Structure

Physi-Chem Properties

Molecular Weight:  906.27
Volume:  922.582
LogP:  7.831
LogD:  3.898
LogS:  -3.082
# Rotatable Bonds:  8
TPSA:  209.76
# H-Bond Aceptor:  12
# H-Bond Donor:  9
# Rings:  11
# Heavy Atoms:  12

MedChem Properties

QED Drug-Likeness Score:  0.065
Synthetic Accessibility Score:  5.071
Fsp3:  0.107
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.086
MDCK Permeability:  6.427414973586565e-06
Pgp-inhibitor:  0.187
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.963
20% Bioavailability (F20%):  0.562
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.002
Plasma Protein Binding (PPB):  93.85558319091797%
Volume Distribution (VD):  0.681
Pgp-substrate:  4.234277248382568%

ADMET: Metabolism

CYP1A2-inhibitor:  0.159
CYP1A2-substrate:  0.139
CYP2C19-inhibitor:  0.974
CYP2C19-substrate:  0.037
CYP2C9-inhibitor:  0.879
CYP2C9-substrate:  0.999
CYP2D6-inhibitor:  0.018
CYP2D6-substrate:  0.92
CYP3A4-inhibitor:  0.894
CYP3A4-substrate:  0.323

ADMET: Excretion

Clearance (CL):  15.367
Half-life (T1/2):  0.204

ADMET: Toxicity

hERG Blockers:  0.128
Human Hepatotoxicity (H-HT):  0.186
Drug-inuced Liver Injury (DILI):  0.893
AMES Toxicity:  0.07
Rat Oral Acute Toxicity:  0.986
Maximum Recommended Daily Dose:  0.996
Skin Sensitization:  0.952
Carcinogencity:  0.033
Eye Corrosion:  0.003
Eye Irritation:  0.909
Respiratory Toxicity:  0.02

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

  Natural Product: NPC112819

Natural Product ID:  NPC112819
Common Name*:   Vitisin C
IUPAC Name:   5-[(2S,3S)-4-[(E)-2-[(3S)-3-[(3S)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-yl]ethenyl]-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol
Synonyms:   Vitisin C
Standard InCHIKey:  WZKKRZSJTLGPHH-GXHOOJFBSA-N
Standard InCHI:  InChI=1S/C56H42O12/c57-35-10-4-29(5-11-35)54-50(33-19-38(60)23-39(61)20-33)49-32(18-42(64)26-47(49)67-54)3-1-28-2-16-46-44(17-28)52(56(66-46)31-8-14-37(59)15-9-31)45-25-43(65)27-48-53(45)51(34-21-40(62)24-41(63)22-34)55(68-48)30-6-12-36(58)13-7-30/h1-27,50-52,54-65H/b3-1+/t50-,51-,52+,54+,55?,56?/m0/s1
SMILES:  C(=Cc1cc(cc2c1[C@H](c1cc(cc(c1)O)O)[C@@H](c1ccc(cc1)O)O2)O)/c1ccc2c(c1)[C@H](c1cc(cc3c1[C@H](c1cc(cc(c1)O)O)C(c1ccc(cc1)O)O3)O)C(c1ccc(cc1)O)O2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1082603
PubChem CID:   46890015
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. Nigeria(latitude 80°N and longitude 4°E) 2005; 2006 DOI[10.1002/ejlt.201000080]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s11306-010-0259-y]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s11306-014-0638-x]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s11746-997-0093-1]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.phytol.2008.07.007]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Seeds Plovdiv, Plovdiv region in South Bulgaria DOI[10.1051/CTV/20163101031]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[11170689]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. fruit n.a. PMID[11312782]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. leaf n.a. PMID[11312782]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[11408943]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[11599360]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. fruit n.a. PMID[12105962]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. Esuela Tecnica Superior de Ingenieros Agrónomos de Albacete 2007 PMID[19256538]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[20826702]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota n.a. seed n.a. PMID[21381697]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[22537213]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[23759170]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Stalks n.a. n.a. PMID[24521157]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Seeds Benedictine Pannonhalma Archabbey, Hungary PMID[29803478]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[31433178]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Fruits n.a. Database[FooDB]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Leaf Essent. Oil n.a. n.a. Database[FooDB]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. Database[FooDB]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. Database[MetaboLights]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17024 Vitis vinifera Species Vitaceae 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 Inhibition = 32.0 % PMID[505017]

☑ 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 NPC112819 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 NPC6702
1.0 High Similarity NPC133209
0.9856 High Similarity NPC149633
0.9716 High Similarity NPC111134
0.965 High Similarity NPC218801
0.9645 High Similarity NPC176804
0.9645 High Similarity NPC71686
0.9583 High Similarity NPC157081
0.9583 High Similarity NPC105073
0.9583 High Similarity NPC233886
0.9583 High Similarity NPC224528
0.9507 High Similarity NPC14468
0.9456 High Similarity NPC202104
0.9444 High Similarity NPC122980
0.9444 High Similarity NPC177172
0.9444 High Similarity NPC148516
0.9444 High Similarity NPC107862
0.9444 High Similarity NPC180605
0.9441 High Similarity NPC242774
0.9441 High Similarity NPC224921
0.9441 High Similarity NPC237546
0.9441 High Similarity NPC231712
0.9384 High Similarity NPC120633
0.9384 High Similarity NPC473018
0.9257 High Similarity NPC157333
0.9209 High Similarity NPC15109
0.9209 High Similarity NPC11727
0.9209 High Similarity NPC125579
0.9078 High Similarity NPC470308
0.9078 High Similarity NPC470307
0.9007 High Similarity NPC471522
0.8993 High Similarity NPC476391
0.8951 High Similarity NPC182509
0.8951 High Similarity NPC213607
0.8951 High Similarity NPC174787
0.8873 High Similarity NPC141717
0.8836 High Similarity NPC15659
0.8836 High Similarity NPC304894
0.8819 High Similarity NPC273623
0.8786 High Similarity NPC473309
0.8774 High Similarity NPC90822
0.8767 High Similarity NPC173203
0.8767 High Similarity NPC163508
0.8742 High Similarity NPC59692
0.8742 High Similarity NPC233467
0.8732 High Similarity NPC476616
0.8732 High Similarity NPC476615
0.8732 High Similarity NPC476617
0.8732 High Similarity NPC473107
0.8725 High Similarity NPC20757
0.8725 High Similarity NPC227516
0.8714 High Similarity NPC254000
0.8681 High Similarity NPC472646
0.8681 High Similarity NPC71465
0.8675 High Similarity NPC324517
0.8675 High Similarity NPC321972
0.8675 High Similarity NPC329343
0.8671 High Similarity NPC37410
0.8671 High Similarity NPC258780
0.8654 High Similarity NPC48880
0.8643 High Similarity NPC471518
0.8643 High Similarity NPC471519
0.863 High Similarity NPC277331
0.863 High Similarity NPC100482
0.8618 High Similarity NPC226809
0.8618 High Similarity NPC279406
0.8611 High Similarity NPC170328
0.8611 High Similarity NPC472647
0.8611 High Similarity NPC206525
0.8611 High Similarity NPC191462
0.8611 High Similarity NPC472648
0.8611 High Similarity NPC133463
0.8611 High Similarity NPC472649
0.8609 High Similarity NPC477612
0.8581 High Similarity NPC475492
0.8562 High Similarity NPC224161
0.8543 High Similarity NPC470098
0.8543 High Similarity NPC473266
0.8543 High Similarity NPC470826
0.8533 High Similarity NPC108811
0.8533 High Similarity NPC153182
0.8533 High Similarity NPC202742
0.8533 High Similarity NPC170103
0.8533 High Similarity NPC262911
0.8533 High Similarity NPC294558
0.8533 High Similarity NPC18185
0.8533 High Similarity NPC70409
0.8533 High Similarity NPC174251
0.8533 High Similarity NPC58190
0.8533 High Similarity NPC328567
0.8533 High Similarity NPC204770
0.8533 High Similarity NPC263940
0.8533 High Similarity NPC327412
0.8533 High Similarity NPC320671
0.8533 High Similarity NPC236202
0.8533 High Similarity NPC82917
0.8533 High Similarity NPC320970
0.8531 High Similarity NPC469610
0.8523 High Similarity NPC181615
0.8521 High Similarity NPC12875
0.8521 High Similarity NPC476166
0.8521 High Similarity NPC207892
0.8521 High Similarity NPC271945
0.8521 High Similarity NPC471517
0.8521 High Similarity NPC280653
0.8521 High Similarity NPC129784
0.8521 High Similarity NPC17343
0.8521 High Similarity NPC181497
0.8521 High Similarity NPC300875
0.8521 High Similarity NPC282508
0.8521 High Similarity NPC129106
0.8521 High Similarity NPC150011
0.8521 High Similarity NPC118114
0.8521 High Similarity NPC8899
0.8521 High Similarity NPC196765
0.8521 High Similarity NPC206224
0.8521 High Similarity NPC164574
0.8521 High Similarity NPC268917
0.8521 High Similarity NPC228369
0.8521 High Similarity NPC236014
0.8506 High Similarity NPC46335
0.8481 Intermediate Similarity NPC261896
0.8477 Intermediate Similarity NPC329836
0.8472 Intermediate Similarity NPC296915
0.8472 Intermediate Similarity NPC225696
0.8472 Intermediate Similarity NPC97834
0.8472 Intermediate Similarity NPC223008
0.8472 Intermediate Similarity NPC198154
0.8472 Intermediate Similarity NPC115335
0.8467 Intermediate Similarity NPC274454
0.8467 Intermediate Similarity NPC317053
0.8467 Intermediate Similarity NPC324492
0.8467 Intermediate Similarity NPC260397
0.8467 Intermediate Similarity NPC96576
0.8467 Intermediate Similarity NPC215678
0.8462 Intermediate Similarity NPC469611
0.8462 Intermediate Similarity NPC13005
0.8451 Intermediate Similarity NPC470225
0.8451 Intermediate Similarity NPC27187
0.8431 Intermediate Similarity NPC471403
0.8425 Intermediate Similarity NPC474687
0.8421 Intermediate Similarity NPC470208
0.8421 Intermediate Similarity NPC476969
0.8421 Intermediate Similarity NPC295573
0.8421 Intermediate Similarity NPC211561
0.8421 Intermediate Similarity NPC321657
0.8421 Intermediate Similarity NPC318373
0.8411 Intermediate Similarity NPC262297
0.8392 Intermediate Similarity NPC237424
0.8392 Intermediate Similarity NPC238168
0.838 Intermediate Similarity NPC93962
0.8366 Intermediate Similarity NPC205501
0.8366 Intermediate Similarity NPC118000
0.8366 Intermediate Similarity NPC162976
0.8357 Intermediate Similarity NPC113495
0.8356 Intermediate Similarity NPC3049
0.8344 Intermediate Similarity NPC248053
0.8344 Intermediate Similarity NPC125495
0.8344 Intermediate Similarity NPC155564
0.8344 Intermediate Similarity NPC470827
0.8344 Intermediate Similarity NPC4809
0.8344 Intermediate Similarity NPC102280
0.8344 Intermediate Similarity NPC73517
0.8344 Intermediate Similarity NPC147743
0.8333 Intermediate Similarity NPC114119
0.8333 Intermediate Similarity NPC470097
0.8333 Intermediate Similarity NPC471415
0.8312 Intermediate Similarity NPC259707
0.8311 Intermediate Similarity NPC472090
0.8311 Intermediate Similarity NPC472092
0.8311 Intermediate Similarity NPC472091
0.831 Intermediate Similarity NPC47283
0.831 Intermediate Similarity NPC53986
0.831 Intermediate Similarity NPC39064
0.831 Intermediate Similarity NPC38664
0.8298 Intermediate Similarity NPC471215
0.8298 Intermediate Similarity NPC262573
0.8291 Intermediate Similarity NPC471404
0.8291 Intermediate Similarity NPC151474
0.8291 Intermediate Similarity NPC205613
0.8291 Intermediate Similarity NPC86630
0.8291 Intermediate Similarity NPC159526
0.8291 Intermediate Similarity NPC106601
0.8291 Intermediate Similarity NPC470828
0.8291 Intermediate Similarity NPC212614
0.828 Intermediate Similarity NPC166116
0.828 Intermediate Similarity NPC55463
0.8276 Intermediate Similarity NPC85435
0.8276 Intermediate Similarity NPC77196
0.8264 Intermediate Similarity NPC244888
0.8264 Intermediate Similarity NPC164804
0.8264 Intermediate Similarity NPC211413
0.8264 Intermediate Similarity NPC472590
0.8264 Intermediate Similarity NPC118683
0.8264 Intermediate Similarity NPC293203
0.8264 Intermediate Similarity NPC68205
0.8258 Intermediate Similarity NPC322899
0.8258 Intermediate Similarity NPC134911
0.8258 Intermediate Similarity NPC46283
0.8258 Intermediate Similarity NPC44192

  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 NPC112819 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
0.8582 High Similarity NPD4907 Clinical (unspecified phase)
0.844 Intermediate Similarity NPD4908 Phase 1
0.8071 Intermediate Similarity NPD1610 Phase 2
0.8 Intermediate Similarity NPD4625 Phase 3
0.7862 Intermediate Similarity NPD2861 Phase 2
0.7786 Intermediate Similarity NPD1548 Phase 1
0.7764 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7744 Intermediate Similarity NPD6959 Discontinued
0.7718 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7718 Intermediate Similarity NPD1613 Approved
0.7703 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7607 Intermediate Similarity NPD7768 Phase 2
0.7586 Intermediate Similarity NPD4749 Approved
0.7568 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7532 Intermediate Similarity NPD7447 Phase 1
0.7515 Intermediate Similarity NPD7228 Approved
0.7515 Intermediate Similarity NPD6234 Discontinued
0.75 Intermediate Similarity NPD4966 Approved
0.75 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD4967 Phase 2
0.75 Intermediate Similarity NPD4965 Approved
0.7485 Intermediate Similarity NPD7819 Suspended
0.7485 Intermediate Similarity NPD7229 Phase 3
0.7484 Intermediate Similarity NPD7037 Approved
0.7483 Intermediate Similarity NPD4060 Phase 1
0.7468 Intermediate Similarity NPD7213 Phase 3
0.7468 Intermediate Similarity NPD7212 Phase 2
0.7466 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7434 Intermediate Similarity NPD5735 Approved
0.7432 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7425 Intermediate Similarity NPD7199 Phase 2
0.74 Intermediate Similarity NPD3027 Phase 3
0.7396 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7389 Intermediate Similarity NPD3892 Phase 2
0.7389 Intermediate Similarity NPD7466 Approved
0.7378 Intermediate Similarity NPD8455 Phase 2
0.7358 Intermediate Similarity NPD7041 Phase 2
0.7358 Intermediate Similarity NPD7040 Clinical (unspecified phase)
0.7347 Intermediate Similarity NPD5327 Phase 3
0.7337 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD5124 Phase 1
0.7317 Intermediate Similarity NPD37 Approved
0.7312 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD6696 Suspended
0.7278 Intermediate Similarity NPD3750 Approved
0.7273 Intermediate Similarity NPD6353 Approved
0.7257 Intermediate Similarity NPD8312 Approved
0.7257 Intermediate Similarity NPD8313 Approved
0.7244 Intermediate Similarity NPD6099 Approved
0.7244 Intermediate Similarity NPD6100 Approved
0.7237 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7215 Intermediate Similarity NPD6674 Discontinued
0.7205 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7181 Intermediate Similarity NPD8651 Approved
0.7169 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7168 Intermediate Similarity NPD5844 Phase 1
0.7161 Intermediate Similarity NPD4097 Suspended
0.7152 Intermediate Similarity NPD7411 Suspended
0.7143 Intermediate Similarity NPD4140 Approved
0.7143 Intermediate Similarity NPD7240 Approved
0.7143 Intermediate Similarity NPD3749 Approved
0.7134 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7119 Intermediate Similarity NPD8054 Approved
0.7119 Intermediate Similarity NPD8053 Approved
0.7102 Intermediate Similarity NPD8453 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7093 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7093 Intermediate Similarity NPD6166 Phase 2
0.7093 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD4380 Phase 2
0.7089 Intermediate Similarity NPD5762 Approved
0.7089 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD5763 Approved
0.7086 Intermediate Similarity NPD6584 Phase 3
0.7086 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD7680 Approved
0.7052 Intermediate Similarity NPD7473 Discontinued
0.7051 Intermediate Similarity NPD2157 Approved
0.7048 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD1549 Phase 2
0.7041 Intermediate Similarity NPD7075 Discontinued
0.7037 Intermediate Similarity NPD7390 Discontinued
0.7013 Intermediate Similarity NPD6812 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD7097 Phase 1
0.7006 Intermediate Similarity NPD7119 Phase 2
0.6994 Remote Similarity NPD7446 Clinical (unspecified phase)
0.698 Remote Similarity NPD422 Phase 1
0.6977 Remote Similarity NPD6232 Discontinued
0.6971 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6971 Remote Similarity NPD8156 Discontinued
0.6966 Remote Similarity NPD6671 Approved
0.6962 Remote Similarity NPD5588 Approved
0.6962 Remote Similarity NPD3748 Approved
0.6959 Remote Similarity NPD5494 Approved
0.6957 Remote Similarity NPD7003 Approved
0.6949 Remote Similarity NPD6559 Discontinued
0.6939 Remote Similarity NPD7741 Discontinued
0.6928 Remote Similarity NPD8158 Clinical (unspecified phase)
0.6928 Remote Similarity NPD3018 Phase 2
0.6923 Remote Similarity NPD3620 Phase 2
0.6923 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6914 Remote Similarity NPD8099 Discontinued
0.6914 Remote Similarity NPD8251 Approved
0.6914 Remote Similarity NPD8252 Approved
0.6905 Remote Similarity NPD1934 Approved
0.6894 Remote Similarity NPD7421 Clinical (unspecified phase)
0.689 Remote Similarity NPD2533 Approved
0.689 Remote Similarity NPD7020 Approved
0.689 Remote Similarity NPD2534 Approved
0.689 Remote Similarity NPD4160 Clinical (unspecified phase)
0.689 Remote Similarity NPD2532 Approved
0.689 Remote Similarity NPD7019 Approved
0.6887 Remote Similarity NPD6582 Phase 2
0.6887 Remote Similarity NPD6583 Phase 3
0.6879 Remote Similarity NPD3787 Discontinued
0.6879 Remote Similarity NPD6355 Discontinued
0.6875 Remote Similarity NPD7843 Approved
0.6875 Remote Similarity NPD6004 Phase 3
0.6875 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6875 Remote Similarity NPD6002 Phase 3
0.6875 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6875 Remote Similarity NPD6005 Phase 3
0.6868 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6864 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6863 Remote Similarity NPD4624 Approved
0.6855 Remote Similarity NPD1510 Phase 2
0.6849 Remote Similarity NPD7157 Approved
0.6848 Remote Similarity NPD6273 Approved
0.6846 Remote Similarity NPD4626 Approved
0.6842 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6836 Remote Similarity NPD7074 Phase 3
0.6832 Remote Similarity NPD970 Clinical (unspecified phase)
0.6824 Remote Similarity NPD3091 Approved
0.6821 Remote Similarity NPD8127 Discontinued
0.6818 Remote Similarity NPD3818 Discontinued
0.6815 Remote Similarity NPD2238 Phase 2
0.6813 Remote Similarity NPD7906 Approved
0.6813 Remote Similarity NPD2796 Approved
0.6803 Remote Similarity NPD7340 Approved
0.6797 Remote Similarity NPD3094 Phase 2
0.6796 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6795 Remote Similarity NPD6798 Discontinued
0.6792 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6792 Remote Similarity NPD4536 Approved
0.6792 Remote Similarity NPD4538 Approved
0.6784 Remote Similarity NPD7773 Phase 2
0.6784 Remote Similarity NPD3882 Suspended
0.6783 Remote Similarity NPD4750 Phase 3
0.678 Remote Similarity NPD7054 Approved
0.6779 Remote Similarity NPD5691 Approved
0.6776 Remote Similarity NPD2982 Phase 2
0.6776 Remote Similarity NPD2983 Phase 2
0.6768 Remote Similarity NPD6667 Approved
0.6768 Remote Similarity NPD5058 Phase 3
0.6768 Remote Similarity NPD6666 Approved
0.6766 Remote Similarity NPD1653 Approved
0.6761 Remote Similarity NPD2342 Discontinued
0.6755 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6755 Remote Similarity NPD1091 Approved
0.6755 Remote Similarity NPD3092 Approved
0.6752 Remote Similarity NPD8032 Phase 2
0.675 Remote Similarity NPD4108 Discontinued
0.675 Remote Similarity NPD5960 Phase 3
0.675 Remote Similarity NPD7033 Discontinued
0.6744 Remote Similarity NPD7833 Phase 2
0.6744 Remote Similarity NPD7831 Phase 2
0.6744 Remote Similarity NPD7832 Clinical (unspecified phase)
0.6743 Remote Similarity NPD8051 Clinical (unspecified phase)
0.6742 Remote Similarity NPD7472 Approved
0.674 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6733 Remote Similarity NPD5846 Approved
0.6733 Remote Similarity NPD6516 Phase 2
0.6731 Remote Similarity NPD7095 Approved
0.6727 Remote Similarity NPD1511 Approved
0.6722 Remote Similarity NPD7549 Discontinued
0.6722 Remote Similarity NPD7808 Phase 3
0.6712 Remote Similarity NPD5283 Phase 1
0.6711 Remote Similarity NPD1840 Phase 2
0.6711 Remote Similarity NPD2981 Phase 2
0.671 Remote Similarity NPD1712 Approved
0.671 Remote Similarity NPD5736 Approved
0.6708 Remote Similarity NPD5406 Approved
0.6708 Remote Similarity NPD5405 Approved
0.6708 Remote Similarity NPD5408 Approved
0.6708 Remote Similarity NPD5404 Approved
0.6707 Remote Similarity NPD7427 Discontinued
0.6706 Remote Similarity NPD6801 Discontinued
0.6703 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6691 Remote Similarity NPD1242 Phase 1
0.669 Remote Similarity NPD968 Approved
0.6688 Remote Similarity NPD2797 Approved
0.6688 Remote Similarity NPD3764 Approved
0.6686 Remote Similarity NPD3051 Approved
0.6685 Remote Similarity NPD4578 Approved
0.6685 Remote Similarity NPD4577 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