Structure

Physi-Chem Properties

Molecular Weight:  975.42
Volume:  954.072
LogP:  -0.445
LogD:  0.111
LogS:  -3.514
# Rotatable Bonds:  9
TPSA:  309.16
# H-Bond Aceptor:  22
# H-Bond Donor:  9
# Rings:  7
# Heavy Atoms:  22

MedChem Properties

QED Drug-Likeness Score:  0.118
Synthetic Accessibility Score:  7.428
Fsp3:  0.479
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:  -6.375
MDCK Permeability:  1.116873954742914e-05
Pgp-inhibitor:  0.994
Pgp-substrate:  0.997
Human Intestinal Absorption (HIA):  0.832
20% Bioavailability (F20%):  0.321
30% Bioavailability (F30%):  0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.116
Plasma Protein Binding (PPB):  65.64769744873047%
Volume Distribution (VD):  0.336
Pgp-substrate:  27.578914642333984%

ADMET: Metabolism

CYP1A2-inhibitor:  0.002
CYP1A2-substrate:  0.024
CYP2C19-inhibitor:  0.03
CYP2C19-substrate:  0.053
CYP2C9-inhibitor:  0.041
CYP2C9-substrate:  0.05
CYP2D6-inhibitor:  0.008
CYP2D6-substrate:  0.199
CYP3A4-inhibitor:  0.36
CYP3A4-substrate:  0.049

ADMET: Excretion

Clearance (CL):  1.561
Half-life (T1/2):  0.199

ADMET: Toxicity

hERG Blockers:  0.067
Human Hepatotoxicity (H-HT):  0.963
Drug-inuced Liver Injury (DILI):  0.918
AMES Toxicity:  0.017
Rat Oral Acute Toxicity:  0.626
Maximum Recommended Daily Dose:  0.947
Skin Sensitization:  0.025
Carcinogencity:  0.02
Eye Corrosion:  0.003
Eye Irritation:  0.003
Respiratory Toxicity:  0.039

Download Data

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

  Natural Product: NPC242728

Natural Product ID:  NPC242728
Common Name*:   Rubiyunnanin F
IUPAC Name:   n.a.
Synonyms:   Rubiyunnanin F
Standard InCHIKey:  YPYSDFAVFSDUFJ-VUYAFSJYSA-N
Standard InCHI:  InChI=1S/C48H61N7O15/c1-24-42(61)52-31(16-18-38(49)57)46(65)53(3)32(19-26-7-12-29(67-6)13-8-26)44(63)51-25(2)45(64)55(5)34-20-27-9-14-30(15-10-27)68-36-22-28(21-33(43(62)50-24)54(4)47(34)66)11-17-35(36)69-48-41(60)40(59)39(58)37(23-56)70-48/h7-15,17,22,24-25,31-34,37,39-41,48,56,58-60H,16,18-21,23H2,1-6H3,(H2,49,57)(H,50,62)(H,51,63)(H,52,61)/t24-,25+,31+,32+,33+,34+,37-,39-,40+,41-,48-/m1/s1
SMILES:  C[C@@H]1C(=N[C@@H](CCC(=N)O)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:   CHEMBL1288985
PubChem CID:   52948965
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 = 38900.0 nM PMID[540341]
NPT181 Cell Line Bel-7402 Homo sapiens IC50 = 20990.0 nM PMID[540341]
NPT659 Cell Line SMMC-7721 Homo sapiens IC50 = 14320.0 nM PMID[540341]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 = 6320.0 nM PMID[540341]
NPT90 Cell Line DU-145 Homo sapiens IC50 = 41620.0 nM PMID[540341]
NPT306 Cell Line PC-3 Homo sapiens IC50 = 22310.0 nM PMID[540341]
NPT81 Cell Line A549 Homo sapiens IC50 = 8180.0 nM PMID[540341]
NPT547 Cell Line BGC-823 Homo sapiens IC50 = 12470.0 nM PMID[540341]
NPT165 Cell Line HeLa Homo sapiens IC50 = 19150.0 nM PMID[540341]
NPT380 Cell Line U-251 Homo sapiens IC50 = 14990.0 nM PMID[540341]
NPT319 Cell Line B16 Mus musculus IC50 = 3440.0 nM PMID[540341]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 1770.0 nM PMID[540341]
NPT2 Others Unspecified IC50 > 25.0 ug.mL-1 PMID[540341]

☑ 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 NPC242728 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
0.9774 High Similarity NPC149962
0.9719 High Similarity NPC144314
0.9665 High Similarity NPC50548
0.9611 High Similarity NPC123859
0.8944 High Similarity NPC138083
0.8814 High Similarity NPC164608
0.875 High Similarity NPC29531
0.8722 High Similarity NPC32064
0.8689 High Similarity NPC276120
0.8663 High Similarity NPC471563
0.8649 High Similarity NPC64140
0.8649 High Similarity NPC174122
0.8595 High Similarity NPC234069
0.8163 Intermediate Similarity NPC311357
0.8115 Intermediate Similarity NPC473407
0.8115 Intermediate Similarity NPC473378
0.803 Intermediate Similarity NPC473460
0.7968 Intermediate Similarity NPC45037
0.7931 Intermediate Similarity NPC326333
0.7903 Intermediate Similarity NPC159767
0.7903 Intermediate Similarity NPC155506
0.79 Intermediate Similarity NPC473422
0.7854 Intermediate Similarity NPC326027
0.7849 Intermediate Similarity NPC273755
0.7849 Intermediate Similarity NPC306804
0.7807 Intermediate Similarity NPC473354
0.7807 Intermediate Similarity NPC473402
0.7801 Intermediate Similarity NPC294951
0.7796 Intermediate Similarity NPC230611
0.7766 Intermediate Similarity NPC50016
0.776 Intermediate Similarity NPC315542
0.7749 Intermediate Similarity NPC471526
0.7739 Intermediate Similarity NPC267414
0.7713 Intermediate Similarity NPC476227
0.7689 Intermediate Similarity NPC475565
0.7689 Intermediate Similarity NPC475349
0.7689 Intermediate Similarity NPC475292
0.7684 Intermediate Similarity NPC269750
0.7684 Intermediate Similarity NPC194671
0.7659 Intermediate Similarity NPC471561
0.7647 Intermediate Similarity NPC196091
0.7634 Intermediate Similarity NPC107938
0.7634 Intermediate Similarity NPC294516
0.7619 Intermediate Similarity NPC471165
0.7606 Intermediate Similarity NPC475442
0.7604 Intermediate Similarity NPC476321
0.7602 Intermediate Similarity NPC473305
0.7602 Intermediate Similarity NPC163961
0.7596 Intermediate Similarity NPC319320
0.7596 Intermediate Similarity NPC287757
0.7581 Intermediate Similarity NPC254700
0.757 Intermediate Similarity NPC475624
0.7566 Intermediate Similarity NPC137627
0.7553 Intermediate Similarity NPC40234
0.7541 Intermediate Similarity NPC56635
0.7526 Intermediate Similarity NPC471048
0.7526 Intermediate Similarity NPC471050
0.7526 Intermediate Similarity NPC471049
0.7526 Intermediate Similarity NPC279871
0.7526 Intermediate Similarity NPC26108
0.7513 Intermediate Similarity NPC89831
0.75 Intermediate Similarity NPC471532
0.75 Intermediate Similarity NPC475421
0.75 Intermediate Similarity NPC248903
0.7487 Intermediate Similarity NPC299806
0.7477 Intermediate Similarity NPC148124
0.746 Intermediate Similarity NPC471568
0.746 Intermediate Similarity NPC473693
0.746 Intermediate Similarity NPC46009
0.7459 Intermediate Similarity NPC471032
0.7459 Intermediate Similarity NPC470935
0.7454 Intermediate Similarity NPC26928
0.7441 Intermediate Similarity NPC471531
0.7438 Intermediate Similarity NPC475654
0.7438 Intermediate Similarity NPC477551
0.743 Intermediate Similarity NPC99724
0.7426 Intermediate Similarity NPC477550
0.7426 Intermediate Similarity NPC477552
0.7409 Intermediate Similarity NPC49353
0.7407 Intermediate Similarity NPC186617
0.7395 Intermediate Similarity NPC470846
0.7394 Intermediate Similarity NPC179250
0.7394 Intermediate Similarity NPC50380
0.7391 Intermediate Similarity NPC257266
0.7387 Intermediate Similarity NPC248822
0.7385 Intermediate Similarity NPC470112
0.7385 Intermediate Similarity NPC470903
0.7385 Intermediate Similarity NPC167763
0.7382 Intermediate Similarity NPC248670
0.7379 Intermediate Similarity NPC477666
0.7376 Intermediate Similarity NPC281629
0.7368 Intermediate Similarity NPC475204
0.7368 Intermediate Similarity NPC475123
0.7356 Intermediate Similarity NPC257728
0.7354 Intermediate Similarity NPC328649
0.7351 Intermediate Similarity NPC197741
0.7351 Intermediate Similarity NPC187028
0.7351 Intermediate Similarity NPC10221
0.7351 Intermediate Similarity NPC305700
0.7351 Intermediate Similarity NPC18249
0.7351 Intermediate Similarity NPC140915
0.735 Intermediate Similarity NPC473716
0.735 Intermediate Similarity NPC475597
0.735 Intermediate Similarity NPC475754
0.734 Intermediate Similarity NPC472923
0.7337 Intermediate Similarity NPC61332
0.7337 Intermediate Similarity NPC240130
0.7323 Intermediate Similarity NPC34780
0.7322 Intermediate Similarity NPC116229
0.7322 Intermediate Similarity NPC139699
0.7322 Intermediate Similarity NPC114659
0.7321 Intermediate Similarity NPC153365
0.7313 Intermediate Similarity NPC314083
0.7313 Intermediate Similarity NPC302715
0.731 Intermediate Similarity NPC102760
0.7308 Intermediate Similarity NPC115144
0.7308 Intermediate Similarity NPC277857
0.7308 Intermediate Similarity NPC476743
0.7308 Intermediate Similarity NPC324081
0.7293 Intermediate Similarity NPC314743
0.7286 Intermediate Similarity NPC230098
0.7286 Intermediate Similarity NPC124626
0.7278 Intermediate Similarity NPC178466
0.7278 Intermediate Similarity NPC63628
0.7277 Intermediate Similarity NPC198741
0.7268 Intermediate Similarity NPC2314
0.7268 Intermediate Similarity NPC476744
0.7268 Intermediate Similarity NPC471031
0.7268 Intermediate Similarity NPC469689
0.7259 Intermediate Similarity NPC473562
0.7249 Intermediate Similarity NPC63931
0.7246 Intermediate Similarity NPC235698
0.7245 Intermediate Similarity NPC329816
0.7243 Intermediate Similarity NPC229882
0.7243 Intermediate Similarity NPC158635
0.724 Intermediate Similarity NPC252960
0.724 Intermediate Similarity NPC328494
0.7238 Intermediate Similarity NPC293347
0.7236 Intermediate Similarity NPC94862
0.7229 Intermediate Similarity NPC319774
0.7225 Intermediate Similarity NPC258128
0.7225 Intermediate Similarity NPC79130
0.7214 Intermediate Similarity NPC477526
0.7209 Intermediate Similarity NPC82056
0.7206 Intermediate Similarity NPC66909
0.7204 Intermediate Similarity NPC471073
0.7204 Intermediate Similarity NPC270811
0.7189 Intermediate Similarity NPC476742
0.7188 Intermediate Similarity NPC90984
0.7188 Intermediate Similarity NPC329717
0.7184 Intermediate Similarity NPC473450
0.7178 Intermediate Similarity NPC318805
0.7178 Intermediate Similarity NPC41122
0.7175 Intermediate Similarity NPC187194
0.7174 Intermediate Similarity NPC233702
0.7173 Intermediate Similarity NPC473502
0.7173 Intermediate Similarity NPC218614
0.7171 Intermediate Similarity NPC323662
0.7165 Intermediate Similarity NPC158277
0.7164 Intermediate Similarity NPC283207
0.7164 Intermediate Similarity NPC237579
0.7158 Intermediate Similarity NPC133984
0.7158 Intermediate Similarity NPC245974
0.7157 Intermediate Similarity NPC473404
0.7157 Intermediate Similarity NPC308709
0.7157 Intermediate Similarity NPC470646
0.7151 Intermediate Similarity NPC476741
0.7149 Intermediate Similarity NPC470847
0.7143 Intermediate Similarity NPC24260
0.7143 Intermediate Similarity NPC328763
0.7143 Intermediate Similarity NPC247298
0.7143 Intermediate Similarity NPC131532
0.7136 Intermediate Similarity NPC248642
0.7136 Intermediate Similarity NPC229234
0.7135 Intermediate Similarity NPC182119
0.7129 Intermediate Similarity NPC169605
0.7128 Intermediate Similarity NPC245615
0.7128 Intermediate Similarity NPC115466
0.7128 Intermediate Similarity NPC137813
0.7128 Intermediate Similarity NPC61604
0.7128 Intermediate Similarity NPC299706
0.7122 Intermediate Similarity NPC234318
0.7122 Intermediate Similarity NPC471592
0.712 Intermediate Similarity NPC290755
0.712 Intermediate Similarity NPC304074
0.712 Intermediate Similarity NPC471771
0.7116 Intermediate Similarity NPC38964
0.7109 Intermediate Similarity NPC478005
0.7108 Intermediate Similarity NPC184933
0.7108 Intermediate Similarity NPC59827
0.7107 Intermediate Similarity NPC474470
0.71 Intermediate Similarity NPC156576
0.7098 Intermediate Similarity NPC474858
0.7097 Intermediate Similarity NPC111785
0.7095 Intermediate Similarity NPC475768
0.7089 Intermediate Similarity NPC92235
0.7085 Intermediate Similarity NPC195538
0.7085 Intermediate Similarity NPC474607
0.7079 Intermediate Similarity NPC476411
0.7077 Intermediate Similarity NPC474953

  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 NPC242728 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
0.7937 Intermediate Similarity NPD7132 Clinical (unspecified phase)
0.7857 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7853 Intermediate Similarity NPD6851 Approved
0.7853 Intermediate Similarity NPD6853 Approved
0.7747 Intermediate Similarity NPD5773 Approved
0.7747 Intermediate Similarity NPD5772 Approved
0.7742 Intermediate Similarity NPD7608 Discontinued
0.7737 Intermediate Similarity NPD6297 Approved
0.7562 Intermediate Similarity NPD7810 Phase 3
0.7562 Intermediate Similarity NPD7811 Phase 3
0.7554 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7526 Intermediate Similarity NPD7280 Phase 3
0.7526 Intermediate Similarity NPD7281 Phase 3
0.7514 Intermediate Similarity NPD7131 Phase 3
0.7513 Intermediate Similarity NPD7039 Approved
0.7513 Intermediate Similarity NPD7038 Approved
0.75 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7459 Intermediate Similarity NPD2978 Approved
0.7459 Intermediate Similarity NPD2977 Approved
0.7433 Intermediate Similarity NPD8031 Discontinued
0.7433 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7427 Intermediate Similarity NPD7607 Clinical (unspecified phase)
0.7424 Intermediate Similarity NPD6377 Clinical (unspecified phase)
0.7418 Intermediate Similarity NPD8318 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD7485 Phase 3
0.7407 Intermediate Similarity NPD7484 Phase 3
0.7391 Intermediate Similarity NPD7583 Approved
0.7387 Intermediate Similarity NPD5525 Clinical (unspecified phase)
0.7381 Intermediate Similarity NPD7827 Phase 1
0.7356 Intermediate Similarity NPD7585 Approved
0.7333 Intermediate Similarity NPD5192 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD7584 Approved
0.7286 Intermediate Similarity NPD7243 Clinical (unspecified phase)
0.724 Intermediate Similarity NPD5137 Approved
0.7222 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.722 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7206 Intermediate Similarity NPD2974 Approved
0.7206 Intermediate Similarity NPD2975 Approved
0.7206 Intermediate Similarity NPD2973 Approved
0.7198 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7192 Intermediate Similarity NPD4413 Clinical (unspecified phase)
0.7189 Intermediate Similarity NPD3687 Approved
0.7189 Intermediate Similarity NPD3686 Approved
0.7182 Intermediate Similarity NPD8058 Clinical (unspecified phase)
0.7182 Intermediate Similarity NPD8059 Phase 3
0.7174 Intermediate Similarity NPD7526 Approved
0.7174 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.7174 Intermediate Similarity NPD52 Approved
0.7166 Intermediate Similarity NPD7118 Clinical (unspecified phase)
0.7166 Intermediate Similarity NPD6386 Approved
0.7166 Intermediate Similarity NPD6385 Approved
0.715 Intermediate Similarity NPD2494 Approved
0.715 Intermediate Similarity NPD2493 Approved
0.7143 Intermediate Similarity NPD8323 Discontinued
0.7135 Intermediate Similarity NPD2122 Discontinued
0.7127 Intermediate Similarity NPD4162 Approved
0.712 Intermediate Similarity NPD4123 Phase 3
0.7114 Intermediate Similarity NPD7291 Discontinued
0.7114 Intermediate Similarity NPD7906 Approved
0.7114 Intermediate Similarity NPD4157 Discontinued
0.7101 Intermediate Similarity NPD4580 Approved
0.7092 Intermediate Similarity NPD6042 Phase 2
0.7092 Intermediate Similarity NPD42 Phase 2
0.7083 Intermediate Similarity NPD5677 Discontinued
0.7083 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7074 Intermediate Similarity NPD7110 Phase 1
0.7074 Intermediate Similarity NPD7109 Clinical (unspecified phase)
0.7072 Intermediate Similarity NPD7596 Clinical (unspecified phase)
0.7069 Intermediate Similarity NPD8153 Approved
0.7069 Intermediate Similarity NPD8152 Approved
0.7067 Intermediate Similarity NPD3452 Approved
0.7067 Intermediate Similarity NPD3450 Approved
0.7049 Intermediate Similarity NPD5241 Discontinued
0.7048 Intermediate Similarity NPD4583 Approved
0.7048 Intermediate Similarity NPD4582 Approved
0.7043 Intermediate Similarity NPD6662 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD3936 Clinical (unspecified phase)
0.7033 Intermediate Similarity NPD3060 Approved
0.7027 Intermediate Similarity NPD3146 Approved
0.7027 Intermediate Similarity NPD3688 Clinical (unspecified phase)
0.7021 Intermediate Similarity NPD4675 Approved
0.7021 Intermediate Similarity NPD4678 Approved
0.7019 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD5457 Discontinued
0.701 Intermediate Similarity NPD3051 Approved
0.7005 Intermediate Similarity NPD4420 Approved
0.7 Intermediate Similarity NPD4004 Approved
0.7 Intermediate Similarity NPD4002 Approved
0.6989 Remote Similarity NPD7613 Discontinued
0.6984 Remote Similarity NPD6072 Discontinued
0.698 Remote Similarity NPD3857 Clinical (unspecified phase)
0.6965 Remote Similarity NPD8053 Approved
0.6965 Remote Similarity NPD8054 Approved
0.6961 Remote Similarity NPD2490 Approved
0.6961 Remote Similarity NPD2488 Approved
0.6959 Remote Similarity NPD7047 Phase 3
0.6959 Remote Similarity NPD8149 Discontinued
0.6957 Remote Similarity NPD2219 Phase 1
0.6946 Remote Similarity NPD6842 Approved
0.6946 Remote Similarity NPD6841 Approved
0.6946 Remote Similarity NPD6843 Phase 3
0.694 Remote Similarity NPD4237 Approved
0.694 Remote Similarity NPD6860 Clinical (unspecified phase)
0.694 Remote Similarity NPD4236 Phase 3
0.6934 Remote Similarity NPD7999 Approved
0.693 Remote Similarity NPD7801 Approved
0.6927 Remote Similarity NPD7296 Approved
0.6919 Remote Similarity NPD8156 Discontinued
0.6919 Remote Similarity NPD5312 Approved
0.6919 Remote Similarity NPD5313 Approved
0.6915 Remote Similarity NPD2971 Approved
0.6915 Remote Similarity NPD2968 Approved
0.6911 Remote Similarity NPD7972 Discontinued
0.6897 Remote Similarity NPD4663 Approved
0.6895 Remote Similarity NPD6677 Suspended
0.6891 Remote Similarity NPD8070 Approved
0.6888 Remote Similarity NPD2969 Approved
0.6888 Remote Similarity NPD2970 Approved
0.6887 Remote Similarity NPD4040 Phase 1
0.6885 Remote Similarity NPD7153 Discontinued
0.6884 Remote Similarity NPD3885 Approved
0.6878 Remote Similarity NPD3808 Clinical (unspecified phase)
0.6872 Remote Similarity NPD5006 Approved
0.6872 Remote Similarity NPD6107 Approved
0.6872 Remote Similarity NPD5005 Approved
0.6869 Remote Similarity NPD8099 Discontinued
0.6869 Remote Similarity NPD8251 Approved
0.6869 Remote Similarity NPD8252 Approved
0.6859 Remote Similarity NPD5722 Discontinued
0.6856 Remote Similarity NPD8245 Clinical (unspecified phase)
0.6854 Remote Similarity NPD5718 Phase 2
0.6854 Remote Similarity NPD8161 Suspended
0.6852 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6852 Remote Similarity NPD7783 Phase 2
0.685 Remote Similarity NPD7007 Discovery
0.6847 Remote Similarity NPD6997 Phase 2
0.6845 Remote Similarity NPD4739 Approved
0.6845 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6845 Remote Similarity NPD3536 Discontinued
0.6842 Remote Similarity NPD6875 Approved
0.6842 Remote Similarity NPD8417 Discontinued
0.6842 Remote Similarity NPD6876 Approved
0.6837 Remote Similarity NPD8151 Discontinued
0.6836 Remote Similarity NPD5752 Clinical (unspecified phase)
0.6834 Remote Similarity NPD7054 Approved
0.6832 Remote Similarity NPD4577 Approved
0.6832 Remote Similarity NPD4578 Approved
0.6829 Remote Similarity NPD7235 Clinical (unspecified phase)
0.6825 Remote Similarity NPD4210 Discontinued
0.6823 Remote Similarity NPD7046 Clinical (unspecified phase)
0.6823 Remote Similarity NPD8455 Phase 2
0.6816 Remote Similarity NPD5745 Approved
0.6814 Remote Similarity NPD3863 Clinical (unspecified phase)
0.6809 Remote Similarity NPD5261 Clinical (unspecified phase)
0.68 Remote Similarity NPD7074 Phase 3
0.68 Remote Similarity NPD7472 Approved
0.6798 Remote Similarity NPD6618 Phase 2
0.6792 Remote Similarity NPD6823 Phase 2
0.6791 Remote Similarity NPD1774 Approved
0.6791 Remote Similarity NPD7701 Phase 2
0.6789 Remote Similarity NPD4005 Discontinued
0.6788 Remote Similarity NPD5967 Approved
0.6782 Remote Similarity NPD7808 Phase 3
0.6776 Remote Similarity NPD2239 Approved
0.6776 Remote Similarity NPD2240 Approved
0.6774 Remote Similarity NPD3692 Discontinued
0.6768 Remote Similarity NPD2489 Approved
0.6768 Remote Similarity NPD27 Approved
0.6768 Remote Similarity NPD4481 Phase 3
0.6757 Remote Similarity NPD2976 Clinical (unspecified phase)
0.6756 Remote Similarity NPD7224 Discontinued
0.6756 Remote Similarity NPD7223 Discontinued
0.6755 Remote Similarity NPD1754 Clinical (unspecified phase)
0.6754 Remote Similarity NPD1337 Clinical (unspecified phase)
0.6753 Remote Similarity NPD6788 Approved
0.6751 Remote Similarity NPD7315 Approved
0.6749 Remote Similarity NPD7311 Approved
0.6749 Remote Similarity NPD7310 Approved
0.6749 Remote Similarity NPD7313 Approved
0.6749 Remote Similarity NPD7312 Approved
0.6739 Remote Similarity NPD1375 Discontinued
0.6736 Remote Similarity NPD6668 Clinical (unspecified phase)
0.6736 Remote Similarity NPD5563 Clinical (unspecified phase)
0.6735 Remote Similarity NPD2904 Discontinued
0.6735 Remote Similarity NPD6746 Phase 2
0.6732 Remote Similarity NPD6089 Clinical (unspecified phase)
0.673 Remote Similarity NPD7565 Approved
0.6726 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6722 Remote Similarity NPD2245 Discovery
0.672 Remote Similarity NPD6331 Phase 2
0.672 Remote Similarity NPD6658 Clinical (unspecified phase)
0.6719 Remote Similarity NPD4772 Phase 2
0.6719 Remote Similarity NPD4773 Phase 2
0.6718 Remote Similarity NPD5604 Discontinued
0.6716 Remote Similarity NPD7309 Approved
0.6716 Remote Similarity NPD5557 Phase 1
0.6714 Remote Similarity NPD6863 Phase 2
0.6704 Remote Similarity NPD5746 Approved
0.6702 Remote Similarity NPD3455 Phase 2
0.6701 Remote Similarity NPD7199 Phase 2

  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