Structure

Physi-Chem Properties

Molecular Weight:  813.37
Volume:  814.902
LogP:  0.406
LogD:  0.954
LogS:  -3.638
# Rotatable Bonds:  6
TPSA:  230.01
# H-Bond Aceptor:  17
# H-Bond Donor:  6
# Rings:  6
# Heavy Atoms:  17

MedChem Properties

QED Drug-Likeness Score:  0.235
Synthetic Accessibility Score:  6.688
Fsp3:  0.405
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:  -5.785
MDCK Permeability:  7.940354407764971e-06
Pgp-inhibitor:  0.999
Pgp-substrate:  0.983
Human Intestinal Absorption (HIA):  0.023
20% Bioavailability (F20%):  0.387
30% Bioavailability (F30%):  0.958

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.069
Plasma Protein Binding (PPB):  69.06166076660156%
Volume Distribution (VD):  0.272
Pgp-substrate:  22.626096725463867%

ADMET: Metabolism

CYP1A2-inhibitor:  0.002
CYP1A2-substrate:  0.041
CYP2C19-inhibitor:  0.084
CYP2C19-substrate:  0.051
CYP2C9-inhibitor:  0.345
CYP2C9-substrate:  0.061
CYP2D6-inhibitor:  0.022
CYP2D6-substrate:  0.267
CYP3A4-inhibitor:  0.911
CYP3A4-substrate:  0.074

ADMET: Excretion

Clearance (CL):  7.063
Half-life (T1/2):  0.255

ADMET: Toxicity

hERG Blockers:  0.046
Human Hepatotoxicity (H-HT):  0.966
Drug-inuced Liver Injury (DILI):  0.917
AMES Toxicity:  0.018
Rat Oral Acute Toxicity:  0.881
Maximum Recommended Daily Dose:  0.961
Skin Sensitization:  0.042
Carcinogencity:  0.031
Eye Corrosion:  0.003
Eye Irritation:  0.004
Respiratory Toxicity:  0.122

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

  Natural Product: NPC138083

Natural Product ID:  NPC138083
Common Name*:   YICIGXQVVJHRDG-YQPHQQCRSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  YICIGXQVVJHRDG-YQPHQQCRSA-N
Standard InCHI:  InChI=1S/C42H51N7O10/c1-23-37(52)46-30(16-18-36(43)51)41(56)47(3)31(19-25-7-12-28(58-6)13-8-25)39(54)45-24(2)40(55)49(5)33-20-26-9-14-29(15-10-26)59-35-22-27(11-17-34(35)50)21-32(38(53)44-23)48(4)42(33)57/h7-15,17,22-24,30-33,50H,16,18-21H2,1-6H3,(H2,43,51)(H,44,53)(H,45,54)(H,46,52)/t23-,24+,30+,31+,32+,33+/m1/s1
SMILES:  COc1ccc(cc1)C[C@H]1C(=N[C@@H](C)C(=O)N(C)[C@H]2Cc3ccc(cc3)Oc3cc(C[C@H](N(C2=O)C)C(=N[C@@H](C(=N[C@H](C(=O)N1C)CCC(=N)O)O)C)O)ccc3O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1288989
PubChem CID:   24881308
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 = 8010.0 nM PMID[456077]
NPT181 Cell Line Bel-7402 Homo sapiens IC50 = 8450.0 nM PMID[456077]
NPT659 Cell Line SMMC-7721 Homo sapiens IC50 = 9090.0 nM PMID[456077]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 = 1440.0 nM PMID[456077]
NPT90 Cell Line DU-145 Homo sapiens IC50 = 2030.0 nM PMID[456077]
NPT306 Cell Line PC-3 Homo sapiens IC50 = 3660.0 nM PMID[456077]
NPT81 Cell Line A549 Homo sapiens IC50 = 2850.0 nM PMID[456077]
NPT547 Cell Line BGC-823 Homo sapiens IC50 = 3260.0 nM PMID[456077]
NPT165 Cell Line HeLa Homo sapiens IC50 = 6160.0 nM PMID[456077]
NPT380 Cell Line U-251 Homo sapiens IC50 = 10810.0 nM PMID[456077]
NPT319 Cell Line B16 Mus musculus IC50 = 1010.0 nM PMID[456077]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 2220.0 nM PMID[456077]
NPT2 Others Unspecified IC50 = 12640.0 nM PMID[456077]

☑ 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 NPC138083 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
0.9756 High Similarity NPC32064
0.9529 High Similarity NPC64140
0.9529 High Similarity NPC174122
0.9512 High Similarity NPC164608
0.9471 High Similarity NPC234069
0.9467 High Similarity NPC276120
0.9302 High Similarity NPC29531
0.8983 High Similarity NPC471563
0.8944 High Similarity NPC242728
0.8833 High Similarity NPC50548
0.8778 High Similarity NPC144314
0.8722 High Similarity NPC149962
0.8595 High Similarity NPC473460
0.8579 High Similarity NPC123859
0.8449 Intermediate Similarity NPC473422
0.8205 Intermediate Similarity NPC471531
0.8197 Intermediate Similarity NPC473407
0.8197 Intermediate Similarity NPC473378
0.8177 Intermediate Similarity NPC471561
0.8176 Intermediate Similarity NPC287757
0.8176 Intermediate Similarity NPC319320
0.8012 Intermediate Similarity NPC56635
0.8 Intermediate Similarity NPC471532
0.7989 Intermediate Similarity NPC124626
0.7944 Intermediate Similarity NPC45037
0.7929 Intermediate Similarity NPC233702
0.7923 Intermediate Similarity NPC315542
0.7921 Intermediate Similarity NPC273755
0.7921 Intermediate Similarity NPC306804
0.7877 Intermediate Similarity NPC155506
0.7877 Intermediate Similarity NPC159767
0.7877 Intermediate Similarity NPC473354
0.787 Intermediate Similarity NPC324081
0.7869 Intermediate Similarity NPC294951
0.7865 Intermediate Similarity NPC89831
0.7841 Intermediate Similarity NPC254700
0.7833 Intermediate Similarity NPC50016
0.7814 Intermediate Similarity NPC471526
0.7798 Intermediate Similarity NPC16188
0.7797 Intermediate Similarity NPC328649
0.7778 Intermediate Similarity NPC26108
0.7778 Intermediate Similarity NPC476227
0.7765 Intermediate Similarity NPC230611
0.7747 Intermediate Similarity NPC194671
0.7747 Intermediate Similarity NPC269750
0.774 Intermediate Similarity NPC290755
0.774 Intermediate Similarity NPC304074
0.774 Intermediate Similarity NPC471771
0.7722 Intermediate Similarity NPC137627
0.7709 Intermediate Similarity NPC196091
0.7709 Intermediate Similarity NPC471568
0.7709 Intermediate Similarity NPC473693
0.7697 Intermediate Similarity NPC294516
0.7697 Intermediate Similarity NPC107938
0.7696 Intermediate Similarity NPC281629
0.7684 Intermediate Similarity NPC223207
0.768 Intermediate Similarity NPC279871
0.768 Intermediate Similarity NPC473402
0.7674 Intermediate Similarity NPC202198
0.7663 Intermediate Similarity NPC476321
0.766 Intermediate Similarity NPC163961
0.766 Intermediate Similarity NPC473305
0.7654 Intermediate Similarity NPC186617
0.7647 Intermediate Similarity NPC5462
0.7647 Intermediate Similarity NPC9373
0.7637 Intermediate Similarity NPC196243
0.7611 Intermediate Similarity NPC40234
0.7611 Intermediate Similarity NPC256012
0.7611 Intermediate Similarity NPC42549
0.7611 Intermediate Similarity NPC317272
0.7611 Intermediate Similarity NPC240841
0.7611 Intermediate Similarity NPC268503
0.7611 Intermediate Similarity NPC250846
0.7598 Intermediate Similarity NPC141957
0.7584 Intermediate Similarity NPC63931
0.7582 Intermediate Similarity NPC471165
0.7581 Intermediate Similarity NPC471048
0.7581 Intermediate Similarity NPC471050
0.7581 Intermediate Similarity NPC471049
0.7577 Intermediate Similarity NPC469689
0.7577 Intermediate Similarity NPC471031
0.7574 Intermediate Similarity NPC222039
0.7574 Intermediate Similarity NPC100478
0.7571 Intermediate Similarity NPC241794
0.7553 Intermediate Similarity NPC94862
0.7541 Intermediate Similarity NPC475215
0.7541 Intermediate Similarity NPC108434
0.7527 Intermediate Similarity NPC248670
0.7515 Intermediate Similarity NPC66518
0.7514 Intermediate Similarity NPC46009
0.7514 Intermediate Similarity NPC153644
0.7514 Intermediate Similarity NPC475544
0.7514 Intermediate Similarity NPC475123
0.7514 Intermediate Similarity NPC469243
0.7514 Intermediate Similarity NPC475204
0.75 Intermediate Similarity NPC476989
0.75 Intermediate Similarity NPC114102
0.7486 Intermediate Similarity NPC472923
0.7486 Intermediate Similarity NPC476268
0.7486 Intermediate Similarity NPC158900
0.7471 Intermediate Similarity NPC56685
0.7459 Intermediate Similarity NPC475421
0.7459 Intermediate Similarity NPC119652
0.7459 Intermediate Similarity NPC97526
0.7458 Intermediate Similarity NPC244336
0.7457 Intermediate Similarity NPC277857
0.7457 Intermediate Similarity NPC115144
0.7457 Intermediate Similarity NPC473491
0.7455 Intermediate Similarity NPC214869
0.7448 Intermediate Similarity NPC302715
0.7447 Intermediate Similarity NPC299806
0.7444 Intermediate Similarity NPC61004
0.7429 Intermediate Similarity NPC478189
0.7418 Intermediate Similarity NPC276506
0.7418 Intermediate Similarity NPC274198
0.7418 Intermediate Similarity NPC198254
0.7414 Intermediate Similarity NPC428
0.7414 Intermediate Similarity NPC476571
0.7414 Intermediate Similarity NPC246587
0.7414 Intermediate Similarity NPC135538
0.7414 Intermediate Similarity NPC24233
0.7414 Intermediate Similarity NPC147390
0.7403 Intermediate Similarity NPC473502
0.7399 Intermediate Similarity NPC245974
0.7396 Intermediate Similarity NPC41122
0.7396 Intermediate Similarity NPC318805
0.7391 Intermediate Similarity NPC136797
0.7386 Intermediate Similarity NPC127402
0.7384 Intermediate Similarity NPC247298
0.7382 Intermediate Similarity NPC240130
0.7382 Intermediate Similarity NPC61332
0.7382 Intermediate Similarity NPC283207
0.7371 Intermediate Similarity NPC262166
0.7363 Intermediate Similarity NPC280022
0.7356 Intermediate Similarity NPC179825
0.7356 Intermediate Similarity NPC191376
0.7356 Intermediate Similarity NPC321505
0.7344 Intermediate Similarity NPC248822
0.734 Intermediate Similarity NPC470112
0.734 Intermediate Similarity NPC470903
0.734 Intermediate Similarity NPC167763
0.7337 Intermediate Similarity NPC66573
0.7333 Intermediate Similarity NPC52029
0.7333 Intermediate Similarity NPC35961
0.7333 Intermediate Similarity NPC195749
0.7323 Intermediate Similarity NPC311357
0.7321 Intermediate Similarity NPC6913
0.7317 Intermediate Similarity NPC111428
0.7314 Intermediate Similarity NPC471032
0.7314 Intermediate Similarity NPC470935
0.7313 Intermediate Similarity NPC478005
0.7305 Intermediate Similarity NPC313737
0.7305 Intermediate Similarity NPC6854
0.7305 Intermediate Similarity NPC285078
0.7297 Intermediate Similarity NPC158277
0.7294 Intermediate Similarity NPC231572
0.7289 Intermediate Similarity NPC257390
0.7288 Intermediate Similarity NPC76213
0.7288 Intermediate Similarity NPC244509
0.7288 Intermediate Similarity NPC473580
0.7288 Intermediate Similarity NPC277669
0.7283 Intermediate Similarity NPC328494
0.7278 Intermediate Similarity NPC242159
0.7278 Intermediate Similarity NPC313694
0.7273 Intermediate Similarity NPC155838
0.7273 Intermediate Similarity NPC5194
0.7273 Intermediate Similarity NPC261934
0.7263 Intermediate Similarity NPC229234
0.7263 Intermediate Similarity NPC107602
0.7263 Intermediate Similarity NPC30779
0.7253 Intermediate Similarity NPC50380
0.7253 Intermediate Similarity NPC179250
0.725 Intermediate Similarity NPC477666
0.7246 Intermediate Similarity NPC82056
0.7246 Intermediate Similarity NPC93882
0.7246 Intermediate Similarity NPC130595
0.7246 Intermediate Similarity NPC244866
0.7245 Intermediate Similarity NPC234318
0.7243 Intermediate Similarity NPC475532
0.7241 Intermediate Similarity NPC185838
0.7235 Intermediate Similarity NPC14600
0.7235 Intermediate Similarity NPC204848
0.7235 Intermediate Similarity NPC312770
0.7235 Intermediate Similarity NPC160607
0.7235 Intermediate Similarity NPC41473
0.7232 Intermediate Similarity NPC220858
0.7232 Intermediate Similarity NPC88249
0.7232 Intermediate Similarity NPC97221
0.7232 Intermediate Similarity NPC192768
0.7232 Intermediate Similarity NPC151895
0.7231 Intermediate Similarity NPC85381
0.7228 Intermediate Similarity NPC90984
0.7222 Intermediate Similarity NPC475654
0.7222 Intermediate Similarity NPC247639
0.7222 Intermediate Similarity NPC477551
0.7222 Intermediate Similarity NPC25084
0.7213 Intermediate Similarity NPC302597
0.7213 Intermediate Similarity NPC475393
0.7212 Intermediate Similarity NPC186898
0.7212 Intermediate Similarity NPC251571

  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 NPC138083 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
0.8212 Intermediate Similarity NPD7132 Clinical (unspecified phase)
0.8122 Intermediate Similarity NPD6851 Approved
0.8122 Intermediate Similarity NPD6853 Approved
0.8101 Intermediate Similarity NPD6297 Approved
0.8095 Intermediate Similarity NPD7131 Phase 3
0.8011 Intermediate Similarity NPD7608 Discontinued
0.7946 Intermediate Similarity NPD6377 Clinical (unspecified phase)
0.7753 Intermediate Similarity NPD7484 Phase 3
0.7753 Intermediate Similarity NPD7485 Phase 3
0.7737 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7713 Intermediate Similarity NPD5525 Clinical (unspecified phase)
0.7614 Intermediate Similarity NPD5772 Approved
0.7614 Intermediate Similarity NPD5773 Approved
0.7581 Intermediate Similarity NPD7280 Phase 3
0.7581 Intermediate Similarity NPD7281 Phase 3
0.7572 Intermediate Similarity NPD6662 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7109 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD4413 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7110 Phase 1
0.75 Intermediate Similarity NPD7118 Clinical (unspecified phase)
0.7473 Intermediate Similarity NPD5137 Approved
0.7412 Intermediate Similarity NPD7596 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD7450 Phase 2
0.7386 Intermediate Similarity NPD824 Approved
0.7384 Intermediate Similarity NPD5241 Discontinued
0.738 Intermediate Similarity NPD7039 Approved
0.738 Intermediate Similarity NPD7038 Approved
0.7368 Intermediate Similarity NPD4162 Approved
0.736 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7356 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7347 Intermediate Similarity NPD7811 Phase 3
0.7347 Intermediate Similarity NPD7810 Phase 3
0.7345 Intermediate Similarity NPD6876 Approved
0.7345 Intermediate Similarity NPD6875 Approved
0.733 Intermediate Similarity NPD7291 Discontinued
0.7318 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD8149 Discontinued
0.731 Intermediate Similarity NPD7153 Discontinued
0.73 Intermediate Similarity NPD7607 Clinical (unspecified phase)
0.7295 Intermediate Similarity NPD8318 Clinical (unspecified phase)
0.7293 Intermediate Similarity NPD8031 Discontinued
0.7289 Intermediate Similarity NPD5718 Phase 2
0.7273 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD3060 Approved
0.7263 Intermediate Similarity NPD8019 Approved
0.7257 Intermediate Similarity NPD4123 Phase 3
0.7255 Intermediate Similarity NPD7827 Phase 1
0.7246 Intermediate Similarity NPD2674 Phase 3
0.7222 Intermediate Similarity NPD2977 Approved
0.7222 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD2978 Approved
0.7219 Intermediate Similarity NPD6042 Phase 2
0.7219 Intermediate Similarity NPD42 Phase 2
0.7216 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.7216 Intermediate Similarity NPD52 Approved
0.7216 Intermediate Similarity NPD7526 Approved
0.7191 Intermediate Similarity NPD3455 Phase 2
0.7182 Intermediate Similarity NPD5967 Approved
0.7173 Intermediate Similarity NPD8053 Approved
0.7173 Intermediate Similarity NPD8054 Approved
0.7165 Intermediate Similarity NPD2490 Approved
0.7165 Intermediate Similarity NPD2488 Approved
0.715 Intermediate Similarity NPD4157 Discontinued
0.7143 Intermediate Similarity NPD5745 Approved
0.7143 Intermediate Similarity NPD2245 Discovery
0.7111 Intermediate Similarity NPD6072 Discontinued
0.7111 Intermediate Similarity NPD6386 Approved
0.7111 Intermediate Similarity NPD6385 Approved
0.711 Intermediate Similarity NPD3655 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD5192 Clinical (unspecified phase)
0.71 Intermediate Similarity NPD2493 Approved
0.71 Intermediate Similarity NPD2494 Approved
0.7086 Intermediate Similarity NPD3692 Discontinued
0.7086 Intermediate Similarity NPD2219 Phase 1
0.7083 Intermediate Similarity NPD3144 Approved
0.7083 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD6618 Phase 2
0.7083 Intermediate Similarity NPD3145 Approved
0.7079 Intermediate Similarity NPD2122 Discontinued
0.7079 Intermediate Similarity NPD4040 Phase 1
0.7069 Intermediate Similarity NPD6860 Clinical (unspecified phase)
0.7068 Intermediate Similarity NPD3936 Clinical (unspecified phase)
0.7065 Intermediate Similarity NPD8245 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD3146 Approved
0.7062 Intermediate Similarity NPD1771 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD3688 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD7906 Approved
0.7056 Intermediate Similarity NPD4675 Approved
0.7056 Intermediate Similarity NPD1337 Clinical (unspecified phase)
0.7056 Intermediate Similarity NPD4678 Approved
0.7043 Intermediate Similarity NPD4166 Phase 2
0.7039 Intermediate Similarity NPD3686 Approved
0.7039 Intermediate Similarity NPD3687 Approved
0.7037 Intermediate Similarity NPD5312 Approved
0.7037 Intermediate Similarity NPD5313 Approved
0.7031 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD6331 Phase 2
0.7024 Intermediate Similarity NPD5746 Approved
0.7022 Intermediate Similarity NPD7303 Discontinued
0.7015 Intermediate Similarity NPD3450 Approved
0.7015 Intermediate Similarity NPD3452 Approved
0.7011 Intermediate Similarity NPD7833 Phase 2
0.7011 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD7831 Phase 2
0.7011 Intermediate Similarity NPD8070 Approved
0.7011 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.7005 Intermediate Similarity NPD4083 Discontinued
0.6995 Remote Similarity NPD4582 Approved
0.6995 Remote Similarity NPD4583 Approved
0.6989 Remote Similarity NPD6107 Approved
0.6983 Remote Similarity NPD3640 Phase 3
0.6983 Remote Similarity NPD3639 Approved
0.6983 Remote Similarity NPD3641 Approved
0.6978 Remote Similarity NPD5722 Discontinued
0.6973 Remote Similarity NPD8303 Discontinued
0.6971 Remote Similarity NPD2459 Approved
0.6971 Remote Similarity NPD2976 Clinical (unspecified phase)
0.6971 Remote Similarity NPD2458 Approved
0.6971 Remote Similarity NPD2460 Phase 3
0.6966 Remote Similarity NPD3985 Discontinued
0.6966 Remote Similarity NPD3536 Discontinued
0.6959 Remote Similarity NPD555 Phase 2
0.6946 Remote Similarity NPD4002 Approved
0.6946 Remote Similarity NPD4004 Approved
0.6946 Remote Similarity NPD6584 Phase 3
0.6941 Remote Similarity NPD259 Phase 1
0.694 Remote Similarity NPD7972 Discontinued
0.694 Remote Similarity NPD7046 Clinical (unspecified phase)
0.6935 Remote Similarity NPD5677 Discontinued
0.6927 Remote Similarity NPD1975 Clinical (unspecified phase)
0.6927 Remote Similarity NPD5261 Clinical (unspecified phase)
0.6927 Remote Similarity NPD3647 Clinical (unspecified phase)
0.6923 Remote Similarity NPD6677 Suspended
0.6919 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6919 Remote Similarity NPD2653 Approved
0.6915 Remote Similarity NPD8051 Clinical (unspecified phase)
0.6905 Remote Similarity NPD7047 Phase 3
0.6904 Remote Similarity NPD6505 Approved
0.6904 Remote Similarity NPD6504 Approved
0.69 Remote Similarity NPD2973 Approved
0.69 Remote Similarity NPD2975 Approved
0.69 Remote Similarity NPD2974 Approved
0.6897 Remote Similarity NPD2161 Phase 2
0.6897 Remote Similarity NPD2239 Approved
0.6897 Remote Similarity NPD2240 Approved
0.6889 Remote Similarity NPD6031 Approved
0.6889 Remote Similarity NPD6030 Approved
0.6888 Remote Similarity NPD7243 Clinical (unspecified phase)
0.6886 Remote Similarity NPD3053 Approved
0.6886 Remote Similarity NPD3055 Approved
0.6885 Remote Similarity NPD7495 Discontinued
0.6882 Remote Similarity NPD6862 Phase 2
0.6881 Remote Similarity NPD5457 Discontinued
0.6879 Remote Similarity NPD6896 Approved
0.6879 Remote Similarity NPD6895 Approved
0.6878 Remote Similarity NPD27 Approved
0.6878 Remote Similarity NPD2489 Approved
0.6875 Remote Similarity NPD4236 Phase 3
0.6875 Remote Similarity NPD4237 Approved
0.6872 Remote Similarity NPD7020 Approved
0.6872 Remote Similarity NPD4739 Approved
0.6872 Remote Similarity NPD2874 Phase 2
0.6872 Remote Similarity NPD7019 Approved
0.6854 Remote Similarity NPD6783 Clinical (unspecified phase)
0.6851 Remote Similarity NPD4124 Clinical (unspecified phase)
0.6842 Remote Similarity NPD1423 Approved
0.6842 Remote Similarity NPD6720 Clinical (unspecified phase)
0.6839 Remote Similarity NPD6028 Clinical (unspecified phase)
0.6839 Remote Similarity NPD6029 Clinical (unspecified phase)
0.6837 Remote Similarity NPD3863 Clinical (unspecified phase)
0.6837 Remote Similarity NPD3857 Clinical (unspecified phase)
0.6837 Remote Similarity NPD6089 Clinical (unspecified phase)
0.6836 Remote Similarity NPD5481 Discontinued
0.6834 Remote Similarity NPD4466 Phase 1
0.6834 Remote Similarity NPD6181 Discontinued
0.6833 Remote Similarity NPD7613 Discontinued
0.6831 Remote Similarity NPD4773 Phase 2
0.6831 Remote Similarity NPD4772 Phase 2
0.6826 Remote Similarity NPD5311 Approved
0.6826 Remote Similarity NPD5310 Approved
0.6823 Remote Similarity NPD5484 Approved
0.6823 Remote Similarity NPD5485 Approved
0.6821 Remote Similarity NPD5314 Approved
0.6821 Remote Similarity NPD3052 Approved
0.6821 Remote Similarity NPD3054 Approved
0.6814 Remote Similarity NPD4971 Clinical (unspecified phase)
0.6813 Remote Similarity NPD6523 Clinical (unspecified phase)
0.6811 Remote Similarity NPD6063 Approved
0.6806 Remote Similarity NPD8099 Discontinued
0.6806 Remote Similarity NPD8252 Approved
0.6806 Remote Similarity NPD8251 Approved
0.6805 Remote Similarity NPD9569 Approved
0.6802 Remote Similarity NPD826 Approved
0.6802 Remote Similarity NPD825 Approved
0.6802 Remote Similarity NPD4435 Approved
0.68 Remote Similarity NPD7669 Phase 3
0.6798 Remote Similarity NPD8323 Discontinued
0.6798 Remote Similarity NPD4580 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