Structure

Physi-Chem Properties

Molecular Weight:  640.2
Volume:  595.466
LogP:  -0.25
LogD:  -0.207
LogS:  -1.829
# Rotatable Bonds:  12
TPSA:  265.52
# H-Bond Aceptor:  16
# H-Bond Donor:  10
# Rings:  4
# Heavy Atoms:  16

MedChem Properties

QED Drug-Likeness Score:  0.072
Synthetic Accessibility Score:  4.72
Fsp3:  0.483
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.637
MDCK Permeability:  2.3204640456242487e-05
Pgp-inhibitor:  0.003
Pgp-substrate:  0.99
Human Intestinal Absorption (HIA):  0.996
20% Bioavailability (F20%):  0.978
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.105
Plasma Protein Binding (PPB):  94.67484283447266%
Volume Distribution (VD):  0.345
Pgp-substrate:  8.292266845703125%

ADMET: Metabolism

CYP1A2-inhibitor:  0.062
CYP1A2-substrate:  0.014
CYP2C19-inhibitor:  0.07
CYP2C19-substrate:  0.049
CYP2C9-inhibitor:  0.071
CYP2C9-substrate:  0.231
CYP2D6-inhibitor:  0.032
CYP2D6-substrate:  0.163
CYP3A4-inhibitor:  0.041
CYP3A4-substrate:  0.01

ADMET: Excretion

Clearance (CL):  1.019
Half-life (T1/2):  0.891

ADMET: Toxicity

hERG Blockers:  0.223
Human Hepatotoxicity (H-HT):  0.108
Drug-inuced Liver Injury (DILI):  0.035
AMES Toxicity:  0.271
Rat Oral Acute Toxicity:  0.087
Maximum Recommended Daily Dose:  0.003
Skin Sensitization:  0.968
Carcinogencity:  0.076
Eye Corrosion:  0.003
Eye Irritation:  0.177
Respiratory Toxicity:  0.011

Download Data

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

  Natural Product: NPC205195

Natural Product ID:  NPC205195
Common Name*:   Plantainoside D
IUPAC Name:   [(2R,3R,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms:   Plantainoside D
Standard InCHIKey:  CBZYUWGJNYOKHT-ZKDZFUIGSA-N
Standard InCHI:  InChI=1S/C29H36O16/c30-11-19-22(36)24(38)25(39)29(43-19)45-27-23(37)20(12-42-21(35)6-3-13-1-4-15(31)17(33)9-13)44-28(26(27)40)41-8-7-14-2-5-16(32)18(34)10-14/h1-6,9-10,19-20,22-34,36-40H,7-8,11-12H2/b6-3+/t19-,20-,22-,23-,24+,25-,26-,27+,28-,29+/m1/s1
SMILES:  OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](COC(=O)/C=C/c3ccc(c(c3)O)O)O[C@H]([C@@H]2O)OCCc2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL452413
PubChem CID:   9986606
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000476] Cinnamic acids and derivatives
        • [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives
          • [CHEMONTID:0000059] Coumaric 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
NPO1097 Bacopa monnieri Species Plantaginaceae Eukaryota n.a. n.a. n.a. PMID[12502309]
NPO30241 Picrorhiza scrophulariiflora Species Plantaginaceae Eukaryota n.a. root n.a. PMID[15133218]
NPO30241 Picrorhiza scrophulariiflora Species Plantaginaceae Eukaryota n.a. root n.a. PMID[15706916]
NPO1097 Bacopa monnieri Species Plantaginaceae Eukaryota whole plant Zhangzhou, Fujian Province, China n.a. PMID[17343408]
NPO30241 Picrorhiza scrophulariiflora Species Plantaginaceae Eukaryota n.a. n.a. n.a. PMID[24035096]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. n.a. n.a. PMID[2488968]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. seed n.a. PMID[2610694]
NPO8918 Plantago depressa Species Plantaginaceae Eukaryota n.a. n.a. n.a. PMID[26562611]
NPO16764 Penstemon linarioides Species Plantaginaceae Eukaryota n.a. n.a. n.a. PMID[9834166]
NPO4443 Digitalis purpurea Species Plantaginaceae Eukaryota n.a. n.a. n.a. PMID[9834166]
NPO30241 Picrorhiza scrophulariiflora Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8416 Picrorhiza kurrooa Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4443 Digitalis purpurea Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4497 Plantago hostifolia Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8918 Plantago depressa Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13325 Plantago lanceolata Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7377 Hemiphragma heterophyllum Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4497 Plantago hostifolia Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13325 Plantago lanceolata Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7377 Hemiphragma heterophyllum Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8918 Plantago depressa Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4443 Digitalis purpurea Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1097 Bacopa monnieri Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14720 Neopicrorhiza scrophulariiflora Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8416 Picrorhiza kurrooa Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO30241 Picrorhiza scrophulariiflora Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4443 Digitalis purpurea Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8918 Plantago depressa Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4443 Digitalis purpurea Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14720 Neopicrorhiza scrophulariiflora Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8416 Picrorhiza kurrooa Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8918 Plantago depressa Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16764 Penstemon linarioides Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8918 Plantago depressa Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8416 Picrorhiza kurrooa Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4443 Digitalis purpurea Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13325 Plantago lanceolata Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1097 Bacopa monnieri Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4497 Plantago hostifolia Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14720 Neopicrorhiza scrophulariiflora Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7377 Hemiphragma heterophyllum Species Plantaginaceae 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
NPT182 Individual Protein Protein kinase C alpha Homo sapiens IC50 = 14800.0 nM PMID[542022]

☑ 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 NPC205195 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
0.9924 High Similarity NPC260425
0.985 High Similarity NPC476385
0.985 High Similarity NPC47471
0.985 High Similarity NPC134405
0.985 High Similarity NPC476377
0.9848 High Similarity NPC81515
0.9848 High Similarity NPC476383
0.9848 High Similarity NPC197316
0.9848 High Similarity NPC89105
0.9848 High Similarity NPC64141
0.9848 High Similarity NPC68092
0.9848 High Similarity NPC472350
0.9774 High Similarity NPC475530
0.9774 High Similarity NPC473799
0.9773 High Similarity NPC78363
0.9704 High Similarity NPC96795
0.9704 High Similarity NPC264632
0.9704 High Similarity NPC476397
0.9704 High Similarity NPC298257
0.9704 High Similarity NPC476380
0.9704 High Similarity NPC476381
0.9704 High Similarity NPC269141
0.9704 High Similarity NPC476384
0.9704 High Similarity NPC119537
0.9704 High Similarity NPC105005
0.9704 High Similarity NPC76406
0.9704 High Similarity NPC112
0.9704 High Similarity NPC476375
0.9704 High Similarity NPC476378
0.9704 High Similarity NPC175214
0.9704 High Similarity NPC247032
0.9704 High Similarity NPC205864
0.9695 High Similarity NPC287597
0.9695 High Similarity NPC886
0.9695 High Similarity NPC34293
0.9632 High Similarity NPC196063
0.9632 High Similarity NPC300894
0.9632 High Similarity NPC296954
0.9632 High Similarity NPC64195
0.9632 High Similarity NPC141455
0.963 High Similarity NPC265648
0.963 High Similarity NPC222433
0.9624 High Similarity NPC476376
0.9552 High Similarity NPC328273
0.9552 High Similarity NPC321638
0.9552 High Similarity NPC171134
0.9552 High Similarity NPC321184
0.9493 High Similarity NPC229505
0.9474 High Similarity NPC476870
0.942 High Similarity NPC100998
0.942 High Similarity NPC34587
0.942 High Similarity NPC252292
0.942 High Similarity NPC34927
0.942 High Similarity NPC476382
0.9416 High Similarity NPC40305
0.9394 High Similarity NPC473285
0.9348 High Similarity NPC476867
0.9318 High Similarity NPC235294
0.9318 High Similarity NPC46137
0.9313 High Similarity NPC477294
0.9313 High Similarity NPC477293
0.9313 High Similarity NPC229784
0.9291 High Similarity NPC470933
0.9291 High Similarity NPC473427
0.9291 High Similarity NPC471062
0.9291 High Similarity NPC94871
0.9291 High Similarity NPC306890
0.9291 High Similarity NPC476398
0.9291 High Similarity NPC259347
0.9291 High Similarity NPC476386
0.9286 High Similarity NPC232992
0.9281 High Similarity NPC476868
0.9281 High Similarity NPC476866
0.9281 High Similarity NPC476869
0.9281 High Similarity NPC476864
0.9254 High Similarity NPC471883
0.9248 High Similarity NPC254275
0.9237 High Similarity NPC232880
0.9225 High Similarity NPC470934
0.9225 High Similarity NPC257970
0.9225 High Similarity NPC188393
0.9225 High Similarity NPC470927
0.9214 High Similarity NPC476865
0.9203 High Similarity NPC140502
0.9185 High Similarity NPC263829
0.9173 High Similarity NPC219677
0.9173 High Similarity NPC225384
0.9173 High Similarity NPC246869
0.9173 High Similarity NPC138777
0.9167 High Similarity NPC184092
0.916 High Similarity NPC288416
0.916 High Similarity NPC476873
0.913 High Similarity NPC186406
0.9104 High Similarity NPC473924
0.9097 High Similarity NPC106818
0.9037 High Similarity NPC254398
0.9034 High Similarity NPC87403
0.9034 High Similarity NPC471874
0.903 High Similarity NPC478255
0.9015 High Similarity NPC264900
0.9015 High Similarity NPC108659
0.9015 High Similarity NPC231607
0.9015 High Similarity NPC79715
0.9008 High Similarity NPC126991
0.9008 High Similarity NPC83218
0.9007 High Similarity NPC216819
0.9007 High Similarity NPC262182
0.9007 High Similarity NPC287615
0.9007 High Similarity NPC83743
0.9 High Similarity NPC478239
0.8958 High Similarity NPC476871
0.8951 High Similarity NPC199311
0.8951 High Similarity NPC192763
0.8951 High Similarity NPC3460
0.8951 High Similarity NPC215095
0.8951 High Similarity NPC261122
0.8951 High Similarity NPC210611
0.8951 High Similarity NPC300262
0.8951 High Similarity NPC28776
0.8951 High Similarity NPC201148
0.8951 High Similarity NPC23677
0.8951 High Similarity NPC80732
0.8951 High Similarity NPC473138
0.8951 High Similarity NPC28651
0.8947 High Similarity NPC225307
0.8939 High Similarity NPC94179
0.8939 High Similarity NPC471157
0.8936 High Similarity NPC292443
0.8936 High Similarity NPC110063
0.8936 High Similarity NPC232228
0.8929 High Similarity NPC296643
0.8929 High Similarity NPC157816
0.8921 High Similarity NPC202700
0.8905 High Similarity NPC123988
0.8897 High Similarity NPC28637
0.8889 High Similarity NPC106138
0.8872 High Similarity NPC106677
0.8841 High Similarity NPC470572
0.8841 High Similarity NPC157554
0.8836 High Similarity NPC478268
0.8811 High Similarity NPC199928
0.8806 High Similarity NPC148982
0.8786 High Similarity NPC106944
0.8779 High Similarity NPC52097
0.8777 High Similarity NPC84789
0.8777 High Similarity NPC310252
0.8777 High Similarity NPC302583
0.8777 High Similarity NPC100558
0.8767 High Similarity NPC143480
0.8767 High Similarity NPC7145
0.8767 High Similarity NPC85192
0.8767 High Similarity NPC125823
0.8759 High Similarity NPC478242
0.8759 High Similarity NPC283839
0.8759 High Similarity NPC90896
0.8732 High Similarity NPC113680
0.8732 High Similarity NPC278961
0.8731 High Similarity NPC35288
0.8731 High Similarity NPC156692
0.8731 High Similarity NPC471882
0.8731 High Similarity NPC173150
0.8731 High Similarity NPC45224
0.8731 High Similarity NPC471881
0.8714 High Similarity NPC220942
0.8714 High Similarity NPC226005
0.8714 High Similarity NPC100389
0.8707 High Similarity NPC472612
0.8707 High Similarity NPC289967
0.8707 High Similarity NPC472611
0.8705 High Similarity NPC199459
0.8705 High Similarity NPC177035
0.8705 High Similarity NPC471664
0.8705 High Similarity NPC52277
0.8705 High Similarity NPC186418
0.8705 High Similarity NPC471665
0.8702 High Similarity NPC147654
0.8702 High Similarity NPC266045
0.8702 High Similarity NPC11724
0.8699 High Similarity NPC69367
0.8696 High Similarity NPC35731
0.8696 High Similarity NPC135127
0.8662 High Similarity NPC473873
0.8662 High Similarity NPC473792
0.8657 High Similarity NPC252114
0.8657 High Similarity NPC61181
0.8643 High Similarity NPC470413
0.8643 High Similarity NPC101686
0.8643 High Similarity NPC469364
0.8643 High Similarity NPC65262
0.8643 High Similarity NPC126206
0.8643 High Similarity NPC138738
0.8639 High Similarity NPC140151
0.8626 High Similarity NPC476872
0.8601 High Similarity NPC204644
0.86 High Similarity NPC11411
0.8593 High Similarity NPC103533
0.8582 High Similarity NPC90318
0.8581 High Similarity NPC53587
0.8581 High Similarity NPC176186
0.8581 High Similarity NPC169404

  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 NPC205195 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
0.9848 High Similarity NPD7266 Discontinued
0.8255 Intermediate Similarity NPD1653 Approved
0.8219 Intermediate Similarity NPD6190 Approved
0.7901 Intermediate Similarity NPD7472 Approved
0.784 Intermediate Similarity NPD7054 Approved
0.7805 Intermediate Similarity NPD7251 Discontinued
0.7805 Intermediate Similarity NPD7685 Pre-registration
0.7791 Intermediate Similarity NPD7074 Phase 3
0.7778 Intermediate Similarity NPD7228 Approved
0.7744 Intermediate Similarity NPD6797 Phase 2
0.7692 Intermediate Similarity NPD3027 Phase 3
0.7658 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7655 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7655 Intermediate Similarity NPD1613 Approved
0.7651 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7651 Intermediate Similarity NPD7808 Phase 3
0.7643 Intermediate Similarity NPD8455 Phase 2
0.7561 Intermediate Similarity NPD3818 Discontinued
0.7516 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD6234 Discontinued
0.7434 Intermediate Similarity NPD8166 Discontinued
0.7425 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7412 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD8313 Approved
0.7396 Intermediate Similarity NPD8312 Approved
0.7394 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7381 Intermediate Similarity NPD7240 Approved
0.7379 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7376 Intermediate Similarity NPD1091 Approved
0.7368 Intermediate Similarity NPD6674 Discontinued
0.7365 Intermediate Similarity NPD230 Phase 1
0.7358 Intermediate Similarity NPD37 Approved
0.7329 Intermediate Similarity NPD4966 Approved
0.7329 Intermediate Similarity NPD4967 Phase 2
0.7329 Intermediate Similarity NPD4965 Approved
0.731 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD4978 Clinical (unspecified phase)
0.7229 Intermediate Similarity NPD6166 Phase 2
0.7229 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7229 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7202 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7185 Intermediate Similarity NPD3021 Approved
0.7185 Intermediate Similarity NPD3022 Approved
0.7176 Intermediate Similarity NPD6559 Discontinued
0.7152 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD1934 Approved
0.7133 Intermediate Similarity NPD3705 Approved
0.7125 Intermediate Similarity NPD4380 Phase 2
0.7124 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD1465 Phase 2
0.7099 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD4628 Phase 3
0.7086 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD3455 Phase 2
0.7048 Intermediate Similarity NPD7199 Phase 2
0.7042 Intermediate Similarity NPD1357 Approved
0.7039 Intermediate Similarity NPD7097 Phase 1
0.702 Intermediate Similarity NPD4340 Discontinued
0.7006 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD5844 Phase 1
0.6993 Remote Similarity NPD5126 Approved
0.6993 Remote Similarity NPD5125 Phase 3
0.697 Remote Similarity NPD7075 Discontinued
0.6961 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6959 Remote Similarity NPD2861 Phase 2
0.6957 Remote Similarity NPD228 Approved
0.6957 Remote Similarity NPD969 Suspended
0.6954 Remote Similarity NPD4060 Phase 1
0.6951 Remote Similarity NPD3817 Phase 2
0.6951 Remote Similarity NPD5402 Approved
0.6946 Remote Similarity NPD8127 Discontinued
0.6933 Remote Similarity NPD3764 Approved
0.6923 Remote Similarity NPD1652 Phase 2
0.6902 Remote Similarity NPD7680 Approved
0.6901 Remote Similarity NPD5536 Phase 2
0.6899 Remote Similarity NPD5058 Phase 3
0.689 Remote Similarity NPD2977 Approved
0.689 Remote Similarity NPD2801 Approved
0.689 Remote Similarity NPD2978 Approved
0.6887 Remote Similarity NPD6233 Phase 2
0.6867 Remote Similarity NPD7095 Approved
0.6864 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6863 Remote Similarity NPD5314 Approved
0.6855 Remote Similarity NPD1511 Approved
0.6853 Remote Similarity NPD9545 Approved
0.6849 Remote Similarity NPD9269 Phase 2
0.6842 Remote Similarity NPD3062 Approved
0.6842 Remote Similarity NPD3061 Approved
0.6842 Remote Similarity NPD3059 Approved
0.6842 Remote Similarity NPD3751 Discontinued
0.6832 Remote Similarity NPD5403 Approved
0.6813 Remote Similarity NPD4160 Clinical (unspecified phase)
0.6807 Remote Similarity NPD3882 Suspended
0.68 Remote Similarity NPD4908 Phase 1
0.6797 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6797 Remote Similarity NPD5124 Phase 1
0.6788 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6788 Remote Similarity NPD1358 Approved
0.677 Remote Similarity NPD1512 Approved
0.6759 Remote Similarity NPD9384 Approved
0.6759 Remote Similarity NPD9381 Approved
0.6753 Remote Similarity NPD6653 Approved
0.6748 Remote Similarity NPD7458 Discontinued
0.6738 Remote Similarity NPD5283 Phase 1
0.6733 Remote Similarity NPD5736 Approved
0.6732 Remote Similarity NPD943 Approved
0.6732 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6732 Remote Similarity NPD3620 Phase 2
0.6731 Remote Similarity NPD9570 Approved
0.6731 Remote Similarity NPD2935 Discontinued
0.6727 Remote Similarity NPD7945 Clinical (unspecified phase)
0.672 Remote Similarity NPD8151 Discontinued
0.6712 Remote Similarity NPD3496 Discontinued
0.6711 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6711 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6711 Remote Similarity NPD3094 Phase 2
0.6711 Remote Similarity NPD6798 Discontinued
0.671 Remote Similarity NPD4536 Approved
0.671 Remote Similarity NPD4537 Clinical (unspecified phase)
0.671 Remote Similarity NPD4538 Approved
0.6709 Remote Similarity NPD5698 Clinical (unspecified phase)
0.6708 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6708 Remote Similarity NPD5401 Approved
0.6706 Remote Similarity NPD6232 Discontinued
0.6706 Remote Similarity NPD3787 Discontinued
0.6689 Remote Similarity NPD2983 Phase 2
0.6689 Remote Similarity NPD2982 Phase 2
0.6688 Remote Similarity NPD1933 Approved
0.6688 Remote Similarity NPD6355 Discontinued
0.6688 Remote Similarity NPD5763 Approved
0.6688 Remote Similarity NPD5762 Approved
0.6687 Remote Similarity NPD3687 Approved
0.6687 Remote Similarity NPD7819 Suspended
0.6687 Remote Similarity NPD3686 Approved
0.6686 Remote Similarity NPD7473 Discontinued
0.6685 Remote Similarity NPD8150 Discontinued
0.6684 Remote Similarity NPD8320 Phase 1
0.6684 Remote Similarity NPD8319 Approved
0.6667 Remote Similarity NPD3750 Approved
0.6667 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5588 Approved
0.6667 Remote Similarity NPD6385 Approved
0.6667 Remote Similarity NPD1610 Phase 2
0.6667 Remote Similarity NPD7843 Approved
0.6667 Remote Similarity NPD422 Phase 1
0.6667 Remote Similarity NPD5960 Phase 3
0.6667 Remote Similarity NPD6386 Approved
0.6648 Remote Similarity NPD6843 Phase 3
0.6648 Remote Similarity NPD6842 Approved
0.6648 Remote Similarity NPD7549 Discontinued
0.6648 Remote Similarity NPD6841 Approved
0.6644 Remote Similarity NPD3225 Approved
0.6643 Remote Similarity NPD7157 Approved
0.6631 Remote Similarity NPD7435 Discontinued
0.663 Remote Similarity NPD7699 Phase 2
0.663 Remote Similarity NPD7700 Phase 2
0.6627 Remote Similarity NPD6801 Discontinued
0.6623 Remote Similarity NPD826 Approved
0.6623 Remote Similarity NPD3018 Phase 2
0.6623 Remote Similarity NPD9494 Approved
0.6623 Remote Similarity NPD825 Approved
0.6623 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6623 Remote Similarity NPD1558 Phase 1
0.6622 Remote Similarity NPD2981 Phase 2
0.6621 Remote Similarity NPD1548 Phase 1
0.6605 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6605 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6604 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6604 Remote Similarity NPD3060 Approved
0.6594 Remote Similarity NPD3134 Approved
0.6593 Remote Similarity NPD1242 Phase 1
0.6591 Remote Similarity NPD2933 Approved
0.6591 Remote Similarity NPD7039 Approved
0.6591 Remote Similarity NPD2934 Approved
0.6591 Remote Similarity NPD7038 Approved
0.6588 Remote Similarity NPD5494 Approved
0.6577 Remote Similarity NPD9622 Approved
0.6575 Remote Similarity NPD9268 Approved
0.6568 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6566 Remote Similarity NPD7411 Suspended
0.6562 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6562 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6562 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6562 Remote Similarity NPD4110 Phase 3
0.6561 Remote Similarity NPD7033 Discontinued
0.6561 Remote Similarity NPD4108 Discontinued
0.6558 Remote Similarity NPD4062 Phase 3
0.6558 Remote Similarity NPD6663 Approved
0.6557 Remote Similarity NPD6534 Approved
0.6557 Remote Similarity NPD6535 Approved
0.6554 Remote Similarity NPD3092 Approved
0.6549 Remote Similarity NPD5535 Approved
0.6545 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6543 Remote Similarity NPD4357 Discontinued
0.6543 Remote Similarity NPD6799 Approved
0.6541 Remote Similarity NPD2860 Approved
0.6541 Remote Similarity NPD2859 Approved
0.6541 Remote Similarity NPD1549 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