Structure

Physi-Chem Properties

Molecular Weight:  934.4
Volume:  911.12
LogP:  -0.205
LogD:  0.438
LogS:  -3.651
# Rotatable Bonds:  7
TPSA:  286.3
# H-Bond Aceptor:  21
# H-Bond Donor:  8
# Rings:  7
# Heavy Atoms:  21

MedChem Properties

QED Drug-Likeness Score:  0.127
Synthetic Accessibility Score:  7.343
Fsp3:  0.478
Lipinski Rule-of-5:  Rejected
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:  -6.603
MDCK Permeability:  1.7324275177088566e-05
Pgp-inhibitor:  0.996
Pgp-substrate:  0.993
Human Intestinal Absorption (HIA):  0.941
20% Bioavailability (F20%):  0.809
30% Bioavailability (F30%):  0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.157
Plasma Protein Binding (PPB):  64.19620513916016%
Volume Distribution (VD):  0.308
Pgp-substrate:  28.71617889404297%

ADMET: Metabolism

CYP1A2-inhibitor:  0.002
CYP1A2-substrate:  0.03
CYP2C19-inhibitor:  0.033
CYP2C19-substrate:  0.067
CYP2C9-inhibitor:  0.027
CYP2C9-substrate:  0.061
CYP2D6-inhibitor:  0.007
CYP2D6-substrate:  0.219
CYP3A4-inhibitor:  0.429
CYP3A4-substrate:  0.048

ADMET: Excretion

Clearance (CL):  1.352
Half-life (T1/2):  0.273

ADMET: Toxicity

hERG Blockers:  0.055
Human Hepatotoxicity (H-HT):  0.969
Drug-inuced Liver Injury (DILI):  0.96
AMES Toxicity:  0.017
Rat Oral Acute Toxicity:  0.521
Maximum Recommended Daily Dose:  0.828
Skin Sensitization:  0.024
Carcinogencity:  0.017
Eye Corrosion:  0.003
Eye Irritation:  0.003
Respiratory Toxicity:  0.018

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

  Natural Product: NPC123859

Natural Product ID:  NPC123859
Common Name*:   FAHSQQJARZIARU-UZNTZRCOSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  FAHSQQJARZIARU-UZNTZRCOSA-N
Standard InCHI:  InChI=1S/C46H58N6O15/c1-23-40(58)49-30(21-53)44(62)50(3)31(17-25-7-12-28(64-6)13-8-25)42(60)48-24(2)43(61)52(5)33-18-26-9-14-29(15-10-26)65-35-20-27(19-32(41(59)47-23)51(4)45(33)63)11-16-34(35)66-46-39(57)38(56)37(55)36(22-54)67-46/h7-16,20,23-24,30-33,36-39,46,53-57H,17-19,21-22H2,1-6H3,(H,47,59)(H,48,60)(H,49,58)/t23-,24+,30+,31+,32+,33+,36-,37-,38+,39-,46-/m1/s1
SMILES:  C[C@@H]1C(=N[C@@H](CO)C(=O)N(C)[C@@H](Cc2ccc(cc2)OC)C(=N[C@@H](C)C(=O)N(C)[C@H]2Cc3ccc(cc3)Oc3cc(ccc3O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)C[C@@H](C(=N1)O)N(C)C2=O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1288991
PubChem CID:   52944623
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000265] Carboxylic acids and derivatives
        • [CHEMONTID:0000013] Amino acids, peptides, and analogues
          • [CHEMONTID:0000348] Peptides
            • [CHEMONTID:0004831] Oligopeptides

*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
NPO16607 Rubia yunnanensis Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[12350148]
NPO16607 Rubia yunnanensis Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[12762798]
NPO16607 Rubia yunnanensis Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[21044847]
NPO16607 Rubia yunnanensis Species Rubiaceae Eukaryota n.a. root n.a. PMID[21973054]
NPO16607 Rubia yunnanensis Species Rubiaceae Eukaryota roots n.a. n.a. PMID[21973054]
NPO16607 Rubia yunnanensis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16607 Rubia yunnanensis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16607 Rubia yunnanensis Species Rubiaceae 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
NPT65 Cell Line HepG2 Homo sapiens IC50 = 12760.0 nM PMID[538000]
NPT181 Cell Line Bel-7402 Homo sapiens IC50 = 11450.0 nM PMID[538000]
NPT659 Cell Line SMMC-7721 Homo sapiens IC50 = 12970.0 nM PMID[538000]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 = 8570.0 nM PMID[538000]
NPT90 Cell Line DU-145 Homo sapiens IC50 = 10650.0 nM PMID[538000]
NPT306 Cell Line PC-3 Homo sapiens IC50 = 14400.0 nM PMID[538000]
NPT81 Cell Line A549 Homo sapiens IC50 = 5020.0 nM PMID[538000]
NPT547 Cell Line BGC-823 Homo sapiens IC50 = 6910.0 nM PMID[538000]
NPT165 Cell Line HeLa Homo sapiens IC50 = 3520.0 nM PMID[538000]
NPT380 Cell Line U-251 Homo sapiens IC50 = 8200.0 nM PMID[538000]
NPT319 Cell Line B16 Mus musculus IC50 = 2890.0 nM PMID[538000]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 1990.0 nM PMID[538000]
NPT2 Others Unspecified IC50 > 25.0 ug.mL-1 PMID[538000]

☑ 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 NPC123859 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
0.983 High Similarity NPC149962
0.9774 High Similarity NPC144314
0.9719 High Similarity NPC50548
0.9611 High Similarity NPC242728
0.905 High Similarity NPC276120
0.8864 High Similarity NPC164608
0.8798 High Similarity NPC29531
0.8771 High Similarity NPC32064
0.861 High Similarity NPC471563
0.8579 High Similarity NPC138083
0.8495 Intermediate Similarity NPC64140
0.8495 Intermediate Similarity NPC174122
0.8441 Intermediate Similarity NPC234069
0.8299 Intermediate Similarity NPC311357
0.7989 Intermediate Similarity NPC315542
0.797 Intermediate Similarity NPC326333
0.7969 Intermediate Similarity NPC473378
0.7969 Intermediate Similarity NPC473407
0.7892 Intermediate Similarity NPC326027
0.7889 Intermediate Similarity NPC473460
0.788 Intermediate Similarity NPC196091
0.785 Intermediate Similarity NPC473422
0.781 Intermediate Similarity NPC475292
0.781 Intermediate Similarity NPC475565
0.781 Intermediate Similarity NPC475349
0.7754 Intermediate Similarity NPC155506
0.7754 Intermediate Similarity NPC159767
0.7725 Intermediate Similarity NPC475442
0.7717 Intermediate Similarity NPC254700
0.7696 Intermediate Similarity NPC471561
0.7689 Intermediate Similarity NPC475624
0.7688 Intermediate Similarity NPC473693
0.7688 Intermediate Similarity NPC471568
0.766 Intermediate Similarity NPC473354
0.766 Intermediate Similarity NPC476227
0.766 Intermediate Similarity NPC473402
0.7656 Intermediate Similarity NPC294951
0.7647 Intermediate Similarity NPC230611
0.7632 Intermediate Similarity NPC45037
0.7632 Intermediate Similarity NPC475421
0.7621 Intermediate Similarity NPC471532
0.7604 Intermediate Similarity NPC471526
0.76 Intermediate Similarity NPC267414
0.7582 Intermediate Similarity NPC56635
0.756 Intermediate Similarity NPC471531
0.754 Intermediate Similarity NPC186617
0.7535 Intermediate Similarity NPC248903
0.7526 Intermediate Similarity NPC50016
0.7513 Intermediate Similarity NPC470112
0.7513 Intermediate Similarity NPC167763
0.7513 Intermediate Similarity NPC470903
0.7513 Intermediate Similarity NPC273755
0.7513 Intermediate Similarity NPC306804
0.7512 Intermediate Similarity NPC148124
0.7512 Intermediate Similarity NPC470846
0.75 Intermediate Similarity NPC471032
0.75 Intermediate Similarity NPC470935
0.75 Intermediate Similarity NPC40234
0.7488 Intermediate Similarity NPC26928
0.7487 Intermediate Similarity NPC294516
0.7487 Intermediate Similarity NPC107938
0.7475 Intermediate Similarity NPC475654
0.7474 Intermediate Similarity NPC471165
0.7474 Intermediate Similarity NPC26108
0.7465 Intermediate Similarity NPC99724
0.7463 Intermediate Similarity NPC477552
0.7463 Intermediate Similarity NPC477550
0.7462 Intermediate Similarity NPC473305
0.7462 Intermediate Similarity NPC163961
0.7461 Intermediate Similarity NPC476321
0.746 Intermediate Similarity NPC89831
0.7449 Intermediate Similarity NPC34780
0.7448 Intermediate Similarity NPC49353
0.7446 Intermediate Similarity NPC287757
0.7446 Intermediate Similarity NPC319320
0.7436 Intermediate Similarity NPC299806
0.7433 Intermediate Similarity NPC50380
0.7433 Intermediate Similarity NPC179250
0.7421 Intermediate Similarity NPC137627
0.7391 Intermediate Similarity NPC10221
0.7391 Intermediate Similarity NPC187028
0.7391 Intermediate Similarity NPC18249
0.7391 Intermediate Similarity NPC197741
0.7391 Intermediate Similarity NPC140915
0.7391 Intermediate Similarity NPC305700
0.7389 Intermediate Similarity NPC477551
0.7387 Intermediate Similarity NPC473716
0.7387 Intermediate Similarity NPC475597
0.7385 Intermediate Similarity NPC471049
0.7385 Intermediate Similarity NPC471050
0.7385 Intermediate Similarity NPC471048
0.7382 Intermediate Similarity NPC279871
0.738 Intermediate Similarity NPC472923
0.7368 Intermediate Similarity NPC252960
0.7366 Intermediate Similarity NPC235698
0.7366 Intermediate Similarity NPC131532
0.7363 Intermediate Similarity NPC116229
0.7363 Intermediate Similarity NPC139699
0.7363 Intermediate Similarity NPC114659
0.7358 Intermediate Similarity NPC194671
0.7358 Intermediate Similarity NPC269750
0.7356 Intermediate Similarity NPC293347
0.7348 Intermediate Similarity NPC277857
0.7348 Intermediate Similarity NPC115144
0.7347 Intermediate Similarity NPC102760
0.7343 Intermediate Similarity NPC79130
0.7343 Intermediate Similarity NPC258128
0.733 Intermediate Similarity NPC477666
0.733 Intermediate Similarity NPC248670
0.7323 Intermediate Similarity NPC230098
0.7318 Intermediate Similarity NPC63628
0.7318 Intermediate Similarity NPC178466
0.7316 Intermediate Similarity NPC198741
0.7316 Intermediate Similarity NPC329717
0.7306 Intermediate Similarity NPC2314
0.7302 Intermediate Similarity NPC218614
0.7302 Intermediate Similarity NPC473502
0.7296 Intermediate Similarity NPC473562
0.7292 Intermediate Similarity NPC158277
0.7292 Intermediate Similarity NPC136797
0.7283 Intermediate Similarity NPC229882
0.7283 Intermediate Similarity NPC158635
0.7282 Intermediate Similarity NPC329816
0.7277 Intermediate Similarity NPC308709
0.7253 Intermediate Similarity NPC473491
0.725 Intermediate Similarity NPC477526
0.7246 Intermediate Similarity NPC169605
0.7243 Intermediate Similarity NPC471073
0.7243 Intermediate Similarity NPC270811
0.7241 Intermediate Similarity NPC471592
0.7225 Intermediate Similarity NPC90984
0.7225 Intermediate Similarity NPC474858
0.7222 Intermediate Similarity NPC475981
0.7222 Intermediate Similarity NPC474746
0.7216 Intermediate Similarity NPC187194
0.7213 Intermediate Similarity NPC233702
0.7211 Intermediate Similarity NPC328649
0.7206 Intermediate Similarity NPC323662
0.72 Intermediate Similarity NPC283207
0.7198 Intermediate Similarity NPC245974
0.7196 Intermediate Similarity NPC4304
0.7188 Intermediate Similarity NPC328494
0.7186 Intermediate Similarity NPC94862
0.7182 Intermediate Similarity NPC247298
0.7182 Intermediate Similarity NPC470847
0.7181 Intermediate Similarity NPC186316
0.7178 Intermediate Similarity NPC328763
0.7178 Intermediate Similarity NPC314083
0.7178 Intermediate Similarity NPC24260
0.7177 Intermediate Similarity NPC257266
0.7174 Intermediate Similarity NPC182119
0.7166 Intermediate Similarity NPC245615
0.7166 Intermediate Similarity NPC61604
0.7166 Intermediate Similarity NPC115466
0.7166 Intermediate Similarity NPC299706
0.7163 Intermediate Similarity NPC82056
0.7158 Intermediate Similarity NPC324081
0.7158 Intermediate Similarity NPC469654
0.7158 Intermediate Similarity NPC469479
0.7158 Intermediate Similarity NPC476743
0.7157 Intermediate Similarity NPC24228
0.7157 Intermediate Similarity NPC234318
0.7157 Intermediate Similarity NPC281629
0.7143 Intermediate Similarity NPC184933
0.7143 Intermediate Similarity NPC474470
0.7143 Intermediate Similarity NPC59827
0.7143 Intermediate Similarity NPC478055
0.7143 Intermediate Similarity NPC257728
0.7136 Intermediate Similarity NPC315253
0.7135 Intermediate Similarity NPC46009
0.7135 Intermediate Similarity NPC475123
0.7135 Intermediate Similarity NPC111785
0.7135 Intermediate Similarity NPC475204
0.7129 Intermediate Similarity NPC41122
0.7129 Intermediate Similarity NPC318805
0.7129 Intermediate Similarity NPC475754
0.7129 Intermediate Similarity NPC475768
0.7129 Intermediate Similarity NPC319549
0.7128 Intermediate Similarity NPC476194
0.7122 Intermediate Similarity NPC70290
0.7122 Intermediate Similarity NPC73020
0.7122 Intermediate Similarity NPC14622
0.7122 Intermediate Similarity NPC215098
0.7122 Intermediate Similarity NPC46744
0.7122 Intermediate Similarity NPC124302
0.7121 Intermediate Similarity NPC474607
0.712 Intermediate Similarity NPC476744
0.7119 Intermediate Similarity NPC476411
0.7114 Intermediate Similarity NPC237579
0.7114 Intermediate Similarity NPC61332
0.7114 Intermediate Similarity NPC240130
0.7113 Intermediate Similarity NPC474953
0.7109 Intermediate Similarity NPC153365
0.7108 Intermediate Similarity NPC477258
0.7105 Intermediate Similarity NPC223335
0.7105 Intermediate Similarity NPC133984
0.7105 Intermediate Similarity NPC63931
0.7105 Intermediate Similarity NPC40920
0.7101 Intermediate Similarity NPC316164
0.71 Intermediate Similarity NPC314743

  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 NPC123859 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
0.7889 Intermediate Similarity NPD5773 Approved
0.7889 Intermediate Similarity NPD5772 Approved
0.7884 Intermediate Similarity NPD7132 Clinical (unspecified phase)
0.7716 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD7810 Phase 3
0.7688 Intermediate Similarity NPD7811 Phase 3
0.7637 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7617 Intermediate Similarity NPD6851 Approved
0.7617 Intermediate Similarity NPD6853 Approved
0.7596 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7565 Intermediate Similarity NPD7280 Phase 3
0.7565 Intermediate Similarity NPD7281 Phase 3
0.7556 Intermediate Similarity NPD7131 Phase 3
0.7549 Intermediate Similarity NPD7607 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7608 Discontinued
0.75 Intermediate Similarity NPD6297 Approved
0.7473 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7371 Intermediate Similarity NPD7038 Approved
0.7371 Intermediate Similarity NPD7039 Approved
0.7368 Intermediate Similarity NPD5137 Approved
0.7323 Intermediate Similarity NPD7243 Clinical (unspecified phase)
0.7312 Intermediate Similarity NPD2978 Approved
0.7312 Intermediate Similarity NPD2977 Approved
0.729 Intermediate Similarity NPD8318 Clinical (unspecified phase)
0.7287 Intermediate Similarity NPD8031 Discontinued
0.7263 Intermediate Similarity NPD7485 Phase 3
0.7263 Intermediate Similarity NPD7484 Phase 3
0.7259 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7251 Intermediate Similarity NPD7827 Phase 1
0.725 Intermediate Similarity NPD5525 Clinical (unspecified phase)
0.7215 Intermediate Similarity NPD8058 Clinical (unspecified phase)
0.7215 Intermediate Similarity NPD8059 Phase 3
0.7182 Intermediate Similarity NPD8323 Discontinued
0.7177 Intermediate Similarity NPD7584 Approved
0.7177 Intermediate Similarity NPD7583 Approved
0.7174 Intermediate Similarity NPD2122 Discontinued
0.7158 Intermediate Similarity NPD4123 Phase 3
0.715 Intermediate Similarity NPD7291 Discontinued
0.7143 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7585 Approved
0.7136 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7129 Intermediate Similarity NPD7296 Approved
0.7128 Intermediate Similarity NPD5312 Approved
0.7128 Intermediate Similarity NPD5313 Approved
0.7122 Intermediate Similarity NPD4420 Approved
0.712 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.712 Intermediate Similarity NPD7526 Approved
0.712 Intermediate Similarity NPD52 Approved
0.7114 Intermediate Similarity NPD6377 Clinical (unspecified phase)
0.7112 Intermediate Similarity NPD7118 Clinical (unspecified phase)
0.7088 Intermediate Similarity NPD5241 Discontinued
0.7087 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD2973 Approved
0.7073 Intermediate Similarity NPD2975 Approved
0.7073 Intermediate Similarity NPD2974 Approved
0.7072 Intermediate Similarity NPD4162 Approved
0.7072 Intermediate Similarity NPD4236 Phase 3
0.7072 Intermediate Similarity NPD4237 Approved
0.7071 Intermediate Similarity NPD3936 Clinical (unspecified phase)
0.7067 Intermediate Similarity NPD5006 Approved
0.7067 Intermediate Similarity NPD5005 Approved
0.7065 Intermediate Similarity NPD7906 Approved
0.7065 Intermediate Similarity NPD8389 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD4675 Approved
0.7059 Intermediate Similarity NPD4678 Approved
0.7043 Intermediate Similarity NPD3686 Approved
0.7043 Intermediate Similarity NPD3687 Approved
0.7037 Intermediate Similarity NPD7972 Discontinued
0.7031 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7031 Intermediate Similarity NPD5677 Discontinued
0.7021 Intermediate Similarity NPD6386 Approved
0.7021 Intermediate Similarity NPD6385 Approved
0.7021 Intermediate Similarity NPD7109 Clinical (unspecified phase)
0.7021 Intermediate Similarity NPD7110 Phase 1
0.702 Intermediate Similarity NPD5192 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD2493 Approved
0.7019 Intermediate Similarity NPD2494 Approved
0.7017 Intermediate Similarity NPD7596 Clinical (unspecified phase)
0.7016 Intermediate Similarity NPD8070 Approved
0.7015 Intermediate Similarity NPD3857 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD8053 Approved
0.7 Intermediate Similarity NPD8054 Approved
0.6995 Remote Similarity NPD2219 Phase 1
0.6989 Remote Similarity NPD6662 Clinical (unspecified phase)
0.6981 Remote Similarity NPD7701 Phase 2
0.698 Remote Similarity NPD6843 Phase 3
0.698 Remote Similarity NPD6842 Approved
0.698 Remote Similarity NPD6841 Approved
0.6976 Remote Similarity NPD4413 Clinical (unspecified phase)
0.6973 Remote Similarity NPD3688 Clinical (unspecified phase)
0.6973 Remote Similarity NPD3146 Approved
0.6971 Remote Similarity NPD4580 Approved
0.6971 Remote Similarity NPD5457 Discontinued
0.6968 Remote Similarity NPD8417 Discontinued
0.6967 Remote Similarity NPD8161 Suspended
0.6963 Remote Similarity NPD7801 Approved
0.6959 Remote Similarity NPD3051 Approved
0.6954 Remote Similarity NPD42 Phase 2
0.6954 Remote Similarity NPD7054 Approved
0.6954 Remote Similarity NPD8156 Discontinued
0.6954 Remote Similarity NPD6042 Phase 2
0.6952 Remote Similarity NPD4210 Discontinued
0.6948 Remote Similarity NPD8151 Discontinued
0.6938 Remote Similarity NPD3452 Approved
0.6938 Remote Similarity NPD3450 Approved
0.6935 Remote Similarity NPD7613 Discontinued
0.6919 Remote Similarity NPD7074 Phase 3
0.6919 Remote Similarity NPD4583 Approved
0.6919 Remote Similarity NPD7472 Approved
0.6919 Remote Similarity NPD4582 Approved
0.6912 Remote Similarity NPD7047 Phase 3
0.6912 Remote Similarity NPD3808 Clinical (unspecified phase)
0.6905 Remote Similarity NPD6823 Phase 2
0.6904 Remote Similarity NPD8252 Approved
0.6904 Remote Similarity NPD8251 Approved
0.6904 Remote Similarity NPD8099 Discontinued
0.69 Remote Similarity NPD7808 Phase 3
0.6897 Remote Similarity NPD4157 Discontinued
0.6893 Remote Similarity NPD5718 Phase 2
0.6885 Remote Similarity NPD6860 Clinical (unspecified phase)
0.6885 Remote Similarity NPD3060 Approved
0.6884 Remote Similarity NPD7007 Discovery
0.6882 Remote Similarity NPD4739 Approved
0.688 Remote Similarity NPD8152 Approved
0.688 Remote Similarity NPD8153 Approved
0.6875 Remote Similarity NPD5752 Clinical (unspecified phase)
0.6872 Remote Similarity NPD4004 Approved
0.6872 Remote Similarity NPD7315 Approved
0.6872 Remote Similarity NPD4002 Approved
0.6859 Remote Similarity NPD8455 Phase 2
0.6856 Remote Similarity NPD2904 Discontinued
0.6854 Remote Similarity NPD5745 Approved
0.6847 Remote Similarity NPD4663 Approved
0.6842 Remote Similarity NPD6677 Suspended
0.6837 Remote Similarity NPD2970 Approved
0.6837 Remote Similarity NPD2969 Approved
0.6834 Remote Similarity NPD3885 Approved
0.6829 Remote Similarity NPD6505 Approved
0.6829 Remote Similarity NPD2490 Approved
0.6829 Remote Similarity NPD2488 Approved
0.6829 Remote Similarity NPD6504 Approved
0.6825 Remote Similarity NPD4005 Discontinued
0.6823 Remote Similarity NPD5967 Approved
0.6823 Remote Similarity NPD6063 Approved
0.6823 Remote Similarity NPD7318 Phase 3
0.6806 Remote Similarity NPD7783 Phase 2
0.6806 Remote Similarity NPD6844 Discontinued
0.6806 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6806 Remote Similarity NPD5722 Discontinued
0.6802 Remote Similarity NPD6997 Phase 2
0.6789 Remote Similarity NPD6875 Approved
0.6789 Remote Similarity NPD6876 Approved
0.6788 Remote Similarity NPD6788 Approved
0.6782 Remote Similarity NPD2968 Approved
0.6782 Remote Similarity NPD2971 Approved
0.6782 Remote Similarity NPD4578 Approved
0.6782 Remote Similarity NPD4577 Approved
0.6776 Remote Similarity NPD1375 Discontinued
0.6771 Remote Similarity NPD5563 Clinical (unspecified phase)
0.6769 Remote Similarity NPD6746 Phase 2
0.6769 Remote Similarity NPD2042 Clinical (unspecified phase)
0.6769 Remote Similarity NPD2041 Clinical (unspecified phase)
0.6766 Remote Similarity NPD7251 Discontinued
0.6762 Remote Similarity NPD7565 Approved
0.6759 Remote Similarity NPD7874 Approved
0.6759 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6758 Remote Similarity NPD8149 Discontinued
0.6757 Remote Similarity NPD6658 Clinical (unspecified phase)
0.6757 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6757 Remote Similarity NPD6331 Phase 2
0.6754 Remote Similarity NPD4772 Phase 2
0.6754 Remote Similarity NPD6072 Discontinued
0.6754 Remote Similarity NPD4773 Phase 2
0.6753 Remote Similarity NPD5604 Discontinued
0.675 Remote Similarity NPD5485 Approved
0.675 Remote Similarity NPD5484 Approved
0.675 Remote Similarity NPD5441 Clinical (unspecified phase)
0.6742 Remote Similarity NPD5746 Approved
0.6738 Remote Similarity NPD1774 Approved
0.6735 Remote Similarity NPD6107 Approved
0.6729 Remote Similarity NPD7999 Approved
0.6721 Remote Similarity NPD2239 Approved
0.6721 Remote Similarity NPD2240 Approved
0.672 Remote Similarity NPD3692 Discontinued
0.6719 Remote Similarity NPD7317 Phase 3
0.6718 Remote Similarity NPD8245 Clinical (unspecified phase)
0.6717 Remote Similarity NPD2489 Approved
0.6717 Remote Similarity NPD27 Approved
0.6717 Remote Similarity NPD4481 Phase 3
0.6716 Remote Similarity NPD6797 Phase 2
0.6711 Remote Similarity NPD7224 Discontinued
0.6711 Remote Similarity NPD7223 Discontinued
0.6702 Remote Similarity NPD3536 Discontinued
0.6702 Remote Similarity NPD1754 Clinical (unspecified phase)
0.67 Remote Similarity NPD7313 Approved
0.67 Remote Similarity NPD7312 Approved
0.67 Remote Similarity NPD7311 Approved
0.67 Remote Similarity NPD7310 Approved
0.6699 Remote Similarity NPD5582 Discontinued
0.6696 Remote Similarity NPD5619 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