Structure

Physi-Chem Properties

Molecular Weight:  1000.4
Volume:  965.211
LogP:  0.258
LogD:  0.37
LogS:  -1.584
# Rotatable Bonds:  16
TPSA:  332.03
# H-Bond Aceptor:  23
# H-Bond Donor:  7
# Rings:  4
# Heavy Atoms:  24

MedChem Properties

QED Drug-Likeness Score:  0.056
Synthetic Accessibility Score:  7.094
Fsp3:  0.522
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:  -6.656
MDCK Permeability:  6.848494649602799e-06
Pgp-inhibitor:  0.971
Pgp-substrate:  0.996
Human Intestinal Absorption (HIA):  0.317
20% Bioavailability (F20%):  0.572
30% Bioavailability (F30%):  0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.057
Plasma Protein Binding (PPB):  63.73666763305664%
Volume Distribution (VD):  0.414
Pgp-substrate:  20.69189453125%

ADMET: Metabolism

CYP1A2-inhibitor:  0.0
CYP1A2-substrate:  0.005
CYP2C19-inhibitor:  0.032
CYP2C19-substrate:  0.039
CYP2C9-inhibitor:  0.031
CYP2C9-substrate:  0.081
CYP2D6-inhibitor:  0.079
CYP2D6-substrate:  0.066
CYP3A4-inhibitor:  0.016
CYP3A4-substrate:  0.04

ADMET: Excretion

Clearance (CL):  2.69
Half-life (T1/2):  0.482

ADMET: Toxicity

hERG Blockers:  0.018
Human Hepatotoxicity (H-HT):  0.976
Drug-inuced Liver Injury (DILI):  0.995
AMES Toxicity:  0.757
Rat Oral Acute Toxicity:  0.783
Maximum Recommended Daily Dose:  0.968
Skin Sensitization:  0.487
Carcinogencity:  0.555
Eye Corrosion:  0.003
Eye Irritation:  0.004
Respiratory Toxicity:  0.909

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

  Natural Product: NPC471050

Natural Product ID:  NPC471050
Common Name*:   Symplostatin 9
IUPAC Name:   sodium;[(2R)-3-[[(2S)-1-[[(2S,5S,8S,11R,12S,15Z,18S,21R)-2-benzyl-15-ethylidene-21-hydroxy-5-[(4-hydroxyphenyl)methyl]-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-8-propan-2-yl-10-oxa-1,4,7,14,17-pentazabicyclo[16.3.1]docosan-12-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-2-methoxy-3-oxopropyl] sulfate
Synonyms:   symplostatin 9
Standard InCHIKey:  NHXDDQPGWZNWED-FYNDLZNZSA-M
Standard InCHI:  InChI=1S/C46H63N7O16S.Na/c1-9-30-39(56)48-31-19-20-35(55)53(44(31)61)33(22-27-13-11-10-12-14-27)45(62)52(7)32(21-28-15-17-29(54)18-16-28)40(57)50-37(25(4)5)46(63)69-26(6)38(43(60)47-30)51-42(59)36(24(2)3)49-41(58)34(67-8)23-68-70(64,65)66;/h9-18,24-26,31-38,54-55H,19-23H2,1-8H3,(H,47,60)(H,48,56)(H,49,58)(H,50,57)(H,51,59)(H,64,65,66);/q;+1/p-1/b30-9-;/t26-,31+,32+,33+,34-,35-,36+,37+,38+;/m1./s1
SMILES:  CO[C@@H](C(=N[C@H](C(=N[C@H]1[C@@H](C)OC(=O)[C@@H](N=C(O)[C@H](Cc2ccc(cc2)[O-])N(C)C(=O)[C@@H](N2C(=O)[C@@H](N=C(/C(=C/C)/N=C1O)O)CC[C@H]2O)Cc1ccccc1)C(C)C)O)C(C)C)O)COS(=O)(=O)O.[Na+]
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2338551
PubChem CID:   71562563
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
NPO33098 cyanobacteria Phylum n.a. Bacteria n.a. n.a. n.a. PMID[19715320]
NPO33098 cyanobacteria Phylum n.a. Bacteria n.a. n.a. n.a. PMID[23350733]

☑ 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
NPT279 Individual Protein Leukocyte elastase Homo sapiens IC50 = 28.0 nM PMID[536131]
NPT2 Others Unspecified Activity = 73.9 % PMID[536131]
NPT2 Others Unspecified IC50 > 10000.0 nM PMID[536131]
NPT2 Others Unspecified IC50 = 324.0 nM PMID[536131]
NPT2 Others Unspecified IC50 = 37.0 nM PMID[536131]

☑ 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 NPC471050 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
1.0 High Similarity NPC471048
1.0 High Similarity NPC471049
0.9586 High Similarity NPC163961
0.9586 High Similarity NPC473305
0.9401 High Similarity NPC476321
0.9345 High Similarity NPC471526
0.9333 High Similarity NPC279871
0.929 High Similarity NPC294951
0.9167 High Similarity NPC269750
0.9167 High Similarity NPC194671
0.9102 High Similarity NPC473354
0.908 High Similarity NPC471051
0.908 High Similarity NPC471053
0.908 High Similarity NPC471052
0.9042 High Similarity NPC273755
0.8971 High Similarity NPC473407
0.8971 High Similarity NPC473378
0.8935 High Similarity NPC50016
0.8929 High Similarity NPC137627
0.8929 High Similarity NPC306804
0.8916 High Similarity NPC107938
0.8916 High Similarity NPC294516
0.8876 High Similarity NPC159767
0.8876 High Similarity NPC155506
0.8876 High Similarity NPC26108
0.887 High Similarity NPC302715
0.883 High Similarity NPC45037
0.881 High Similarity NPC40234
0.8765 High Similarity NPC476227
0.8757 High Similarity NPC230611
0.8655 High Similarity NPC473402
0.8644 High Similarity NPC102959
0.8596 High Similarity NPC60516
0.8488 Intermediate Similarity NPC248670
0.848 Intermediate Similarity NPC475204
0.848 Intermediate Similarity NPC475123
0.848 Intermediate Similarity NPC46009
0.8352 Intermediate Similarity NPC65714
0.8333 Intermediate Similarity NPC471165
0.8287 Intermediate Similarity NPC240130
0.8287 Intermediate Similarity NPC61332
0.8284 Intermediate Similarity NPC471527
0.8261 Intermediate Similarity NPC473371
0.8246 Intermediate Similarity NPC63931
0.8218 Intermediate Similarity NPC89831
0.8216 Intermediate Similarity NPC471592
0.8125 Intermediate Similarity NPC158277
0.8101 Intermediate Similarity NPC473404
0.8075 Intermediate Similarity NPC323662
0.8057 Intermediate Similarity NPC196091
0.7967 Intermediate Similarity NPC315542
0.7957 Intermediate Similarity NPC328763
0.7927 Intermediate Similarity NPC220060
0.7914 Intermediate Similarity NPC163392
0.7914 Intermediate Similarity NPC239762
0.7895 Intermediate Similarity NPC477551
0.7884 Intermediate Similarity NPC477550
0.7884 Intermediate Similarity NPC477552
0.788 Intermediate Similarity NPC94862
0.787 Intermediate Similarity NPC233702
0.7844 Intermediate Similarity NPC16188
0.7824 Intermediate Similarity NPC473341
0.7824 Intermediate Similarity NPC262166
0.7821 Intermediate Similarity NPC477462
0.7796 Intermediate Similarity NPC174122
0.7796 Intermediate Similarity NPC64140
0.7791 Intermediate Similarity NPC127741
0.7784 Intermediate Similarity NPC81026
0.7766 Intermediate Similarity NPC469445
0.7753 Intermediate Similarity NPC471568
0.7753 Intermediate Similarity NPC473693
0.7742 Intermediate Similarity NPC234069
0.774 Intermediate Similarity NPC63040
0.774 Intermediate Similarity NPC302597
0.7727 Intermediate Similarity NPC22883
0.7727 Intermediate Similarity NPC5719
0.7727 Intermediate Similarity NPC472923
0.7727 Intermediate Similarity NPC217804
0.7727 Intermediate Similarity NPC210377
0.7725 Intermediate Similarity NPC266741
0.7719 Intermediate Similarity NPC202198
0.7719 Intermediate Similarity NPC122590
0.7708 Intermediate Similarity NPC469443
0.7706 Intermediate Similarity NPC473491
0.7704 Intermediate Similarity NPC469444
0.7697 Intermediate Similarity NPC186617
0.7692 Intermediate Similarity NPC475421
0.7688 Intermediate Similarity NPC326027
0.7684 Intermediate Similarity NPC15068
0.7684 Intermediate Similarity NPC254700
0.7684 Intermediate Similarity NPC61004
0.7683 Intermediate Similarity NPC6570
0.7677 Intermediate Similarity NPC326333
0.7674 Intermediate Similarity NPC39431
0.766 Intermediate Similarity NPC248822
0.7657 Intermediate Similarity NPC469243
0.7654 Intermediate Similarity NPC198254
0.7654 Intermediate Similarity NPC274198
0.7633 Intermediate Similarity NPC135121
0.763 Intermediate Similarity NPC476268
0.7627 Intermediate Similarity NPC223207
0.7619 Intermediate Similarity NPC477217
0.7619 Intermediate Similarity NPC201244
0.7614 Intermediate Similarity NPC478005
0.76 Intermediate Similarity NPC25539
0.7598 Intermediate Similarity NPC280022
0.7588 Intermediate Similarity NPC469442
0.7588 Intermediate Similarity NPC277306
0.7584 Intermediate Similarity NPC290755
0.7584 Intermediate Similarity NPC471771
0.7584 Intermediate Similarity NPC304074
0.7582 Intermediate Similarity NPC196243
0.7581 Intermediate Similarity NPC138083
0.7574 Intermediate Similarity NPC262077
0.7568 Intermediate Similarity NPC470903
0.7568 Intermediate Similarity NPC470112
0.7568 Intermediate Similarity NPC167763
0.7566 Intermediate Similarity NPC477526
0.7557 Intermediate Similarity NPC475544
0.7556 Intermediate Similarity NPC276506
0.7554 Intermediate Similarity NPC32064
0.7552 Intermediate Similarity NPC144314
0.7545 Intermediate Similarity NPC476989
0.7544 Intermediate Similarity NPC2501
0.7543 Intermediate Similarity NPC56635
0.7543 Intermediate Similarity NPC197743
0.7543 Intermediate Similarity NPC297145
0.7542 Intermediate Similarity NPC209463
0.7542 Intermediate Similarity NPC141957
0.754 Intermediate Similarity NPC276120
0.7527 Intermediate Similarity NPC136797
0.7527 Intermediate Similarity NPC164608
0.7526 Intermediate Similarity NPC242728
0.7514 Intermediate Similarity NPC477637
0.7514 Intermediate Similarity NPC328494
0.7513 Intermediate Similarity NPC50548
0.75 Intermediate Similarity NPC119652
0.75 Intermediate Similarity NPC62104
0.75 Intermediate Similarity NPC7817
0.75 Intermediate Similarity NPC97526
0.75 Intermediate Similarity NPC1390
0.75 Intermediate Similarity NPC149962
0.75 Intermediate Similarity NPC244336
0.75 Intermediate Similarity NPC4910
0.75 Intermediate Similarity NPC91953
0.75 Intermediate Similarity NPC475168
0.7487 Intermediate Similarity NPC299806
0.7463 Intermediate Similarity NPC478007
0.7456 Intermediate Similarity NPC52748
0.7448 Intermediate Similarity NPC184933
0.7448 Intermediate Similarity NPC59827
0.7444 Intermediate Similarity NPC328649
0.7444 Intermediate Similarity NPC473502
0.744 Intermediate Similarity NPC197921
0.7439 Intermediate Similarity NPC257390
0.7429 Intermediate Similarity NPC473580
0.7416 Intermediate Similarity NPC241794
0.7414 Intermediate Similarity NPC5194
0.7414 Intermediate Similarity NPC261934
0.7407 Intermediate Similarity NPC329731
0.7401 Intermediate Similarity NPC319320
0.7401 Intermediate Similarity NPC287757
0.7396 Intermediate Similarity NPC161069
0.7396 Intermediate Similarity NPC469360
0.7396 Intermediate Similarity NPC314083
0.7391 Intermediate Similarity NPC478008
0.7387 Intermediate Similarity NPC219350
0.7387 Intermediate Similarity NPC194699
0.7385 Intermediate Similarity NPC123859
0.7384 Intermediate Similarity NPC9373
0.7384 Intermediate Similarity NPC471820
0.7384 Intermediate Similarity NPC471821
0.7381 Intermediate Similarity NPC307357
0.7381 Intermediate Similarity NPC46098
0.7381 Intermediate Similarity NPC268841
0.7374 Intermediate Similarity NPC191863
0.7374 Intermediate Similarity NPC133470
0.7374 Intermediate Similarity NPC289776
0.7371 Intermediate Similarity NPC470902
0.7366 Intermediate Similarity NPC153554
0.7365 Intermediate Similarity NPC68865
0.736 Intermediate Similarity NPC311357
0.7358 Intermediate Similarity NPC477632
0.7358 Intermediate Similarity NPC477638
0.7356 Intermediate Similarity NPC162104
0.7347 Intermediate Similarity NPC473450
0.7333 Intermediate Similarity NPC45191
0.7333 Intermediate Similarity NPC477527
0.733 Intermediate Similarity NPC29531
0.733 Intermediate Similarity NPC244509
0.7314 Intermediate Similarity NPC56685
0.731 Intermediate Similarity NPC209509
0.7283 Intermediate Similarity NPC475532
0.7267 Intermediate Similarity NPC314358
0.7251 Intermediate Similarity NPC476978
0.7243 Intermediate Similarity NPC165285
0.7243 Intermediate Similarity NPC17698
0.7225 Intermediate Similarity NPC145113
0.7225 Intermediate Similarity NPC138775
0.7219 Intermediate Similarity NPC313694

  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 NPC471050 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
0.7753 Intermediate Similarity NPD7608 Discontinued
0.7644 Intermediate Similarity NPD7118 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD7131 Phase 3
0.7296 Intermediate Similarity NPD7811 Phase 3
0.7296 Intermediate Similarity NPD7810 Phase 3
0.7225 Intermediate Similarity NPD8323 Discontinued
0.7211 Intermediate Similarity NPD6851 Approved
0.7211 Intermediate Similarity NPD6853 Approved
0.7211 Intermediate Similarity NPD5946 Clinical (unspecified phase)
0.7207 Intermediate Similarity NPD8019 Approved
0.7198 Intermediate Similarity NPD8303 Discontinued
0.712 Intermediate Similarity NPD7484 Phase 3
0.712 Intermediate Similarity NPD7485 Phase 3
0.7111 Intermediate Similarity NPD7495 Discontinued
0.7105 Intermediate Similarity NPD7132 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD8417 Discontinued
0.7035 Intermediate Similarity NPD7565 Approved
0.7011 Intermediate Similarity NPD6860 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6297 Approved
0.6994 Remote Similarity NPD7978 Discontinued
0.6981 Remote Similarity NPD8356 Approved
0.6964 Remote Similarity NPD3136 Phase 2
0.6959 Remote Similarity NPD8172 Phase 2
0.6959 Remote Similarity NPD8173 Phase 2
0.6957 Remote Similarity NPD8031 Discontinued
0.6936 Remote Similarity NPD7450 Phase 2
0.6882 Remote Similarity NPD5729 Clinical (unspecified phase)
0.6872 Remote Similarity NPD8103 Clinical (unspecified phase)
0.6872 Remote Similarity NPD7303 Discontinued
0.6867 Remote Similarity NPD3125 Approved
0.6852 Remote Similarity NPD8430 Approved
0.6805 Remote Similarity NPD5203 Approved
0.6805 Remote Similarity NPD4620 Approved
0.6805 Remote Similarity NPD5201 Approved
0.6805 Remote Similarity NPD4617 Approved
0.6805 Remote Similarity NPD5202 Clinical (unspecified phase)
0.6786 Remote Similarity NPD6089 Clinical (unspecified phase)
0.6778 Remote Similarity NPD7613 Discontinued
0.6776 Remote Similarity NPD7749 Clinical (unspecified phase)
0.6772 Remote Similarity NPD5137 Approved
0.6761 Remote Similarity NPD6681 Discovery
0.6761 Remote Similarity NPD7596 Clinical (unspecified phase)
0.6755 Remote Similarity NPD2017 Approved
0.6755 Remote Similarity NPD2890 Approved
0.6755 Remote Similarity NPD2889 Approved
0.6755 Remote Similarity NPD2888 Approved
0.6751 Remote Similarity NPD8025 Phase 2
0.6744 Remote Similarity NPD6346 Approved
0.6744 Remote Similarity NPD5119 Approved
0.6744 Remote Similarity NPD5120 Approved
0.6744 Remote Similarity NPD5121 Approved
0.674 Remote Similarity NPD7523 Phase 3
0.6716 Remote Similarity NPD7667 Clinical (unspecified phase)
0.6707 Remote Similarity NPD4659 Approved
0.6703 Remote Similarity NPD7972 Discontinued
0.6686 Remote Similarity NPD6866 Clinical (unspecified phase)
0.6686 Remote Similarity NPD6867 Clinical (unspecified phase)
0.6686 Remote Similarity NPD5745 Approved
0.6685 Remote Similarity NPD5481 Discontinued
0.6685 Remote Similarity NPD6390 Discontinued
0.6685 Remote Similarity NPD3400 Discontinued
0.6684 Remote Similarity NPD7695 Clinical (unspecified phase)
0.6684 Remote Similarity NPD2098 Approved
0.6684 Remote Similarity NPD5218 Approved
0.6684 Remote Similarity NPD5219 Approved
0.6667 Remote Similarity NPD6682 Clinical (unspecified phase)
0.6667 Remote Similarity NPD2097 Approved
0.6649 Remote Similarity NPD5445 Approved
0.6648 Remote Similarity NPD6897 Clinical (unspecified phase)
0.6647 Remote Similarity NPD2584 Suspended
0.6633 Remote Similarity NPD7281 Phase 3
0.6633 Remote Similarity NPD7617 Discontinued
0.6633 Remote Similarity NPD7280 Phase 3
0.6632 Remote Similarity NPD4652 Approved
0.6629 Remote Similarity NPD6852 Discontinued
0.6629 Remote Similarity NPD2976 Clinical (unspecified phase)
0.6628 Remote Similarity NPD1329 Clinical (unspecified phase)
0.6628 Remote Similarity NPD4619 Approved
0.6628 Remote Similarity NPD4621 Approved
0.6628 Remote Similarity NPD1330 Phase 2
0.6612 Remote Similarity NPD8315 Phase 1
0.6611 Remote Similarity NPD6884 Clinical (unspecified phase)
0.6599 Remote Similarity NPD6237 Clinical (unspecified phase)
0.6598 Remote Similarity NPD5485 Approved
0.6598 Remote Similarity NPD5484 Approved
0.6592 Remote Similarity NPD6676 Phase 2
0.6578 Remote Similarity NPD5967 Approved
0.6578 Remote Similarity NPD7080 Clinical (unspecified phase)
0.6571 Remote Similarity NPD6073 Approved
0.657 Remote Similarity NPD5746 Approved
0.6564 Remote Similarity NPD6211 Clinical (unspecified phase)
0.6561 Remote Similarity NPD8245 Clinical (unspecified phase)
0.6559 Remote Similarity NPD5355 Approved
0.6559 Remote Similarity NPD5356 Approved
0.6559 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6555 Remote Similarity NPD7583 Approved
0.6546 Remote Similarity NPD5313 Approved
0.6546 Remote Similarity NPD5312 Approved
0.6534 Remote Similarity NPD6295 Approved
0.6534 Remote Similarity NPD6294 Approved
0.6531 Remote Similarity NPD5192 Clinical (unspecified phase)
0.6529 Remote Similarity NPD4103 Phase 2
0.6529 Remote Similarity NPD2159 Approved
0.6529 Remote Similarity NPD2160 Approved
0.6529 Remote Similarity NPD2625 Approved
0.6529 Remote Similarity NPD2627 Approved
0.6529 Remote Similarity NPD4104 Clinical (unspecified phase)
0.6529 Remote Similarity NPD2628 Approved
0.6529 Remote Similarity NPD2626 Approved
0.6526 Remote Similarity NPD5823 Approved
0.6524 Remote Similarity NPD7585 Approved
0.6522 Remote Similarity NPD6863 Phase 2
0.6514 Remote Similarity NPD7113 Clinical (unspecified phase)
0.6509 Remote Similarity NPD3878 Approved
0.6508 Remote Similarity NPD4521 Clinical (unspecified phase)
0.6507 Remote Similarity NPD8161 Suspended
0.6505 Remote Similarity NPD7110 Phase 1
0.6505 Remote Similarity NPD7109 Clinical (unspecified phase)
0.65 Remote Similarity NPD6608 Clinical (unspecified phase)
0.6486 Remote Similarity NPD3455 Phase 2
0.6484 Remote Similarity NPD6088 Approved
0.648 Remote Similarity NPD7959 Clinical (unspecified phase)
0.6479 Remote Similarity NPD3879 Approved
0.6474 Remote Similarity NPD4738 Phase 2
0.6474 Remote Similarity NPD6862 Phase 2
0.6467 Remote Similarity NPD5723 Approved
0.6464 Remote Similarity NPD7910 Clinical (unspecified phase)
0.6462 Remote Similarity NPD3965 Phase 1
0.6461 Remote Similarity NPD2240 Approved
0.6461 Remote Similarity NPD4173 Approved
0.6461 Remote Similarity NPD4172 Approved
0.6461 Remote Similarity NPD2239 Approved
0.6457 Remote Similarity NPD8265 Approved
0.6457 Remote Similarity NPD5296 Approved
0.6457 Remote Similarity NPD8416 Discontinued
0.6453 Remote Similarity NPD4177 Approved
0.6453 Remote Similarity NPD4175 Approved
0.6448 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6448 Remote Similarity NPD3536 Discontinued
0.6447 Remote Similarity NPD8014 Clinical (unspecified phase)
0.6442 Remote Similarity NPD8163 Clinical (unspecified phase)
0.6442 Remote Similarity NPD8162 Phase 2
0.644 Remote Similarity NPD2904 Discontinued
0.6436 Remote Similarity NPD6504 Approved
0.6436 Remote Similarity NPD5772 Approved
0.6436 Remote Similarity NPD5773 Approved
0.6436 Remote Similarity NPD6505 Approved
0.6436 Remote Similarity NPD6668 Clinical (unspecified phase)
0.6433 Remote Similarity NPD2585 Clinical (unspecified phase)
0.6425 Remote Similarity NPD6253 Approved
0.6422 Remote Similarity NPD4413 Clinical (unspecified phase)
0.6422 Remote Similarity NPD6312 Discontinued
0.6421 Remote Similarity NPD8070 Approved
0.642 Remote Similarity NPD555 Phase 2
0.642 Remote Similarity NPD8643 Discontinued
0.6418 Remote Similarity NPD4435 Approved
0.6418 Remote Similarity NPD5558 Clinical (unspecified phase)
0.6417 Remote Similarity NPD6677 Suspended
0.6417 Remote Similarity NPD2541 Clinical (unspecified phase)
0.6412 Remote Similarity NPD4677 Discontinued
0.6409 Remote Similarity NPD2575 Approved
0.6402 Remote Similarity NPD7600 Phase 2
0.64 Remote Similarity NPD7715 Approved
0.64 Remote Similarity NPD7714 Approved
0.6396 Remote Similarity NPD4086 Phase 1
0.6395 Remote Similarity NPD5339 Clinical (unspecified phase)
0.6394 Remote Similarity NPD6254 Approved
0.6394 Remote Similarity NPD6256 Approved
0.6394 Remote Similarity NPD6255 Approved
0.6391 Remote Similarity NPD4806 Approved
0.6391 Remote Similarity NPD4807 Approved
0.6389 Remote Similarity NPD6119 Clinical (unspecified phase)
0.6389 Remote Similarity NPD8149 Discontinued
0.6386 Remote Similarity NPD6377 Clinical (unspecified phase)
0.6385 Remote Similarity NPD3803 Clinical (unspecified phase)
0.6384 Remote Similarity NPD5725 Approved
0.6383 Remote Similarity NPD2515 Approved
0.6383 Remote Similarity NPD3007 Approved
0.6383 Remote Similarity NPD7011 Discontinued
0.6374 Remote Similarity NPD6552 Clinical (unspecified phase)
0.6369 Remote Similarity NPD1725 Approved
0.6369 Remote Similarity NPD5238 Clinical (unspecified phase)
0.6368 Remote Similarity NPD8351 Phase 2
0.6368 Remote Similarity NPD4434 Approved
0.6364 Remote Similarity NPD6824 Clinical (unspecified phase)
0.6364 Remote Similarity NPD6309 Approved
0.6364 Remote Similarity NPD6623 Phase 3
0.6364 Remote Similarity NPD6310 Approved
0.6364 Remote Similarity NPD6502 Phase 2
0.6364 Remote Similarity NPD6311 Approved
0.6359 Remote Similarity NPD5200 Clinical (unspecified phase)
0.6359 Remote Similarity NPD5556 Clinical (unspecified phase)
0.6358 Remote Similarity NPD5204 Approved
0.6358 Remote Similarity NPD3626 Phase 3
0.6353 Remote Similarity NPD5108 Clinical (unspecified phase)
0.6349 Remote Similarity NPD6818 Clinical (unspecified phase)
0.6349 Remote Similarity NPD7089 Clinical (unspecified phase)
0.6349 Remote Similarity NPD7599 Phase 2
0.6348 Remote Similarity NPD3553 Approved
0.6348 Remote Similarity NPD3554 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