Structure

Physi-Chem Properties

Molecular Weight:  514.22
Volume:  516.639
LogP:  4.549
LogD:  3.341
LogS:  -5.192
# Rotatable Bonds:  7
TPSA:  101.91
# H-Bond Aceptor:  9
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.437
Synthetic Accessibility Score:  4.104
Fsp3:  0.464
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.638
MDCK Permeability:  2.6261650418746285e-05
Pgp-inhibitor:  0.987
Pgp-substrate:  0.004
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.001
30% Bioavailability (F30%):  0.044

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.039
Plasma Protein Binding (PPB):  76.0810317993164%
Volume Distribution (VD):  0.947
Pgp-substrate:  17.010801315307617%

ADMET: Metabolism

CYP1A2-inhibitor:  0.114
CYP1A2-substrate:  0.979
CYP2C19-inhibitor:  0.963
CYP2C19-substrate:  0.893
CYP2C9-inhibitor:  0.894
CYP2C9-substrate:  0.842
CYP2D6-inhibitor:  0.087
CYP2D6-substrate:  0.783
CYP3A4-inhibitor:  0.923
CYP3A4-substrate:  0.846

ADMET: Excretion

Clearance (CL):  7.727
Half-life (T1/2):  0.076

ADMET: Toxicity

hERG Blockers:  0.027
Human Hepatotoxicity (H-HT):  0.145
Drug-inuced Liver Injury (DILI):  0.243
AMES Toxicity:  0.029
Rat Oral Acute Toxicity:  0.082
Maximum Recommended Daily Dose:  0.796
Skin Sensitization:  0.75
Carcinogencity:  0.084
Eye Corrosion:  0.003
Eye Irritation:  0.397
Respiratory Toxicity:  0.833

Download Data

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

  Natural Product: NPC224472

Natural Product ID:  NPC224472
Common Name*:   Gomisin F
IUPAC Name:   n.a.
Synonyms:   Gomisin F
Standard InCHIKey:  LCQKYZXWCLBYHK-WIKKSFEZSA-N
Standard InCHI:  InChI=1S/C28H34O9/c1-14(2)9-20(29)37-27-17-12-19-24(36-13-35-19)26(34-8)22(17)21-16(10-15(3)28(27,4)30)11-18(31-5)23(32-6)25(21)33-7/h9,11-12,15,27,30H,10,13H2,1-8H3/t15-,27-,28-/m0/s1
SMILES:  COc1c2OCOc2cc2c1c1c(cc(c(c1OC)OC)OC)C[C@@H]([C@]([C@H]2OC(=O)C=C(C)C)(C)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1081698
PubChem CID:   6325287
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
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. PMID[16562834]
NPO8584 Schisandra arisanensis Species Schisandraceae Eukaryota fruits n.a. n.a. PMID[19673515]
NPO8584 Schisandra arisanensis Species Schisandraceae Eukaryota fruits n.a. n.a. PMID[20536188]
NPO8584 Schisandra arisanensis Species Schisandraceae Eukaryota fruits n.a. n.a. PMID[23265871]
NPO29191 Schisandra neglecta Species Schisandraceae Eukaryota Stems Luoji Mountain Village, Xichang County, Sicuan Province, China 2011-Sep PMID[23738539]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. fruit n.a. PMID[24155209]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. PMID[24959987]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. PMID[25302569]
NPO8584 Schisandra arisanensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8584 Schisandra arisanensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8584 Schisandra arisanensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29191 Schisandra neglecta Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8187 Schisandra chinensis Species Schisandraceae 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
NPT927 Cell Line PBMC Homo sapiens Inhibition = 36.1 % PMID[481705]
NPT927 Cell Line PBMC Homo sapiens Inhibition = 75.2 % PMID[481705]
NPT927 Cell Line PBMC Homo sapiens Inhibition = 58.9 % PMID[481705]
NPT1452 Cell Line C8166 Homo sapiens CC50 = 61900.0 nM PMID[481706]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 10000.0 nM PMID[481706]
NPT306 Cell Line PC-3 Homo sapiens IC50 > 10000.0 nM PMID[481706]
NPT81 Cell Line A549 Homo sapiens IC50 > 10000.0 nM PMID[481706]
NPT2678 Cell Line NB-4 Homo sapiens IC50 > 10000.0 nM PMID[481706]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 = 8300.0 nM PMID[481706]
NPT27 Others Unspecified Ratio CC50/EC50 = 7.5 n.a. PMID[481706]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 10000.0 nM PMID[481706]

☑ 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 NPC224472 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
0.9862 High Similarity NPC297271
0.9862 High Similarity NPC77237
0.9862 High Similarity NPC308739
0.9862 High Similarity NPC217708
0.9862 High Similarity NPC53669
0.9862 High Similarity NPC126405
0.9862 High Similarity NPC16791
0.966 High Similarity NPC198461
0.9597 High Similarity NPC475592
0.9595 High Similarity NPC476065
0.9592 High Similarity NPC24562
0.9524 High Similarity NPC471154
0.9517 High Similarity NPC477375
0.9517 High Similarity NPC252281
0.9517 High Similarity NPC325720
0.9517 High Similarity NPC316676
0.9517 High Similarity NPC198129
0.9517 High Similarity NPC327352
0.951 High Similarity NPC326144
0.9459 High Similarity NPC474606
0.9456 High Similarity NPC475756
0.9452 High Similarity NPC477376
0.9452 High Similarity NPC477374
0.9452 High Similarity NPC322426
0.9448 High Similarity NPC295297
0.9444 High Similarity NPC318286
0.9444 High Similarity NPC327651
0.9441 High Similarity NPC76415
0.9441 High Similarity NPC218510
0.9404 High Similarity NPC230531
0.9404 High Similarity NPC215400
0.94 High Similarity NPC29727
0.94 High Similarity NPC473323
0.9396 High Similarity NPC312763
0.9388 High Similarity NPC316989
0.9388 High Similarity NPC473989
0.9379 High Similarity NPC321958
0.9379 High Similarity NPC321696
0.9333 High Similarity NPC238834
0.932 High Similarity NPC85141
0.9267 High Similarity NPC473425
0.9262 High Similarity NPC475229
0.9262 High Similarity NPC477378
0.9257 High Similarity NPC470916
0.92 High Similarity NPC477377
0.9189 High Similarity NPC474393
0.9189 High Similarity NPC474347
0.9172 High Similarity NPC324962
0.9167 High Similarity NPC320471
0.9167 High Similarity NPC83049
0.9167 High Similarity NPC118162
0.9161 High Similarity NPC201404
0.9161 High Similarity NPC53722
0.9161 High Similarity NPC290714
0.9116 High Similarity NPC474054
0.911 High Similarity NPC121661
0.911 High Similarity NPC73467
0.911 High Similarity NPC87883
0.9103 High Similarity NPC103637
0.9103 High Similarity NPC230538
0.9103 High Similarity NPC36531
0.9103 High Similarity NPC229172
0.9091 High Similarity NPC63061
0.9091 High Similarity NPC865
0.9054 High Similarity NPC183083
0.9054 High Similarity NPC137352
0.9048 High Similarity NPC110763
0.9048 High Similarity NPC475868
0.9048 High Similarity NPC197352
0.9048 High Similarity NPC166506
0.9048 High Similarity NPC189239
0.902 High Similarity NPC477380
0.9013 High Similarity NPC178195
0.9013 High Similarity NPC348849
0.9013 High Similarity NPC473736
0.9 High Similarity NPC24425
0.9 High Similarity NPC477381
0.8987 High Similarity NPC79322
0.8986 High Similarity NPC154971
0.8986 High Similarity NPC252286
0.898 High Similarity NPC172171
0.898 High Similarity NPC239254
0.8973 High Similarity NPC287124
0.8973 High Similarity NPC184684
0.8973 High Similarity NPC184641
0.8973 High Similarity NPC133934
0.8961 High Similarity NPC477885
0.8947 High Similarity NPC475141
0.8947 High Similarity NPC149735
0.894 High Similarity NPC477379
0.894 High Similarity NPC303519
0.8931 High Similarity NPC88557
0.8919 High Similarity NPC477702
0.8889 High Similarity NPC143895
0.8882 High Similarity NPC302610
0.8881 High Similarity NPC185680
0.8881 High Similarity NPC145722
0.8881 High Similarity NPC256776
0.8875 High Similarity NPC477883
0.8868 High Similarity NPC311912
0.8867 High Similarity NPC477879
0.8859 High Similarity NPC212890
0.8851 High Similarity NPC477701
0.8851 High Similarity NPC141569
0.8851 High Similarity NPC166884
0.879 High Similarity NPC319749
0.8782 High Similarity NPC325122
0.8767 High Similarity NPC471183
0.8765 High Similarity NPC477881
0.8759 High Similarity NPC32189
0.8759 High Similarity NPC11453
0.8742 High Similarity NPC304821
0.8741 High Similarity NPC102256
0.8734 High Similarity NPC469512
0.8734 High Similarity NPC280778
0.8707 High Similarity NPC216434
0.8707 High Similarity NPC103448
0.8701 High Similarity NPC474514
0.869 High Similarity NPC236522
0.8679 High Similarity NPC469518
0.8679 High Similarity NPC469475
0.8671 High Similarity NPC191352
0.8671 High Similarity NPC184928
0.8671 High Similarity NPC141493
0.8671 High Similarity NPC258322
0.8662 High Similarity NPC241600
0.8662 High Similarity NPC173726
0.8634 High Similarity NPC471180
0.863 High Similarity NPC133025
0.8625 High Similarity NPC477884
0.8618 High Similarity NPC270751
0.8618 High Similarity NPC252402
0.8618 High Similarity NPC93924
0.8618 High Similarity NPC102934
0.8616 High Similarity NPC42797
0.8606 High Similarity NPC477882
0.8606 High Similarity NPC477880
0.86 High Similarity NPC472713
0.86 High Similarity NPC118385
0.86 High Similarity NPC187774
0.86 High Similarity NPC473046
0.86 High Similarity NPC472712
0.8599 High Similarity NPC207584
0.8599 High Similarity NPC19947
0.8591 High Similarity NPC41782
0.8591 High Similarity NPC474295
0.859 High Similarity NPC117154
0.8589 High Similarity NPC471181
0.8581 High Similarity NPC245948
0.8581 High Similarity NPC177868
0.8581 High Similarity NPC46591
0.8571 High Similarity NPC86605
0.8571 High Similarity NPC301765
0.8571 High Similarity NPC46277
0.8571 High Similarity NPC156948
0.8571 High Similarity NPC474039
0.8571 High Similarity NPC3072
0.8571 High Similarity NPC283949
0.8562 High Similarity NPC55239
0.8562 High Similarity NPC214853
0.8562 High Similarity NPC475865
0.8562 High Similarity NPC240279
0.8562 High Similarity NPC291977
0.8562 High Similarity NPC150534
0.8562 High Similarity NPC180602
0.8553 High Similarity NPC152424
0.8553 High Similarity NPC100465
0.8552 High Similarity NPC1474
0.8552 High Similarity NPC196937
0.8535 High Similarity NPC32373
0.8535 High Similarity NPC237946
0.8533 High Similarity NPC469630
0.8533 High Similarity NPC12728
0.8533 High Similarity NPC185071
0.8516 High Similarity NPC470264
0.8514 High Similarity NPC6369
0.8514 High Similarity NPC30951
0.8509 High Similarity NPC222531
0.8506 High Similarity NPC469707
0.8506 High Similarity NPC182368
0.8506 High Similarity NPC472709
0.8506 High Similarity NPC472710
0.8506 High Similarity NPC225815
0.8506 High Similarity NPC185955
0.8506 High Similarity NPC214326
0.8506 High Similarity NPC9933
0.8506 High Similarity NPC260781
0.8506 High Similarity NPC218041
0.8506 High Similarity NPC145979
0.8506 High Similarity NPC469706
0.8503 High Similarity NPC471988
0.8503 High Similarity NPC197166
0.8503 High Similarity NPC121651
0.85 High Similarity NPC473445
0.8493 Intermediate Similarity NPC555
0.8493 Intermediate Similarity NPC206737
0.8493 Intermediate Similarity NPC469659
0.8493 Intermediate Similarity NPC7515
0.8493 Intermediate Similarity NPC56764
0.8493 Intermediate Similarity NPC188378

  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 NPC224472 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
0.8581 High Similarity NPD37 Approved
0.8544 High Similarity NPD6234 Discontinued
0.8535 High Similarity NPD4967 Phase 2
0.8535 High Similarity NPD4965 Approved
0.8535 High Similarity NPD4966 Approved
0.8323 Intermediate Similarity NPD7199 Phase 2
0.8293 Intermediate Similarity NPD7228 Approved
0.8221 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.8095 Intermediate Similarity NPD7240 Approved
0.7975 Intermediate Similarity NPD1653 Approved
0.7972 Intermediate Similarity NPD3705 Approved
0.7905 Intermediate Similarity NPD3027 Phase 3
0.7806 Intermediate Similarity NPD6674 Discontinued
0.7799 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7792 Intermediate Similarity NPD7266 Discontinued
0.7751 Intermediate Similarity NPD3818 Discontinued
0.7722 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7701 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD7473 Discontinued
0.7661 Intermediate Similarity NPD7074 Phase 3
0.7636 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7632 Intermediate Similarity NPD1613 Approved
0.7632 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7619 Intermediate Similarity NPD6232 Discontinued
0.7602 Intermediate Similarity NPD5844 Phase 1
0.7602 Intermediate Similarity NPD7054 Approved
0.7576 Intermediate Similarity NPD3817 Phase 2
0.7558 Intermediate Similarity NPD7472 Approved
0.7543 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7533 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD4060 Phase 1
0.7515 Intermediate Similarity NPD1465 Phase 2
0.7485 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD6559 Discontinued
0.7455 Intermediate Similarity NPD1934 Approved
0.7452 Intermediate Similarity NPD5762 Approved
0.7452 Intermediate Similarity NPD5763 Approved
0.7432 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7429 Intermediate Similarity NPD7808 Phase 3
0.7429 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7417 Intermediate Similarity NPD3018 Phase 2
0.7416 Intermediate Similarity NPD6843 Phase 3
0.7416 Intermediate Similarity NPD6841 Approved
0.7416 Intermediate Similarity NPD6842 Approved
0.741 Intermediate Similarity NPD7819 Suspended
0.7407 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7371 Intermediate Similarity NPD7685 Pre-registration
0.7371 Intermediate Similarity NPD7251 Discontinued
0.7355 Intermediate Similarity NPD6355 Discontinued
0.7321 Intermediate Similarity NPD3882 Suspended
0.7314 Intermediate Similarity NPD6797 Phase 2
0.731 Intermediate Similarity NPD7229 Phase 3
0.7305 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD8455 Phase 2
0.7301 Intermediate Similarity NPD7314 Clinical (unspecified phase)
0.7296 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7294 Intermediate Similarity NPD5494 Approved
0.7278 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD7680 Approved
0.7267 Intermediate Similarity NPD2983 Phase 2
0.7267 Intermediate Similarity NPD2982 Phase 2
0.7255 Intermediate Similarity NPD4908 Phase 1
0.7251 Intermediate Similarity NPD8127 Discontinued
0.725 Intermediate Similarity NPD1652 Phase 2
0.7244 Intermediate Similarity NPD5124 Phase 1
0.7244 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7239 Intermediate Similarity NPD2532 Approved
0.7239 Intermediate Similarity NPD2534 Approved
0.7239 Intermediate Similarity NPD2533 Approved
0.7232 Intermediate Similarity NPD7549 Discontinued
0.7225 Intermediate Similarity NPD6166 Phase 2
0.7225 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7225 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD5283 Phase 1
0.7209 Intermediate Similarity NPD3787 Discontinued
0.7208 Intermediate Similarity NPD4625 Phase 3
0.7205 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7202 Intermediate Similarity NPD2801 Approved
0.7202 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD2981 Phase 2
0.7176 Intermediate Similarity NPD7075 Discontinued
0.7162 Intermediate Similarity NPD5691 Approved
0.7162 Intermediate Similarity NPD1357 Approved
0.7161 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD7097 Phase 1
0.7143 Intermediate Similarity NPD3751 Discontinued
0.7133 Intermediate Similarity NPD1610 Phase 2
0.7133 Intermediate Similarity NPD422 Phase 1
0.7133 Intermediate Similarity NPD1091 Approved
0.7126 Intermediate Similarity NPD7028 Phase 2
0.7124 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7119 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7114 Intermediate Similarity NPD4626 Approved
0.7104 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7102 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD4110 Phase 3
0.7099 Intermediate Similarity NPD3750 Approved
0.7097 Intermediate Similarity NPD7095 Approved
0.7078 Intermediate Similarity NPD2861 Phase 2
0.7073 Intermediate Similarity NPD6799 Approved
0.707 Intermediate Similarity NPD3620 Phase 2
0.707 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7066 Intermediate Similarity NPD6055 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD2438 Suspended
0.7059 Intermediate Similarity NPD6374 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD6190 Approved
0.7051 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD4749 Approved
0.7037 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD919 Approved
0.7025 Intermediate Similarity NPD230 Phase 1
0.7024 Intermediate Similarity NPD4380 Phase 2
0.7024 Intermediate Similarity NPD6599 Discontinued
0.7012 Intermediate Similarity NPD5058 Phase 3
0.7011 Intermediate Similarity NPD7296 Approved
0.7 Intermediate Similarity NPD3748 Approved
0.7 Intermediate Similarity NPD8312 Approved
0.7 Intermediate Similarity NPD5563 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD8313 Approved
0.6994 Remote Similarity NPD4628 Phase 3
0.6994 Remote Similarity NPD7982 Clinical (unspecified phase)
0.6982 Remote Similarity NPD5090 Approved
0.6982 Remote Similarity NPD5089 Approved
0.6978 Remote Similarity NPD8434 Phase 2
0.6971 Remote Similarity NPD3926 Phase 2
0.697 Remote Similarity NPD1511 Approved
0.697 Remote Similarity NPD4357 Discontinued
0.6964 Remote Similarity NPD4005 Discontinued
0.6962 Remote Similarity NPD4140 Approved
0.6959 Remote Similarity NPD5353 Approved
0.6959 Remote Similarity NPD5402 Approved
0.6957 Remote Similarity NPD6099 Approved
0.6957 Remote Similarity NPD6100 Approved
0.6954 Remote Similarity NPD6959 Discontinued
0.6951 Remote Similarity NPD5307 Clinical (unspecified phase)
0.6947 Remote Similarity NPD5005 Approved
0.6947 Remote Similarity NPD5006 Approved
0.6943 Remote Similarity NPD6798 Discontinued
0.6941 Remote Similarity NPD6801 Discontinued
0.6928 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6919 Remote Similarity NPD7768 Phase 2
0.6914 Remote Similarity NPD1375 Discontinued
0.6914 Remote Similarity NPD3540 Phase 1
0.6913 Remote Similarity NPD5536 Phase 2
0.6907 Remote Similarity NPD8151 Discontinued
0.6894 Remote Similarity NPD4108 Discontinued
0.689 Remote Similarity NPD3892 Phase 2
0.6887 Remote Similarity NPD5126 Approved
0.6887 Remote Similarity NPD5125 Phase 3
0.6886 Remote Similarity NPD1512 Approved
0.6883 Remote Similarity NPD1283 Approved
0.6882 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6879 Remote Similarity NPD3749 Approved
0.6879 Remote Similarity NPD4055 Discovery
0.6875 Remote Similarity NPD6653 Approved
0.6875 Remote Similarity NPD5242 Approved
0.6871 Remote Similarity NPD2424 Discontinued
0.6867 Remote Similarity NPD1548 Phase 1
0.6864 Remote Similarity NPD7458 Discontinued
0.686 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6855 Remote Similarity NPD2979 Phase 3
0.6852 Remote Similarity NPD3539 Phase 1
0.6852 Remote Similarity NPD2935 Discontinued
0.6848 Remote Similarity NPD5084 Clinical (unspecified phase)
0.6845 Remote Similarity NPD5403 Approved
0.6842 Remote Similarity NPD3496 Discontinued
0.6839 Remote Similarity NPD2797 Approved
0.6826 Remote Similarity NPD5401 Approved
0.6826 Remote Similarity NPD7446 Clinical (unspecified phase)
0.6825 Remote Similarity NPD4420 Approved
0.6818 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6813 Remote Similarity NPD5735 Approved
0.6813 Remote Similarity NPD1933 Approved
0.6807 Remote Similarity NPD7124 Phase 2
0.6802 Remote Similarity NPD2977 Approved
0.6802 Remote Similarity NPD2978 Approved
0.6797 Remote Similarity NPD1611 Approved
0.6792 Remote Similarity NPD6233 Phase 2
0.679 Remote Similarity NPD7033 Discontinued
0.6788 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6784 Remote Similarity NPD7411 Suspended
0.6779 Remote Similarity NPD7157 Approved
0.6774 Remote Similarity NPD6696 Suspended
0.6765 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6761 Remote Similarity NPD1247 Approved
0.6753 Remote Similarity NPD1608 Approved
0.675 Remote Similarity NPD2238 Phase 2
0.6748 Remote Similarity NPD2796 Approved
0.6748 Remote Similarity NPD6032 Approved
0.6747 Remote Similarity NPD2677 Approved
0.6742 Remote Similarity NPD4481 Phase 3
0.6736 Remote Similarity NPD7435 Discontinued
0.6735 Remote Similarity NPD228 Approved
0.6734 Remote Similarity NPD7930 Approved
0.673 Remote Similarity NPD1699 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