Structure

Physi-Chem Properties

Molecular Weight:  826.29
Volume:  775.098
LogP:  0.053
LogD:  -0.101
LogS:  -2.476
# Rotatable Bonds:  17
TPSA:  310.28
# H-Bond Aceptor:  20
# H-Bond Donor:  10
# Rings:  5
# Heavy Atoms:  20

MedChem Properties

QED Drug-Likeness Score:  0.051
Synthetic Accessibility Score:  5.443
Fsp3:  0.579
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:  -6.694
MDCK Permeability:  8.93335381988436e-05
Pgp-inhibitor:  0.003
Pgp-substrate:  0.997
Human Intestinal Absorption (HIA):  0.999
20% Bioavailability (F20%):  0.793
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.139
Plasma Protein Binding (PPB):  74.13855743408203%
Volume Distribution (VD):  0.257
Pgp-substrate:  16.92475700378418%

ADMET: Metabolism

CYP1A2-inhibitor:  0.018
CYP1A2-substrate:  0.006
CYP2C19-inhibitor:  0.031
CYP2C19-substrate:  0.05
CYP2C9-inhibitor:  0.011
CYP2C9-substrate:  0.037
CYP2D6-inhibitor:  0.047
CYP2D6-substrate:  0.096
CYP3A4-inhibitor:  0.061
CYP3A4-substrate:  0.014

ADMET: Excretion

Clearance (CL):  0.619
Half-life (T1/2):  0.847

ADMET: Toxicity

hERG Blockers:  0.484
Human Hepatotoxicity (H-HT):  0.42
Drug-inuced Liver Injury (DILI):  0.513
AMES Toxicity:  0.15
Rat Oral Acute Toxicity:  0.119
Maximum Recommended Daily Dose:  0.003
Skin Sensitization:  0.961
Carcinogencity:  0.051
Eye Corrosion:  0.003
Eye Irritation:  0.014
Respiratory Toxicity:  0.025

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

  Natural Product: NPC476378

Natural Product ID:  NPC476378
Common Name*:   Kankanoside H2
IUPAC Name:   [(2R,3R,4S,5R,6R)-5-acetyloxy-6-[2-(3,4-dihydroxyphenyl)ethoxy]-2-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-4-[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]methoxy]oxan-3-yl] (Z)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:   Kankanoside H2
Standard InCHIKey:  YVEWOLFCBHXGFW-GBSNAEPKSA-N
Standard InCHI:  InChI=1S/C38H50O20/c1-17-28(45)31(48)30(47)25(54-17)15-52-35-34(58-27(44)10-6-19-3-7-21(41)8-4-19)26(16-53-37-33(50)32(49)29(46)24(14-39)56-37)57-38(36(35)55-18(2)40)51-12-11-20-5-9-22(42)23(43)13-20/h3-10,13,17,24-26,28-39,41-43,45-50H,11-12,14-16H2,1-2H3/b10-6-/t17-,24+,25-,26+,28-,29+,30-,31+,32-,33+,34+,35-,36+,37+,38+/m0/s1
SMILES:  CC1C(C(C(C(O1)COC2C(C(OC(C2OC(=O)C)OCCC3=CC(=C(C=C3)O)O)COC4C(C(C(C(O4)CO)O)O)O)OC(=O)C=CC5=CC=C(C=C5)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL590308
PubChem CID:   46228747
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000476] Cinnamic acids and derivatives
        • [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives
          • [CHEMONTID:0003002] Hydroxycinnamic acid esters
            • [CHEMONTID:0000465] Coumaric acid esters

*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
NPO6964 Cistanche tubulosa Species Orobanchaceae Eukaryota fresh stems n.a. n.a. PMID[20159656]
NPO6964 Cistanche tubulosa Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6964 Cistanche tubulosa Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6964 Cistanche tubulosa Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO6964 Cistanche tubulosa Species Orobanchaceae 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
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 4.4 % PMID[450631]
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 11.6 % PMID[450631]
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 18.2 % PMID[450631]
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 26.3 % PMID[450631]

☑ 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 NPC476378 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 NPC96795
1.0 High Similarity NPC264632
1.0 High Similarity NPC476375
1.0 High Similarity NPC76406
1.0 High Similarity NPC269141
1.0 High Similarity NPC247032
1.0 High Similarity NPC476380
1.0 High Similarity NPC175214
1.0 High Similarity NPC205864
1.0 High Similarity NPC119537
1.0 High Similarity NPC112
1.0 High Similarity NPC476381
1.0 High Similarity NPC476384
1.0 High Similarity NPC298257
1.0 High Similarity NPC476397
0.9926 High Similarity NPC64195
0.9852 High Similarity NPC476377
0.9852 High Similarity NPC47471
0.9783 High Similarity NPC229505
0.9779 High Similarity NPC265648
0.9779 High Similarity NPC222433
0.9778 High Similarity NPC475530
0.9778 High Similarity NPC473799
0.9706 High Similarity NPC476385
0.9706 High Similarity NPC134405
0.9704 High Similarity NPC64141
0.9704 High Similarity NPC205195
0.9704 High Similarity NPC472350
0.9704 High Similarity NPC89105
0.9704 High Similarity NPC81515
0.9704 High Similarity NPC476383
0.9704 High Similarity NPC197316
0.9704 High Similarity NPC68092
0.9638 High Similarity NPC196063
0.9638 High Similarity NPC296954
0.9638 High Similarity NPC300894
0.9638 High Similarity NPC141455
0.963 High Similarity NPC260425
0.963 High Similarity NPC476376
0.9574 High Similarity NPC94871
0.9574 High Similarity NPC471062
0.9574 High Similarity NPC476398
0.9574 High Similarity NPC476386
0.9574 High Similarity NPC473427
0.9574 High Similarity NPC306890
0.9574 High Similarity NPC259347
0.9574 High Similarity NPC470933
0.9565 High Similarity NPC105005
0.9507 High Similarity NPC470927
0.9507 High Similarity NPC257970
0.9485 High Similarity NPC78363
0.9481 High Similarity NPC263829
0.9433 High Similarity NPC232992
0.9407 High Similarity NPC287597
0.9407 High Similarity NPC34293
0.9407 High Similarity NPC886
0.9291 High Similarity NPC252292
0.9291 High Similarity NPC34927
0.9291 High Similarity NPC34587
0.9291 High Similarity NPC476382
0.9291 High Similarity NPC100998
0.9286 High Similarity NPC40305
0.9275 High Similarity NPC171134
0.9275 High Similarity NPC328273
0.9275 High Similarity NPC321184
0.9275 High Similarity NPC321638
0.9259 High Similarity NPC473285
0.9241 High Similarity NPC106818
0.9236 High Similarity NPC188393
0.9236 High Similarity NPC470934
0.9197 High Similarity NPC476870
0.9185 High Similarity NPC235294
0.9185 High Similarity NPC46137
0.9178 High Similarity NPC87403
0.9124 High Similarity NPC471883
0.9097 High Similarity NPC23677
0.9091 High Similarity NPC476865
0.9085 High Similarity NPC476867
0.9078 High Similarity NPC140502
0.9048 High Similarity NPC471874
0.9044 High Similarity NPC138777
0.9044 High Similarity NPC246869
0.9044 High Similarity NPC225384
0.9037 High Similarity NPC477293
0.9037 High Similarity NPC229784
0.9037 High Similarity NPC477294
0.9021 High Similarity NPC216819
0.9021 High Similarity NPC262182
0.9021 High Similarity NPC476864
0.9021 High Similarity NPC287615
0.9021 High Similarity NPC476868
0.9021 High Similarity NPC476869
0.9021 High Similarity NPC476866
0.9021 High Similarity NPC83743
0.8978 High Similarity NPC254275
0.8973 High Similarity NPC476871
0.8966 High Similarity NPC192763
0.8966 High Similarity NPC201148
0.8966 High Similarity NPC80732
0.8966 High Similarity NPC28651
0.8966 High Similarity NPC261122
0.8966 High Similarity NPC199311
0.8966 High Similarity NPC3460
0.8966 High Similarity NPC215095
0.8966 High Similarity NPC300262
0.8966 High Similarity NPC210611
0.8963 High Similarity NPC232880
0.8913 High Similarity NPC254398
0.8912 High Similarity NPC7145
0.8912 High Similarity NPC143480
0.8912 High Similarity NPC125823
0.8912 High Similarity NPC85192
0.8905 High Similarity NPC219677
0.8897 High Similarity NPC184092
0.8889 High Similarity NPC288416
0.8889 High Similarity NPC476873
0.8881 High Similarity NPC478239
0.8873 High Similarity NPC186406
0.8851 High Similarity NPC478268
0.8841 High Similarity NPC473924
0.8836 High Similarity NPC473138
0.8836 High Similarity NPC28776
0.8819 High Similarity NPC110063
0.8815 High Similarity NPC471157
0.8811 High Similarity NPC296643
0.8811 High Similarity NPC157816
0.8777 High Similarity NPC28637
0.8776 High Similarity NPC90896
0.8776 High Similarity NPC106138
0.8776 High Similarity NPC283839
0.8768 High Similarity NPC478255
0.875 High Similarity NPC106677
0.875 High Similarity NPC278961
0.875 High Similarity NPC113680
0.875 High Similarity NPC108659
0.875 High Similarity NPC231607
0.875 High Similarity NPC264900
0.875 High Similarity NPC79715
0.8741 High Similarity NPC83218
0.8741 High Similarity NPC126991
0.8725 High Similarity NPC472611
0.8725 High Similarity NPC472612
0.8725 High Similarity NPC289967
0.8723 High Similarity NPC157554
0.8716 High Similarity NPC69367
0.8701 High Similarity NPC246024
0.8699 High Similarity NPC199928
0.869 High Similarity NPC292443
0.869 High Similarity NPC232228
0.8686 High Similarity NPC225307
0.8681 High Similarity NPC473792
0.8681 High Similarity NPC473873
0.8676 High Similarity NPC94179
0.8671 High Similarity NPC202700
0.8652 High Similarity NPC123988
0.8649 High Similarity NPC478242
0.8636 High Similarity NPC149873
0.8636 High Similarity NPC7191
0.8618 High Similarity NPC11411
0.8613 High Similarity NPC45224
0.8613 High Similarity NPC35288
0.8613 High Similarity NPC103533
0.8613 High Similarity NPC173150
0.8613 High Similarity NPC471881
0.8613 High Similarity NPC156692
0.8613 High Similarity NPC471882
0.8601 High Similarity NPC220942
0.8601 High Similarity NPC226005
0.8601 High Similarity NPC100389
0.8592 High Similarity NPC199459
0.8592 High Similarity NPC52277
0.8592 High Similarity NPC470572
0.8592 High Similarity NPC177035
0.8582 High Similarity NPC35731
0.8582 High Similarity NPC135127
0.8581 High Similarity NPC471873
0.8562 High Similarity NPC471878
0.8553 High Similarity NPC131532
0.8551 High Similarity NPC148982
0.8542 High Similarity NPC106944
0.854 High Similarity NPC61181
0.8533 High Similarity NPC473621
0.8531 High Similarity NPC84789
0.8531 High Similarity NPC126206
0.8531 High Similarity NPC302583
0.8531 High Similarity NPC101686
0.8531 High Similarity NPC100558
0.8531 High Similarity NPC469364
0.8531 High Similarity NPC470413
0.8531 High Similarity NPC138738
0.8531 High Similarity NPC310252
0.8531 High Similarity NPC65262
0.8519 High Similarity NPC52097
0.8516 High Similarity NPC471869
0.8506 High Similarity NPC478269
0.8503 High Similarity NPC274960
0.8503 High Similarity NPC143120
0.8503 High Similarity NPC473909
0.8493 Intermediate Similarity NPC204644
0.8477 Intermediate Similarity NPC215060

  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 NPC476378 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
0.9704 High Similarity NPD7266 Discontinued
0.8039 Intermediate Similarity NPD1653 Approved
0.8 Intermediate Similarity NPD6190 Approved
0.7927 Intermediate Similarity NPD7074 Phase 3
0.7927 Intermediate Similarity NPD7472 Approved
0.7866 Intermediate Similarity NPD7054 Approved
0.7831 Intermediate Similarity NPD7685 Pre-registration
0.7831 Intermediate Similarity NPD7251 Discontinued
0.7805 Intermediate Similarity NPD7228 Approved
0.7784 Intermediate Similarity NPD7808 Phase 3
0.7771 Intermediate Similarity NPD6797 Phase 2
0.7673 Intermediate Similarity NPD8455 Phase 2
0.7603 Intermediate Similarity NPD3027 Phase 3
0.7582 Intermediate Similarity NPD8166 Discontinued
0.7471 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7469 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7456 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.745 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.745 Intermediate Similarity NPD1613 Approved
0.7442 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7427 Intermediate Similarity NPD8312 Approved
0.7427 Intermediate Similarity NPD8313 Approved
0.7412 Intermediate Similarity NPD7240 Approved
0.7381 Intermediate Similarity NPD3818 Discontinued
0.7378 Intermediate Similarity NPD6234 Discontinued
0.7337 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.729 Intermediate Similarity NPD6674 Discontinued
0.7285 Intermediate Similarity NPD230 Phase 1
0.7284 Intermediate Similarity NPD37 Approved
0.7262 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7262 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7262 Intermediate Similarity NPD6166 Phase 2
0.7256 Intermediate Similarity NPD4966 Approved
0.7256 Intermediate Similarity NPD4967 Phase 2
0.7256 Intermediate Similarity NPD4965 Approved
0.7216 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7181 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD1091 Approved
0.7135 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7114 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.711 Intermediate Similarity NPD6559 Discontinued
0.7101 Intermediate Similarity NPD3022 Approved
0.7101 Intermediate Similarity NPD3021 Approved
0.7081 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7078 Intermediate Similarity NPD4978 Clinical (unspecified phase)
0.7078 Intermediate Similarity NPD7097 Phase 1
0.7073 Intermediate Similarity NPD1934 Approved
0.7055 Intermediate Similarity NPD3705 Approved
0.703 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD7680 Approved
0.7025 Intermediate Similarity NPD4628 Phase 3
0.6995 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6994 Remote Similarity NPD3455 Phase 2
0.6982 Remote Similarity NPD7199 Phase 2
0.6982 Remote Similarity NPD8127 Discontinued
0.6966 Remote Similarity NPD1357 Approved
0.6951 Remote Similarity NPD4380 Phase 2
0.6943 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6936 Remote Similarity NPD5844 Phase 1
0.6928 Remote Similarity NPD1465 Phase 2
0.6918 Remote Similarity NPD5126 Approved
0.6918 Remote Similarity NPD5125 Phase 3
0.6905 Remote Similarity NPD7075 Discontinued
0.6898 Remote Similarity NPD8320 Phase 1
0.6898 Remote Similarity NPD8319 Approved
0.6886 Remote Similarity NPD3817 Phase 2
0.6883 Remote Similarity NPD4060 Phase 1
0.6879 Remote Similarity NPD228 Approved
0.6855 Remote Similarity NPD1652 Phase 2
0.6842 Remote Similarity NPD8151 Discontinued
0.6839 Remote Similarity NPD4340 Discontinued
0.6832 Remote Similarity NPD5058 Phase 3
0.6828 Remote Similarity NPD5536 Phase 2
0.6826 Remote Similarity NPD2801 Approved
0.6826 Remote Similarity NPD2978 Approved
0.6826 Remote Similarity NPD2977 Approved
0.6818 Remote Similarity NPD6233 Phase 2
0.6816 Remote Similarity NPD8150 Discontinued
0.6802 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6797 Remote Similarity NPD7095 Approved
0.6788 Remote Similarity NPD7458 Discontinued
0.6786 Remote Similarity NPD5402 Approved
0.6782 Remote Similarity NPD3751 Discontinued
0.6781 Remote Similarity NPD9545 Approved
0.6776 Remote Similarity NPD2861 Phase 2
0.6766 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6761 Remote Similarity NPD969 Suspended
0.6757 Remote Similarity NPD7700 Phase 2
0.6757 Remote Similarity NPD7699 Phase 2
0.6753 Remote Similarity NPD3764 Approved
0.6748 Remote Similarity NPD4160 Clinical (unspecified phase)
0.6746 Remote Similarity NPD3882 Suspended
0.6732 Remote Similarity NPD4908 Phase 1
0.6731 Remote Similarity NPD5124 Phase 1
0.6731 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6726 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6726 Remote Similarity NPD7819 Suspended
0.6714 Remote Similarity NPD1358 Approved
0.6713 Remote Similarity NPD7843 Approved
0.6688 Remote Similarity NPD6653 Approved
0.6688 Remote Similarity NPD5314 Approved
0.6687 Remote Similarity NPD1511 Approved
0.6685 Remote Similarity NPD7549 Discontinued
0.6684 Remote Similarity NPD7783 Phase 2
0.6684 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6667 Remote Similarity NPD3062 Approved
0.6667 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6667 Remote Similarity NPD3059 Approved
0.6667 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5403 Approved
0.6667 Remote Similarity NPD7435 Discontinued
0.6667 Remote Similarity NPD2935 Discontinued
0.6667 Remote Similarity NPD3061 Approved
0.6667 Remote Similarity NPD3620 Phase 2
0.6667 Remote Similarity NPD5736 Approved
0.6667 Remote Similarity NPD9269 Phase 2
0.6667 Remote Similarity NPD5283 Phase 1
0.6647 Remote Similarity NPD6232 Discontinued
0.6647 Remote Similarity NPD3787 Discontinued
0.6646 Remote Similarity NPD4538 Approved
0.6646 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6646 Remote Similarity NPD5698 Clinical (unspecified phase)
0.6646 Remote Similarity NPD4536 Approved
0.6646 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6645 Remote Similarity NPD6798 Discontinued
0.6645 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6645 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6645 Remote Similarity NPD3094 Phase 2
0.6644 Remote Similarity NPD3496 Discontinued
0.6629 Remote Similarity NPD7473 Discontinued
0.6627 Remote Similarity NPD3687 Approved
0.6627 Remote Similarity NPD3686 Approved
0.6625 Remote Similarity NPD5762 Approved
0.6625 Remote Similarity NPD5763 Approved
0.6624 Remote Similarity NPD1933 Approved
0.6624 Remote Similarity NPD6355 Discontinued
0.6623 Remote Similarity NPD2982 Phase 2
0.6623 Remote Similarity NPD2983 Phase 2
0.6611 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6608 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6607 Remote Similarity NPD6386 Approved
0.6607 Remote Similarity NPD6385 Approved
0.6606 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6606 Remote Similarity NPD1512 Approved
0.66 Remote Similarity NPD422 Phase 1
0.6595 Remote Similarity NPD6534 Approved
0.6595 Remote Similarity NPD6535 Approved
0.6593 Remote Similarity NPD6842 Approved
0.6593 Remote Similarity NPD6841 Approved
0.6593 Remote Similarity NPD6843 Phase 3
0.6579 Remote Similarity NPD7697 Approved
0.6579 Remote Similarity NPD7698 Approved
0.6579 Remote Similarity NPD7696 Phase 3
0.6577 Remote Similarity NPD9384 Approved
0.6577 Remote Similarity NPD9381 Approved
0.6575 Remote Similarity NPD7157 Approved
0.6568 Remote Similarity NPD6801 Discontinued
0.6562 Remote Similarity NPD9570 Approved
0.6561 Remote Similarity NPD943 Approved
0.6561 Remote Similarity NPD1558 Phase 1
0.6561 Remote Similarity NPD826 Approved
0.6561 Remote Similarity NPD825 Approved
0.6558 Remote Similarity NPD9494 Approved
0.6558 Remote Similarity NPD3018 Phase 2
0.6556 Remote Similarity NPD2981 Phase 2
0.6554 Remote Similarity NPD8470 Clinical (unspecified phase)
0.655 Remote Similarity NPD7768 Phase 2
0.6546 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6546 Remote Similarity NPD7874 Approved
0.6545 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6545 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6545 Remote Similarity NPD5401 Approved
0.6543 Remote Similarity NPD3060 Approved
0.6543 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6536 Remote Similarity NPD7039 Approved
0.6536 Remote Similarity NPD7038 Approved
0.6532 Remote Similarity NPD5494 Approved
0.6528 Remote Similarity NPD7701 Phase 2
0.6526 Remote Similarity NPD6823 Phase 2
0.6525 Remote Similarity NPD3134 Approved
0.6519 Remote Similarity NPD2934 Approved
0.6519 Remote Similarity NPD2933 Approved
0.6513 Remote Similarity NPD9622 Approved
0.6509 Remote Similarity NPD7411 Suspended
0.6508 Remote Similarity NPD6778 Approved
0.6508 Remote Similarity NPD6779 Approved
0.6508 Remote Similarity NPD6780 Approved
0.6508 Remote Similarity NPD6782 Approved
0.6508 Remote Similarity NPD6777 Approved
0.6508 Remote Similarity NPD6781 Approved
0.6508 Remote Similarity NPD6776 Approved
0.6503 Remote Similarity NPD4110 Phase 3
0.6503 Remote Similarity NPD3750 Approved
0.6503 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6503 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6503 Remote Similarity NPD4109 Clinical (unspecified phase)
0.65 Remote Similarity NPD5588 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