Structure

Physi-Chem Properties

Molecular Weight:  1014.59
Volume:  1039.685
LogP:  3.952
LogD:  3.263
LogS:  -3.633
# Rotatable Bonds:  16
TPSA:  267.59
# H-Bond Aceptor:  20
# H-Bond Donor:  5
# Rings:  3
# Heavy Atoms:  20

MedChem Properties

QED Drug-Likeness Score:  0.132
Synthetic Accessibility Score:  6.37
Fsp3:  0.712
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:  -5.314
MDCK Permeability:  5.815300391986966e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.999
Human Intestinal Absorption (HIA):  0.64
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.691

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.04
Plasma Protein Binding (PPB):  81.60845184326172%
Volume Distribution (VD):  0.566
Pgp-substrate:  4.912437438964844%

ADMET: Metabolism

CYP1A2-inhibitor:  0.001
CYP1A2-substrate:  0.016
CYP2C19-inhibitor:  0.086
CYP2C19-substrate:  0.091
CYP2C9-inhibitor:  0.105
CYP2C9-substrate:  0.018
CYP2D6-inhibitor:  0.006
CYP2D6-substrate:  0.055
CYP3A4-inhibitor:  0.916
CYP3A4-substrate:  0.364

ADMET: Excretion

Clearance (CL):  8.057
Half-life (T1/2):  0.09

ADMET: Toxicity

hERG Blockers:  0.006
Human Hepatotoxicity (H-HT):  0.99
Drug-inuced Liver Injury (DILI):  0.949
AMES Toxicity:  0.006
Rat Oral Acute Toxicity:  0.61
Maximum Recommended Daily Dose:  0.79
Skin Sensitization:  0.054
Carcinogencity:  0.121
Eye Corrosion:  0.003
Eye Irritation:  0.004
Respiratory Toxicity:  0.159

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

  Natural Product: NPC475421

Natural Product ID:  NPC475421
Common Name*:   Didemnin C
IUPAC Name:   (2R)-N-[(3S,6S,8S,12S,13R,16S,17R,20S,23S)-13-[(2S)-butan-2-yl]-12-hydroxy-20-[(4-methoxyphenyl)methyl]-6,17,21-trimethyl-3-(2-methylpropyl)-2,5,7,10,15,19,22-heptaoxo-8-propan-2-yl-9,18-dioxa-1,4,14,21-tetrazabicyclo[21.3.0]hexacosan-16-yl]-2-[[(2S)-2-hydroxypropanoyl]-methylamino]-4-methylpentanamide
Synonyms:   Didemnin C
Standard InCHIKey:  ZRSXZCRRAOVIJD-KNKJEZLASA-N
Standard InCHI:  InChI=1S/C52H82N6O14/c1-15-30(8)42-40(60)26-41(61)72-45(29(6)7)44(62)31(9)46(63)53-36(23-27(2)3)50(67)58-22-16-17-37(58)51(68)57(13)39(25-34-18-20-35(70-14)21-19-34)52(69)71-33(11)43(48(65)54-42)55-47(64)38(24-28(4)5)56(12)49(66)32(10)59/h18-21,27-33,36-40,42-43,45,59-60H,15-17,22-26H2,1-14H3,(H,53,63)(H,54,65)(H,55,64)/t30-,31-,32-,33+,36-,37-,38+,39-,40-,42+,43-,45-/m0/s1
SMILES:  CC[C@@H]([C@H]1N=C(O)[C@@H](N=C([C@H](N(C(=O)[C@@H](O)C)C)CC(C)C)O)[C@@H](C)OC(=O)[C@H](Cc2ccc(cc2)OC)N(C)C(=O)[C@@H]2CCCN2C(=O)[C@@H](N=C([C@H](C(=O)[C@@H](OC(=O)C[C@@H]1O)C(C)C)C)O)CC(C)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL505317
PubChem CID:   9963211
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0001813] Peptidomimetics
        • [CHEMONTID:0001961] Depsipeptides
          • [CHEMONTID:0001994] Cyclic depsipeptides

*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
NPO28186 Trididemnum solidum Species Didemnidae Eukaryota n.a. n.a. n.a. PMID[21341712]
NPO28186 Trididemnum solidum Species Didemnidae Eukaryota n.a. n.a. n.a. PMID[21770369]
NPO28186 Trididemnum solidum Species Didemnidae Eukaryota n.a. n.a. n.a. PMID[3373220]
NPO28186 Trididemnum solidum Species Didemnidae 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
NPT137 Cell Line L1210 Mus musculus ID50 = 0.002 ug ml-1 PMID[494368]
NPT137 Cell Line L1210 Mus musculus IC50 = 0.011 ug.mL-1 PMID[494369]

☑ 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 NPC475421 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
0.9815 High Similarity NPC470903
0.9815 High Similarity NPC470112
0.9815 High Similarity NPC167763
0.9695 High Similarity NPC299806
0.9141 High Similarity NPC196091
0.9012 High Similarity NPC472923
0.8675 High Similarity NPC473502
0.8571 High Similarity NPC473693
0.8571 High Similarity NPC471568
0.8402 Intermediate Similarity NPC186617
0.8363 Intermediate Similarity NPC137627
0.8314 Intermediate Similarity NPC26108
0.8258 Intermediate Similarity NPC4910
0.8249 Intermediate Similarity NPC315542
0.8246 Intermediate Similarity NPC475204
0.8246 Intermediate Similarity NPC475123
0.8176 Intermediate Similarity NPC254700
0.8129 Intermediate Similarity NPC107938
0.8129 Intermediate Similarity NPC294516
0.811 Intermediate Similarity NPC324081
0.8103 Intermediate Similarity NPC155506
0.8103 Intermediate Similarity NPC159767
0.8087 Intermediate Similarity NPC59827
0.8087 Intermediate Similarity NPC184933
0.8056 Intermediate Similarity NPC329731
0.8046 Intermediate Similarity NPC306804
0.8037 Intermediate Similarity NPC145113
0.8035 Intermediate Similarity NPC40234
0.8035 Intermediate Similarity NPC46009
0.8022 Intermediate Similarity NPC473407
0.8022 Intermediate Similarity NPC473378
0.8012 Intermediate Similarity NPC63931
0.8012 Intermediate Similarity NPC262166
0.8 Intermediate Similarity NPC476227
0.8 Intermediate Similarity NPC471165
0.8 Intermediate Similarity NPC279871
0.7988 Intermediate Similarity NPC319320
0.7988 Intermediate Similarity NPC287757
0.7957 Intermediate Similarity NPC477527
0.7952 Intermediate Similarity NPC162104
0.7927 Intermediate Similarity NPC329761
0.7927 Intermediate Similarity NPC225648
0.7923 Intermediate Similarity NPC477526
0.7923 Intermediate Similarity NPC248822
0.7898 Intermediate Similarity NPC473402
0.7898 Intermediate Similarity NPC473354
0.7886 Intermediate Similarity NPC230611
0.7866 Intermediate Similarity NPC81026
0.7865 Intermediate Similarity NPC269750
0.7865 Intermediate Similarity NPC194671
0.7853 Intermediate Similarity NPC50016
0.7844 Intermediate Similarity NPC233702
0.7841 Intermediate Similarity NPC273755
0.784 Intermediate Similarity NPC263493
0.784 Intermediate Similarity NPC269398
0.7805 Intermediate Similarity NPC5620
0.7805 Intermediate Similarity NPC266741
0.779 Intermediate Similarity NPC294951
0.7784 Intermediate Similarity NPC473491
0.7772 Intermediate Similarity NPC64140
0.7772 Intermediate Similarity NPC174122
0.7751 Intermediate Similarity NPC39431
0.7742 Intermediate Similarity NPC328763
0.774 Intermediate Similarity NPC248670
0.7719 Intermediate Similarity NPC207675
0.7719 Intermediate Similarity NPC212699
0.7719 Intermediate Similarity NPC297145
0.7719 Intermediate Similarity NPC197743
0.7717 Intermediate Similarity NPC234069
0.7711 Intermediate Similarity NPC16188
0.7706 Intermediate Similarity NPC244509
0.7705 Intermediate Similarity NPC276120
0.7697 Intermediate Similarity NPC164608
0.7697 Intermediate Similarity NPC158277
0.7692 Intermediate Similarity NPC471050
0.7692 Intermediate Similarity NPC471049
0.7692 Intermediate Similarity NPC471048
0.7684 Intermediate Similarity NPC328494
0.7684 Intermediate Similarity NPC477551
0.7684 Intermediate Similarity NPC89831
0.768 Intermediate Similarity NPC476321
0.768 Intermediate Similarity NPC473404
0.7672 Intermediate Similarity NPC477550
0.7672 Intermediate Similarity NPC477552
0.7669 Intermediate Similarity NPC46098
0.7669 Intermediate Similarity NPC268841
0.7669 Intermediate Similarity NPC307357
0.7667 Intermediate Similarity NPC45037
0.7665 Intermediate Similarity NPC471821
0.7665 Intermediate Similarity NPC471820
0.7657 Intermediate Similarity NPC469479
0.7637 Intermediate Similarity NPC471526
0.7632 Intermediate Similarity NPC123859
0.7619 Intermediate Similarity NPC132771
0.7619 Intermediate Similarity NPC129666
0.7614 Intermediate Similarity NPC209463
0.7614 Intermediate Similarity NPC302597
0.7607 Intermediate Similarity NPC178662
0.7607 Intermediate Similarity NPC476133
0.7607 Intermediate Similarity NPC470884
0.7607 Intermediate Similarity NPC98424
0.7607 Intermediate Similarity NPC92784
0.7605 Intermediate Similarity NPC135121
0.7592 Intermediate Similarity NPC473450
0.759 Intermediate Similarity NPC477217
0.759 Intermediate Similarity NPC201244
0.759 Intermediate Similarity NPC209509
0.7588 Intermediate Similarity NPC202198
0.7588 Intermediate Similarity NPC5194
0.7588 Intermediate Similarity NPC261934
0.7581 Intermediate Similarity NPC473305
0.7581 Intermediate Similarity NPC163961
0.7581 Intermediate Similarity NPC240130
0.7581 Intermediate Similarity NPC61332
0.7579 Intermediate Similarity NPC323662
0.7578 Intermediate Similarity NPC470392
0.7576 Intermediate Similarity NPC161069
0.7576 Intermediate Similarity NPC91953
0.7572 Intermediate Similarity NPC244336
0.7571 Intermediate Similarity NPC469505
0.7566 Intermediate Similarity NPC149962
0.7563 Intermediate Similarity NPC326333
0.7557 Intermediate Similarity NPC61004
0.7546 Intermediate Similarity NPC471265
0.7546 Intermediate Similarity NPC471264
0.7545 Intermediate Similarity NPC314358
0.753 Intermediate Similarity NPC476978
0.7527 Intermediate Similarity NPC32064
0.7526 Intermediate Similarity NPC144314
0.7515 Intermediate Similarity NPC2501
0.7515 Intermediate Similarity NPC197921
0.7514 Intermediate Similarity NPC56635
0.75 Intermediate Similarity NPC473580
0.75 Intermediate Similarity NPC136797
0.75 Intermediate Similarity NPC242728
0.7487 Intermediate Similarity NPC50548
0.7487 Intermediate Similarity NPC326027
0.7485 Intermediate Similarity NPC316008
0.7485 Intermediate Similarity NPC313867
0.7485 Intermediate Similarity NPC56685
0.747 Intermediate Similarity NPC469360
0.747 Intermediate Similarity NPC139326
0.747 Intermediate Similarity NPC251439
0.7459 Intermediate Similarity NPC138083
0.7455 Intermediate Similarity NPC163392
0.7455 Intermediate Similarity NPC239762
0.7439 Intermediate Similarity NPC68865
0.7429 Intermediate Similarity NPC475544
0.7429 Intermediate Similarity NPC469243
0.7425 Intermediate Similarity NPC315283
0.7425 Intermediate Similarity NPC314388
0.7425 Intermediate Similarity NPC52748
0.7423 Intermediate Similarity NPC248283
0.741 Intermediate Similarity NPC476989
0.7396 Intermediate Similarity NPC138775
0.7391 Intermediate Similarity NPC477637
0.7386 Intermediate Similarity NPC241794
0.7384 Intermediate Similarity NPC122590
0.7368 Intermediate Similarity NPC65714
0.7368 Intermediate Similarity NPC302715
0.7365 Intermediate Similarity NPC212850
0.7365 Intermediate Similarity NPC83289
0.7365 Intermediate Similarity NPC189724
0.736 Intermediate Similarity NPC471771
0.736 Intermediate Similarity NPC304074
0.736 Intermediate Similarity NPC194699
0.736 Intermediate Similarity NPC290755
0.736 Intermediate Similarity NPC219350
0.7353 Intermediate Similarity NPC240848
0.7353 Intermediate Similarity NPC9373
0.734 Intermediate Similarity NPC102959
0.7333 Intermediate Similarity NPC6570
0.733 Intermediate Similarity NPC471563
0.7318 Intermediate Similarity NPC328649
0.7318 Intermediate Similarity NPC141957
0.731 Intermediate Similarity NPC245974
0.7303 Intermediate Similarity NPC223207
0.7302 Intermediate Similarity NPC29531
0.7302 Intermediate Similarity NPC60516
0.7301 Intermediate Similarity NPC246079
0.7299 Intermediate Similarity NPC476268
0.7294 Intermediate Similarity NPC247298
0.7292 Intermediate Similarity NPC473371
0.7289 Intermediate Similarity NPC242159
0.7289 Intermediate Similarity NPC313694
0.7287 Intermediate Similarity NPC94862
0.7283 Intermediate Similarity NPC473341
0.7278 Intermediate Similarity NPC129486
0.7267 Intermediate Similarity NPC7817
0.7267 Intermediate Similarity NPC475168
0.7262 Intermediate Similarity NPC176226
0.7256 Intermediate Similarity NPC274732
0.7254 Intermediate Similarity NPC471592
0.7246 Intermediate Similarity NPC476259
0.7238 Intermediate Similarity NPC198254
0.7238 Intermediate Similarity NPC276506
0.7238 Intermediate Similarity NPC274198
0.7229 Intermediate Similarity NPC109580
0.7229 Intermediate Similarity NPC127741
0.7219 Intermediate Similarity NPC204546

  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 NPC475421 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
0.7929 Intermediate Similarity NPD7118 Clinical (unspecified phase)
0.7904 Intermediate Similarity NPD7131 Phase 3
0.7836 Intermediate Similarity NPD7972 Discontinued
0.7727 Intermediate Similarity NPD7608 Discontinued
0.7578 Intermediate Similarity NPD5745 Approved
0.7571 Intermediate Similarity NPD7485 Phase 3
0.7571 Intermediate Similarity NPD7484 Phase 3
0.7546 Intermediate Similarity NPD8173 Phase 2
0.7546 Intermediate Similarity NPD8172 Phase 2
0.7529 Intermediate Similarity NPD6390 Discontinued
0.75 Intermediate Similarity NPD8031 Discontinued
0.7473 Intermediate Similarity NPD5484 Approved
0.7473 Intermediate Similarity NPD5485 Approved
0.7453 Intermediate Similarity NPD5746 Approved
0.7378 Intermediate Similarity NPD7113 Clinical (unspecified phase)
0.736 Intermediate Similarity NPD8303 Discontinued
0.7358 Intermediate Similarity NPD7811 Phase 3
0.7358 Intermediate Similarity NPD7810 Phase 3
0.7354 Intermediate Similarity NPD6504 Approved
0.7354 Intermediate Similarity NPD6505 Approved
0.7326 Intermediate Similarity NPD7613 Discontinued
0.7321 Intermediate Similarity NPD7596 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD6860 Clinical (unspecified phase)
0.7268 Intermediate Similarity NPD7565 Approved
0.7262 Intermediate Similarity NPD7978 Discontinued
0.7219 Intermediate Similarity NPD7280 Phase 3
0.7219 Intermediate Similarity NPD7281 Phase 3
0.7184 Intermediate Similarity NPD1670 Discontinued
0.7181 Intermediate Similarity NPD6853 Approved
0.7181 Intermediate Similarity NPD6851 Approved
0.7166 Intermediate Similarity NPD7132 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD5772 Approved
0.7135 Intermediate Similarity NPD5773 Approved
0.7101 Intermediate Similarity NPD1725 Approved
0.7081 Intermediate Similarity NPD3676 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD2976 Clinical (unspecified phase)
0.7069 Intermediate Similarity NPD5348 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD7959 Clinical (unspecified phase)
0.7033 Intermediate Similarity NPD2042 Clinical (unspecified phase)
0.7033 Intermediate Similarity NPD2041 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD3136 Phase 2
0.7022 Intermediate Similarity NPD2513 Approved
0.7021 Intermediate Similarity NPD8014 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD6681 Discovery
0.7016 Intermediate Similarity NPD6089 Clinical (unspecified phase)
0.7016 Intermediate Similarity NPD4434 Approved
0.7006 Intermediate Similarity NPD8416 Discontinued
0.7 Intermediate Similarity NPD2239 Approved
0.7 Intermediate Similarity NPD2240 Approved
0.7 Intermediate Similarity NPD7318 Phase 3
0.6995 Remote Similarity NPD2516 Approved
0.6983 Remote Similarity NPD3007 Approved
0.6983 Remote Similarity NPD5355 Approved
0.6983 Remote Similarity NPD2515 Approved
0.6983 Remote Similarity NPD5356 Approved
0.6979 Remote Similarity NPD4435 Approved
0.6971 Remote Similarity NPD3688 Clinical (unspecified phase)
0.6971 Remote Similarity NPD3146 Approved
0.6968 Remote Similarity NPD6297 Approved
0.6965 Remote Similarity NPD8161 Suspended
0.6957 Remote Similarity NPD2517 Approved
0.6946 Remote Similarity NPD5729 Clinical (unspecified phase)
0.6944 Remote Similarity NPD6668 Clinical (unspecified phase)
0.6932 Remote Similarity NPD4186 Clinical (unspecified phase)
0.6919 Remote Similarity NPD3655 Clinical (unspecified phase)
0.6915 Remote Similarity NPD5557 Phase 1
0.6914 Remote Similarity NPD2584 Suspended
0.6911 Remote Similarity NPD6556 Clinical (unspecified phase)
0.691 Remote Similarity NPD2052 Approved
0.6906 Remote Similarity NPD2097 Approved
0.6906 Remote Similarity NPD5967 Approved
0.6897 Remote Similarity NPD8323 Discontinued
0.6889 Remote Similarity NPD7317 Phase 3
0.6885 Remote Similarity NPD8245 Clinical (unspecified phase)
0.6878 Remote Similarity NPD3878 Approved
0.6875 Remote Similarity NPD3536 Discontinued
0.6872 Remote Similarity NPD22 Approved
0.6872 Remote Similarity NPD2053 Approved
0.6865 Remote Similarity NPD7315 Approved
0.6865 Remote Similarity NPD4652 Approved
0.6862 Remote Similarity NPD5312 Approved
0.6862 Remote Similarity NPD5313 Approved
0.6845 Remote Similarity NPD3879 Approved
0.6839 Remote Similarity NPD3400 Discontinued
0.6833 Remote Similarity NPD2541 Clinical (unspecified phase)
0.6831 Remote Similarity NPD2098 Approved
0.6828 Remote Similarity NPD5137 Approved
0.6825 Remote Similarity NPD7695 Clinical (unspecified phase)
0.6821 Remote Similarity NPD5525 Clinical (unspecified phase)
0.6816 Remote Similarity NPD6863 Phase 2
0.6809 Remote Similarity NPD3909 Discontinued
0.6807 Remote Similarity NPD4175 Approved
0.6807 Remote Similarity NPD4177 Approved
0.6806 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6792 Remote Similarity NPD5292 Approved
0.6792 Remote Similarity NPD5291 Approved
0.6786 Remote Similarity NPD1330 Phase 2
0.6786 Remote Similarity NPD1329 Clinical (unspecified phase)
0.6786 Remote Similarity NPD7296 Approved
0.6782 Remote Similarity NPD4237 Approved
0.6782 Remote Similarity NPD4236 Phase 3
0.6769 Remote Similarity NPD7861 Discontinued
0.6766 Remote Similarity NPD6238 Discontinued
0.6757 Remote Similarity NPD2904 Discontinued
0.6754 Remote Similarity NPD5192 Clinical (unspecified phase)
0.6753 Remote Similarity NPD8103 Clinical (unspecified phase)
0.6742 Remote Similarity NPD1975 Clinical (unspecified phase)
0.674 Remote Similarity NPD6677 Suspended
0.6727 Remote Similarity NPD196 Phase 1
0.6725 Remote Similarity NPD6073 Approved
0.6725 Remote Similarity NPD5725 Approved
0.6723 Remote Similarity NPD6682 Clinical (unspecified phase)
0.6721 Remote Similarity NPD7080 Clinical (unspecified phase)
0.6717 Remote Similarity NPD4413 Clinical (unspecified phase)
0.6706 Remote Similarity NPD8265 Approved
0.6705 Remote Similarity NPD3692 Discontinued
0.6704 Remote Similarity NPD7523 Phase 3
0.6703 Remote Similarity NPD4227 Discontinued
0.6703 Remote Similarity NPD7495 Discontinued
0.6703 Remote Similarity NPD8019 Approved
0.6686 Remote Similarity NPD3374 Clinical (unspecified phase)
0.6686 Remote Similarity NPD5689 Approved
0.6686 Remote Similarity NPD5688 Approved
0.6686 Remote Similarity NPD1048 Approved
0.6685 Remote Similarity NPD8417 Discontinued
0.6684 Remote Similarity NPD42 Phase 2
0.6684 Remote Similarity NPD6042 Phase 2
0.6684 Remote Similarity NPD3965 Phase 1
0.6667 Remote Similarity NPD8643 Discontinued
0.6667 Remote Similarity NPD6666 Approved
0.6667 Remote Similarity NPD5865 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4210 Discontinued
0.6667 Remote Similarity NPD6667 Approved
0.665 Remote Similarity NPD5994 Discontinued
0.665 Remote Similarity NPD8162 Phase 2
0.665 Remote Similarity NPD8163 Clinical (unspecified phase)
0.6649 Remote Similarity NPD8051 Clinical (unspecified phase)
0.6649 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6649 Remote Similarity NPD5946 Clinical (unspecified phase)
0.6648 Remote Similarity NPD7527 Clinical (unspecified phase)
0.6648 Remote Similarity NPD7526 Approved
0.6648 Remote Similarity NPD6386 Approved
0.6648 Remote Similarity NPD2575 Approved
0.6648 Remote Similarity NPD52 Approved
0.6648 Remote Similarity NPD6385 Approved
0.6648 Remote Similarity NPD5481 Discontinued
0.6648 Remote Similarity NPD6676 Phase 2
0.6648 Remote Similarity NPD7749 Clinical (unspecified phase)
0.6647 Remote Similarity NPD2245 Discovery
0.6647 Remote Similarity NPD5747 Discontinued
0.6647 Remote Similarity NPD1423 Approved
0.6628 Remote Similarity NPD4579 Clinical (unspecified phase)
0.6627 Remote Similarity NPD4738 Phase 2
0.6627 Remote Similarity NPD3125 Approved
0.6615 Remote Similarity NPD3153 Approved
0.6615 Remote Similarity NPD3154 Approved
0.6614 Remote Similarity NPD3451 Clinical (unspecified phase)
0.6613 Remote Similarity NPD6862 Phase 2
0.6612 Remote Similarity NPD4018 Clinical (unspecified phase)
0.661 Remote Similarity NPD2219 Phase 1
0.6609 Remote Similarity NPD7450 Phase 2
0.6609 Remote Similarity NPD6032 Approved
0.66 Remote Similarity NPD7667 Clinical (unspecified phase)
0.6599 Remote Similarity NPD5114 Approved
0.6599 Remote Similarity NPD5112 Approved
0.6599 Remote Similarity NPD5113 Approved
0.6592 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6592 Remote Similarity NPD3158 Phase 1
0.6592 Remote Similarity NPD3157 Approved
0.6591 Remote Similarity NPD2654 Approved
0.6588 Remote Similarity NPD3056 Clinical (unspecified phase)
0.6587 Remote Similarity NPD2585 Clinical (unspecified phase)
0.6578 Remote Similarity NPD6746 Phase 2
0.6576 Remote Similarity NPD3465 Clinical (unspecified phase)
0.6576 Remote Similarity NPD5563 Clinical (unspecified phase)
0.6571 Remote Similarity NPD3656 Approved
0.657 Remote Similarity NPD4618 Approved
0.657 Remote Similarity NPD6355 Discontinued
0.657 Remote Similarity NPD4622 Approved
0.6569 Remote Similarity NPD4971 Clinical (unspecified phase)
0.6568 Remote Similarity NPD2614 Approved
0.6568 Remote Similarity NPD2613 Approved
0.6566 Remote Similarity NPD3808 Clinical (unspecified phase)
0.6566 Remote Similarity NPD3685 Discontinued
0.6562 Remote Similarity NPD5441 Clinical (unspecified phase)
0.6559 Remote Similarity NPD8070 Approved
0.6558 Remote Similarity NPD6824 Clinical (unspecified phase)
0.6556 Remote Similarity NPD7303 Discontinued
0.6552 Remote Similarity NPD6519 Phase 2
0.655 Remote Similarity NPD3090 Approved
0.655 Remote Similarity NPD2566 Approved
0.655 Remote Similarity NPD3087 Approved
0.655 Remote Similarity NPD4745 Approved
0.655 Remote Similarity NPD2574 Discontinued
0.655 Remote Similarity NPD3088 Approved
0.655 Remote Similarity NPD2573 Approved
0.655 Remote Similarity NPD839 Approved
0.655 Remote Similarity NPD4746 Phase 3
0.655 Remote Similarity NPD2571 Approved
0.655 Remote Similarity NPD2572 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