Structure

Physi-Chem Properties

Molecular Weight:  940.12
Volume:  842.17
LogP:  2.092
LogD:  1.12
LogS:  -2.04
# Rotatable Bonds:  16
TPSA:  444.18
# H-Bond Aceptor:  26
# H-Bond Donor:  15
# Rings:  6
# Heavy Atoms:  26

MedChem Properties

QED Drug-Likeness Score:  0.051
Synthetic Accessibility Score:  4.753
Fsp3:  0.146
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -7.271
MDCK Permeability:  8.346079994225875e-06
Pgp-inhibitor:  0.079
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.998
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.002
Plasma Protein Binding (PPB):  83.55686950683594%
Volume Distribution (VD):  0.282
Pgp-substrate:  32.289459228515625%

ADMET: Metabolism

CYP1A2-inhibitor:  0.697
CYP1A2-substrate:  0.003
CYP2C19-inhibitor:  0.013
CYP2C19-substrate:  0.01
CYP2C9-inhibitor:  0.207
CYP2C9-substrate:  0.012
CYP2D6-inhibitor:  0.0
CYP2D6-substrate:  0.049
CYP3A4-inhibitor:  0.012
CYP3A4-substrate:  0.001

ADMET: Excretion

Clearance (CL):  15.671
Half-life (T1/2):  0.977

ADMET: Toxicity

hERG Blockers:  0.075
Human Hepatotoxicity (H-HT):  0.151
Drug-inuced Liver Injury (DILI):  0.99
AMES Toxicity:  0.045
Rat Oral Acute Toxicity:  0.0
Maximum Recommended Daily Dose:  0.003
Skin Sensitization:  0.978
Carcinogencity:  0.006
Eye Corrosion:  0.003
Eye Irritation:  0.955
Respiratory Toxicity:  0.001

Download Data

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

  Natural Product: NPC318826

Natural Product ID:  NPC318826
Common Name*:   Beta-D-Allopyranose Pentakis(3,4,5-Trihydroxybenzoate)
IUPAC Name:   [(2R,3R,4R,5R,6S)-3,4,5,6-tetrakis[(3,4,5-trihydroxybenzoyl)oxy]oxan-2-yl]methyl 3,4,5-trihydroxybenzoate
Synonyms:  
Standard InCHIKey:  QJYNZEYHSMRWBK-ZZYOXLQRSA-N
Standard InCHI:  InChI=1S/C41H32O26/c42-17-1-12(2-18(43)28(17)52)36(57)62-11-27-33(64-37(58)13-3-19(44)29(53)20(45)4-13)34(65-38(59)14-5-21(46)30(54)22(47)6-14)35(66-39(60)15-7-23(48)31(55)24(49)8-15)41(63-27)67-40(61)16-9-25(50)32(56)26(51)10-16/h1-10,27,33-35,41-56H,11H2/t27-,33-,34-,35-,41+/m1/s1
SMILES:  O=C(c1cc(O)c(c(c1)O)O)O[C@@H]1O[C@H](COC(=O)c2cc(O)c(c(c2)O)O)[C@H]([C@H]([C@H]1OC(=O)c1cc(O)c(c(c1)O)O)OC(=O)c1cc(O)c(c(c1)O)O)OC(=O)c1cc(O)c(c(c1)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL207164
PubChem CID:   11600488
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000238] Tannins

*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
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Seeds Gansu province, China DOI[10.1016/j.foodres.2020.109416]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Seeds Henan province, China DOI[10.1016/j.foodres.2020.109416]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Seeds Shandong province, China DOI[10.1016/j.foodres.2020.109416]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Seeds Shanxi province, China DOI[10.1016/j.foodres.2020.109416]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Seeds Anhui province, China DOI[10.1016/j.foodres.2020.109416]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. DOI[10.2174/092986712800229032]
NPO22550 Paeonia suffruticosa Species Paeoniaceae Eukaryota n.a. n.a. n.a. PMID[11339628]
NPO22550 Paeonia suffruticosa Species Paeoniaceae Eukaryota n.a. bark n.a. PMID[17260795]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. n.a. n.a. PMID[19402674]
NPO22550 Paeonia suffruticosa Species Paeoniaceae Eukaryota n.a. Daejeon, Korea 2007-Jan PMID[19670875]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. PMID[19721258]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. PMID[19772486]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Roots n.a. n.a. PMID[20806783]
NPO22550 Paeonia suffruticosa Species Paeoniaceae Eukaryota n.a. seed n.a. PMID[20822014]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. PMID[21782011]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. PMID[22190295]
NPO22550 Paeonia suffruticosa Species Paeoniaceae Eukaryota n.a. root n.a. PMID[22547314]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. seed n.a. PMID[23497864]
NPO22550 Paeonia suffruticosa Species Paeoniaceae Eukaryota root bark Bozhou, Anhui Province, China 2010-AUG PMID[24377852]
NPO22550 Paeonia suffruticosa Species Paeoniaceae Eukaryota n.a. flower n.a. PMID[24504864]
NPO22550 Paeonia suffruticosa Species Paeoniaceae Eukaryota Flowers LuoYang, HeNan, China n.a. PMID[24621197]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. PMID[26838074]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. PMID[27313650]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. PMID[27429639]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Roots n.a. n.a. PMID[29741372]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Seeds HeZe, ShanDong, China early autumn (from August to the beginning of September PMID[32545196]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Roots n.a. n.a. PMID[32951423]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Seeds Xinjiang,China PMID[33063333]
NPO17385 Magnolia acuminata Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26910 Quercus infectoria Species Fagaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12328 Ampelopsis japonica Species Vitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29741 Paeonia moutan Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17385 Magnolia acuminata Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12328 Ampelopsis japonica Species Vitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26910 Quercus infectoria Species Fagaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22550 Paeonia suffruticosa Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26910 Quercus infectoria Species Fagaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22550 Paeonia suffruticosa Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12328 Ampelopsis japonica Species Vitaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17385 Magnolia acuminata Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29741 Paeonia moutan Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22550 Paeonia suffruticosa Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26910 Quercus infectoria Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17385 Magnolia acuminata Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22550 Paeonia suffruticosa Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12328 Ampelopsis japonica 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
NPT520 Cell Line 3T3-L1 Mus musculus Activity = 34.0 Bq PMID[538399]

☑ 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 NPC318826 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 NPC114791
1.0 High Similarity NPC141331
1.0 High Similarity NPC210501
1.0 High Similarity NPC104222
0.9801 High Similarity NPC172419
0.9801 High Similarity NPC238419
0.9735 High Similarity NPC239019
0.9735 High Similarity NPC247629
0.9536 High Similarity NPC44260
0.9536 High Similarity NPC3746
0.9536 High Similarity NPC205037
0.9536 High Similarity NPC61152
0.9536 High Similarity NPC16024
0.9494 High Similarity NPC149300
0.943 High Similarity NPC43918
0.943 High Similarity NPC190204
0.943 High Similarity NPC261411
0.9313 High Similarity NPC47521
0.9308 High Similarity NPC470271
0.9308 High Similarity NPC311389
0.9272 High Similarity NPC92117
0.925 High Similarity NPC198125
0.925 High Similarity NPC95421
0.9245 High Similarity NPC175793
0.9226 High Similarity NPC134925
0.9205 High Similarity NPC142528
0.9205 High Similarity NPC120621
0.9205 High Similarity NPC248257
0.9193 High Similarity NPC470272
0.915 High Similarity NPC140151
0.913 High Similarity NPC658
0.913 High Similarity NPC197708
0.9068 High Similarity NPC31034
0.9057 High Similarity NPC14030
0.9057 High Similarity NPC291957
0.9051 High Similarity NPC289346
0.9026 High Similarity NPC252979
0.9018 High Similarity NPC102851
0.9018 High Similarity NPC5786
0.9007 High Similarity NPC108455
0.9 High Similarity NPC470898
0.897 High Similarity NPC472723
0.894 High Similarity NPC229036
0.894 High Similarity NPC22176
0.894 High Similarity NPC190587
0.894 High Similarity NPC226738
0.894 High Similarity NPC121573
0.8938 High Similarity NPC90905
0.8938 High Similarity NPC285108
0.8938 High Similarity NPC4013
0.8938 High Similarity NPC33298
0.8922 High Similarity NPC8940
0.8896 High Similarity NPC75945
0.8862 High Similarity NPC80956
0.8834 High Similarity NPC217781
0.8834 High Similarity NPC473818
0.8824 High Similarity NPC260521
0.8824 High Similarity NPC65489
0.8824 High Similarity NPC469649
0.8805 High Similarity NPC1913
0.8805 High Similarity NPC472860
0.8797 High Similarity NPC172920
0.8797 High Similarity NPC156624
0.8788 High Similarity NPC100251
0.8782 High Similarity NPC477334
0.8773 High Similarity NPC26536
0.8773 High Similarity NPC49983
0.8773 High Similarity NPC142707
0.8773 High Similarity NPC317671
0.8772 High Similarity NPC158214
0.8772 High Similarity NPC240200
0.8772 High Similarity NPC290289
0.8772 High Similarity NPC223534
0.8757 High Similarity NPC135831
0.8757 High Similarity NPC297503
0.8757 High Similarity NPC97119
0.875 High Similarity NPC471030
0.875 High Similarity NPC287872
0.875 High Similarity NPC74319
0.875 High Similarity NPC160780
0.875 High Similarity NPC289811
0.8735 High Similarity NPC98583
0.8721 High Similarity NPC31208
0.8721 High Similarity NPC93065
0.8721 High Similarity NPC472724
0.8721 High Similarity NPC472720
0.8721 High Similarity NPC469652
0.8721 High Similarity NPC160543
0.8721 High Similarity NPC187632
0.8721 High Similarity NPC472721
0.8713 High Similarity NPC475179
0.8712 High Similarity NPC166851
0.8712 High Similarity NPC162169
0.871 High Similarity NPC43123
0.8706 High Similarity NPC231254
0.8696 High Similarity NPC119125
0.8696 High Similarity NPC203020
0.8696 High Similarity NPC476373
0.8696 High Similarity NPC166277
0.8696 High Similarity NPC239966
0.8688 High Similarity NPC4747
0.8688 High Similarity NPC104275
0.8688 High Similarity NPC133984
0.8679 High Similarity NPC203757
0.8675 High Similarity NPC75763
0.8675 High Similarity NPC225036
0.8675 High Similarity NPC65333
0.8675 High Similarity NPC12218
0.8675 High Similarity NPC105525
0.8671 High Similarity NPC97924
0.8671 High Similarity NPC40078
0.8671 High Similarity NPC471091
0.8663 High Similarity NPC142291
0.8663 High Similarity NPC7839
0.8655 High Similarity NPC104910
0.8655 High Similarity NPC111490
0.8655 High Similarity NPC474093
0.8655 High Similarity NPC261623
0.8655 High Similarity NPC469650
0.8654 High Similarity NPC42464
0.865 High Similarity NPC227297
0.865 High Similarity NPC121290
0.865 High Similarity NPC469651
0.8642 High Similarity NPC311803
0.8642 High Similarity NPC472859
0.8642 High Similarity NPC25389
0.8639 High Similarity NPC198902
0.8631 High Similarity NPC67629
0.8631 High Similarity NPC297574
0.8631 High Similarity NPC79736
0.8625 High Similarity NPC291948
0.8625 High Similarity NPC250436
0.8625 High Similarity NPC104983
0.8625 High Similarity NPC300845
0.8625 High Similarity NPC88803
0.8623 High Similarity NPC163165
0.8623 High Similarity NPC172033
0.8623 High Similarity NPC88560
0.8623 High Similarity NPC175230
0.8614 High Similarity NPC149011
0.8614 High Similarity NPC204937
0.8605 High Similarity NPC97817
0.8605 High Similarity NPC30011
0.8605 High Similarity NPC72554
0.8599 High Similarity NPC306343
0.8589 High Similarity NPC476372
0.8589 High Similarity NPC476371
0.8589 High Similarity NPC246024
0.8588 High Similarity NPC469371
0.8581 High Similarity NPC473867
0.858 High Similarity NPC253521
0.858 High Similarity NPC267549
0.858 High Similarity NPC113836
0.858 High Similarity NPC258044
0.858 High Similarity NPC293626
0.858 High Similarity NPC267680
0.858 High Similarity NPC217387
0.858 High Similarity NPC37668
0.858 High Similarity NPC196127
0.8571 High Similarity NPC289322
0.8571 High Similarity NPC68324
0.8571 High Similarity NPC38779
0.8571 High Similarity NPC135222
0.8571 High Similarity NPC474010
0.8571 High Similarity NPC476358
0.8571 High Similarity NPC114179
0.8571 High Similarity NPC187205
0.8571 High Similarity NPC156818
0.8571 High Similarity NPC160512
0.8571 High Similarity NPC49173
0.8563 High Similarity NPC264302
0.8563 High Similarity NPC47140
0.8563 High Similarity NPC67134
0.8555 High Similarity NPC173872
0.8555 High Similarity NPC269046
0.8555 High Similarity NPC119094
0.8553 High Similarity NPC87403
0.8553 High Similarity NPC105827
0.8553 High Similarity NPC310661
0.8538 High Similarity NPC162394
0.8538 High Similarity NPC35924
0.8538 High Similarity NPC123259
0.8538 High Similarity NPC156785
0.8538 High Similarity NPC199172
0.8538 High Similarity NPC129533
0.8538 High Similarity NPC241781
0.8538 High Similarity NPC470718
0.8528 High Similarity NPC266365
0.8521 High Similarity NPC144097
0.8521 High Similarity NPC472991
0.8521 High Similarity NPC472992
0.8521 High Similarity NPC61904
0.8519 High Similarity NPC87317
0.8516 High Similarity NPC477333
0.8512 High Similarity NPC472993
0.8509 High Similarity NPC318432
0.8506 High Similarity NPC201814
0.8503 High Similarity NPC476365
0.85 High Similarity NPC327032
0.85 High Similarity NPC191046

  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 NPC318826 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
0.8625 High Similarity NPD4868 Clinical (unspecified phase)
0.8563 High Similarity NPD7993 Clinical (unspecified phase)
0.8284 Intermediate Similarity NPD7472 Approved
0.8278 Intermediate Similarity NPD230 Phase 1
0.8225 Intermediate Similarity NPD7054 Approved
0.8187 Intermediate Similarity NPD7251 Discontinued
0.8176 Intermediate Similarity NPD7074 Phase 3
0.8153 Intermediate Similarity NPD6190 Approved
0.814 Intermediate Similarity NPD7808 Phase 3
0.814 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8129 Intermediate Similarity NPD6797 Phase 2
0.8129 Intermediate Similarity NPD7266 Discontinued
0.8081 Intermediate Similarity NPD7685 Pre-registration
0.8059 Intermediate Similarity NPD3818 Discontinued
0.7953 Intermediate Similarity NPD7228 Approved
0.7904 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7901 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7886 Intermediate Similarity NPD8312 Approved
0.7886 Intermediate Similarity NPD8313 Approved
0.7865 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7836 Intermediate Similarity NPD6166 Phase 2
0.7836 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7836 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7751 Intermediate Similarity NPD6234 Discontinued
0.7725 Intermediate Similarity NPD1465 Phase 2
0.7725 Intermediate Similarity NPD8455 Phase 2
0.7725 Intermediate Similarity NPD8151 Discontinued
0.7701 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7697 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.768 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7667 Intermediate Similarity NPD9269 Phase 2
0.7665 Intermediate Similarity NPD1934 Approved
0.7636 Intermediate Similarity NPD1653 Approved
0.7619 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7607 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD5844 Phase 1
0.7571 Intermediate Similarity NPD7240 Approved
0.756 Intermediate Similarity NPD37 Approved
0.7545 Intermediate Similarity NPD4380 Phase 2
0.7529 Intermediate Similarity NPD4967 Phase 2
0.7529 Intermediate Similarity NPD4966 Approved
0.7529 Intermediate Similarity NPD4965 Approved
0.7515 Intermediate Similarity NPD2801 Approved
0.7514 Intermediate Similarity NPD6232 Discontinued
0.7486 Intermediate Similarity NPD7473 Discontinued
0.7485 Intermediate Similarity NPD7075 Discontinued
0.7472 Intermediate Similarity NPD6559 Discontinued
0.7471 Intermediate Similarity NPD3817 Phase 2
0.7429 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7427 Intermediate Similarity NPD3882 Suspended
0.7423 Intermediate Similarity NPD8166 Discontinued
0.74 Intermediate Similarity NPD9268 Approved
0.7394 Intermediate Similarity NPD1511 Approved
0.7356 Intermediate Similarity NPD7199 Phase 2
0.7356 Intermediate Similarity NPD6959 Discontinued
0.7326 Intermediate Similarity NPD7768 Phase 2
0.731 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD7819 Suspended
0.7305 Intermediate Similarity NPD1512 Approved
0.7296 Intermediate Similarity NPD943 Approved
0.7294 Intermediate Similarity NPD7411 Suspended
0.7278 Intermediate Similarity NPD7458 Discontinued
0.7273 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD5402 Approved
0.7267 Intermediate Similarity NPD5353 Approved
0.724 Intermediate Similarity NPD8320 Phase 1
0.724 Intermediate Similarity NPD8319 Approved
0.7196 Intermediate Similarity NPD7700 Phase 2
0.7196 Intermediate Similarity NPD7699 Phase 2
0.7188 Intermediate Similarity NPD7680 Approved
0.7188 Intermediate Similarity NPD7435 Discontinued
0.7186 Intermediate Similarity NPD7390 Discontinued
0.7174 Intermediate Similarity NPD8150 Discontinued
0.717 Intermediate Similarity NPD3764 Approved
0.7158 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7151 Intermediate Similarity NPD3751 Discontinued
0.715 Intermediate Similarity NPD7871 Phase 2
0.715 Intermediate Similarity NPD7870 Phase 2
0.7128 Intermediate Similarity NPD6535 Approved
0.7128 Intermediate Similarity NPD6534 Approved
0.7119 Intermediate Similarity NPD3787 Discontinued
0.7108 Intermediate Similarity NPD4628 Phase 3
0.7105 Intermediate Similarity NPD9545 Approved
0.7102 Intermediate Similarity NPD5494 Approved
0.7091 Intermediate Similarity NPD1549 Phase 2
0.7086 Intermediate Similarity NPD3749 Approved
0.7083 Intermediate Similarity NPD6799 Approved
0.7059 Intermediate Similarity NPD5403 Approved
0.7056 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7056 Intermediate Similarity NPD7874 Approved
0.7052 Intermediate Similarity NPD6801 Discontinued
0.7041 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7031 Intermediate Similarity NPD6781 Approved
0.7031 Intermediate Similarity NPD6780 Approved
0.7031 Intermediate Similarity NPD6776 Approved
0.7031 Intermediate Similarity NPD6777 Approved
0.7031 Intermediate Similarity NPD6779 Approved
0.7031 Intermediate Similarity NPD6778 Approved
0.7031 Intermediate Similarity NPD6782 Approved
0.703 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.702 Intermediate Similarity NPD7783 Phase 2
0.702 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7012 Intermediate Similarity NPD1510 Phase 2
0.701 Intermediate Similarity NPD7698 Approved
0.701 Intermediate Similarity NPD7696 Phase 3
0.701 Intermediate Similarity NPD7697 Approved
0.7006 Intermediate Similarity NPD3750 Approved
0.7 Intermediate Similarity NPD3027 Phase 3
0.6988 Remote Similarity NPD970 Clinical (unspecified phase)
0.6981 Remote Similarity NPD9494 Approved
0.6977 Remote Similarity NPD3455 Phase 2
0.6975 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6975 Remote Similarity NPD1613 Approved
0.6973 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6957 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6954 Remote Similarity NPD7701 Phase 2
0.6946 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6941 Remote Similarity NPD5401 Approved
0.6941 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6909 Remote Similarity NPD651 Clinical (unspecified phase)
0.6905 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6897 Remote Similarity NPD6385 Approved
0.6897 Remote Similarity NPD6386 Approved
0.6895 Remote Similarity NPD6212 Phase 3
0.6895 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6895 Remote Similarity NPD6213 Phase 3
0.6889 Remote Similarity NPD5242 Approved
0.6878 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6875 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6872 Remote Similarity NPD6823 Phase 2
0.6867 Remote Similarity NPD5404 Approved
0.6867 Remote Similarity NPD5406 Approved
0.6867 Remote Similarity NPD5408 Approved
0.6867 Remote Similarity NPD5405 Approved
0.6867 Remote Similarity NPD1551 Phase 2
0.685 Remote Similarity NPD7801 Approved
0.6842 Remote Similarity NPD2532 Approved
0.6842 Remote Similarity NPD2534 Approved
0.6842 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6842 Remote Similarity NPD2533 Approved
0.6842 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6839 Remote Similarity NPD6599 Discontinued
0.6832 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6829 Remote Similarity NPD1933 Approved
0.6784 Remote Similarity NPD7585 Approved
0.6778 Remote Similarity NPD8127 Discontinued
0.6768 Remote Similarity NPD1240 Approved
0.6766 Remote Similarity NPD2796 Approved
0.6766 Remote Similarity NPD2935 Discontinued
0.6747 Remote Similarity NPD7097 Phase 1
0.6734 Remote Similarity NPD7583 Approved
0.673 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6727 Remote Similarity NPD447 Suspended
0.672 Remote Similarity NPD8434 Phase 2
0.6707 Remote Similarity NPD1509 Clinical (unspecified phase)
0.6707 Remote Similarity NPD6233 Phase 2
0.6707 Remote Similarity NPD3748 Approved
0.6706 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6701 Remote Similarity NPD8090 Clinical (unspecified phase)
0.6687 Remote Similarity NPD1607 Approved
0.6686 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6683 Remote Similarity NPD7211 Clinical (unspecified phase)
0.665 Remote Similarity NPD7584 Approved
0.6647 Remote Similarity NPD4978 Clinical (unspecified phase)
0.6631 Remote Similarity NPD7038 Approved
0.6631 Remote Similarity NPD7039 Approved
0.6612 Remote Similarity NPD3926 Phase 2
0.6608 Remote Similarity NPD7003 Approved
0.6575 Remote Similarity NPD919 Approved
0.6559 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6557 Remote Similarity NPD7229 Phase 3
0.655 Remote Similarity NPD6674 Discontinued
0.6545 Remote Similarity NPD6798 Discontinued
0.6532 Remote Similarity NPD7440 Discontinued
0.6524 Remote Similarity NPD4908 Phase 1
0.6519 Remote Similarity NPD6971 Discontinued
0.6517 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6514 Remote Similarity NPD6273 Approved
0.6508 Remote Similarity NPD7549 Discontinued
0.6505 Remote Similarity NPD7799 Discontinued
0.65 Remote Similarity NPD1091 Approved
0.6497 Remote Similarity NPD3226 Approved
0.6494 Remote Similarity NPD4357 Discontinued
0.649 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6489 Remote Similarity NPD5953 Discontinued
0.6485 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6471 Remote Similarity NPD6099 Approved
0.6471 Remote Similarity NPD6100 Approved
0.6471 Remote Similarity NPD7286 Phase 2
0.6467 Remote Similarity NPD5711 Approved
0.6467 Remote Similarity NPD5710 Approved
0.6467 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6455 Remote Similarity NPD8368 Discontinued
0.6446 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6442 Remote Similarity NPD1203 Approved
0.6436 Remote Similarity NPD7999 Approved
0.6433 Remote Similarity NPD9493 Approved
0.6432 Remote Similarity NPD8486 Clinical (unspecified phase)

  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