Structure

Physi-Chem Properties

Molecular Weight:  970.29
Volume:  933.252
LogP:  6.75
LogD:  2.417
LogS:  -5.393
# Rotatable Bonds:  13
TPSA:  303.96
# H-Bond Aceptor:  20
# H-Bond Donor:  8
# Rings:  8
# Heavy Atoms:  20

MedChem Properties

QED Drug-Likeness Score:  0.05
Synthetic Accessibility Score:  5.6
Fsp3:  0.36
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.594
MDCK Permeability:  5.290874105412513e-05
Pgp-inhibitor:  0.622
Pgp-substrate:  0.846
Human Intestinal Absorption (HIA):  0.97
20% Bioavailability (F20%):  0.0
30% Bioavailability (F30%):  0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.003
Plasma Protein Binding (PPB):  83.37445831298828%
Volume Distribution (VD):  0.44
Pgp-substrate:  19.439830780029297%

ADMET: Metabolism

CYP1A2-inhibitor:  0.611
CYP1A2-substrate:  0.084
CYP2C19-inhibitor:  0.02
CYP2C19-substrate:  0.043
CYP2C9-inhibitor:  0.293
CYP2C9-substrate:  0.133
CYP2D6-inhibitor:  0.421
CYP2D6-substrate:  0.099
CYP3A4-inhibitor:  0.025
CYP3A4-substrate:  0.024

ADMET: Excretion

Clearance (CL):  0.596
Half-life (T1/2):  0.385

ADMET: Toxicity

hERG Blockers:  0.016
Human Hepatotoxicity (H-HT):  0.996
Drug-inuced Liver Injury (DILI):  0.994
AMES Toxicity:  0.339
Rat Oral Acute Toxicity:  0.012
Maximum Recommended Daily Dose:  0.901
Skin Sensitization:  0.754
Carcinogencity:  0.068
Eye Corrosion:  0.003
Eye Irritation:  0.084
Respiratory Toxicity:  0.212

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

  Natural Product: NPC475220

Natural Product ID:  NPC475220
Common Name*:   [(2S,3R,4R,5R,6S)-5-Acetyloxy-6-[[(9S)-9-[(9R)-2-[(2S,3R,4R,5S,6S)-3,4-Diacetyloxy-5-Hydroxy-6-Methyloxan-2-Yl]Oxy-4,5-Dihydroxy-7-Methyl-10-Oxo-9H-Anthracen-9-Yl]-4,5-Dihydroxy-7-Methyl-10-Oxo-9H-Anthracen-2-Yl]Oxy]-4-Hydroxy-2-Methyloxan-3-Yl] Acetate
IUPAC Name:   [(2S,3R,4R,5R,6S)-5-acetyloxy-6-[[(9S)-9-[(9R)-2-[(2S,3R,4R,5S,6S)-3,4-diacetyloxy-5-hydroxy-6-methyloxan-2-yl]oxy-4,5-dihydroxy-7-methyl-10-oxo-9H-anthracen-9-yl]-4,5-dihydroxy-7-methyl-10-oxo-9H-anthracen-2-yl]oxy]-4-hydroxy-2-methyloxan-3-yl] acetate
Synonyms:  
Standard InCHIKey:  JEXQJQKTBMMMPJ-RELBTLKZSA-N
Standard InCHI:  InChI=1S/C50H50O20/c1-17-9-27-35(29-13-25(15-33(57)39(29)42(60)37(27)31(55)11-17)69-49-47(67-23(7)53)44(62)45(20(4)64-49)65-21(5)51)36-28-10-18(2)12-32(56)38(28)43(61)40-30(36)14-26(16-34(40)58)70-50-48(68-24(8)54)46(66-22(6)52)41(59)19(3)63-50/h9-16,19-20,35-36,41,44-50,55-59,62H,1-8H3/t19-,20-,35-,36+,41-,44+,45-,46+,47+,48+,49-,50-/m0/s1
SMILES:  CC(=O)O[C@H]1[C@H](Oc2cc(O)c3c(c2)[C@H](c2c(C3=O)c(O)cc(c2)C)[C@@H]2c3cc(C)cc(c3C(=O)c3c2cc(O[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2OC(=O)C)OC(=O)C)O)cc3O)O)O[C@H]([C@@H]([C@H]1O)OC(=O)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL501310
PubChem CID:   44567188
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates
          • [CHEMONTID:0002105] Glycosyl compounds
            • [CHEMONTID:0004165] Phenolic 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
NPO32935 rhamnus nepalensis Species Rhamnaceae Eukaryota Leaves Pa Co, Mai Chau, Hoa Binh Province, 150 km west of Hanoi, Vietnam 1995-Nov PMID[11575949]

☑ 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
NPT91 Cell Line KB Homo sapiens IC50 = 800.0 nM PMID[510613]

☑ 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 NPC475220 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 NPC473686
1.0 High Similarity NPC475352
1.0 High Similarity NPC229817
1.0 High Similarity NPC221140
0.9882 High Similarity NPC293227
0.9882 High Similarity NPC473717
0.9882 High Similarity NPC473631
0.9882 High Similarity NPC475662
0.9425 High Similarity NPC87583
0.9408 High Similarity NPC298778
0.9364 High Similarity NPC477860
0.9364 High Similarity NPC475161
0.9357 High Similarity NPC474345
0.9357 High Similarity NPC63105
0.9322 High Similarity NPC264302
0.9302 High Similarity NPC170018
0.9302 High Similarity NPC76112
0.9302 High Similarity NPC66820
0.9302 High Similarity NPC46958
0.9302 High Similarity NPC92403
0.9298 High Similarity NPC213052
0.9253 High Similarity NPC470448
0.9253 High Similarity NPC470453
0.9253 High Similarity NPC470452
0.9253 High Similarity NPC164047
0.9244 High Similarity NPC68381
0.9195 High Similarity NPC277710
0.9195 High Similarity NPC153578
0.9195 High Similarity NPC245059
0.9195 High Similarity NPC84494
0.9195 High Similarity NPC299149
0.9195 High Similarity NPC114257
0.9191 High Similarity NPC475246
0.9186 High Similarity NPC168789
0.9176 High Similarity NPC249977
0.9167 High Similarity NPC470193
0.9167 High Similarity NPC470198
0.9167 High Similarity NPC282474
0.9167 High Similarity NPC316274
0.9167 High Similarity NPC470200
0.9167 High Similarity NPC470194
0.9167 High Similarity NPC470195
0.9167 High Similarity NPC470197
0.9167 High Similarity NPC470196
0.9153 High Similarity NPC65489
0.9153 High Similarity NPC105591
0.9148 High Similarity NPC75574
0.9148 High Similarity NPC318119
0.9133 High Similarity NPC3718
0.9128 High Similarity NPC111536
0.9128 High Similarity NPC30432
0.9128 High Similarity NPC76128
0.9128 High Similarity NPC5029
0.9128 High Similarity NPC271385
0.9123 High Similarity NPC259905
0.9118 High Similarity NPC178851
0.9096 High Similarity NPC241847
0.9091 High Similarity NPC321916
0.9091 High Similarity NPC132111
0.907 High Similarity NPC76047
0.9059 High Similarity NPC7752
0.9056 High Similarity NPC314459
0.9056 High Similarity NPC470199
0.905 High Similarity NPC472721
0.905 High Similarity NPC31208
0.905 High Similarity NPC160543
0.905 High Similarity NPC469652
0.905 High Similarity NPC93065
0.905 High Similarity NPC472720
0.905 High Similarity NPC472724
0.904 High Similarity NPC231254
0.9023 High Similarity NPC199533
0.9023 High Similarity NPC470454
0.9017 High Similarity NPC288152
0.9017 High Similarity NPC9002
0.9017 High Similarity NPC257011
0.9017 High Similarity NPC137871
0.9016 High Similarity NPC174140
0.9 High Similarity NPC48474
0.8994 High Similarity NPC290289
0.8994 High Similarity NPC223534
0.8994 High Similarity NPC240200
0.8994 High Similarity NPC158214
0.8971 High Similarity NPC289876
0.8971 High Similarity NPC475233
0.8966 High Similarity NPC25724
0.8966 High Similarity NPC203751
0.8966 High Similarity NPC85368
0.8966 High Similarity NPC472054
0.896 High Similarity NPC199079
0.896 High Similarity NPC210808
0.8947 High Similarity NPC99216
0.8944 High Similarity NPC187632
0.8941 High Similarity NPC15374
0.8939 High Similarity NPC64755
0.8939 High Similarity NPC469649
0.8939 High Similarity NPC260521
0.8927 High Similarity NPC197357
0.8927 High Similarity NPC85316
0.8907 High Similarity NPC3474
0.8902 High Similarity NPC222455
0.8902 High Similarity NPC473202
0.8901 High Similarity NPC477082
0.8895 High Similarity NPC260504
0.8895 High Similarity NPC471091
0.8895 High Similarity NPC473278
0.8895 High Similarity NPC89809
0.8895 High Similarity NPC40078
0.8895 High Similarity NPC97924
0.8889 High Similarity NPC257566
0.8889 High Similarity NPC124155
0.8889 High Similarity NPC473618
0.8883 High Similarity NPC111490
0.8883 High Similarity NPC469650
0.8883 High Similarity NPC112380
0.8883 High Similarity NPC261623
0.8876 High Similarity NPC313452
0.887 High Similarity NPC212290
0.887 High Similarity NPC471030
0.887 High Similarity NPC179862
0.887 High Similarity NPC58538
0.8864 High Similarity NPC102053
0.8864 High Similarity NPC255799
0.8864 High Similarity NPC231787
0.8857 High Similarity NPC98776
0.8851 High Similarity NPC188815
0.8851 High Similarity NPC469344
0.8844 High Similarity NPC472622
0.884 High Similarity NPC201814
0.884 High Similarity NPC314672
0.8837 High Similarity NPC469664
0.8837 High Similarity NPC475979
0.8833 High Similarity NPC72554
0.8833 High Similarity NPC179947
0.8833 High Similarity NPC97817
0.8833 High Similarity NPC475179
0.8833 High Similarity NPC30011
0.883 High Similarity NPC472876
0.883 High Similarity NPC44947
0.883 High Similarity NPC187934
0.883 High Similarity NPC97637
0.883 High Similarity NPC216752
0.883 High Similarity NPC190450
0.883 High Similarity NPC298171
0.8827 High Similarity NPC292706
0.8827 High Similarity NPC224557
0.8824 High Similarity NPC328093
0.882 High Similarity NPC315221
0.882 High Similarity NPC469371
0.8817 High Similarity NPC257309
0.8807 High Similarity NPC470667
0.8807 High Similarity NPC146803
0.88 High Similarity NPC100251
0.88 High Similarity NPC67134
0.88 High Similarity NPC47140
0.88 High Similarity NPC101399
0.88 High Similarity NPC217822
0.88 High Similarity NPC221288
0.88 High Similarity NPC65333
0.88 High Similarity NPC474522
0.88 High Similarity NPC477836
0.88 High Similarity NPC11847
0.8798 High Similarity NPC476358
0.8793 High Similarity NPC470206
0.8793 High Similarity NPC470207
0.8793 High Similarity NPC5319
0.8786 High Similarity NPC262222
0.8786 High Similarity NPC477835
0.8786 High Similarity NPC68592
0.8786 High Similarity NPC70441
0.8786 High Similarity NPC298666
0.8786 High Similarity NPC472621
0.8785 High Similarity NPC7839
0.8785 High Similarity NPC269046
0.8785 High Similarity NPC477083
0.8785 High Similarity NPC142291
0.8785 High Similarity NPC477081
0.8779 High Similarity NPC473644
0.8778 High Similarity NPC104910
0.8778 High Similarity NPC474093
0.8772 High Similarity NPC101636
0.8772 High Similarity NPC47923
0.8772 High Similarity NPC18380
0.8771 High Similarity NPC241781
0.8771 High Similarity NPC476203
0.8771 High Similarity NPC129533
0.8771 High Similarity NPC123259
0.8771 High Similarity NPC156785
0.8771 High Similarity NPC162394
0.8765 High Similarity NPC308265
0.8765 High Similarity NPC53139
0.8765 High Similarity NPC51247
0.8764 High Similarity NPC472725
0.8764 High Similarity NPC80956
0.8764 High Similarity NPC472726
0.8763 High Similarity NPC470450
0.8757 High Similarity NPC472723
0.8757 High Similarity NPC324220
0.8757 High Similarity NPC312630
0.875 High Similarity NPC470335

  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 NPC475220 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
0.9302 High Similarity NPD8313 Approved
0.9302 High Similarity NPD8312 Approved
0.8882 High Similarity NPD6959 Discontinued
0.8793 High Similarity NPD7804 Clinical (unspecified phase)
0.873 High Similarity NPD8151 Discontinued
0.8729 High Similarity NPD7879 Clinical (unspecified phase)
0.8636 High Similarity NPD7074 Phase 3
0.8636 High Similarity NPD7472 Approved
0.8596 High Similarity NPD7808 Phase 3
0.858 High Similarity NPD7054 Approved
0.8539 High Similarity NPD7251 Discontinued
0.8539 High Similarity NPD6559 Discontinued
0.8488 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8483 Intermediate Similarity NPD6797 Phase 2
0.8421 Intermediate Similarity NPD8455 Phase 2
0.8421 Intermediate Similarity NPD7819 Suspended
0.8415 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.838 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8372 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8362 Intermediate Similarity NPD7473 Discontinued
0.8305 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8305 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8305 Intermediate Similarity NPD6166 Phase 2
0.8305 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8276 Intermediate Similarity NPD7075 Discontinued
0.8268 Intermediate Similarity NPD5844 Phase 1
0.8256 Intermediate Similarity NPD7783 Phase 2
0.8256 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.8212 Intermediate Similarity NPD7228 Approved
0.8192 Intermediate Similarity NPD6232 Discontinued
0.8187 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8177 Intermediate Similarity NPD7435 Discontinued
0.814 Intermediate Similarity NPD4380 Phase 2
0.8135 Intermediate Similarity NPD7870 Phase 2
0.8135 Intermediate Similarity NPD7871 Phase 2
0.8114 Intermediate Similarity NPD7768 Phase 2
0.8114 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8111 Intermediate Similarity NPD3818 Discontinued
0.8103 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8103 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8092 Intermediate Similarity NPD7411 Suspended
0.8083 Intermediate Similarity NPD7696 Phase 3
0.8083 Intermediate Similarity NPD7697 Approved
0.8083 Intermediate Similarity NPD7698 Approved
0.8041 Intermediate Similarity NPD8320 Phase 1
0.8041 Intermediate Similarity NPD8319 Approved
0.8021 Intermediate Similarity NPD6782 Approved
0.8021 Intermediate Similarity NPD6776 Approved
0.8021 Intermediate Similarity NPD6780 Approved
0.8021 Intermediate Similarity NPD6777 Approved
0.8021 Intermediate Similarity NPD6781 Approved
0.8021 Intermediate Similarity NPD6778 Approved
0.8021 Intermediate Similarity NPD6779 Approved
0.802 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.802 Intermediate Similarity NPD7874 Approved
0.801 Intermediate Similarity NPD7701 Phase 2
0.8 Intermediate Similarity NPD7390 Discontinued
0.7977 Intermediate Similarity NPD7458 Discontinued
0.7943 Intermediate Similarity NPD1934 Approved
0.7943 Intermediate Similarity NPD6801 Discontinued
0.7935 Intermediate Similarity NPD7240 Approved
0.7917 Intermediate Similarity NPD7699 Phase 2
0.7917 Intermediate Similarity NPD7700 Phase 2
0.7889 Intermediate Similarity NPD7801 Approved
0.7849 Intermediate Similarity NPD2533 Approved
0.7849 Intermediate Similarity NPD2532 Approved
0.7849 Intermediate Similarity NPD2534 Approved
0.7846 Intermediate Similarity NPD6823 Phase 2
0.7841 Intermediate Similarity NPD37 Approved
0.7833 Intermediate Similarity NPD7199 Phase 2
0.7821 Intermediate Similarity NPD6234 Discontinued
0.7819 Intermediate Similarity NPD8150 Discontinued
0.7809 Intermediate Similarity NPD4965 Approved
0.7809 Intermediate Similarity NPD4966 Approved
0.7809 Intermediate Similarity NPD4967 Phase 2
0.7805 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD5494 Approved
0.7765 Intermediate Similarity NPD3749 Approved
0.776 Intermediate Similarity NPD6534 Approved
0.776 Intermediate Similarity NPD6535 Approved
0.7753 Intermediate Similarity NPD3817 Phase 2
0.7746 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7746 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD6599 Discontinued
0.7706 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7697 Intermediate Similarity NPD1465 Phase 2
0.7692 Intermediate Similarity NPD3787 Discontinued
0.7672 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.767 Intermediate Similarity NPD3226 Approved
0.767 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7654 Intermediate Similarity NPD5402 Approved
0.765 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD3751 Discontinued
0.7602 Intermediate Similarity NPD1549 Phase 2
0.7598 Intermediate Similarity NPD2801 Approved
0.7586 Intermediate Similarity NPD6799 Approved
0.7557 Intermediate Similarity NPD5403 Approved
0.7543 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7526 Intermediate Similarity NPD6213 Phase 3
0.7526 Intermediate Similarity NPD6212 Phase 3
0.7526 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD3750 Approved
0.7514 Intermediate Similarity NPD4628 Phase 3
0.75 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7486 Intermediate Similarity NPD1511 Approved
0.746 Intermediate Similarity NPD7685 Pre-registration
0.7458 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7457 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7457 Intermediate Similarity NPD6674 Discontinued
0.745 Intermediate Similarity NPD7680 Approved
0.7448 Intermediate Similarity NPD8434 Phase 2
0.7443 Intermediate Similarity NPD5401 Approved
0.7442 Intermediate Similarity NPD2346 Discontinued
0.7426 Intermediate Similarity NPD7584 Approved
0.7424 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7418 Intermediate Similarity NPD3882 Suspended
0.7414 Intermediate Similarity NPD7003 Approved
0.7414 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7405 Intermediate Similarity NPD5711 Approved
0.7405 Intermediate Similarity NPD5710 Approved
0.7401 Intermediate Similarity NPD1512 Approved
0.7384 Intermediate Similarity NPD5406 Approved
0.7384 Intermediate Similarity NPD6099 Approved
0.7384 Intermediate Similarity NPD5405 Approved
0.7384 Intermediate Similarity NPD5404 Approved
0.7384 Intermediate Similarity NPD6100 Approved
0.7384 Intermediate Similarity NPD2796 Approved
0.7384 Intermediate Similarity NPD5408 Approved
0.7345 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7343 Intermediate Similarity NPD7930 Approved
0.7326 Intermediate Similarity NPD1510 Phase 2
0.7326 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7312 Intermediate Similarity NPD7229 Phase 3
0.731 Intermediate Similarity NPD1607 Approved
0.729 Intermediate Similarity NPD8058 Clinical (unspecified phase)
0.729 Intermediate Similarity NPD8059 Phase 3
0.7283 Intermediate Similarity NPD2935 Discontinued
0.7283 Intermediate Similarity NPD1551 Phase 2
0.7249 Intermediate Similarity NPD7177 Discontinued
0.7225 Intermediate Similarity NPD3748 Approved
0.7222 Intermediate Similarity NPD1653 Approved
0.722 Intermediate Similarity NPD7585 Approved
0.7216 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7207 Intermediate Similarity NPD6273 Approved
0.7206 Intermediate Similarity NPD7211 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD1240 Approved
0.7191 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7171 Intermediate Similarity NPD7583 Approved
0.7166 Intermediate Similarity NPD8127 Discontinued
0.7164 Intermediate Similarity NPD8285 Discontinued
0.7159 Intermediate Similarity NPD2800 Approved
0.7143 Intermediate Similarity NPD7266 Discontinued
0.7135 Intermediate Similarity NPD5953 Discontinued
0.7126 Intermediate Similarity NPD2799 Discontinued
0.712 Intermediate Similarity NPD7286 Phase 2
0.711 Intermediate Similarity NPD6651 Approved
0.7072 Intermediate Similarity NPD920 Approved
0.7069 Intermediate Similarity NPD7097 Phase 1
0.7062 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD1243 Approved
0.7059 Intermediate Similarity NPD4908 Phase 1
0.7059 Intermediate Similarity NPD919 Approved
0.705 Intermediate Similarity NPD4360 Phase 2
0.705 Intermediate Similarity NPD4363 Phase 3
0.7044 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD7999 Approved
0.7022 Intermediate Similarity NPD8166 Discontinued
0.7011 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.6994 Remote Similarity NPD4060 Phase 1
0.699 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6979 Remote Similarity NPD7799 Discontinued
0.6977 Remote Similarity NPD8366 Approved
0.6961 Remote Similarity NPD642 Clinical (unspecified phase)
0.6955 Remote Similarity NPD8067 Phase 3
0.6954 Remote Similarity NPD5124 Phase 1
0.6954 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6944 Remote Similarity NPD643 Clinical (unspecified phase)
0.6935 Remote Similarity NPD4287 Approved
0.6919 Remote Similarity NPD4625 Phase 3
0.6912 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6911 Remote Similarity NPD3926 Phase 2
0.6897 Remote Similarity NPD1613 Approved
0.6897 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6893 Remote Similarity NPD2438 Suspended
0.6891 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6879 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6879 Remote Similarity NPD6798 Discontinued
0.6879 Remote Similarity NPD2313 Discontinued
0.6872 Remote Similarity NPD5698 Clinical (unspecified phase)
0.686 Remote Similarity NPD6832 Phase 2
0.6857 Remote Similarity NPD6355 Discontinued
0.6857 Remote Similarity NPD230 Phase 1
0.6857 Remote Similarity NPD1933 Approved
0.6849 Remote Similarity NPD8491 Approved
0.6836 Remote Similarity NPD7033 Discontinued
0.6818 Remote Similarity NPD8469 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