Structure

Physi-Chem Properties

Molecular Weight:  828.25
Volume:  781.797
LogP:  0.056
LogD:  -0.026
LogS:  -3.648
# Rotatable Bonds:  12
TPSA:  340.37
# H-Bond Aceptor:  19
# H-Bond Donor:  15
# Rings:  6
# Heavy Atoms:  19

MedChem Properties

QED Drug-Likeness Score:  0.079
Synthetic Accessibility Score:  5.527
Fsp3:  0.35
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  2
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.718
MDCK Permeability:  3.5122786812280538e-06
Pgp-inhibitor:  0.012
Pgp-substrate:  0.969
Human Intestinal Absorption (HIA):  0.969
20% Bioavailability (F20%):  0.192
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.032
Plasma Protein Binding (PPB):  95.79552459716797%
Volume Distribution (VD):  0.285
Pgp-substrate:  7.364707946777344%

ADMET: Metabolism

CYP1A2-inhibitor:  0.153
CYP1A2-substrate:  0.008
CYP2C19-inhibitor:  0.009
CYP2C19-substrate:  0.051
CYP2C9-inhibitor:  0.007
CYP2C9-substrate:  0.578
CYP2D6-inhibitor:  0.016
CYP2D6-substrate:  0.196
CYP3A4-inhibitor:  0.039
CYP3A4-substrate:  0.021

ADMET: Excretion

Clearance (CL):  2.175
Half-life (T1/2):  0.785

ADMET: Toxicity

hERG Blockers:  0.274
Human Hepatotoxicity (H-HT):  0.206
Drug-inuced Liver Injury (DILI):  0.354
AMES Toxicity:  0.196
Rat Oral Acute Toxicity:  0.095
Maximum Recommended Daily Dose:  0.016
Skin Sensitization:  0.959
Carcinogencity:  0.039
Eye Corrosion:  0.003
Eye Irritation:  0.053
Respiratory Toxicity:  0.006

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

  Natural Product: NPC100936

Natural Product ID:  NPC100936
Common Name*:   5-[(2R)-Hydroxy-(1S)-(4-Hydroxyphenyl)-2-(3,5-Dihydroxy-2-Beta-D-Glucopyranosyloxyphenyl)Ethyl]-6-[(E)-4-Hydroxystyryl]Benzene-2,4-Diol-1-O-Beta-D-Glucopyranoside
IUPAC Name:   (2S,3R,4S,5S,6R)-2-[2-[(1R,2S)-2-[4,6-dihydroxy-2-[(E)-2-(4-hydroxyphenyl)ethenyl]-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-1-hydroxy-2-(4-hydroxyphenyl)ethyl]-4,6-dihydroxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:  
Standard InCHIKey:  VQQCZBVAZZGBOJ-CQJFAUMQSA-N
Standard InCHI:  InChI=1S/C40H44O19/c41-14-26-31(50)33(52)35(54)39(56-26)58-37-21(10-3-16-1-6-18(43)7-2-16)29(23(46)13-25(37)48)28(17-4-8-19(44)9-5-17)30(49)22-11-20(45)12-24(47)38(22)59-40-36(55)34(53)32(51)27(15-42)57-40/h1-13,26-28,30-36,39-55H,14-15H2/b10-3+/t26-,27-,28+,30+,31-,32-,33+,34+,35-,36-,39+,40+/m1/s1
SMILES:  OC[C@H]1O[C@@H](Oc2c(O)cc(cc2[C@@H]([C@H](c2c(O)cc(c(c2/C=C/c2ccc(cc2)O)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)O)c2ccc(cc2)O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3109429
PubChem CID:   76335691
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000253] Stilbenes
        • [CHEMONTID:0000142] Stilbene 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
NPO31520 Polygonum multiflorum Species Polygonaceae Eukaryota roots n.a. n.a. PMID[24499304]
NPO31520 Polygonum multiflorum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31520 Polygonum multiflorum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]

☑ 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
NPT1 Others Radical scavenging activity IC50 > 2000000.0 nM PMID[520386]

☑ 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 NPC100936 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 NPC1253
0.9419 High Similarity NPC185231
0.9281 High Similarity NPC233467
0.9231 High Similarity NPC4809
0.9231 High Similarity NPC147743
0.9231 High Similarity NPC73517
0.9211 High Similarity NPC476969
0.9172 High Similarity NPC159526
0.9172 High Similarity NPC471404
0.9172 High Similarity NPC86630
0.9172 High Similarity NPC106601
0.9172 High Similarity NPC205613
0.9172 High Similarity NPC212614
0.9172 High Similarity NPC151474
0.9156 High Similarity NPC469944
0.9156 High Similarity NPC226108
0.9156 High Similarity NPC272552
0.9156 High Similarity NPC322899
0.9156 High Similarity NPC44192
0.9156 High Similarity NPC134911
0.9156 High Similarity NPC46283
0.9145 High Similarity NPC280945
0.9145 High Similarity NPC281549
0.9097 High Similarity NPC20050
0.9097 High Similarity NPC306267
0.9097 High Similarity NPC78809
0.9091 High Similarity NPC473621
0.9085 High Similarity NPC318373
0.9085 High Similarity NPC321657
0.9079 High Similarity NPC227902
0.9032 High Similarity NPC226809
0.9032 High Similarity NPC279406
0.9032 High Similarity NPC21902
0.9032 High Similarity NPC59692
0.9026 High Similarity NPC477612
0.9026 High Similarity NPC225815
0.9026 High Similarity NPC469707
0.9026 High Similarity NPC214326
0.9026 High Similarity NPC260781
0.9026 High Similarity NPC218041
0.9026 High Similarity NPC145979
0.9026 High Similarity NPC185955
0.9026 High Similarity NPC182368
0.9026 High Similarity NPC9933
0.9026 High Similarity NPC469706
0.902 High Similarity NPC175976
0.9013 High Similarity NPC125755
0.9007 High Similarity NPC469313
0.9007 High Similarity NPC76176
0.9007 High Similarity NPC171932
0.9007 High Similarity NPC168579
0.9007 High Similarity NPC28440
0.9007 High Similarity NPC138227
0.8974 High Similarity NPC224161
0.8968 High Similarity NPC259707
0.8961 High Similarity NPC211561
0.8954 High Similarity NPC236202
0.8954 High Similarity NPC204770
0.8954 High Similarity NPC82917
0.8954 High Similarity NPC58190
0.8954 High Similarity NPC263940
0.8954 High Similarity NPC108811
0.8954 High Similarity NPC70409
0.8954 High Similarity NPC202742
0.8954 High Similarity NPC15538
0.8954 High Similarity NPC473480
0.8954 High Similarity NPC18185
0.8954 High Similarity NPC262911
0.8954 High Similarity NPC294558
0.8954 High Similarity NPC170103
0.8947 High Similarity NPC161700
0.8947 High Similarity NPC277867
0.8947 High Similarity NPC475096
0.894 High Similarity NPC37793
0.894 High Similarity NPC252169
0.8938 High Similarity NPC48880
0.8917 High Similarity NPC46335
0.8903 High Similarity NPC238140
0.8889 High Similarity NPC95652
0.8889 High Similarity NPC190714
0.8889 High Similarity NPC150714
0.8889 High Similarity NPC96576
0.8889 High Similarity NPC99515
0.8846 High Similarity NPC329343
0.8846 High Similarity NPC324517
0.8846 High Similarity NPC321972
0.8839 High Similarity NPC44452
0.8834 High Similarity NPC59516
0.8831 High Similarity NPC39657
0.8824 High Similarity NPC23807
0.8816 High Similarity NPC113680
0.8816 High Similarity NPC472451
0.8816 High Similarity NPC278961
0.8808 High Similarity NPC469661
0.8808 High Similarity NPC178054
0.8797 High Similarity NPC157333
0.8782 High Similarity NPC472709
0.8782 High Similarity NPC472710
0.8774 High Similarity NPC329836
0.8774 High Similarity NPC227516
0.8774 High Similarity NPC20757
0.8766 High Similarity NPC155564
0.8766 High Similarity NPC102280
0.8766 High Similarity NPC248053
0.8765 High Similarity NPC12326
0.8758 High Similarity NPC304894
0.8758 High Similarity NPC25292
0.8758 High Similarity NPC15659
0.8758 High Similarity NPC473045
0.875 High Similarity NPC472714
0.875 High Similarity NPC475084
0.875 High Similarity NPC189115
0.875 High Similarity NPC5262
0.875 High Similarity NPC469559
0.8742 High Similarity NPC262189
0.8742 High Similarity NPC106944
0.8734 High Similarity NPC200645
0.8734 High Similarity NPC475227
0.8734 High Similarity NPC106669
0.8726 High Similarity NPC471403
0.8718 High Similarity NPC55715
0.8718 High Similarity NPC473266
0.8718 High Similarity NPC55158
0.8718 High Similarity NPC470826
0.8718 High Similarity NPC95392
0.8718 High Similarity NPC51328
0.8718 High Similarity NPC286235
0.8718 High Similarity NPC470098
0.8718 High Similarity NPC35877
0.8701 High Similarity NPC272619
0.8701 High Similarity NPC307466
0.8701 High Similarity NPC286245
0.8701 High Similarity NPC271076
0.8693 High Similarity NPC473044
0.8693 High Similarity NPC173203
0.8693 High Similarity NPC163508
0.8684 High Similarity NPC471389
0.8662 High Similarity NPC475224
0.8654 High Similarity NPC301961
0.8654 High Similarity NPC270751
0.8654 High Similarity NPC130449
0.8654 High Similarity NPC166584
0.8654 High Similarity NPC226153
0.8654 High Similarity NPC248132
0.8654 High Similarity NPC304048
0.8645 High Similarity NPC226540
0.8636 High Similarity NPC187774
0.8636 High Similarity NPC50250
0.8636 High Similarity NPC118385
0.8636 High Similarity NPC473108
0.8636 High Similarity NPC253015
0.8636 High Similarity NPC151704
0.8636 High Similarity NPC471063
0.8636 High Similarity NPC473046
0.8636 High Similarity NPC471065
0.8636 High Similarity NPC472712
0.8636 High Similarity NPC472713
0.8625 High Similarity NPC202104
0.8618 High Similarity NPC291101
0.8618 High Similarity NPC22317
0.8618 High Similarity NPC472090
0.8618 High Similarity NPC472091
0.8618 High Similarity NPC266197
0.8618 High Similarity NPC472092
0.8609 High Similarity NPC474390
0.8609 High Similarity NPC59324
0.8609 High Similarity NPC65530
0.859 High Similarity NPC320970
0.859 High Similarity NPC31325
0.859 High Similarity NPC15956
0.859 High Similarity NPC193473
0.859 High Similarity NPC320671
0.859 High Similarity NPC275284
0.859 High Similarity NPC327412
0.859 High Similarity NPC224674
0.859 High Similarity NPC114505
0.859 High Similarity NPC213074
0.859 High Similarity NPC328567
0.8589 High Similarity NPC149873
0.8589 High Similarity NPC7191
0.8581 High Similarity NPC11422
0.8581 High Similarity NPC178014
0.8581 High Similarity NPC42716
0.8581 High Similarity NPC474749
0.8571 High Similarity NPC185307
0.8571 High Similarity NPC470950
0.8563 High Similarity NPC472724
0.8563 High Similarity NPC31208
0.8563 High Similarity NPC160543
0.8563 High Similarity NPC93065
0.8563 High Similarity NPC472721
0.8563 High Similarity NPC469652
0.8563 High Similarity NPC472720
0.8562 High Similarity NPC257095
0.8562 High Similarity NPC273932
0.8562 High Similarity NPC159922
0.8562 High Similarity NPC89686
0.8562 High Similarity NPC100482
0.8562 High Similarity NPC277331
0.8553 High Similarity NPC471388

  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 NPC100936 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
0.8333 Intermediate Similarity NPD7228 Approved
0.8278 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8278 Intermediate Similarity NPD1613 Approved
0.825 Intermediate Similarity NPD1653 Approved
0.8205 Intermediate Similarity NPD6674 Discontinued
0.8129 Intermediate Similarity NPD7472 Approved
0.8129 Intermediate Similarity NPD7074 Phase 3
0.811 Intermediate Similarity NPD8455 Phase 2
0.807 Intermediate Similarity NPD7054 Approved
0.8013 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7989 Intermediate Similarity NPD7808 Phase 3
0.7961 Intermediate Similarity NPD3027 Phase 3
0.7947 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7931 Intermediate Similarity NPD7251 Discontinued
0.7931 Intermediate Similarity NPD7240 Approved
0.7929 Intermediate Similarity NPD7199 Phase 2
0.7917 Intermediate Similarity NPD6234 Discontinued
0.7895 Intermediate Similarity NPD4908 Phase 1
0.7874 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7874 Intermediate Similarity NPD6797 Phase 2
0.7841 Intermediate Similarity NPD8313 Approved
0.7841 Intermediate Similarity NPD8312 Approved
0.7831 Intermediate Similarity NPD37 Approved
0.7798 Intermediate Similarity NPD4966 Approved
0.7798 Intermediate Similarity NPD4965 Approved
0.7798 Intermediate Similarity NPD4967 Phase 2
0.7792 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7791 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7791 Intermediate Similarity NPD6166 Phase 2
0.7791 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7784 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7736 Intermediate Similarity NPD7266 Discontinued
0.7733 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7701 Intermediate Similarity NPD3818 Discontinued
0.7692 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7657 Intermediate Similarity NPD5844 Phase 1
0.7606 Intermediate Similarity NPD7680 Approved
0.7598 Intermediate Similarity NPD8054 Approved
0.7598 Intermediate Similarity NPD8053 Approved
0.7597 Intermediate Similarity NPD2861 Phase 2
0.7572 Intermediate Similarity NPD3787 Discontinued
0.7557 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.755 Intermediate Similarity NPD1091 Approved
0.755 Intermediate Similarity NPD1610 Phase 2
0.7544 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7527 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7487 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7412 Intermediate Similarity NPD1934 Approved
0.7368 Intermediate Similarity NPD1465 Phase 2
0.7363 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7351 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7314 Intermediate Similarity NPD6959 Discontinued
0.7303 Intermediate Similarity NPD3751 Discontinued
0.7293 Intermediate Similarity NPD7549 Discontinued
0.7278 Intermediate Similarity NPD4625 Phase 3
0.7267 Intermediate Similarity NPD2801 Approved
0.7267 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7263 Intermediate Similarity NPD8156 Discontinued
0.7241 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7238 Intermediate Similarity NPD6559 Discontinued
0.7233 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7208 Intermediate Similarity NPD3705 Approved
0.7207 Intermediate Similarity NPD8099 Discontinued
0.7207 Intermediate Similarity NPD8251 Approved
0.7207 Intermediate Similarity NPD8252 Approved
0.7171 Intermediate Similarity NPD1548 Phase 1
0.7159 Intermediate Similarity NPD5494 Approved
0.7151 Intermediate Similarity NPD7473 Discontinued
0.7143 Intermediate Similarity NPD7685 Pre-registration
0.7143 Intermediate Similarity NPD3620 Phase 2
0.7143 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD8151 Discontinued
0.7143 Intermediate Similarity NPD4060 Phase 1
0.7126 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD7097 Phase 1
0.7115 Intermediate Similarity NPD4749 Approved
0.7101 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD7447 Phase 1
0.7097 Intermediate Similarity NPD7906 Approved
0.7097 Intermediate Similarity NPD6842 Approved
0.7097 Intermediate Similarity NPD6841 Approved
0.7097 Intermediate Similarity NPD6843 Phase 3
0.7079 Intermediate Similarity NPD6232 Discontinued
0.7071 Intermediate Similarity NPD7783 Phase 2
0.7071 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD3018 Phase 2
0.7043 Intermediate Similarity NPD4663 Approved
0.7041 Intermediate Similarity NPD7213 Phase 3
0.7041 Intermediate Similarity NPD7212 Phase 2
0.7027 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7022 Intermediate Similarity NPD8127 Discontinued
0.7 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.6994 Remote Similarity NPD4380 Phase 2
0.6989 Remote Similarity NPD7768 Phase 2
0.6988 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6974 Remote Similarity NPD7696 Phase 3
0.6974 Remote Similarity NPD7697 Approved
0.6974 Remote Similarity NPD7698 Approved
0.6971 Remote Similarity NPD7819 Suspended
0.6959 Remote Similarity NPD1940 Clinical (unspecified phase)
0.6941 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6941 Remote Similarity NPD1511 Approved
0.6939 Remote Similarity NPD7871 Phase 2
0.6939 Remote Similarity NPD7870 Phase 2
0.6932 Remote Similarity NPD5402 Approved
0.6932 Remote Similarity NPD3817 Phase 2
0.6923 Remote Similarity NPD6823 Phase 2
0.6919 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6919 Remote Similarity NPD7701 Phase 2
0.6907 Remote Similarity NPD6781 Approved
0.6907 Remote Similarity NPD6778 Approved
0.6907 Remote Similarity NPD6782 Approved
0.6907 Remote Similarity NPD6780 Approved
0.6907 Remote Similarity NPD6777 Approved
0.6907 Remote Similarity NPD6776 Approved
0.6907 Remote Similarity NPD6779 Approved
0.6906 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6899 Remote Similarity NPD2983 Phase 2
0.6899 Remote Similarity NPD2982 Phase 2
0.6893 Remote Similarity NPD3882 Suspended
0.689 Remote Similarity NPD5123 Clinical (unspecified phase)
0.689 Remote Similarity NPD5735 Approved
0.689 Remote Similarity NPD5124 Phase 1
0.6888 Remote Similarity NPD7435 Discontinued
0.6886 Remote Similarity NPD5762 Approved
0.6886 Remote Similarity NPD5763 Approved
0.6882 Remote Similarity NPD7311 Approved
0.6882 Remote Similarity NPD5058 Phase 3
0.6882 Remote Similarity NPD7310 Approved
0.6882 Remote Similarity NPD7313 Approved
0.6882 Remote Similarity NPD4577 Approved
0.6882 Remote Similarity NPD4578 Approved
0.6882 Remote Similarity NPD7312 Approved
0.6875 Remote Similarity NPD6917 Clinical (unspecified phase)
0.6864 Remote Similarity NPD3892 Phase 2
0.6864 Remote Similarity NPD3750 Approved
0.6863 Remote Similarity NPD6671 Approved
0.686 Remote Similarity NPD1512 Approved
0.6855 Remote Similarity NPD8651 Approved
0.6854 Remote Similarity NPD7075 Discontinued
0.6845 Remote Similarity NPD7309 Approved
0.6842 Remote Similarity NPD5283 Phase 1
0.6835 Remote Similarity NPD2981 Phase 2
0.6826 Remote Similarity NPD6100 Approved
0.6826 Remote Similarity NPD6099 Approved
0.6824 Remote Similarity NPD6190 Approved
0.6818 Remote Similarity NPD3382 Approved
0.6818 Remote Similarity NPD3383 Approved
0.6818 Remote Similarity NPD3384 Approved
0.6816 Remote Similarity NPD7801 Approved
0.6813 Remote Similarity NPD27 Approved
0.6813 Remote Similarity NPD2489 Approved
0.681 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6805 Remote Similarity NPD1652 Phase 2
0.6804 Remote Similarity NPD7699 Phase 2
0.6804 Remote Similarity NPD7700 Phase 2
0.6802 Remote Similarity NPD7446 Clinical (unspecified phase)
0.6796 Remote Similarity NPD3051 Approved
0.6796 Remote Similarity NPD7229 Phase 3
0.6795 Remote Similarity NPD1357 Approved
0.6776 Remote Similarity NPD7843 Approved
0.6768 Remote Similarity NPD6233 Phase 2
0.6766 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6766 Remote Similarity NPD6028 Clinical (unspecified phase)
0.6766 Remote Similarity NPD6029 Clinical (unspecified phase)
0.6766 Remote Similarity NPD4108 Discontinued
0.6766 Remote Similarity NPD7874 Approved
0.6765 Remote Similarity NPD7466 Approved
0.6758 Remote Similarity NPD2970 Approved
0.6758 Remote Similarity NPD2969 Approved
0.6753 Remote Similarity NPD7157 Approved
0.6744 Remote Similarity NPD7041 Phase 2
0.6744 Remote Similarity NPD7040 Clinical (unspecified phase)
0.6743 Remote Similarity NPD4005 Discontinued
0.6743 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6742 Remote Similarity NPD6374 Clinical (unspecified phase)
0.6725 Remote Similarity NPD2677 Approved
0.6723 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6711 Remote Similarity NPD228 Approved
0.6707 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6707 Remote Similarity NPD4536 Approved
0.6707 Remote Similarity NPD6798 Discontinued
0.6707 Remote Similarity NPD4538 Approved
0.6706 Remote Similarity NPD5177 Phase 3
0.6687 Remote Similarity NPD6355 Discontinued
0.6687 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6686 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6686 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6685 Remote Similarity NPD2978 Approved
0.6685 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6685 Remote Similarity NPD2977 Approved
0.6667 Remote Similarity NPD5588 Approved
0.6667 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7831 Phase 2
0.6667 Remote Similarity NPD7832 Clinical (unspecified phase)
0.6667 Remote Similarity NPD3749 Approved
0.6667 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6667 Remote Similarity NPD8166 Discontinued
0.6667 Remote Similarity NPD7833 Phase 2

  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