Structure

Physi-Chem Properties

Molecular Weight:  998.28
Volume:  968.542
LogP:  4.447
LogD:  2.623
LogS:  -3.57
# Rotatable Bonds:  24
TPSA:  310.03
# H-Bond Aceptor:  21
# H-Bond Donor:  7
# Rings:  6
# Heavy Atoms:  21

MedChem Properties

QED Drug-Likeness Score:  0.04
Synthetic Accessibility Score:  5.564
Fsp3:  0.275
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.101
MDCK Permeability:  4.0814913518261164e-05
Pgp-inhibitor:  0.037
Pgp-substrate:  0.985
Human Intestinal Absorption (HIA):  0.961
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.029
Plasma Protein Binding (PPB):  103.26887512207031%
Volume Distribution (VD):  0.369
Pgp-substrate:  1.260632038116455%

ADMET: Metabolism

CYP1A2-inhibitor:  0.062
CYP1A2-substrate:  0.016
CYP2C19-inhibitor:  0.567
CYP2C19-substrate:  0.047
CYP2C9-inhibitor:  0.705
CYP2C9-substrate:  0.872
CYP2D6-inhibitor:  0.681
CYP2D6-substrate:  0.347
CYP3A4-inhibitor:  0.852
CYP3A4-substrate:  0.342

ADMET: Excretion

Clearance (CL):  3.618
Half-life (T1/2):  0.945

ADMET: Toxicity

hERG Blockers:  0.181
Human Hepatotoxicity (H-HT):  0.069
Drug-inuced Liver Injury (DILI):  0.048
AMES Toxicity:  0.293
Rat Oral Acute Toxicity:  0.098
Maximum Recommended Daily Dose:  0.378
Skin Sensitization:  0.988
Carcinogencity:  0.156
Eye Corrosion:  0.003
Eye Irritation:  0.04
Respiratory Toxicity:  0.007

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

  Natural Product: NPC85192

Natural Product ID:  NPC85192
Common Name*:   Vanicoside A
IUPAC Name:   [(2R,3R,4S,5S)-5-[(2S,3R,4S,5S,6R)-3-acetyloxy-4,5-dihydroxy-6-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxymethyl]oxan-2-yl]oxy-3-hydroxy-4-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-5-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]oxolan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:  
Standard InCHIKey:  RNXDQKHOEWIRNH-FSZFHJIYSA-N
Standard InCHI:  InChI=1S/C51H50O21/c1-29(52)68-48-47(63)45(61)39(26-65-42(58)23-13-33-9-20-37(56)38(25-33)64-2)69-50(48)72-51(28-67-43(59)22-11-31-5-16-35(54)17-6-31)49(70-44(60)24-12-32-7-18-36(55)19-8-32)46(62)40(71-51)27-66-41(57)21-10-30-3-14-34(53)15-4-30/h3-25,39-40,45-50,53-56,61-63H,26-28H2,1-2H3/b21-10+,22-11+,23-13+,24-12+/t39-,40-,45-,46-,47+,48-,49+,50+,51+/m1/s1
SMILES:  CC(=O)O[C@@H]1[C@H]([C@@H]([C@@H](COC(=O)/C=C/c2ccc(c(c2)OC)O)O[C@H]1O[C@@]1(COC(=O)/C=C/c2ccc(cc2)O)[C@H]([C@@H]([C@@H](COC(=O)/C=C/c2ccc(cc2)O)O1)O)OC(=O)/C=C/c1ccc(cc1)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL454490
PubChem CID:   44575681
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000265] Carboxylic acids and derivatives
        • [CHEMONTID:0002995] Pentacarboxylic acids and derivatives

*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
NPO40997 Polygonum pensylvanicum Species Polygonaceae Eukaryota n.a. n.a. n.a. PMID[8176400]
NPO6826 Persicaria perfoliata Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6826 Persicaria perfoliata Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO6826 Persicaria perfoliata Species Polygonaceae 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
NPT2 Others Unspecified IC50 = 44.0 ug.mL-1 PMID[455760]

☑ 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 NPC85192 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 NPC125823
1.0 High Similarity NPC7145
1.0 High Similarity NPC143480
0.979 High Similarity NPC80732
0.979 High Similarity NPC3460
0.979 High Similarity NPC215095
0.979 High Similarity NPC199311
0.979 High Similarity NPC192763
0.979 High Similarity NPC300262
0.979 High Similarity NPC210611
0.979 High Similarity NPC28651
0.979 High Similarity NPC261122
0.979 High Similarity NPC201148
0.958 High Similarity NPC83743
0.958 High Similarity NPC287615
0.958 High Similarity NPC216819
0.958 High Similarity NPC262182
0.9524 High Similarity NPC472612
0.9524 High Similarity NPC289967
0.9524 High Similarity NPC472611
0.9408 High Similarity NPC149873
0.9408 High Similarity NPC7191
0.9392 High Similarity NPC478268
0.9388 High Similarity NPC476871
0.9388 High Similarity NPC470934
0.9388 High Similarity NPC188393
0.9375 High Similarity NPC110063
0.932 High Similarity NPC476386
0.932 High Similarity NPC473427
0.932 High Similarity NPC470933
0.932 High Similarity NPC283839
0.932 High Similarity NPC90896
0.932 High Similarity NPC476398
0.932 High Similarity NPC94871
0.932 High Similarity NPC259347
0.932 High Similarity NPC471062
0.932 High Similarity NPC306890
0.9257 High Similarity NPC257970
0.9257 High Similarity NPC470927
0.9247 High Similarity NPC476865
0.9184 High Similarity NPC232992
0.9178 High Similarity NPC34587
0.9178 High Similarity NPC476868
0.9178 High Similarity NPC100998
0.9178 High Similarity NPC34927
0.9178 High Similarity NPC476866
0.9178 High Similarity NPC476864
0.9178 High Similarity NPC476869
0.9178 High Similarity NPC476382
0.9178 High Similarity NPC252292
0.9167 High Similarity NPC59516
0.9161 High Similarity NPC226005
0.9145 High Similarity NPC11411
0.911 High Similarity NPC476867
0.9103 High Similarity NPC157816
0.9103 High Similarity NPC140502
0.9097 High Similarity NPC246024
0.9048 High Similarity NPC274960
0.9048 High Similarity NPC143120
0.9048 High Similarity NPC473909
0.9041 High Similarity NPC478239
0.9026 High Similarity NPC478269
0.9021 High Similarity NPC157554
0.8986 High Similarity NPC229505
0.898 High Similarity NPC297342
0.898 High Similarity NPC196063
0.898 High Similarity NPC141455
0.898 High Similarity NPC296954
0.898 High Similarity NPC300894
0.8912 High Similarity NPC298257
0.8912 High Similarity NPC476375
0.8912 High Similarity NPC269141
0.8912 High Similarity NPC112
0.8912 High Similarity NPC76406
0.8912 High Similarity NPC105005
0.8912 High Similarity NPC476381
0.8912 High Similarity NPC119537
0.8912 High Similarity NPC264632
0.8912 High Similarity NPC476384
0.8912 High Similarity NPC96795
0.8912 High Similarity NPC476378
0.8912 High Similarity NPC205864
0.8912 High Similarity NPC247032
0.8912 High Similarity NPC175214
0.8912 High Similarity NPC476380
0.8912 High Similarity NPC476397
0.891 High Similarity NPC478267
0.8904 High Similarity NPC134405
0.8904 High Similarity NPC476385
0.8904 High Similarity NPC186406
0.8904 High Similarity NPC476377
0.8904 High Similarity NPC47471
0.8897 High Similarity NPC100389
0.8881 High Similarity NPC471883
0.8859 High Similarity NPC199928
0.8851 High Similarity NPC232228
0.8851 High Similarity NPC64195
0.8844 High Similarity NPC222433
0.8844 High Similarity NPC265648
0.8836 High Similarity NPC475530
0.8836 High Similarity NPC473799
0.8836 High Similarity NPC202700
0.8831 High Similarity NPC131532
0.8819 High Similarity NPC476870
0.8811 High Similarity NPC28637
0.8808 High Similarity NPC475250
0.8808 High Similarity NPC106138
0.8784 High Similarity NPC40305
0.8774 High Similarity NPC478266
0.8767 High Similarity NPC476383
0.8767 High Similarity NPC68092
0.8767 High Similarity NPC89105
0.8767 High Similarity NPC472350
0.8767 High Similarity NPC81515
0.8767 High Similarity NPC321184
0.8767 High Similarity NPC328273
0.8767 High Similarity NPC321638
0.8767 High Similarity NPC197316
0.8767 High Similarity NPC64141
0.8767 High Similarity NPC171134
0.8767 High Similarity NPC205195
0.8759 High Similarity NPC37468
0.8759 High Similarity NPC186418
0.8742 High Similarity NPC478237
0.8726 High Similarity NPC478265
0.8725 High Similarity NPC292443
0.8718 High Similarity NPC471878
0.8716 High Similarity NPC67467
0.8701 High Similarity NPC115203
0.8699 High Similarity NPC260425
0.8699 High Similarity NPC78363
0.8699 High Similarity NPC476376
0.8684 High Similarity NPC478242
0.8681 High Similarity NPC254398
0.8679 High Similarity NPC227297
0.8671 High Similarity NPC219677
0.8667 High Similarity NPC138915
0.8658 High Similarity NPC113680
0.8658 High Similarity NPC278961
0.8649 High Similarity NPC472711
0.863 High Similarity NPC52277
0.863 High Similarity NPC199459
0.863 High Similarity NPC177035
0.8621 High Similarity NPC34293
0.8621 High Similarity NPC886
0.8621 High Similarity NPC135127
0.8621 High Similarity NPC287597
0.8618 High Similarity NPC252402
0.8618 High Similarity NPC226153
0.8618 High Similarity NPC304048
0.8618 High Similarity NPC102934
0.8611 High Similarity NPC473924
0.8611 High Similarity NPC252833
0.8611 High Similarity NPC473285
0.8599 High Similarity NPC133984
0.8599 High Similarity NPC226759
0.8591 High Similarity NPC473792
0.8591 High Similarity NPC473873
0.8581 High Similarity NPC110699
0.8581 High Similarity NPC106055
0.858 High Similarity NPC197708
0.858 High Similarity NPC658
0.8571 High Similarity NPC126206
0.8571 High Similarity NPC138738
0.8571 High Similarity NPC470413
0.8571 High Similarity NPC478249
0.8571 High Similarity NPC269914
0.8552 High Similarity NPC6836
0.8535 High Similarity NPC228357
0.8533 High Similarity NPC185307
0.8533 High Similarity NPC46092
0.8533 High Similarity NPC477898
0.8533 High Similarity NPC470950
0.8531 High Similarity NPC477294
0.8531 High Similarity NPC477293
0.8531 High Similarity NPC307110
0.8531 High Similarity NPC229784
0.8519 High Similarity NPC128403
0.8519 High Similarity NPC286809
0.8516 High Similarity NPC106818
0.8516 High Similarity NPC203664
0.8506 High Similarity NPC475224
0.8503 High Similarity NPC471664
0.8503 High Similarity NPC471665
0.8493 Intermediate Similarity NPC35731
0.8493 Intermediate Similarity NPC470881
0.8487 Intermediate Similarity NPC93610
0.8487 Intermediate Similarity NPC241846
0.8485 Intermediate Similarity NPC473630
0.8481 Intermediate Similarity NPC125495
0.8477 Intermediate Similarity NPC283995
0.8477 Intermediate Similarity NPC471063
0.8477 Intermediate Similarity NPC470235
0.8477 Intermediate Similarity NPC129417
0.8477 Intermediate Similarity NPC84181
0.8476 Intermediate Similarity NPC102851
0.8476 Intermediate Similarity NPC5786
0.8467 Intermediate Similarity NPC476356
0.8466 Intermediate Similarity NPC149300
0.8466 Intermediate Similarity NPC95421

  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 NPC85192 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
0.8767 High Similarity NPD7266 Discontinued
0.8205 Intermediate Similarity NPD1653 Approved
0.8095 Intermediate Similarity NPD7685 Pre-registration
0.8072 Intermediate Similarity NPD7228 Approved
0.795 Intermediate Similarity NPD8455 Phase 2
0.7949 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.787 Intermediate Similarity NPD7472 Approved
0.7811 Intermediate Similarity NPD7054 Approved
0.7803 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7765 Intermediate Similarity NPD7074 Phase 3
0.7758 Intermediate Similarity NPD6234 Discontinued
0.7733 Intermediate Similarity NPD7808 Phase 3
0.7719 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD8312 Approved
0.7688 Intermediate Similarity NPD8313 Approved
0.7674 Intermediate Similarity NPD7251 Discontinued
0.7674 Intermediate Similarity NPD7240 Approved
0.767 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7669 Intermediate Similarity NPD37 Approved
0.7667 Intermediate Similarity NPD3027 Phase 3
0.7647 Intermediate Similarity NPD3818 Discontinued
0.7636 Intermediate Similarity NPD4966 Approved
0.7636 Intermediate Similarity NPD4965 Approved
0.7636 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7636 Intermediate Similarity NPD4967 Phase 2
0.7619 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7616 Intermediate Similarity NPD6797 Phase 2
0.7595 Intermediate Similarity NPD6190 Approved
0.7578 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7517 Intermediate Similarity NPD1357 Approved
0.7468 Intermediate Similarity NPD6674 Discontinued
0.7456 Intermediate Similarity NPD7199 Phase 2
0.7427 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7427 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7427 Intermediate Similarity NPD6166 Phase 2
0.7403 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD1613 Approved
0.7371 Intermediate Similarity NPD6559 Discontinued
0.7366 Intermediate Similarity NPD7680 Approved
0.7365 Intermediate Similarity NPD3705 Approved
0.7353 Intermediate Similarity NPD8127 Discontinued
0.7293 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7261 Intermediate Similarity NPD7097 Phase 1
0.7248 Intermediate Similarity NPD1091 Approved
0.7243 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD8166 Discontinued
0.72 Intermediate Similarity NPD5844 Phase 1
0.72 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD1934 Approved
0.7143 Intermediate Similarity NPD5536 Phase 2
0.7143 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD2977 Approved
0.7101 Intermediate Similarity NPD2978 Approved
0.7078 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD3882 Suspended
0.7012 Intermediate Similarity NPD5058 Phase 3
0.7006 Intermediate Similarity NPD6233 Phase 2
0.7 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.6995 Remote Similarity NPD8151 Discontinued
0.6994 Remote Similarity NPD4628 Phase 3
0.6966 Remote Similarity NPD228 Approved
0.6964 Remote Similarity NPD7458 Discontinued
0.6962 Remote Similarity NPD3620 Phase 2
0.6962 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6961 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6959 Remote Similarity NPD3817 Phase 2
0.6944 Remote Similarity NPD7549 Discontinued
0.6928 Remote Similarity NPD2983 Phase 2
0.6928 Remote Similarity NPD2982 Phase 2
0.6923 Remote Similarity NPD4908 Phase 1
0.6923 Remote Similarity NPD1358 Approved
0.6923 Remote Similarity NPD4380 Phase 2
0.6919 Remote Similarity NPD7768 Phase 2
0.6918 Remote Similarity NPD230 Phase 1
0.6914 Remote Similarity NPD6232 Discontinued
0.6901 Remote Similarity NPD2801 Approved
0.6901 Remote Similarity NPD1465 Phase 2
0.6893 Remote Similarity NPD7473 Discontinued
0.6879 Remote Similarity NPD7095 Approved
0.6879 Remote Similarity NPD7075 Discontinued
0.6867 Remote Similarity NPD4357 Discontinued
0.6863 Remote Similarity NPD2981 Phase 2
0.6859 Remote Similarity NPD2861 Phase 2
0.6859 Remote Similarity NPD9494 Approved
0.6855 Remote Similarity NPD4060 Phase 1
0.6854 Remote Similarity NPD3751 Discontinued
0.6836 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6835 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6835 Remote Similarity NPD6798 Discontinued
0.6829 Remote Similarity NPD1652 Phase 2
0.6826 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6823 Remote Similarity NPD7435 Discontinued
0.6818 Remote Similarity NPD3787 Discontinued
0.6813 Remote Similarity NPD4340 Discontinued
0.6813 Remote Similarity NPD1933 Approved
0.6807 Remote Similarity NPD6783 Clinical (unspecified phase)
0.6796 Remote Similarity NPD7038 Approved
0.6796 Remote Similarity NPD7039 Approved
0.677 Remote Similarity NPD2492 Phase 1
0.677 Remote Similarity NPD6653 Approved
0.6763 Remote Similarity NPD5402 Approved
0.6757 Remote Similarity NPD5283 Phase 1
0.6752 Remote Similarity NPD3018 Phase 2
0.6736 Remote Similarity NPD3134 Approved
0.673 Remote Similarity NPD3764 Approved
0.6727 Remote Similarity NPD4237 Approved
0.6727 Remote Similarity NPD4236 Phase 3
0.6727 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6725 Remote Similarity NPD7028 Phase 2
0.6708 Remote Similarity NPD6355 Discontinued
0.6708 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6708 Remote Similarity NPD5124 Phase 1
0.6707 Remote Similarity NPD5762 Approved
0.6707 Remote Similarity NPD5763 Approved
0.6706 Remote Similarity NPD3687 Approved
0.6706 Remote Similarity NPD3686 Approved
0.6705 Remote Similarity NPD7819 Suspended
0.6705 Remote Similarity NPD5563 Clinical (unspecified phase)
0.6705 Remote Similarity NPD5494 Approved
0.6705 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6705 Remote Similarity NPD6818 Clinical (unspecified phase)
0.6701 Remote Similarity NPD7874 Approved
0.6701 Remote Similarity NPD7870 Phase 2
0.6701 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6701 Remote Similarity NPD7871 Phase 2
0.6689 Remote Similarity NPD7843 Approved
0.6687 Remote Similarity NPD4110 Phase 3
0.6687 Remote Similarity NPD5588 Approved
0.6687 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6686 Remote Similarity NPD6273 Approved
0.6686 Remote Similarity NPD6386 Approved
0.6686 Remote Similarity NPD7411 Suspended
0.6686 Remote Similarity NPD6385 Approved
0.6686 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6684 Remote Similarity NPD6823 Phase 2
0.6667 Remote Similarity NPD6777 Approved
0.6667 Remote Similarity NPD7783 Phase 2
0.6667 Remote Similarity NPD6781 Approved
0.6667 Remote Similarity NPD6780 Approved
0.6667 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6841 Approved
0.6667 Remote Similarity NPD6779 Approved
0.6667 Remote Similarity NPD6776 Approved
0.6667 Remote Similarity NPD1511 Approved
0.6667 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6959 Discontinued
0.6667 Remote Similarity NPD5125 Phase 3
0.6667 Remote Similarity NPD6843 Phase 3
0.6667 Remote Similarity NPD6782 Approved
0.6667 Remote Similarity NPD6778 Approved
0.6667 Remote Similarity NPD5126 Approved
0.6667 Remote Similarity NPD6842 Approved
0.6649 Remote Similarity NPD7698 Approved
0.6649 Remote Similarity NPD7696 Phase 3
0.6649 Remote Similarity NPD7697 Approved
0.6647 Remote Similarity NPD5403 Approved
0.6646 Remote Similarity NPD1558 Phase 1
0.6646 Remote Similarity NPD4140 Approved
0.6646 Remote Similarity NPD2935 Discontinued
0.6627 Remote Similarity NPD5698 Clinical (unspecified phase)
0.6627 Remote Similarity NPD3060 Approved
0.6626 Remote Similarity NPD4536 Approved
0.6626 Remote Similarity NPD4978 Clinical (unspecified phase)
0.6626 Remote Similarity NPD4538 Approved
0.6626 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6625 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6623 Remote Similarity NPD3496 Discontinued
0.6622 Remote Similarity NPD969 Suspended
0.6613 Remote Similarity NPD8434 Phase 2
0.6605 Remote Similarity NPD447 Suspended
0.6599 Remote Similarity NPD7701 Phase 2
0.6595 Remote Similarity NPD8054 Approved
0.6595 Remote Similarity NPD8053 Approved
0.6588 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6588 Remote Similarity NPD1512 Approved
0.6585 Remote Similarity NPD7033 Discontinued
0.6581 Remote Similarity NPD422 Phase 1
0.6578 Remote Similarity NPD7906 Approved
0.6577 Remote Similarity NPD5535 Approved
0.6571 Remote Similarity NPD5353 Approved
0.657 Remote Similarity NPD3455 Phase 2
0.657 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6561 Remote Similarity NPD3225 Approved
0.6556 Remote Similarity NPD7157 Approved
0.6552 Remote Similarity NPD6801 Discontinued
0.6531 Remote Similarity NPD8319 Approved
0.6531 Remote Similarity NPD8320 Phase 1
0.6529 Remote Similarity NPD4160 Clinical (unspecified phase)
0.6529 Remote Similarity NPD5401 Approved
0.6529 Remote Similarity NPD7446 Clinical (unspecified phase)
0.6524 Remote Similarity NPD8150 Discontinued
0.6514 Remote Similarity NPD5773 Approved
0.6514 Remote Similarity NPD5772 Approved
0.6506 Remote Similarity NPD1375 Discontinued
0.6506 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6503 Remote Similarity NPD5735 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