Structure

Physi-Chem Properties

Molecular Weight:  956.11
Volume:  845.04
LogP:  1.031
LogD:  0.49
LogS:  -3.513
# Rotatable Bonds:  12
TPSA:  454.16
# H-Bond Aceptor:  27
# H-Bond Donor:  14
# Rings:  7
# Heavy Atoms:  27

MedChem Properties

QED Drug-Likeness Score:  0.042
Synthetic Accessibility Score:  6.853
Fsp3:  0.22
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  2
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -7.009
MDCK Permeability:  1.0092478078149725e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.008
Human Intestinal Absorption (HIA):  0.991
20% Bioavailability (F20%):  0.981
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.002
Plasma Protein Binding (PPB):  83.89599609375%
Volume Distribution (VD):  0.416
Pgp-substrate:  38.25809097290039%

ADMET: Metabolism

CYP1A2-inhibitor:  0.031
CYP1A2-substrate:  0.005
CYP2C19-inhibitor:  0.009
CYP2C19-substrate:  0.015
CYP2C9-inhibitor:  0.436
CYP2C9-substrate:  0.025
CYP2D6-inhibitor:  0.0
CYP2D6-substrate:  0.044
CYP3A4-inhibitor:  0.011
CYP3A4-substrate:  0.001

ADMET: Excretion

Clearance (CL):  6.605
Half-life (T1/2):  0.98

ADMET: Toxicity

hERG Blockers:  0.021
Human Hepatotoxicity (H-HT):  0.306
Drug-inuced Liver Injury (DILI):  0.997
AMES Toxicity:  0.067
Rat Oral Acute Toxicity:  0.0
Maximum Recommended Daily Dose:  0.04
Skin Sensitization:  0.938
Carcinogencity:  0.017
Eye Corrosion:  0.003
Eye Irritation:  0.919
Respiratory Toxicity:  0.002

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

  Natural Product: NPC142291

Natural Product ID:  NPC142291
Common Name*:   Chebulinic Acid
IUPAC Name:   n.a.
Synonyms:   Chebulinic Acid
Standard InCHIKey:  YGVHOSGNOYKRIH-JHSYUSIXSA-N
Standard InCHI:  InChI=1S/C41H32O27/c42-15-1-10(2-16(43)26(15)51)35(56)62-9-22-31-33(66-36(57)11-3-17(44)27(52)18(45)4-11)34(41(63-22)68-37(58)12-5-19(46)28(53)20(47)6-12)67-38(59)13-7-21(48)29(54)32-25(13)24(30(55)40(61)65-32)14(8-23(49)50)39(60)64-31/h1-7,14,22,24,30-31,33-34,41-48,51-55H,8-9H2,(H,49,50)/t14-,22-,24+,30+,31-,33+,34-,41+/m1/s1
SMILES:  OC(=O)C[C@H]1C(=O)O[C@@H]2[C@@H](COC(=O)c3cc(O)c(c(c3)O)O)O[C@H]([C@@H]([C@H]2OC(=O)c2cc(O)c(c(c2)O)O)OC(=O)c2c3[C@H]1[C@H](O)C(=O)Oc3c(c(c2)O)O)OC(=O)c1cc(O)c(c(c1)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL501154
PubChem CID:   452240
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000238] Tannins
        • [CHEMONTID:0001710] Hydrolyzable 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
NPO26650 Terminalia chebula Species Combretaceae Eukaryota n.a. n.a. n.a. PMID[11520216]
NPO28450 Phyllanthus emblica Species Phyllanthaceae Eukaryota n.a. n.a. n.a. PMID[11754604]
NPO28450 Phyllanthus emblica Species Phyllanthaceae Eukaryota Roots Simao city, Yunnan Province, China 2007-MAY PMID[19374435]
NPO26650 Terminalia chebula Species Combretaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28450 Phyllanthus emblica Species Phyllanthaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28450 Phyllanthus emblica Species Phyllanthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26650 Terminalia chebula Species Combretaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26650 Terminalia chebula Species Combretaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28450 Phyllanthus emblica Species Phyllanthaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26650 Terminalia chebula Species Combretaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28450 Phyllanthus emblica Species Phyllanthaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22244 Terminalia bellirica Species Combretaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28450 Phyllanthus emblica Species Phyllanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26650 Terminalia chebula Species Combretaceae 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
NPT326 Individual Protein Squalene monooxygenase Rattus norvegicus IC50 = 12000.0 nM PMID[534419]
NPT672 Cell Line TE-671 Homo sapiens ED50 > 10.0 ug ml-1 PMID[534420]
NPT180 Cell Line HCT-8 Homo sapiens ED50 > 10.0 ug ml-1 PMID[534420]
NPT81 Cell Line A549 Homo sapiens ED50 > 10.0 ug ml-1 PMID[534420]
NPT91 Cell Line KB Homo sapiens ED50 > 10.0 ug ml-1 PMID[534420]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 Inhibition > 50.0 % PMID[534417]
NPT2 Others Unspecified IC50 > 50.0 ug.mL-1 PMID[534418]
NPT20 Organism Candida albicans Candida albicans IC50 > 50.0 ug.mL-1 PMID[534418]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans IC50 > 50.0 ug.mL-1 PMID[534418]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 > 10.0 ug ml-1 PMID[534420]
NPT2 Others Unspecified Activity = 67.0 % PMID[534421]
NPT2 Others Unspecified Activity = 75.0 % PMID[534421]
NPT2 Others Unspecified Activity = 8.0 % PMID[534421]
NPT2 Others Unspecified Activity = 24.0 % PMID[534421]
NPT2 Others Unspecified Activity = 22.0 % PMID[534421]
NPT2 Others Unspecified Activity = 71.0 % PMID[534421]
NPT2 Others Unspecified Activity = 109.0 % PMID[534421]
NPT2 Others Unspecified Activity = 46.0 % PMID[534421]
NPT2 Others Unspecified Activity = 27.0 % PMID[534421]
NPT2 Others Unspecified Activity = 1.0 % PMID[534421]
NPT29 Organism Rattus norvegicus Rattus norvegicus ED50 = 3.2 mg.kg-1 PMID[534422]
NPT29 Organism Rattus norvegicus Rattus norvegicus ED50 = 3.4 mg.kg-1 PMID[534422]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = -76.9 mmHg PMID[534422]

☑ 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 NPC142291 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 NPC7839
0.9884 High Similarity NPC119094
0.9884 High Similarity NPC173872
0.9535 High Similarity NPC80956
0.9419 High Similarity NPC297574
0.9379 High Similarity NPC201814
0.9314 High Similarity NPC129533
0.9314 High Similarity NPC123259
0.9306 High Similarity NPC472723
0.927 High Similarity NPC472721
0.927 High Similarity NPC472720
0.927 High Similarity NPC31208
0.927 High Similarity NPC160543
0.927 High Similarity NPC93065
0.927 High Similarity NPC469652
0.927 High Similarity NPC472724
0.9227 High Similarity NPC3474
0.9213 High Similarity NPC477081
0.9213 High Similarity NPC269046
0.9213 High Similarity NPC477083
0.9213 High Similarity NPC240200
0.9213 High Similarity NPC158214
0.9213 High Similarity NPC223534
0.9213 High Similarity NPC290289
0.9209 High Similarity NPC111490
0.9209 High Similarity NPC261623
0.9195 High Similarity NPC473713
0.9162 High Similarity NPC187632
0.9157 High Similarity NPC65489
0.9157 High Similarity NPC237202
0.9157 High Similarity NPC469649
0.9157 High Similarity NPC260521
0.9153 High Similarity NPC231254
0.9148 High Similarity NPC8940
0.9128 High Similarity NPC149300
0.9116 High Similarity NPC477082
0.9116 High Similarity NPC476358
0.9111 High Similarity NPC97924
0.9111 High Similarity NPC264302
0.9111 High Similarity NPC40078
0.9111 High Similarity NPC471091
0.9101 High Similarity NPC469650
0.908 High Similarity NPC166674
0.908 High Similarity NPC46640
0.908 High Similarity NPC34436
0.908 High Similarity NPC263119
0.908 High Similarity NPC219600
0.908 High Similarity NPC473550
0.9075 High Similarity NPC181778
0.9075 High Similarity NPC470272
0.907 High Similarity NPC311389
0.907 High Similarity NPC470271
0.907 High Similarity NPC473818
0.904 High Similarity NPC170203
0.904 High Similarity NPC208797
0.904 High Similarity NPC53680
0.9023 High Similarity NPC100251
0.9023 High Similarity NPC65333
0.9017 High Similarity NPC658
0.9017 High Similarity NPC197708
0.9016 High Similarity NPC189312
0.9012 High Similarity NPC175793
0.8994 High Similarity NPC104910
0.8994 High Similarity NPC474093
0.8989 High Similarity NPC470718
0.8989 High Similarity NPC297503
0.8989 High Similarity NPC97119
0.8989 High Similarity NPC135831
0.8983 High Similarity NPC198902
0.8977 High Similarity NPC67629
0.8977 High Similarity NPC79736
0.8973 High Similarity NPC470450
0.8971 High Similarity NPC98583
0.896 High Similarity NPC261411
0.896 High Similarity NPC190204
0.896 High Similarity NPC43918
0.8944 High Similarity NPC475360
0.8944 High Similarity NPC72554
0.8944 High Similarity NPC30011
0.8944 High Similarity NPC97817
0.8944 High Similarity NPC475179
0.8939 High Similarity NPC25946
0.8939 High Similarity NPC470720
0.8939 High Similarity NPC470713
0.8939 High Similarity NPC21359
0.8939 High Similarity NPC460984
0.8939 High Similarity NPC470717
0.8933 High Similarity NPC125352
0.8927 High Similarity NPC267549
0.892 High Similarity NPC473630
0.8914 High Similarity NPC5786
0.8914 High Similarity NPC102851
0.8908 High Similarity NPC198125
0.8908 High Similarity NPC95421
0.8895 High Similarity NPC121290
0.8889 High Similarity NPC473554
0.8889 High Similarity NPC295625
0.8889 High Similarity NPC470719
0.8889 High Similarity NPC112380
0.8883 High Similarity NPC162394
0.8883 High Similarity NPC241781
0.8883 High Similarity NPC156785
0.8883 High Similarity NPC132111
0.8876 High Similarity NPC471030
0.8864 High Similarity NPC163165
0.8857 High Similarity NPC47521
0.8851 High Similarity NPC31034
0.884 High Similarity NPC105591
0.884 High Similarity NPC269625
0.8837 High Similarity NPC291957
0.8837 High Similarity NPC14030
0.8833 High Similarity NPC223860
0.8833 High Similarity NPC275977
0.8833 High Similarity NPC249560
0.8833 High Similarity NPC318119
0.8827 High Similarity NPC117668
0.8827 High Similarity NPC469371
0.882 High Similarity NPC113836
0.882 High Similarity NPC476620
0.882 High Similarity NPC37668
0.882 High Similarity NPC476622
0.882 High Similarity NPC293626
0.882 High Similarity NPC476618
0.882 High Similarity NPC476623
0.882 High Similarity NPC476619
0.882 High Similarity NPC253521
0.882 High Similarity NPC258044
0.882 High Similarity NPC267680
0.882 High Similarity NPC217387
0.882 High Similarity NPC196127
0.882 High Similarity NPC476621
0.8817 High Similarity NPC174140
0.8807 High Similarity NPC47140
0.8807 High Similarity NPC38438
0.8807 High Similarity NPC67134
0.8786 High Similarity NPC470898
0.8785 High Similarity NPC221140
0.8785 High Similarity NPC473686
0.8785 High Similarity NPC33083
0.8785 High Similarity NPC475352
0.8785 High Similarity NPC475220
0.8785 High Similarity NPC229817
0.8778 High Similarity NPC321916
0.8771 High Similarity NPC472726
0.8771 High Similarity NPC472725
0.8764 High Similarity NPC144097
0.8764 High Similarity NPC61904
0.8757 High Similarity NPC175230
0.8757 High Similarity NPC88560
0.8757 High Similarity NPC316539
0.8757 High Similarity NPC172033
0.875 High Similarity NPC204937
0.875 High Similarity NPC149011
0.8743 High Similarity NPC249977
0.8736 High Similarity NPC179947
0.8736 High Similarity NPC64755
0.8729 High Similarity NPC470451
0.8729 High Similarity NPC470416
0.8729 High Similarity NPC470455
0.8728 High Similarity NPC476371
0.8728 High Similarity NPC285108
0.8728 High Similarity NPC33298
0.8728 High Similarity NPC476372
0.8721 High Similarity NPC289346
0.8721 High Similarity NPC24627
0.8721 High Similarity NPC24164
0.8715 High Similarity NPC477895
0.8715 High Similarity NPC217520
0.8715 High Similarity NPC35167
0.8715 High Similarity NPC472387
0.8715 High Similarity NPC139571
0.8715 High Similarity NPC173837
0.8713 High Similarity NPC238419
0.8713 High Similarity NPC172419
0.8708 High Similarity NPC34267
0.8708 High Similarity NPC81042
0.8708 High Similarity NPC253685
0.8708 High Similarity NPC214621
0.8708 High Similarity NPC171706
0.8708 High Similarity NPC223426
0.8689 High Similarity NPC205721
0.8689 High Similarity NPC473618
0.8681 High Similarity NPC87583
0.8678 High Similarity NPC227297
0.8674 High Similarity NPC473717
0.8674 High Similarity NPC473631
0.8674 High Similarity NPC199172
0.8674 High Similarity NPC470445
0.8674 High Similarity NPC470446
0.8674 High Similarity NPC470447
0.8674 High Similarity NPC470449
0.8674 High Similarity NPC36138
0.8674 High Similarity NPC35924
0.8674 High Similarity NPC293227
0.8674 High Similarity NPC475662
0.8667 High Similarity NPC212290
0.8663 High Similarity NPC104222
0.8663 High Similarity NPC87317
0.8663 High Similarity NPC114791
0.8663 High Similarity NPC210501

  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 NPC142291 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
0.9023 High Similarity NPD7993 Clinical (unspecified phase)
0.8655 High Similarity NPD4868 Clinical (unspecified phase)
0.8603 High Similarity NPD7808 Phase 3
0.8547 High Similarity NPD7251 Discontinued
0.8539 High Similarity NPD7472 Approved
0.8539 High Similarity NPD7074 Phase 3
0.85 High Similarity NPD4338 Clinical (unspecified phase)
0.8492 Intermediate Similarity NPD6797 Phase 2
0.8483 Intermediate Similarity NPD7054 Approved
0.8453 Intermediate Similarity NPD8313 Approved
0.8453 Intermediate Similarity NPD8312 Approved
0.843 Intermediate Similarity NPD1465 Phase 2
0.8427 Intermediate Similarity NPD7228 Approved
0.8418 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8418 Intermediate Similarity NPD6166 Phase 2
0.8418 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8324 Intermediate Similarity NPD3818 Discontinued
0.8278 Intermediate Similarity NPD5844 Phase 1
0.8235 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8177 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8128 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.8114 Intermediate Similarity NPD8455 Phase 2
0.8079 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8071 Intermediate Similarity NPD8151 Discontinued
0.8065 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.8056 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.8045 Intermediate Similarity NPD7199 Phase 2
0.8043 Intermediate Similarity NPD7240 Approved
0.8034 Intermediate Similarity NPD6234 Discontinued
0.7967 Intermediate Similarity NPD7473 Discontinued
0.7955 Intermediate Similarity NPD37 Approved
0.7946 Intermediate Similarity NPD7685 Pre-registration
0.7921 Intermediate Similarity NPD4966 Approved
0.7921 Intermediate Similarity NPD4965 Approved
0.7921 Intermediate Similarity NPD4967 Phase 2
0.7901 Intermediate Similarity NPD6232 Discontinued
0.7853 Intermediate Similarity NPD1934 Approved
0.7845 Intermediate Similarity NPD6959 Discontinued
0.7829 Intermediate Similarity NPD1653 Approved
0.7826 Intermediate Similarity NPD3751 Discontinued
0.7778 Intermediate Similarity NPD7075 Discontinued
0.7765 Intermediate Similarity NPD3817 Phase 2
0.7727 Intermediate Similarity NPD7435 Discontinued
0.7722 Intermediate Similarity NPD3882 Suspended
0.7717 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7709 Intermediate Similarity NPD7819 Suspended
0.7709 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7705 Intermediate Similarity NPD3787 Discontinued
0.767 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7667 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.766 Intermediate Similarity NPD6559 Discontinued
0.7638 Intermediate Similarity NPD7697 Approved
0.7638 Intermediate Similarity NPD7696 Phase 3
0.7638 Intermediate Similarity NPD7680 Approved
0.7638 Intermediate Similarity NPD7698 Approved
0.7635 Intermediate Similarity NPD7783 Phase 2
0.7635 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7614 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7611 Intermediate Similarity NPD2801 Approved
0.7611 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD7870 Phase 2
0.76 Intermediate Similarity NPD8320 Phase 1
0.76 Intermediate Similarity NPD8319 Approved
0.76 Intermediate Similarity NPD7871 Phase 2
0.7596 Intermediate Similarity NPD5494 Approved
0.7586 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7586 Intermediate Similarity NPD7874 Approved
0.7582 Intermediate Similarity NPD3749 Approved
0.7576 Intermediate Similarity NPD6779 Approved
0.7576 Intermediate Similarity NPD6781 Approved
0.7576 Intermediate Similarity NPD6778 Approved
0.7576 Intermediate Similarity NPD6782 Approved
0.7576 Intermediate Similarity NPD6777 Approved
0.7576 Intermediate Similarity NPD6780 Approved
0.7576 Intermediate Similarity NPD6776 Approved
0.7574 Intermediate Similarity NPD7701 Phase 2
0.7569 Intermediate Similarity NPD5402 Approved
0.7542 Intermediate Similarity NPD4380 Phase 2
0.7527 Intermediate Similarity NPD7768 Phase 2
0.7514 Intermediate Similarity NPD1512 Approved
0.75 Intermediate Similarity NPD7411 Suspended
0.7486 Intermediate Similarity NPD6190 Approved
0.7475 Intermediate Similarity NPD7700 Phase 2
0.7475 Intermediate Similarity NPD7699 Phase 2
0.7463 Intermediate Similarity NPD7801 Approved
0.7461 Intermediate Similarity NPD8434 Phase 2
0.7459 Intermediate Similarity NPD6801 Discontinued
0.7457 Intermediate Similarity NPD7266 Discontinued
0.7429 Intermediate Similarity NPD3750 Approved
0.7401 Intermediate Similarity NPD1511 Approved
0.7401 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7374 Intermediate Similarity NPD5403 Approved
0.7371 Intermediate Similarity NPD8150 Discontinued
0.7366 Intermediate Similarity NPD8127 Discontinued
0.7323 Intermediate Similarity NPD6534 Approved
0.7323 Intermediate Similarity NPD6535 Approved
0.7311 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7303 Intermediate Similarity NPD6799 Approved
0.7293 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7293 Intermediate Similarity NPD7458 Discontinued
0.7273 Intermediate Similarity NPD6674 Discontinued
0.7267 Intermediate Similarity NPD230 Phase 1
0.7263 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7263 Intermediate Similarity NPD5401 Approved
0.7253 Intermediate Similarity NPD6599 Discontinued
0.7232 Intermediate Similarity NPD4628 Phase 3
0.7216 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7216 Intermediate Similarity NPD1549 Phase 2
0.7209 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD1613 Approved
0.7198 Intermediate Similarity NPD3226 Approved
0.7196 Intermediate Similarity NPD3926 Phase 2
0.7179 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7175 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7167 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7159 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7159 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7157 Intermediate Similarity NPD6823 Phase 2
0.7143 Intermediate Similarity NPD3748 Approved
0.7083 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.7079 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7074 Intermediate Similarity NPD919 Approved
0.7072 Intermediate Similarity NPD2534 Approved
0.7072 Intermediate Similarity NPD2533 Approved
0.7072 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7072 Intermediate Similarity NPD2532 Approved
0.7067 Intermediate Similarity NPD7585 Approved
0.7053 Intermediate Similarity NPD7229 Phase 3
0.7039 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7033 Intermediate Similarity NPD6273 Approved
0.7019 Intermediate Similarity NPD7583 Approved
0.7018 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7005 Intermediate Similarity NPD5353 Approved
0.6994 Remote Similarity NPD6859 Clinical (unspecified phase)
0.699 Remote Similarity NPD7549 Discontinued
0.6989 Remote Similarity NPD7097 Phase 1
0.6978 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6977 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6976 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6949 Remote Similarity NPD1510 Phase 2
0.6944 Remote Similarity NPD8166 Discontinued
0.6944 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6936 Remote Similarity NPD3027 Phase 3
0.6931 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6931 Remote Similarity NPD6213 Phase 3
0.6931 Remote Similarity NPD6212 Phase 3
0.6923 Remote Similarity NPD7390 Discontinued
0.6911 Remote Similarity NPD1247 Approved
0.691 Remote Similarity NPD2796 Approved
0.691 Remote Similarity NPD6100 Approved
0.691 Remote Similarity NPD6099 Approved
0.6897 Remote Similarity NPD6798 Discontinued
0.6879 Remote Similarity NPD4908 Phase 1
0.6875 Remote Similarity NPD447 Suspended
0.6875 Remote Similarity NPD1933 Approved
0.6875 Remote Similarity NPD6355 Discontinued
0.6857 Remote Similarity NPD7584 Approved
0.6854 Remote Similarity NPD651 Clinical (unspecified phase)
0.6851 Remote Similarity NPD7003 Approved
0.6839 Remote Similarity NPD5242 Approved
0.6821 Remote Similarity NPD7177 Discontinued
0.6818 Remote Similarity NPD943 Approved
0.6818 Remote Similarity NPD4060 Phase 1
0.6816 Remote Similarity NPD6841 Approved
0.6816 Remote Similarity NPD6843 Phase 3
0.6816 Remote Similarity NPD1551 Phase 2
0.6816 Remote Similarity NPD6842 Approved
0.681 Remote Similarity NPD7211 Clinical (unspecified phase)
0.68 Remote Similarity NPD3764 Approved
0.68 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6791 Remote Similarity NPD7930 Approved
0.6782 Remote Similarity NPD4287 Approved
0.678 Remote Similarity NPD7667 Clinical (unspecified phase)
0.6768 Remote Similarity NPD7039 Approved
0.6768 Remote Similarity NPD7038 Approved
0.6763 Remote Similarity NPD8285 Discontinued
0.6761 Remote Similarity NPD6233 Phase 2
0.6757 Remote Similarity NPD8058 Clinical (unspecified phase)
0.6757 Remote Similarity NPD8059 Phase 3
0.6755 Remote Similarity NPD7615 Clinical (unspecified phase)
0.675 Remote Similarity NPD8053 Approved
0.675 Remote Similarity NPD8054 Approved
0.6737 Remote Similarity NPD4288 Approved
0.6725 Remote Similarity NPD9269 Phase 2
0.6723 Remote Similarity NPD1240 Approved
0.6722 Remote Similarity NPD5404 Approved
0.6722 Remote Similarity NPD5405 Approved
0.6722 Remote Similarity NPD2935 Discontinued
0.6722 Remote Similarity NPD5406 Approved
0.6722 Remote Similarity NPD5408 Approved
0.6717 Remote Similarity NPD5953 Discontinued
0.6705 Remote Similarity NPD3268 Approved
0.6701 Remote Similarity NPD5710 Approved
0.6701 Remote Similarity NPD5711 Approved
0.6685 Remote Similarity NPD5124 Phase 1
0.6685 Remote Similarity NPD2346 Discontinued
0.6685 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6385 Approved
0.6667 Remote Similarity NPD1509 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5005 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