Structure

Physi-Chem Properties

Molecular Weight:  682.25
Volume:  641.434
LogP:  0.831
LogD:  0.071
LogS:  -2.794
# Rotatable Bonds:  9
TPSA:  257.68
# H-Bond Aceptor:  16
# H-Bond Donor:  10
# Rings:  5
# Heavy Atoms:  16

MedChem Properties

QED Drug-Likeness Score:  0.13
Synthetic Accessibility Score:  5.142
Fsp3:  0.562
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:  -6.556
MDCK Permeability:  4.052973599755205e-05
Pgp-inhibitor:  0.006
Pgp-substrate:  0.999
Human Intestinal Absorption (HIA):  0.991
20% Bioavailability (F20%):  0.079
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.113
Plasma Protein Binding (PPB):  93.4753189086914%
Volume Distribution (VD):  0.19
Pgp-substrate:  7.235490322113037%

ADMET: Metabolism

CYP1A2-inhibitor:  0.058
CYP1A2-substrate:  0.027
CYP2C19-inhibitor:  0.038
CYP2C19-substrate:  0.063
CYP2C9-inhibitor:  0.003
CYP2C9-substrate:  0.063
CYP2D6-inhibitor:  0.022
CYP2D6-substrate:  0.151
CYP3A4-inhibitor:  0.047
CYP3A4-substrate:  0.005

ADMET: Excretion

Clearance (CL):  0.667
Half-life (T1/2):  0.676

ADMET: Toxicity

hERG Blockers:  0.552
Human Hepatotoxicity (H-HT):  0.091
Drug-inuced Liver Injury (DILI):  0.078
AMES Toxicity:  0.179
Rat Oral Acute Toxicity:  0.168
Maximum Recommended Daily Dose:  0.004
Skin Sensitization:  0.96
Carcinogencity:  0.072
Eye Corrosion:  0.003
Eye Irritation:  0.077
Respiratory Toxicity:  0.39

Download Data

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

  Natural Product: NPC257095

Natural Product ID:  NPC257095
Common Name*:   Lysidiside Q
IUPAC Name:   (2R,3R,4R,5R,6S)-2-[[(2R,3S,4S,5R,6S)-3,4-dihydroxy-6-[3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy]-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]methoxy]-6-methyloxane-3,4,5-triol
Synonyms:   lysidiside Q
Standard InCHIKey:  OBHAZHJCJUWHRN-IVUAMTHTSA-N
Standard InCHI:  InChI=1S/C32H42O16/c1-13-21(35)24(38)27(41)30(44-13)43-12-20-23(37)26(40)29(48-31-28(42)25(39)22(36)14(2)45-31)32(47-20)46-19-10-16(9-18(34)11-19)4-3-15-5-7-17(33)8-6-15/h3-11,13-14,20-42H,12H2,1-2H3/b4-3+/t13-,14-,20+,21-,22-,23+,24+,25+,26-,27+,28+,29+,30+,31-,32+/m0/s1
SMILES:  Oc1cc(cc(c1)/C=C/c1ccc(cc1)O)O[C@@H]1O[C@H](CO[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)[C@H]([C@@H]([C@H]1O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL575147
PubChem CID:   25155859
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates
          • [CHEMONTID:0000198] Oligosaccharides

*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
NPO33047 lysidice brevicalyx wei Species n.a. Eukaryota Barks n.a. n.a. PMID[18847246]

☑ 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
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 5.0 % PMID[473472]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 39.0 % PMID[473472]

☑ 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 NPC257095 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 NPC89686
1.0 High Similarity NPC273932
0.9699 High Similarity NPC197723
0.9699 High Similarity NPC3293
0.9699 High Similarity NPC138350
0.9699 High Similarity NPC40664
0.9699 High Similarity NPC165482
0.9624 High Similarity NPC238243
0.9549 High Similarity NPC130496
0.9549 High Similarity NPC188555
0.9474 High Similarity NPC115022
0.9474 High Similarity NPC294166
0.9398 High Similarity NPC26080
0.9398 High Similarity NPC303422
0.9398 High Similarity NPC85799
0.9398 High Similarity NPC165686
0.9323 High Similarity NPC121376
0.9301 High Similarity NPC473621
0.9225 High Similarity NPC280945
0.9214 High Similarity NPC225445
0.9197 High Similarity NPC124149
0.9173 High Similarity NPC218003
0.9155 High Similarity NPC473480
0.9155 High Similarity NPC15538
0.9143 High Similarity NPC116922
0.913 High Similarity NPC98777
0.913 High Similarity NPC212770
0.9124 High Similarity NPC242028
0.9124 High Similarity NPC164857
0.9124 High Similarity NPC203230
0.9071 High Similarity NPC469559
0.9058 High Similarity NPC87777
0.9058 High Similarity NPC262328
0.9058 High Similarity NPC59324
0.9058 High Similarity NPC65530
0.9051 High Similarity NPC470236
0.9 High Similarity NPC210192
0.8951 High Similarity NPC125755
0.8944 High Similarity NPC138227
0.8944 High Similarity NPC76176
0.8944 High Similarity NPC469313
0.8944 High Similarity NPC177597
0.8944 High Similarity NPC168579
0.8936 High Similarity NPC189115
0.8936 High Similarity NPC475084
0.8905 High Similarity NPC49074
0.8897 High Similarity NPC475067
0.8881 High Similarity NPC277867
0.8881 High Similarity NPC161700
0.8881 High Similarity NPC475096
0.8873 High Similarity NPC37793
0.8873 High Similarity NPC473044
0.8872 High Similarity NPC12308
0.8865 High Similarity NPC469661
0.8849 High Similarity NPC469383
0.8832 High Similarity NPC162093
0.8824 High Similarity NPC262606
0.8811 High Similarity NPC473045
0.8811 High Similarity NPC25292
0.8803 High Similarity NPC128337
0.8803 High Similarity NPC230718
0.8803 High Similarity NPC5253
0.8803 High Similarity NPC49542
0.8803 High Similarity NPC139976
0.8803 High Similarity NPC84207
0.8803 High Similarity NPC472353
0.8794 High Similarity NPC106944
0.8786 High Similarity NPC134260
0.8786 High Similarity NPC470413
0.8786 High Similarity NPC138738
0.8776 High Similarity NPC259707
0.8768 High Similarity NPC132895
0.8767 High Similarity NPC55715
0.8767 High Similarity NPC35877
0.8767 High Similarity NPC95392
0.8759 High Similarity NPC227902
0.8759 High Similarity NPC39657
0.8759 High Similarity NPC469698
0.8759 High Similarity NPC473412
0.8742 High Similarity NPC185231
0.8741 High Similarity NPC278961
0.8741 High Similarity NPC252169
0.8741 High Similarity NPC113680
0.8732 High Similarity NPC108674
0.8716 High Similarity NPC233467
0.8716 High Similarity NPC59692
0.8705 High Similarity NPC251981
0.8705 High Similarity NPC48863
0.8705 High Similarity NPC187194
0.8705 High Similarity NPC13745
0.8696 High Similarity NPC299144
0.869 High Similarity NPC190714
0.869 High Similarity NPC99515
0.869 High Similarity NPC476865
0.8681 High Similarity NPC471063
0.8681 High Similarity NPC476867
0.8671 High Similarity NPC472714
0.8671 High Similarity NPC5262
0.8652 High Similarity NPC195196
0.8643 High Similarity NPC185778
0.8639 High Similarity NPC470933
0.8639 High Similarity NPC51328
0.8639 High Similarity NPC94871
0.8639 High Similarity NPC473427
0.8639 High Similarity NPC306890
0.8639 High Similarity NPC471062
0.8639 High Similarity NPC286235
0.8639 High Similarity NPC106138
0.8639 High Similarity NPC55158
0.8639 High Similarity NPC259347
0.8639 High Similarity NPC283839
0.8639 High Similarity NPC476386
0.8639 High Similarity NPC476398
0.8639 High Similarity NPC90896
0.8633 High Similarity NPC215833
0.8633 High Similarity NPC69513
0.8621 High Similarity NPC476864
0.8621 High Similarity NPC476869
0.8621 High Similarity NPC476866
0.8621 High Similarity NPC476868
0.8613 High Similarity NPC248355
0.8591 High Similarity NPC472612
0.8591 High Similarity NPC289967
0.8591 High Similarity NPC472611
0.8582 High Similarity NPC52277
0.8582 High Similarity NPC199459
0.8582 High Similarity NPC177035
0.8582 High Similarity NPC172818
0.8582 High Similarity NPC25695
0.8581 High Similarity NPC475224
0.8581 High Similarity NPC257970
0.8581 High Similarity NPC476871
0.8581 High Similarity NPC470927
0.8571 High Similarity NPC130449
0.8571 High Similarity NPC478237
0.8571 High Similarity NPC35731
0.8571 High Similarity NPC170694
0.8571 High Similarity NPC107478
0.8571 High Similarity NPC175976
0.8571 High Similarity NPC476411
0.8571 High Similarity NPC248132
0.8562 High Similarity NPC100936
0.8562 High Similarity NPC205796
0.8562 High Similarity NPC74320
0.8562 High Similarity NPC248053
0.8562 High Similarity NPC155564
0.8562 High Similarity NPC1253
0.8562 High Similarity NPC276753
0.8562 High Similarity NPC107120
0.8562 High Similarity NPC102280
0.8561 High Similarity NPC470270
0.8553 High Similarity NPC4809
0.8553 High Similarity NPC73517
0.8553 High Similarity NPC147743
0.8552 High Similarity NPC472712
0.8552 High Similarity NPC472713
0.8552 High Similarity NPC118385
0.8552 High Similarity NPC187774
0.8552 High Similarity NPC473046
0.854 High Similarity NPC302378
0.8533 High Similarity NPC246893
0.8523 High Similarity NPC471403
0.8503 High Similarity NPC232992
0.8497 Intermediate Similarity NPC471404
0.8497 Intermediate Similarity NPC159526
0.8497 Intermediate Similarity NPC205613
0.8497 Intermediate Similarity NPC106601
0.8497 Intermediate Similarity NPC212614
0.8497 Intermediate Similarity NPC151474
0.8497 Intermediate Similarity NPC86630
0.8493 Intermediate Similarity NPC226722
0.8489 Intermediate Similarity NPC469613
0.8489 Intermediate Similarity NPC30043
0.8489 Intermediate Similarity NPC469625
0.8489 Intermediate Similarity NPC9912
0.8483 Intermediate Similarity NPC470950
0.8483 Intermediate Similarity NPC46092
0.8483 Intermediate Similarity NPC185307
0.8478 Intermediate Similarity NPC307110
0.8478 Intermediate Similarity NPC166040
0.8467 Intermediate Similarity NPC176186
0.8467 Intermediate Similarity NPC53587
0.8467 Intermediate Similarity NPC44192
0.8467 Intermediate Similarity NPC476352
0.8467 Intermediate Similarity NPC469944
0.8467 Intermediate Similarity NPC46283
0.8467 Intermediate Similarity NPC169404
0.8467 Intermediate Similarity NPC226108
0.8467 Intermediate Similarity NPC272552
0.8467 Intermediate Similarity NPC21902
0.8467 Intermediate Similarity NPC322899
0.8467 Intermediate Similarity NPC215060
0.8467 Intermediate Similarity NPC134911
0.8456 Intermediate Similarity NPC472709
0.8456 Intermediate Similarity NPC472710
0.8451 Intermediate Similarity NPC104167
0.8446 Intermediate Similarity NPC114659
0.8446 Intermediate Similarity NPC270751
0.8446 Intermediate Similarity NPC139699
0.844 Intermediate Similarity NPC87696

  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 NPC257095 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
0.8169 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8169 Intermediate Similarity NPD1613 Approved
0.8162 Intermediate Similarity NPD1091 Approved
0.8137 Intermediate Similarity NPD7074 Phase 3
0.8137 Intermediate Similarity NPD7472 Approved
0.8098 Intermediate Similarity NPD7808 Phase 3
0.8085 Intermediate Similarity NPD3027 Phase 3
0.8082 Intermediate Similarity NPD7266 Discontinued
0.8075 Intermediate Similarity NPD7054 Approved
0.8037 Intermediate Similarity NPD7251 Discontinued
0.8026 Intermediate Similarity NPD1653 Approved
0.7975 Intermediate Similarity NPD6797 Phase 2
0.7963 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7887 Intermediate Similarity NPD4908 Phase 1
0.7887 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7885 Intermediate Similarity NPD8455 Phase 2
0.7848 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7817 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7791 Intermediate Similarity NPD7228 Approved
0.7778 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7643 Intermediate Similarity NPD1610 Phase 2
0.7616 Intermediate Similarity NPD6674 Discontinued
0.7609 Intermediate Similarity NPD1548 Phase 1
0.75 Intermediate Similarity NPD7240 Approved
0.75 Intermediate Similarity NPD6559 Discontinued
0.747 Intermediate Similarity NPD3818 Discontinued
0.7468 Intermediate Similarity NPD5058 Phase 3
0.7456 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7455 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7455 Intermediate Similarity NPD6166 Phase 2
0.7455 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7448 Intermediate Similarity NPD2861 Phase 2
0.7426 Intermediate Similarity NPD7843 Approved
0.7415 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7413 Intermediate Similarity NPD2983 Phase 2
0.7413 Intermediate Similarity NPD2982 Phase 2
0.7375 Intermediate Similarity NPD37 Approved
0.7362 Intermediate Similarity NPD6234 Discontinued
0.7347 Intermediate Similarity NPD4625 Phase 3
0.7346 Intermediate Similarity NPD4967 Phase 2
0.7346 Intermediate Similarity NPD4965 Approved
0.7346 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7346 Intermediate Similarity NPD4966 Approved
0.7343 Intermediate Similarity NPD2981 Phase 2
0.7337 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD8313 Approved
0.731 Intermediate Similarity NPD8312 Approved
0.7305 Intermediate Similarity NPD1357 Approved
0.7297 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7292 Intermediate Similarity NPD4749 Approved
0.7285 Intermediate Similarity NPD4538 Approved
0.7285 Intermediate Similarity NPD7097 Phase 1
0.7285 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7285 Intermediate Similarity NPD4536 Approved
0.7273 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD7199 Phase 2
0.7273 Intermediate Similarity NPD1652 Phase 2
0.7267 Intermediate Similarity NPD1934 Approved
0.7266 Intermediate Similarity NPD7157 Approved
0.7261 Intermediate Similarity NPD7447 Phase 1
0.725 Intermediate Similarity NPD4380 Phase 2
0.7229 Intermediate Similarity NPD3787 Discontinued
0.7222 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD3018 Phase 2
0.7197 Intermediate Similarity NPD7213 Phase 3
0.7197 Intermediate Similarity NPD7212 Phase 2
0.7195 Intermediate Similarity NPD7075 Discontinued
0.7193 Intermediate Similarity NPD7685 Pre-registration
0.7153 Intermediate Similarity NPD3705 Approved
0.7152 Intermediate Similarity NPD5124 Phase 1
0.7152 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7132 Intermediate Similarity NPD2684 Approved
0.7124 Intermediate Similarity NPD5588 Approved
0.7124 Intermediate Similarity NPD5960 Phase 3
0.7123 Intermediate Similarity NPD8651 Approved
0.7091 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD4060 Phase 1
0.7083 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD5402 Approved
0.7059 Intermediate Similarity NPD290 Approved
0.7059 Intermediate Similarity NPD3751 Discontinued
0.7034 Intermediate Similarity NPD422 Phase 1
0.7022 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7021 Intermediate Similarity NPD6671 Approved
0.702 Intermediate Similarity NPD6233 Phase 2
0.7012 Intermediate Similarity NPD2801 Approved
0.7012 Intermediate Similarity NPD7819 Suspended
0.7012 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD7680 Approved
0.7 Intermediate Similarity NPD7095 Approved
0.6992 Remote Similarity NPD1242 Phase 1
0.6985 Remote Similarity NPD968 Approved
0.6978 Remote Similarity NPD7237 Clinical (unspecified phase)
0.697 Remote Similarity NPD3817 Phase 2
0.6964 Remote Similarity NPD6959 Discontinued
0.6957 Remote Similarity NPD5403 Approved
0.6939 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6933 Remote Similarity NPD4675 Approved
0.6933 Remote Similarity NPD4678 Approved
0.6928 Remote Similarity NPD5735 Approved
0.6923 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6923 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6919 Remote Similarity NPD5844 Phase 1
0.6913 Remote Similarity NPD6584 Phase 3
0.6913 Remote Similarity NPD6917 Clinical (unspecified phase)
0.6903 Remote Similarity NPD4108 Discontinued
0.6899 Remote Similarity NPD4628 Phase 3
0.6897 Remote Similarity NPD5125 Phase 3
0.6897 Remote Similarity NPD5126 Approved
0.6897 Remote Similarity NPD6516 Phase 2
0.6897 Remote Similarity NPD5846 Approved
0.689 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6883 Remote Similarity NPD6653 Approved
0.6879 Remote Similarity NPD1549 Phase 2
0.6875 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6875 Remote Similarity NPD1511 Approved
0.6867 Remote Similarity NPD6374 Clinical (unspecified phase)
0.6859 Remote Similarity NPD6100 Approved
0.6859 Remote Similarity NPD6099 Approved
0.6857 Remote Similarity NPD228 Approved
0.6855 Remote Similarity NPD6190 Approved
0.6852 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6848 Remote Similarity NPD6801 Discontinued
0.6842 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6842 Remote Similarity NPD6798 Discontinued
0.6842 Remote Similarity NPD7783 Phase 2
0.6836 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6832 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6832 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6832 Remote Similarity NPD5401 Approved
0.6826 Remote Similarity NPD3882 Suspended
0.6826 Remote Similarity NPD7768 Phase 2
0.6825 Remote Similarity NPD8151 Discontinued
0.6818 Remote Similarity NPD6355 Discontinued
0.6818 Remote Similarity NPD4340 Discontinued
0.6815 Remote Similarity NPD5762 Approved
0.6815 Remote Similarity NPD5763 Approved
0.6807 Remote Similarity NPD7089 Clinical (unspecified phase)
0.6807 Remote Similarity NPD2977 Approved
0.6807 Remote Similarity NPD2978 Approved
0.6807 Remote Similarity NPD1465 Phase 2
0.6792 Remote Similarity NPD4535 Phase 3
0.6792 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6792 Remote Similarity NPD3750 Approved
0.679 Remote Similarity NPD1512 Approved
0.6788 Remote Similarity NPD7411 Suspended
0.678 Remote Similarity NPD8053 Approved
0.678 Remote Similarity NPD8054 Approved
0.677 Remote Similarity NPD6799 Approved
0.6768 Remote Similarity NPD6055 Clinical (unspecified phase)
0.6768 Remote Similarity NPD8158 Clinical (unspecified phase)
0.6761 Remote Similarity NPD5283 Phase 1
0.676 Remote Similarity NPD6842 Approved
0.676 Remote Similarity NPD6841 Approved
0.676 Remote Similarity NPD6843 Phase 3
0.6757 Remote Similarity NPD2231 Phase 2
0.6757 Remote Similarity NPD2235 Phase 2
0.6753 Remote Similarity NPD1558 Phase 1
0.675 Remote Similarity NPD2677 Approved
0.6744 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6731 Remote Similarity NPD4978 Clinical (unspecified phase)
0.6711 Remote Similarity NPD6582 Phase 2
0.6711 Remote Similarity NPD3685 Discontinued
0.6711 Remote Similarity NPD6583 Phase 3
0.6709 Remote Similarity NPD3540 Phase 1
0.6706 Remote Similarity NPD5494 Approved
0.669 Remote Similarity NPD5535 Approved
0.6688 Remote Similarity NPD4062 Phase 3
0.6688 Remote Similarity NPD7033 Discontinued
0.6687 Remote Similarity NPD3892 Phase 2
0.6687 Remote Similarity NPD7466 Approved
0.6667 Remote Similarity NPD2424 Discontinued
0.6667 Remote Similarity NPD3225 Approved
0.6667 Remote Similarity NPD3180 Approved
0.6667 Remote Similarity NPD3179 Approved
0.6667 Remote Similarity NPD4357 Discontinued
0.6667 Remote Similarity NPD7549 Discontinued
0.6649 Remote Similarity NPD7698 Approved
0.6649 Remote Similarity NPD7696 Phase 3
0.6649 Remote Similarity NPD7697 Approved
0.6647 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6646 Remote Similarity NPD3539 Phase 1
0.6646 Remote Similarity NPD5307 Clinical (unspecified phase)
0.6646 Remote Similarity NPD1551 Phase 2
0.6646 Remote Similarity NPD2122 Discontinued
0.6646 Remote Similarity NPD2796 Approved
0.6645 Remote Similarity NPD3620 Phase 2
0.6645 Remote Similarity NPD2238 Phase 2
0.6645 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6645 Remote Similarity NPD5837 Clinical (unspecified phase)
0.6645 Remote Similarity NPD4140 Approved
0.6632 Remote Similarity NPD7584 Approved
0.6626 Remote Similarity NPD4123 Phase 3
0.6626 Remote Similarity NPD3536 Discontinued
0.6626 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6625 Remote Similarity NPD3060 Approved
0.6622 Remote Similarity NPD3496 Discontinued
0.6605 Remote Similarity NPD5756 Phase 2
0.6604 Remote Similarity NPD1375 Discontinued

  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