Structure

Physi-Chem Properties

Molecular Weight:  610.15
Volume:  552.318
LogP:  -0.038
LogD:  -0.21
LogS:  -3.742
# Rotatable Bonds:  6
TPSA:  269.43
# H-Bond Aceptor:  16
# H-Bond Donor:  10
# Rings:  5
# Heavy Atoms:  16

MedChem Properties

QED Drug-Likeness Score:  0.14
Synthetic Accessibility Score:  4.783
Fsp3:  0.444
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.47
MDCK Permeability:  1.9190752936992794e-05
Pgp-inhibitor:  0.005
Pgp-substrate:  0.997
Human Intestinal Absorption (HIA):  0.876
20% Bioavailability (F20%):  0.038
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.041
Plasma Protein Binding (PPB):  87.11073303222656%
Volume Distribution (VD):  0.701
Pgp-substrate:  17.0244140625%

ADMET: Metabolism

CYP1A2-inhibitor:  0.121
CYP1A2-substrate:  0.041
CYP2C19-inhibitor:  0.035
CYP2C19-substrate:  0.048
CYP2C9-inhibitor:  0.018
CYP2C9-substrate:  0.139
CYP2D6-inhibitor:  0.056
CYP2D6-substrate:  0.129
CYP3A4-inhibitor:  0.039
CYP3A4-substrate:  0.003

ADMET: Excretion

Clearance (CL):  1.502
Half-life (T1/2):  0.728

ADMET: Toxicity

hERG Blockers:  0.227
Human Hepatotoxicity (H-HT):  0.083
Drug-inuced Liver Injury (DILI):  0.982
AMES Toxicity:  0.851
Rat Oral Acute Toxicity:  0.053
Maximum Recommended Daily Dose:  0.01
Skin Sensitization:  0.929
Carcinogencity:  0.055
Eye Corrosion:  0.003
Eye Irritation:  0.609
Respiratory Toxicity:  0.025

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

  Natural Product: NPC203259

Natural Product ID:  NPC203259
Common Name*:   2-(3,4-Dihydroxyphenyl)-5,7-Dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-Trihydroxy-6-Methyloxan-2-Yl]Oxymethyl]Oxan-2-Yl]Oxychromen-4-One;Hydrate
IUPAC Name:   2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one;hydrate
Synonyms:  
Standard InCHIKey:  PGHSKTKIQIBATG-ZAAWVBGYSA-N
Standard InCHI:  InChI=1S/C27H30O16.H2O/c1-8-17(32)20(35)22(37)26(40-8)39-7-15-18(33)21(36)23(38)27(42-15)43-25-19(34)16-13(31)5-10(28)6-14(16)41-24(25)9-2-3-11(29)12(30)4-9;/h2-6,8,15,17-18,20-23,26-33,35-38H,7H2,1H3;1H2/t8-,15+,17-,18+,20+,21-,22+,23+,26+,27-;/m0./s1
SMILES:  C[C@H]1[C@@H]([C@H]([C@H]([C@H](OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)Oc2c(=O)c3c(cc(cc3oc2c2ccc(c(c2)O)O)O)O)O)O)O)O1)O)O)O.O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1883743
PubChem CID:   45479757
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
NPO26293 Ginkgo biloba Species Ginkgoaceae Eukaryota n.a. leaf n.a. DOI[10.1016/S0031-9422(01)00320-X]
NPO26293 Ginkgo biloba Species Ginkgoaceae Eukaryota n.a. leaf n.a. PMID[11738417]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota Fruits n.a. n.a. PMID[16309325]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota n.a. Seoul, Korea 2000-Jun PMID[16643034]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota fruit n.a. n.a. PMID[18505286]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota fruit n.a. n.a. PMID[19650637]
NPO26293 Ginkgo biloba Species Ginkgoaceae Eukaryota n.a. fruit n.a. PMID[21462031]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota fruits n.a. n.a. PMID[23305920]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[32141747]
NPO26293 Ginkgo biloba Species Ginkgoaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26293 Ginkgo biloba Species Ginkgoaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26293 Ginkgo biloba Species Ginkgoaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26293 Ginkgo biloba Species Ginkgoaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26293 Ginkgo biloba Species Ginkgoaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9518 Gardenia jasminoides 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
NPT135 Individual Protein Chromobox protein homolog 1 Homo sapiens Potency n.a. 89125.1 nM PMID[568495]
NPT1356 Individual Protein Protein disulfide-isomerase Homo sapiens AC50 = 7620.0 nM PMID[568495]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 2059.6 nM PMID[568495]
NPT100 Individual Protein Glutaminase kidney isoform, mitochondrial Homo sapiens Potency n.a. 11220.2 nM PMID[568495]
NPT478 Individual Protein Ataxin-2 Homo sapiens Potency n.a. 39810.7 nM PMID[568495]
NPT1356 Individual Protein Protein disulfide-isomerase Homo sapiens AC50 n.a. 7620.0 nM PMID[568495]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 6513.1 nM PMID[568495]
NPT84 Individual Protein Dual specificity tyrosine-phosphorylation-regulated kinase 1A Rattus norvegicus AC50 = 4076.0 nM PMID[568495]
NPT2 Others Unspecified IC50 > 67547.0 nM PMID[568495]
NPT24148 PROTEIN-PROTEIN INTERACTION Ras and Rab interactor 1/Tyrosine-protein kinase ABL1 Homo sapiens IC50 > 73464.0 nM PMID[568495]
NPT2 Others Unspecified Potency n.a. 19952.6 nM PMID[568495]
NPT471 Organism Trypanosoma brucei brucei Trypanosoma brucei brucei IC50 < 30000.0 nM PMID[568496]

☑ 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 NPC203259 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 NPC471748
1.0 High Similarity NPC155877
1.0 High Similarity NPC134532
1.0 High Similarity NPC33054
1.0 High Similarity NPC176740
1.0 High Similarity NPC471725
0.9938 High Similarity NPC156869
0.9938 High Similarity NPC67326
0.9938 High Similarity NPC254855
0.9938 High Similarity NPC259896
0.9938 High Similarity NPC255157
0.9938 High Similarity NPC95866
0.9938 High Similarity NPC67105
0.9938 High Similarity NPC136042
0.9938 High Similarity NPC29958
0.9877 High Similarity NPC16194
0.9877 High Similarity NPC476472
0.9877 High Similarity NPC294815
0.9877 High Similarity NPC19108
0.9877 High Similarity NPC473327
0.9877 High Similarity NPC220173
0.9876 High Similarity NPC26230
0.9876 High Similarity NPC60735
0.9875 High Similarity NPC227508
0.9816 High Similarity NPC14187
0.9816 High Similarity NPC65563
0.9816 High Similarity NPC470949
0.9816 High Similarity NPC292019
0.9816 High Similarity NPC122467
0.9816 High Similarity NPC89127
0.9816 High Similarity NPC202908
0.9816 High Similarity NPC471669
0.9814 High Similarity NPC285197
0.9812 High Similarity NPC127546
0.9812 High Similarity NPC275454
0.9812 High Similarity NPC223424
0.9812 High Similarity NPC317489
0.9812 High Similarity NPC52550
0.9812 High Similarity NPC84362
0.9812 High Similarity NPC173637
0.9756 High Similarity NPC173837
0.9756 High Similarity NPC251417
0.9756 High Similarity NPC89052
0.9755 High Similarity NPC253685
0.9755 High Similarity NPC294629
0.9752 High Similarity NPC223747
0.9752 High Similarity NPC270578
0.9752 High Similarity NPC225434
0.9752 High Similarity NPC203050
0.9752 High Similarity NPC52382
0.9752 High Similarity NPC120099
0.9752 High Similarity NPC219904
0.975 High Similarity NPC274618
0.975 High Similarity NPC115674
0.975 High Similarity NPC276222
0.975 High Similarity NPC56077
0.975 High Similarity NPC328940
0.975 High Similarity NPC281131
0.975 High Similarity NPC8856
0.975 High Similarity NPC210073
0.975 High Similarity NPC118284
0.975 High Similarity NPC145038
0.975 High Similarity NPC179950
0.975 High Similarity NPC253662
0.975 High Similarity NPC277174
0.975 High Similarity NPC88789
0.975 High Similarity NPC308404
0.975 High Similarity NPC135599
0.975 High Similarity NPC73855
0.975 High Similarity NPC113968
0.9697 High Similarity NPC241423
0.9697 High Similarity NPC473571
0.9697 High Similarity NPC473682
0.9697 High Similarity NPC470443
0.9697 High Similarity NPC126784
0.9697 High Similarity NPC192539
0.9697 High Similarity NPC110941
0.9697 High Similarity NPC470444
0.9695 High Similarity NPC169733
0.9695 High Similarity NPC473862
0.9695 High Similarity NPC219043
0.9695 High Similarity NPC8573
0.9695 High Similarity NPC48984
0.9691 High Similarity NPC206123
0.9691 High Similarity NPC244776
0.9691 High Similarity NPC116864
0.9689 High Similarity NPC265530
0.9689 High Similarity NPC92565
0.9689 High Similarity NPC226304
0.9689 High Similarity NPC160156
0.9689 High Similarity NPC325555
0.9688 High Similarity NPC240431
0.9688 High Similarity NPC277205
0.9688 High Similarity NPC55786
0.9688 High Similarity NPC19388
0.9639 High Similarity NPC473073
0.9639 High Similarity NPC473071
0.9632 High Similarity NPC245452
0.9632 High Similarity NPC153755
0.9632 High Similarity NPC175107
0.9632 High Similarity NPC190003
0.963 High Similarity NPC195257
0.963 High Similarity NPC86008
0.963 High Similarity NPC209296
0.9627 High Similarity NPC197285
0.9627 High Similarity NPC21100
0.9625 High Similarity NPC19709
0.9581 High Similarity NPC470445
0.9581 High Similarity NPC470447
0.9581 High Similarity NPC470449
0.9581 High Similarity NPC241781
0.9581 High Similarity NPC473072
0.9581 High Similarity NPC156785
0.9581 High Similarity NPC162394
0.9581 High Similarity NPC470446
0.9573 High Similarity NPC42773
0.9573 High Similarity NPC101026
0.9573 High Similarity NPC4390
0.9573 High Similarity NPC21666
0.9573 High Similarity NPC45522
0.9573 High Similarity NPC24043
0.9573 High Similarity NPC169977
0.9571 High Similarity NPC78734
0.9571 High Similarity NPC20505
0.9571 High Similarity NPC51326
0.9571 High Similarity NPC235260
0.9571 High Similarity NPC218488
0.9571 High Similarity NPC155763
0.9571 High Similarity NPC231194
0.9571 High Similarity NPC150767
0.9565 High Similarity NPC311830
0.9565 High Similarity NPC22832
0.9563 High Similarity NPC473043
0.9563 High Similarity NPC189142
0.9563 High Similarity NPC77660
0.9524 High Similarity NPC249560
0.9524 High Similarity NPC470451
0.9524 High Similarity NPC25946
0.9524 High Similarity NPC470720
0.9524 High Similarity NPC223860
0.9524 High Similarity NPC460984
0.9524 High Similarity NPC470717
0.9524 High Similarity NPC275977
0.9524 High Similarity NPC470455
0.9524 High Similarity NPC470713
0.9524 High Similarity NPC148710
0.9524 High Similarity NPC21359
0.9518 High Similarity NPC217387
0.9518 High Similarity NPC258044
0.9518 High Similarity NPC35167
0.9518 High Similarity NPC196127
0.9518 High Similarity NPC37668
0.9518 High Similarity NPC217520
0.9518 High Similarity NPC267680
0.9518 High Similarity NPC113836
0.9518 High Similarity NPC139571
0.9518 High Similarity NPC253521
0.9518 High Similarity NPC293626
0.9515 High Similarity NPC223426
0.9515 High Similarity NPC81042
0.9515 High Similarity NPC198199
0.9515 High Similarity NPC34267
0.9515 High Similarity NPC214621
0.9512 High Similarity NPC180918
0.9512 High Similarity NPC476405
0.9512 High Similarity NPC3583
0.9512 High Similarity NPC259152
0.9512 High Similarity NPC117260
0.9512 High Similarity NPC256760
0.9509 High Similarity NPC43587
0.9509 High Similarity NPC138927
0.9509 High Similarity NPC105283
0.9506 High Similarity NPC255615
0.9506 High Similarity NPC67037
0.9506 High Similarity NPC236934
0.9506 High Similarity NPC5778
0.9503 High Similarity NPC88023
0.9503 High Similarity NPC222936
0.9503 High Similarity NPC270335
0.9503 High Similarity NPC168822
0.9503 High Similarity NPC243930
0.9503 High Similarity NPC284960
0.9503 High Similarity NPC309025
0.9503 High Similarity NPC29830
0.9503 High Similarity NPC191306
0.95 High Similarity NPC181465
0.95 High Similarity NPC116458
0.95 High Similarity NPC215710
0.95 High Similarity NPC170052
0.95 High Similarity NPC265885
0.95 High Similarity NPC64305
0.95 High Similarity NPC253788
0.95 High Similarity NPC139320
0.95 High Similarity NPC249281
0.95 High Similarity NPC246943
0.95 High Similarity NPC476215
0.95 High Similarity NPC297987
0.95 High Similarity NPC173582
0.95 High Similarity NPC473438
0.95 High Similarity NPC135846

  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 NPC203259 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
1.0 High Similarity NPD6797 Phase 2
0.9938 High Similarity NPD7251 Discontinued
0.9755 High Similarity NPD7808 Phase 3
0.9691 High Similarity NPD7472 Approved
0.963 High Similarity NPD7054 Approved
0.9451 High Similarity NPD7074 Phase 3
0.9398 High Similarity NPD4338 Clinical (unspecified phase)
0.9273 High Similarity NPD7804 Clinical (unspecified phase)
0.9207 High Similarity NPD6166 Phase 2
0.9207 High Similarity NPD6167 Clinical (unspecified phase)
0.9207 High Similarity NPD6168 Clinical (unspecified phase)
0.9096 High Similarity NPD3818 Discontinued
0.9074 High Similarity NPD4381 Clinical (unspecified phase)
0.8834 High Similarity NPD3817 Phase 2
0.8827 High Similarity NPD1934 Approved
0.8773 High Similarity NPD2393 Clinical (unspecified phase)
0.8688 High Similarity NPD1512 Approved
0.8667 High Similarity NPD3882 Suspended
0.8659 High Similarity NPD2801 Approved
0.8605 High Similarity NPD7993 Clinical (unspecified phase)
0.8562 High Similarity NPD1511 Approved
0.8503 High Similarity NPD7075 Discontinued
0.8476 Intermediate Similarity NPD4380 Phase 2
0.8443 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8383 Intermediate Similarity NPD5402 Approved
0.8373 Intermediate Similarity NPD6801 Discontinued
0.8343 Intermediate Similarity NPD6559 Discontinued
0.8323 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8293 Intermediate Similarity NPD5403 Approved
0.8282 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8221 Intermediate Similarity NPD6799 Approved
0.8171 Intermediate Similarity NPD5401 Approved
0.8132 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8114 Intermediate Similarity NPD3751 Discontinued
0.8092 Intermediate Similarity NPD3787 Discontinued
0.8081 Intermediate Similarity NPD5494 Approved
0.8075 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8075 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8035 Intermediate Similarity NPD6959 Discontinued
0.8025 Intermediate Similarity NPD1549 Phase 2
0.8024 Intermediate Similarity NPD1653 Approved
0.7953 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7944 Intermediate Similarity NPD8312 Approved
0.7944 Intermediate Similarity NPD8313 Approved
0.7929 Intermediate Similarity NPD6599 Discontinued
0.791 Intermediate Similarity NPD7228 Approved
0.7901 Intermediate Similarity NPD2796 Approved
0.7895 Intermediate Similarity NPD7819 Suspended
0.7895 Intermediate Similarity NPD1465 Phase 2
0.7882 Intermediate Similarity NPD7411 Suspended
0.7865 Intermediate Similarity NPD5844 Phase 1
0.7844 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7841 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.784 Intermediate Similarity NPD1510 Phase 2
0.7833 Intermediate Similarity NPD7685 Pre-registration
0.7784 Intermediate Similarity NPD6232 Discontinued
0.7753 Intermediate Similarity NPD7473 Discontinued
0.7751 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7744 Intermediate Similarity NPD7266 Discontinued
0.7737 Intermediate Similarity NPD6777 Approved
0.7737 Intermediate Similarity NPD6779 Approved
0.7737 Intermediate Similarity NPD6778 Approved
0.7737 Intermediate Similarity NPD6776 Approved
0.7737 Intermediate Similarity NPD6780 Approved
0.7737 Intermediate Similarity NPD6782 Approved
0.7737 Intermediate Similarity NPD6781 Approved
0.7727 Intermediate Similarity NPD7199 Phase 2
0.7714 Intermediate Similarity NPD919 Approved
0.7708 Intermediate Similarity NPD7435 Discontinued
0.7702 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7702 Intermediate Similarity NPD1613 Approved
0.7697 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD8151 Discontinued
0.7688 Intermediate Similarity NPD8455 Phase 2
0.7665 Intermediate Similarity NPD6190 Approved
0.7663 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7634 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7627 Intermediate Similarity NPD1247 Approved
0.7617 Intermediate Similarity NPD7698 Approved
0.7617 Intermediate Similarity NPD7697 Approved
0.7617 Intermediate Similarity NPD7696 Phase 3
0.7614 Intermediate Similarity NPD6234 Discontinued
0.7605 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7593 Intermediate Similarity NPD1240 Approved
0.759 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.759 Intermediate Similarity NPD7584 Approved
0.7551 Intermediate Similarity NPD7701 Phase 2
0.7542 Intermediate Similarity NPD3926 Phase 2
0.7541 Intermediate Similarity NPD7240 Approved
0.7529 Intermediate Similarity NPD37 Approved
0.75 Intermediate Similarity NPD3750 Approved
0.75 Intermediate Similarity NPD4966 Approved
0.75 Intermediate Similarity NPD4965 Approved
0.75 Intermediate Similarity NPD4967 Phase 2
0.75 Intermediate Similarity NPD1607 Approved
0.7487 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7487 Intermediate Similarity NPD7870 Phase 2
0.7487 Intermediate Similarity NPD7871 Phase 2
0.7485 Intermediate Similarity NPD943 Approved
0.7475 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7475 Intermediate Similarity NPD7874 Approved
0.7474 Intermediate Similarity NPD6535 Approved
0.7474 Intermediate Similarity NPD6534 Approved
0.7471 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7448 Intermediate Similarity NPD7699 Phase 2
0.7448 Intermediate Similarity NPD7700 Phase 2
0.7439 Intermediate Similarity NPD230 Phase 1
0.7439 Intermediate Similarity NPD1933 Approved
0.7437 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7437 Intermediate Similarity NPD7783 Phase 2
0.7407 Intermediate Similarity NPD3027 Phase 3
0.7401 Intermediate Similarity NPD7768 Phase 2
0.7398 Intermediate Similarity NPD8319 Approved
0.7398 Intermediate Similarity NPD8320 Phase 1
0.7396 Intermediate Similarity NPD4628 Phase 3
0.7391 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD1551 Phase 2
0.7362 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.736 Intermediate Similarity NPD3749 Approved
0.735 Intermediate Similarity NPD7801 Approved
0.7305 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7296 Intermediate Similarity NPD6823 Phase 2
0.7262 Intermediate Similarity NPD2935 Discontinued
0.7249 Intermediate Similarity NPD8150 Discontinued
0.7249 Intermediate Similarity NPD8434 Phase 2
0.7235 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7229 Intermediate Similarity NPD447 Suspended
0.7225 Intermediate Similarity NPD2533 Approved
0.7225 Intermediate Similarity NPD2534 Approved
0.7225 Intermediate Similarity NPD2532 Approved
0.7213 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7202 Intermediate Similarity NPD3748 Approved
0.72 Intermediate Similarity NPD7585 Approved
0.7159 Intermediate Similarity NPD7458 Discontinued
0.7152 Intermediate Similarity NPD6798 Discontinued
0.715 Intermediate Similarity NPD7583 Approved
0.7143 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD920 Approved
0.7135 Intermediate Similarity NPD2800 Approved
0.7129 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.7128 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD1091 Approved
0.7115 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7113 Intermediate Similarity NPD4360 Phase 2
0.7113 Intermediate Similarity NPD4363 Phase 3
0.7112 Intermediate Similarity NPD5953 Discontinued
0.7108 Intermediate Similarity NPD6233 Phase 2
0.7107 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD7033 Discontinued
0.7085 Intermediate Similarity NPD7680 Approved
0.7069 Intermediate Similarity NPD7390 Discontinued
0.7062 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD6213 Phase 3
0.7062 Intermediate Similarity NPD6212 Phase 3
0.7062 Intermediate Similarity NPD3226 Approved
0.7059 Intermediate Similarity NPD6100 Approved
0.7059 Intermediate Similarity NPD6099 Approved
0.7039 Intermediate Similarity NPD6844 Discontinued
0.7035 Intermediate Similarity NPD6674 Discontinued
0.7035 Intermediate Similarity NPD1652 Phase 2
0.7035 Intermediate Similarity NPD1243 Approved
0.703 Intermediate Similarity NPD6832 Phase 2
0.703 Intermediate Similarity NPD4908 Phase 1
0.7029 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7024 Intermediate Similarity NPD6355 Discontinued
0.7012 Intermediate Similarity NPD2798 Approved
0.7011 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7005 Intermediate Similarity NPD7286 Phase 2
0.6982 Remote Similarity NPD6651 Approved
0.697 Remote Similarity NPD9494 Approved
0.6951 Remote Similarity NPD1203 Approved
0.6946 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6946 Remote Similarity NPD2313 Discontinued
0.6933 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6931 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6923 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6923 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6923 Remote Similarity NPD5124 Phase 1
0.6919 Remote Similarity NPD2346 Discontinued
0.6919 Remote Similarity NPD2344 Approved
0.6914 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6901 Remote Similarity NPD2799 Discontinued
0.6897 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6875 Remote Similarity NPD1548 Phase 1
0.6872 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6868 Remote Similarity NPD5353 Approved
0.6864 Remote Similarity NPD4060 Phase 1
0.6862 Remote Similarity NPD2163 Approved
0.6845 Remote Similarity NPD3268 Approved
0.6845 Remote Similarity NPD2403 Approved
0.6836 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6828 Remote Similarity NPD5711 Approved
0.6828 Remote Similarity NPD5710 Approved
0.6827 Remote Similarity NPD7930 Approved
0.681 Remote Similarity NPD1610 Phase 2
0.681 Remote Similarity NPD422 Phase 1
0.6805 Remote Similarity NPD4062 Phase 3
0.6802 Remote Similarity NPD1509 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