem Properties

Molecular Weight:  1048.28
Volume:  985.709
LogP:  3.498
LogD:  1.765
LogS:  -4.762
# Rotatable Bonds:  16
TPSA:  380.95
# H-Bond Aceptor:  24
# H-Bond Donor:  12
# Rings:  8
# Heavy Atoms:  24

MedChem Properties

QED Drug-Likeness Score:  0.042
Synthetic Accessibility Score:  6.063
Fsp3:  0.353
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.583
MDCK Permeability:  4.1332623368361965e-05
Pgp-inhibitor:  0.006
Pgp-substrate:  0.999
Human Intestinal Absorption (HIA):  0.915
20% Bioavailability (F20%):  0.085
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.019
Plasma Protein Binding (PPB):  99.23094940185547%
Volume Distribution (VD):  0.362
Pgp-substrate:  5.7993597984313965%

ADMET: Metabolism

CYP1A2-inhibitor:  0.072
CYP1A2-substrate:  0.007
CYP2C19-inhibitor:  0.2
CYP2C19-substrate:  0.039
CYP2C9-inhibitor:  0.421
CYP2C9-substrate:  0.287
CYP2D6-inhibitor:  0.443
CYP2D6-substrate:  0.127
CYP3A4-inhibitor:  0.162
CYP3A4-substrate:  0.012

ADMET: Excretion

Clearance (CL):  1.995
Half-life (T1/2):  0.712

ADMET: Toxicity

hERG Blockers:  0.219
Human Hepatotoxicity (H-HT):  0.16
Drug-inuced Liver Injury (DILI):  0.987
AMES Toxicity:  0.684
Rat Oral Acute Toxicity:  0.059
Maximum Recommended Daily Dose:  0.023
Skin Sensitization:  0.97
Carcinogencity:  0.065
Eye Corrosion:  0.003
Eye Irritation:  0.198
Respiratory Toxicity:  0.015

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

  Natural Product: NPC72554

Natural Product ID:  NPC72554
Common Name*:   Quercetin 3-O-Alpha-L-Rhamnopyranosyl(1->6)-[(4-O-Trans-P-Coumaroyl)-Alpha-L-Rhamnopyranosyl(1->2)]-(3-O-Trans-P-Coumaroyl)-Beta-D-Galactopyranoside
IUPAC Name:   [(2S,3R,4S,5R,6S)-6-[(2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-5-hydroxy-4-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-3-yl]oxy-4,5-dihydroxy-2-methyloxan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:  
Standard InCHIKey:  NSOXFPIGIUWTDU-SCYPOZLLSA-N
Standard InCHI:  InChI=1S/C51H52O24/c1-21-37(60)40(63)42(65)49(68-21)67-20-33-38(61)46(73-35(59)16-8-24-5-12-27(53)13-6-24)48(75-50-43(66)41(64)44(22(2)69-50)72-34(58)15-7-23-3-10-26(52)11-4-23)51(71-33)74-47-39(62)36-31(57)18-28(54)19-32(36)70-45(47)25-9-14-29(55)30(56)17-25/h3-19,21-22,33,37-38,40-44,46,48-57,60-61,63-66H,20H2,1-2H3/b15-7+,16-8+/t21-,22-,33+,37-,38-,40+,41-,42+,43+,44-,46-,48+,49+,50-,51-/m0/s1
SMILES:  Oc1ccc(cc1)/C=C/C(=O)O[C@H]1[C@H](C)O[C@H]([C@@H]([C@@H]1O)O)O[C@H]1[C@@H](O[C@@H]([C@@H]([C@@H]1OC(=O)/C=C/c1ccc(cc1)O)O)CO[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)Oc1c(oc2c(c1=O)c(O)cc(c2)O)c1ccc(c(c1)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL461396
PubChem CID:   21576262
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
NPO10828 Adina racemosa Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[15043423]
NPO10828 Adina racemosa Species Rubiaceae 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
NPT2 Others Unspecified FC = 10.0 n.a. PMID[468226]

☑ 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 NPC72554 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 NPC97817
1.0 High Similarity NPC30011
0.9882 High Similarity NPC249560
0.9882 High Similarity NPC223860
0.9882 High Similarity NPC275977
0.9825 High Similarity NPC474093
0.9825 High Similarity NPC33083
0.9825 High Similarity NPC104910
0.9825 High Similarity NPC295625
0.9825 High Similarity NPC473554
0.9825 High Similarity NPC470719
0.9824 High Similarity NPC162394
0.9824 High Similarity NPC241781
0.9824 High Similarity NPC156785
0.9767 High Similarity NPC475179
0.9766 High Similarity NPC470717
0.9766 High Similarity NPC470713
0.9766 High Similarity NPC460984
0.9766 High Similarity NPC21359
0.9766 High Similarity NPC25946
0.9766 High Similarity NPC470720
0.9708 High Similarity NPC470718
0.9708 High Similarity NPC297503
0.9708 High Similarity NPC97119
0.9708 High Similarity NPC135831
0.9591 High Similarity NPC471030
0.9588 High Similarity NPC292019
0.9588 High Similarity NPC14187
0.9588 High Similarity NPC89127
0.9588 High Similarity NPC471669
0.9588 High Similarity NPC122467
0.9588 High Similarity NPC473862
0.9588 High Similarity NPC202908
0.9588 High Similarity NPC231787
0.954 High Similarity NPC64755
0.9532 High Similarity NPC477895
0.9532 High Similarity NPC217520
0.9532 High Similarity NPC37668
0.9532 High Similarity NPC196127
0.9532 High Similarity NPC251417
0.9532 High Similarity NPC267680
0.9532 High Similarity NPC113836
0.9532 High Similarity NPC35167
0.9532 High Similarity NPC139571
0.9532 High Similarity NPC253521
0.9532 High Similarity NPC293626
0.9532 High Similarity NPC89052
0.9532 High Similarity NPC173837
0.9532 High Similarity NPC217387
0.9532 High Similarity NPC258044
0.9529 High Similarity NPC214621
0.9529 High Similarity NPC34267
0.9529 High Similarity NPC223426
0.9529 High Similarity NPC81042
0.9477 High Similarity NPC192539
0.9474 High Similarity NPC144097
0.9474 High Similarity NPC61904
0.9474 High Similarity NPC219043
0.9474 High Similarity NPC48984
0.9425 High Similarity NPC470416
0.9425 High Similarity NPC470455
0.9425 High Similarity NPC470451
0.9419 High Similarity NPC120952
0.9415 High Similarity NPC294815
0.9415 High Similarity NPC473327
0.9415 High Similarity NPC253685
0.9415 High Similarity NPC220173
0.9415 High Similarity NPC19108
0.9415 High Similarity NPC16194
0.9415 High Similarity NPC476472
0.9412 High Similarity NPC217822
0.9412 High Similarity NPC470714
0.9412 High Similarity NPC471725
0.9412 High Similarity NPC155877
0.9412 High Similarity NPC470715
0.9412 High Similarity NPC470716
0.9412 High Similarity NPC134532
0.9412 High Similarity NPC11847
0.9412 High Similarity NPC33054
0.9412 High Similarity NPC101399
0.9412 High Similarity NPC471748
0.9412 High Similarity NPC221288
0.9412 High Similarity NPC203259
0.9412 High Similarity NPC176740
0.9412 High Similarity NPC474522
0.9368 High Similarity NPC470449
0.9368 High Similarity NPC199172
0.9368 High Similarity NPC470447
0.9368 High Similarity NPC470445
0.9368 High Similarity NPC36138
0.9368 High Similarity NPC35924
0.9368 High Similarity NPC470446
0.9357 High Similarity NPC472993
0.9353 High Similarity NPC470712
0.9353 High Similarity NPC156869
0.9353 High Similarity NPC116864
0.9353 High Similarity NPC164704
0.9353 High Similarity NPC95866
0.9353 High Similarity NPC259896
0.9353 High Similarity NPC244776
0.9353 High Similarity NPC188815
0.9353 High Similarity NPC96605
0.9353 High Similarity NPC92815
0.9353 High Similarity NPC254855
0.9353 High Similarity NPC255157
0.9353 High Similarity NPC218161
0.9353 High Similarity NPC469344
0.9353 High Similarity NPC280642
0.9353 High Similarity NPC136042
0.9353 High Similarity NPC29958
0.9353 High Similarity NPC67326
0.9353 High Similarity NPC67105
0.931 High Similarity NPC469371
0.9302 High Similarity NPC198199
0.9298 High Similarity NPC175107
0.9298 High Similarity NPC180918
0.9298 High Similarity NPC47140
0.9298 High Similarity NPC67134
0.9298 High Similarity NPC60735
0.9298 High Similarity NPC153755
0.9298 High Similarity NPC26230
0.9298 High Similarity NPC190003
0.9294 High Similarity NPC227508
0.927 High Similarity NPC264302
0.9253 High Similarity NPC470444
0.9253 High Similarity NPC473571
0.9253 High Similarity NPC470443
0.9253 High Similarity NPC473682
0.9253 High Similarity NPC110941
0.9253 High Similarity NPC241423
0.9253 High Similarity NPC126784
0.9249 High Similarity NPC154741
0.9249 High Similarity NPC470949
0.9249 High Similarity NPC65563
0.9249 High Similarity NPC296018
0.9244 High Similarity NPC476374
0.9244 High Similarity NPC4390
0.9244 High Similarity NPC88560
0.9244 High Similarity NPC172033
0.9244 High Similarity NPC175230
0.924 High Similarity NPC285197
0.924 High Similarity NPC206123
0.924 High Similarity NPC235260
0.924 High Similarity NPC155763
0.924 High Similarity NPC20505
0.9235 High Similarity NPC84362
0.9235 High Similarity NPC223424
0.9235 High Similarity NPC317489
0.9235 High Similarity NPC127546
0.9235 High Similarity NPC173637
0.9235 High Similarity NPC52550
0.9235 High Similarity NPC275454
0.9231 High Similarity NPC470450
0.9209 High Similarity NPC65489
0.9205 High Similarity NPC75574
0.9205 High Similarity NPC318119
0.9205 High Similarity NPC231254
0.9195 High Similarity NPC476773
0.9191 High Similarity NPC294629
0.9186 High Similarity NPC476370
0.9181 High Similarity NPC138927
0.9181 High Similarity NPC86008
0.9181 High Similarity NPC120099
0.9181 High Similarity NPC223747
0.9181 High Similarity NPC219904
0.9181 High Similarity NPC225434
0.9181 High Similarity NPC195257
0.9181 High Similarity NPC209296
0.9181 High Similarity NPC203050
0.9181 High Similarity NPC52382
0.9181 High Similarity NPC43587
0.9181 High Similarity NPC105283
0.9181 High Similarity NPC270578
0.9176 High Similarity NPC179950
0.9176 High Similarity NPC277174
0.9176 High Similarity NPC221342
0.9176 High Similarity NPC73855
0.9176 High Similarity NPC12013
0.9176 High Similarity NPC88789
0.9176 High Similarity NPC118284
0.9176 High Similarity NPC253662
0.9176 High Similarity NPC281131
0.9176 High Similarity NPC8856
0.9176 High Similarity NPC135599
0.9176 High Similarity NPC476470
0.9176 High Similarity NPC32641
0.9176 High Similarity NPC56077
0.9176 High Similarity NPC115674
0.9176 High Similarity NPC473278
0.9176 High Similarity NPC328940
0.9176 High Similarity NPC308404
0.9176 High Similarity NPC256188
0.9176 High Similarity NPC210073
0.9176 High Similarity NPC189564
0.9176 High Similarity NPC274618
0.9176 High Similarity NPC260504
0.9176 High Similarity NPC11432
0.9176 High Similarity NPC203145
0.9176 High Similarity NPC145038
0.9176 High Similarity NPC64425

  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 NPC72554 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
0.9471 High Similarity NPD7251 Discontinued
0.9415 High Similarity NPD7808 Phase 3
0.9412 High Similarity NPD6797 Phase 2
0.924 High Similarity NPD7472 Approved
0.9181 High Similarity NPD7054 Approved
0.9128 High Similarity NPD7074 Phase 3
0.908 High Similarity NPD4338 Clinical (unspecified phase)
0.8966 High Similarity NPD7993 Clinical (unspecified phase)
0.896 High Similarity NPD7804 Clinical (unspecified phase)
0.8895 High Similarity NPD6166 Phase 2
0.8895 High Similarity NPD6167 Clinical (unspecified phase)
0.8895 High Similarity NPD6168 Clinical (unspecified phase)
0.8686 High Similarity NPD3818 Discontinued
0.8655 High Similarity NPD4381 Clinical (unspecified phase)
0.8538 High Similarity NPD3817 Phase 2
0.8488 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8439 Intermediate Similarity NPD7075 Discontinued
0.8398 Intermediate Similarity NPD8313 Approved
0.8398 Intermediate Similarity NPD8312 Approved
0.8378 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8314 Intermediate Similarity NPD1934 Approved
0.8276 Intermediate Similarity NPD3882 Suspended
0.8266 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8266 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8218 Intermediate Similarity NPD5402 Approved
0.8208 Intermediate Similarity NPD6801 Discontinued
0.8187 Intermediate Similarity NPD6559 Discontinued
0.8176 Intermediate Similarity NPD1512 Approved
0.8161 Intermediate Similarity NPD2801 Approved
0.8129 Intermediate Similarity NPD5403 Approved
0.8092 Intermediate Similarity NPD4380 Phase 2
0.8075 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.8059 Intermediate Similarity NPD1511 Approved
0.8059 Intermediate Similarity NPD6799 Approved
0.8057 Intermediate Similarity NPD8455 Phase 2
0.8056 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.802 Intermediate Similarity NPD8151 Discontinued
0.8012 Intermediate Similarity NPD5401 Approved
0.7989 Intermediate Similarity NPD6959 Discontinued
0.7955 Intermediate Similarity NPD7819 Suspended
0.7943 Intermediate Similarity NPD7411 Suspended
0.7923 Intermediate Similarity NPD5844 Phase 1
0.791 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7892 Intermediate Similarity NPD7685 Pre-registration
0.7874 Intermediate Similarity NPD1653 Approved
0.7869 Intermediate Similarity NPD7228 Approved
0.7869 Intermediate Similarity NPD3751 Discontinued
0.7865 Intermediate Similarity NPD7768 Phase 2
0.7857 Intermediate Similarity NPD7435 Discontinued
0.7845 Intermediate Similarity NPD3787 Discontinued
0.7819 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7816 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7814 Intermediate Similarity NPD7473 Discontinued
0.7803 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7802 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7784 Intermediate Similarity NPD6599 Discontinued
0.7753 Intermediate Similarity NPD1465 Phase 2
0.7747 Intermediate Similarity NPD6232 Discontinued
0.7735 Intermediate Similarity NPD5494 Approved
0.7732 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD8320 Phase 1
0.7727 Intermediate Similarity NPD8319 Approved
0.7711 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7711 Intermediate Similarity NPD7874 Approved
0.7706 Intermediate Similarity NPD7266 Discontinued
0.7701 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD7199 Phase 2
0.7677 Intermediate Similarity NPD7696 Phase 3
0.7677 Intermediate Similarity NPD7698 Approved
0.7677 Intermediate Similarity NPD7697 Approved
0.7673 Intermediate Similarity NPD7783 Phase 2
0.7673 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7661 Intermediate Similarity NPD1549 Phase 2
0.7638 Intermediate Similarity NPD7870 Phase 2
0.7638 Intermediate Similarity NPD7871 Phase 2
0.763 Intermediate Similarity NPD6190 Approved
0.7614 Intermediate Similarity NPD6776 Approved
0.7614 Intermediate Similarity NPD6781 Approved
0.7614 Intermediate Similarity NPD6779 Approved
0.7614 Intermediate Similarity NPD6780 Approved
0.7614 Intermediate Similarity NPD6782 Approved
0.7614 Intermediate Similarity NPD6778 Approved
0.7614 Intermediate Similarity NPD6777 Approved
0.7612 Intermediate Similarity NPD7701 Phase 2
0.7602 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7602 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7582 Intermediate Similarity NPD919 Approved
0.7544 Intermediate Similarity NPD2796 Approved
0.7527 Intermediate Similarity NPD3749 Approved
0.7513 Intermediate Similarity NPD7240 Approved
0.7513 Intermediate Similarity NPD7700 Phase 2
0.7513 Intermediate Similarity NPD7699 Phase 2
0.7486 Intermediate Similarity NPD6234 Discontinued
0.7485 Intermediate Similarity NPD1510 Phase 2
0.7471 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7443 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7429 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7415 Intermediate Similarity NPD7801 Approved
0.7409 Intermediate Similarity NPD8150 Discontinued
0.7403 Intermediate Similarity NPD37 Approved
0.7389 Intermediate Similarity NPD7584 Approved
0.7377 Intermediate Similarity NPD4965 Approved
0.7377 Intermediate Similarity NPD4966 Approved
0.7377 Intermediate Similarity NPD4967 Phase 2
0.7371 Intermediate Similarity NPD3750 Approved
0.736 Intermediate Similarity NPD6534 Approved
0.736 Intermediate Similarity NPD6535 Approved
0.7356 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD7458 Discontinued
0.7326 Intermediate Similarity NPD3926 Phase 2
0.732 Intermediate Similarity NPD8434 Phase 2
0.7314 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7312 Intermediate Similarity NPD1247 Approved
0.731 Intermediate Similarity NPD230 Phase 1
0.731 Intermediate Similarity NPD1933 Approved
0.7287 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7277 Intermediate Similarity NPD6823 Phase 2
0.7273 Intermediate Similarity NPD4628 Phase 3
0.7251 Intermediate Similarity NPD1240 Approved
0.7251 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7251 Intermediate Similarity NPD1613 Approved
0.7241 Intermediate Similarity NPD7680 Approved
0.7241 Intermediate Similarity NPD1551 Phase 2
0.7235 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7184 Intermediate Similarity NPD7585 Approved
0.7168 Intermediate Similarity NPD1607 Approved
0.7151 Intermediate Similarity NPD943 Approved
0.7143 Intermediate Similarity NPD2935 Discontinued
0.7136 Intermediate Similarity NPD7583 Approved
0.7135 Intermediate Similarity NPD6798 Discontinued
0.7129 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7111 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.711 Intermediate Similarity NPD447 Suspended
0.7093 Intermediate Similarity NPD6233 Phase 2
0.7086 Intermediate Similarity NPD3748 Approved
0.7056 Intermediate Similarity NPD7390 Discontinued
0.7049 Intermediate Similarity NPD3226 Approved
0.7037 Intermediate Similarity NPD8127 Discontinued
0.7037 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.7033 Intermediate Similarity NPD920 Approved
0.7018 Intermediate Similarity NPD6832 Phase 2
0.7018 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7017 Intermediate Similarity NPD2532 Approved
0.7017 Intermediate Similarity NPD2533 Approved
0.7017 Intermediate Similarity NPD2534 Approved
0.701 Intermediate Similarity NPD5953 Discontinued
0.6995 Remote Similarity NPD7286 Phase 2
0.6989 Remote Similarity NPD651 Clinical (unspecified phase)
0.6977 Remote Similarity NPD3027 Phase 3
0.6965 Remote Similarity NPD6213 Phase 3
0.6965 Remote Similarity NPD6212 Phase 3
0.6965 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6959 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6957 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6927 Remote Similarity NPD1243 Approved
0.6927 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6923 Remote Similarity NPD642 Clinical (unspecified phase)
0.6914 Remote Similarity NPD6355 Discontinued
0.6906 Remote Similarity NPD643 Clinical (unspecified phase)
0.6893 Remote Similarity NPD7033 Discontinued
0.6889 Remote Similarity NPD8166 Discontinued
0.6889 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6862 Remote Similarity NPD5353 Approved
0.6853 Remote Similarity NPD7549 Discontinued
0.6845 Remote Similarity NPD6844 Discontinued
0.6842 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6842 Remote Similarity NPD1203 Approved
0.6839 Remote Similarity NPD2313 Discontinued
0.6836 Remote Similarity NPD7097 Phase 1
0.6833 Remote Similarity NPD6674 Discontinued
0.6833 Remote Similarity NPD1652 Phase 2
0.6831 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6822 Remote Similarity NPD7930 Approved
0.6821 Remote Similarity NPD4908 Phase 1
0.6818 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6816 Remote Similarity NPD2346 Discontinued
0.6802 Remote Similarity NPD7038 Approved
0.6802 Remote Similarity NPD7039 Approved
0.6798 Remote Similarity NPD2799 Discontinued
0.6787 Remote Similarity NPD8059 Phase 3
0.6787 Remote Similarity NPD8058 Clinical (unspecified phase)
0.6769 Remote Similarity NPD7799 Discontinued
0.6768 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6765 Remote Similarity NPD4363 Phase 3
0.6765 Remote Similarity NPD4360 Phase 2
0.676 Remote Similarity NPD5406 Approved
0.676 Remote Similarity NPD6099 Approved
0.676 Remote Similarity NPD6100 Approved
0.676 Remote Similarity NPD5405 Approved
0.676 Remote Similarity NPD5408 Approved
0.676 Remote Similarity NPD5404 Approved
0.6743 Remote Similarity NPD4907 Clinical (unspecified phase)
0.674 Remote Similarity NPD2800 Approved
0.6736 Remote Similarity NPD7229 Phase 3
0.6733 Remote Similarity NPD4287 Approved
0.6723 Remote Similarity NPD5124 Phase 1
0.6723 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6722 Remote Similarity NPD2344 Approved
0.6715 Remote Similarity NPD8285 Discontinued
0.6706 Remote Similarity NPD1091 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