Structure

Physi-Chem Properties

Molecular Weight:  989.39
Volume:  927.566
LogP:  -0.269
LogD:  -0.072
LogS:  -0.691
# Rotatable Bonds:  18
TPSA:  358.51
# H-Bond Aceptor:  24
# H-Bond Donor:  11
# Rings:  3
# Heavy Atoms:  26

MedChem Properties

QED Drug-Likeness Score:  0.029
Synthetic Accessibility Score:  6.99
Fsp3:  0.659
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:  -6.551
MDCK Permeability:  2.399637014605105e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.999
Human Intestinal Absorption (HIA):  0.991
20% Bioavailability (F20%):  0.999
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.048
Plasma Protein Binding (PPB):  70.63311004638672%
Volume Distribution (VD):  0.351
Pgp-substrate:  15.138171195983887%

ADMET: Metabolism

CYP1A2-inhibitor:  0.0
CYP1A2-substrate:  0.011
CYP2C19-inhibitor:  0.038
CYP2C19-substrate:  0.035
CYP2C9-inhibitor:  0.078
CYP2C9-substrate:  0.025
CYP2D6-inhibitor:  0.005
CYP2D6-substrate:  0.068
CYP3A4-inhibitor:  0.008
CYP3A4-substrate:  0.005

ADMET: Excretion

Clearance (CL):  2.541
Half-life (T1/2):  0.221

ADMET: Toxicity

hERG Blockers:  0.062
Human Hepatotoxicity (H-HT):  0.737
Drug-inuced Liver Injury (DILI):  0.834
AMES Toxicity:  0.007
Rat Oral Acute Toxicity:  0.286
Maximum Recommended Daily Dose:  0.966
Skin Sensitization:  0.253
Carcinogencity:  0.381
Eye Corrosion:  0.003
Eye Irritation:  0.003
Respiratory Toxicity:  0.851

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

  Natural Product: NPC277306

Natural Product ID:  NPC277306
Common Name*:   (R)-3-((2S,5S,8S,11R,12S,15S,18S,21R)-15-(3-(Amino(Iminio)Methylamino)Propyl)-2,8-Di-Sec-Butyl-5-(3-Chloro-4-Methoxybenzyl)-21-Hydroxy-4,11-Dimethyl-3,6,9,13,16,22-Hexaoxo-10-Oxa-1,4,7,14,17-Pentaazabicyclo[16.3.1]Docosan-12-Ylamino)-2-Hydroxy-3-Oxopropyl Sulfate
IUPAC Name:   [(2R)-3-[[(2S,5S,8S,11R,12S,15S,18S,21R)-2,8-bis[(2S)-butan-2-yl]-5-[(3-chloro-4-methoxyphenyl)methyl]-15-[3-(diaminomethylideneamino)propyl]-21-hydroxy-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-10-oxa-1,4,7,14,17-pentazabicyclo[16.3.1]docosan-12-yl]amino]-2-hydroxy-3-oxopropyl] hydrogen sulfate
Synonyms:  
Standard InCHIKey:  OMLCFIGVAFGCAB-WNVWBQEDSA-N
Standard InCHI:  InChI=1S/C41H64ClN9O15S/c1-8-20(3)31-40(60)66-22(5)32(49-36(56)28(52)19-65-67(61,62)63)37(57)46-25(11-10-16-45-41(43)44)34(54)47-26-13-15-30(53)51(38(26)58)33(21(4)9-2)39(59)50(6)27(35(55)48-31)18-23-12-14-29(64-7)24(42)17-23/h12,14,17,20-22,25-28,30-33,52-53H,8-11,13,15-16,18-19H2,1-7H3,(H,46,57)(H,47,54)(H,48,55)(H,49,56)(H4,43,44,45)(H,61,62,63)/t20-,21-,22+,25-,26-,27-,28+,30+,31-,32-,33-/m0/s1
SMILES:  CC[C@@H]([C@@H]1N=C(O)[C@H](Cc2ccc(c(c2)Cl)OC)N(C)C(=O)[C@H]([C@H](CC)C)N2[C@H](O)CC[C@@H](C2=O)N=C([C@@H](N=C([C@H]([C@H](OC1=O)C)N=C([C@@H](COS(=O)(=O)O)O)O)O)CCCNC(=N)N)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1078911
PubChem CID:   44254975
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
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. n.a. n.a. PMID[11000050]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. n.a. n.a. PMID[11374973]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. n.a. n.a. PMID[12141855]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. Einan Reservoir in Israel n.a. PMID[12141855]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. n.a. n.a. PMID[18163584]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. n.a. n.a. PMID[18558743]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. n.a. n.a. PMID[18973386]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria water bloom of the cyanobacterium Microcystis aeruginosa n.a. n.a. PMID[19650639]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria bloom material Lake Kinneret, Israel n.a. PMID[22280481]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. Kibbutz Geva, Israel n.a. PMID[23153007]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. Water Reservoir near Kibbutz Hafetz Haim, Israel n.a. PMID[23718637]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria Bloom n.a. n.a. PMID[24261937]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. n.a. n.a. PMID[24642434]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. n.a. n.a. PMID[24868986]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. n.a. n.a. PMID[29405714]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria Bloom n.a. n.a. PMID[29847132]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. n.a. n.a. PMID[9249979]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. n.a. n.a. PMID[9842728]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. n.a. n.a. Database[Title]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria 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
NPT2 Others Unspecified IC50 = 700.0 nM PMID[560084]
NPT2 Others Unspecified IC50 = 18200.0 nM PMID[560084]

☑ 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 NPC277306 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 NPC469442
0.9894 High Similarity NPC25539
0.9786 High Similarity NPC194699
0.9786 High Similarity NPC219350
0.9372 High Similarity NPC220060
0.9259 High Similarity NPC469443
0.9223 High Similarity NPC469444
0.9179 High Similarity NPC469445
0.8632 High Similarity NPC102959
0.8586 High Similarity NPC60516
0.8454 Intermediate Similarity NPC302715
0.8274 Intermediate Similarity NPC473371
0.822 Intermediate Similarity NPC473404
0.802 Intermediate Similarity NPC51047
0.802 Intermediate Similarity NPC473450
0.802 Intermediate Similarity NPC477551
0.801 Intermediate Similarity NPC477552
0.801 Intermediate Similarity NPC477550
0.798 Intermediate Similarity NPC473407
0.798 Intermediate Similarity NPC473378
0.7968 Intermediate Similarity NPC217804
0.7968 Intermediate Similarity NPC210377
0.7968 Intermediate Similarity NPC5719
0.7968 Intermediate Similarity NPC22883
0.7929 Intermediate Similarity NPC61332
0.7929 Intermediate Similarity NPC240130
0.7884 Intermediate Similarity NPC63040
0.7831 Intermediate Similarity NPC15068
0.7801 Intermediate Similarity NPC46009
0.78 Intermediate Similarity NPC248822
0.78 Intermediate Similarity NPC470728
0.7754 Intermediate Similarity NPC1390
0.7754 Intermediate Similarity NPC62104
0.7732 Intermediate Similarity NPC50016
0.772 Intermediate Similarity NPC273755
0.7665 Intermediate Similarity NPC476321
0.7653 Intermediate Similarity NPC45037
0.7626 Intermediate Similarity NPC471526
0.7617 Intermediate Similarity NPC475204
0.7617 Intermediate Similarity NPC475123
0.7594 Intermediate Similarity NPC295795
0.7588 Intermediate Similarity NPC471048
0.7588 Intermediate Similarity NPC471049
0.7588 Intermediate Similarity NPC471050
0.7573 Intermediate Similarity NPC323662
0.7538 Intermediate Similarity NPC306804
0.75 Intermediate Similarity NPC473354
0.7488 Intermediate Similarity NPC473305
0.7488 Intermediate Similarity NPC163961
0.7463 Intermediate Similarity NPC299806
0.7463 Intermediate Similarity NPC328763
0.7436 Intermediate Similarity NPC198254
0.7436 Intermediate Similarity NPC196091
0.7436 Intermediate Similarity NPC274198
0.7436 Intermediate Similarity NPC473693
0.7436 Intermediate Similarity NPC471568
0.7423 Intermediate Similarity NPC107938
0.7423 Intermediate Similarity NPC294516
0.7409 Intermediate Similarity NPC472923
0.7407 Intermediate Similarity NPC326027
0.7398 Intermediate Similarity NPC230611
0.7395 Intermediate Similarity NPC326333
0.7389 Intermediate Similarity NPC94862
0.7387 Intermediate Similarity NPC269750
0.7387 Intermediate Similarity NPC194671
0.7385 Intermediate Similarity NPC186617
0.736 Intermediate Similarity NPC137627
0.7358 Intermediate Similarity NPC81845
0.7347 Intermediate Similarity NPC40234
0.7347 Intermediate Similarity NPC276506
0.7344 Intermediate Similarity NPC471527
0.7327 Intermediate Similarity NPC294951
0.7323 Intermediate Similarity NPC471165
0.7323 Intermediate Similarity NPC473402
0.7323 Intermediate Similarity NPC26108
0.7323 Intermediate Similarity NPC279871
0.7296 Intermediate Similarity NPC280022
0.7286 Intermediate Similarity NPC196243
0.726 Intermediate Similarity NPC477632
0.726 Intermediate Similarity NPC477638
0.7259 Intermediate Similarity NPC269383
0.7259 Intermediate Similarity NPC151030
0.7236 Intermediate Similarity NPC476227
0.7236 Intermediate Similarity NPC155506
0.7236 Intermediate Similarity NPC159767
0.7214 Intermediate Similarity NPC475421
0.7186 Intermediate Similarity NPC248670
0.7178 Intermediate Similarity NPC263507
0.7178 Intermediate Similarity NPC153554
0.7178 Intermediate Similarity NPC271958
0.7178 Intermediate Similarity NPC45112
0.7178 Intermediate Similarity NPC134413
0.7163 Intermediate Similarity NPC477631
0.7157 Intermediate Similarity NPC209463
0.715 Intermediate Similarity NPC477636
0.7143 Intermediate Similarity NPC63931
0.7129 Intermediate Similarity NPC119652
0.7129 Intermediate Similarity NPC97526
0.7121 Intermediate Similarity NPC129486
0.7108 Intermediate Similarity NPC470112
0.7108 Intermediate Similarity NPC167763
0.7108 Intermediate Similarity NPC470903
0.71 Intermediate Similarity NPC49315
0.71 Intermediate Similarity NPC475532
0.7077 Intermediate Similarity NPC469243
0.7065 Intermediate Similarity NPC17698
0.7065 Intermediate Similarity NPC165285
0.7048 Intermediate Similarity NPC65714
0.7047 Intermediate Similarity NPC473580
0.7039 Intermediate Similarity NPC315542
0.7031 Intermediate Similarity NPC473341
0.7024 Intermediate Similarity NPC86678
0.702 Intermediate Similarity NPC254700
0.7018 Intermediate Similarity NPC478005
0.7005 Intermediate Similarity NPC471053
0.7005 Intermediate Similarity NPC471052
0.7005 Intermediate Similarity NPC471051
0.699 Remote Similarity NPC475544
0.6985 Remote Similarity NPC473502
0.6981 Remote Similarity NPC477639
0.6971 Remote Similarity NPC4910
0.697 Remote Similarity NPC223207
0.6952 Remote Similarity NPC477526
0.6948 Remote Similarity NPC471592
0.6939 Remote Similarity NPC287757
0.6939 Remote Similarity NPC319320
0.6935 Remote Similarity NPC304074
0.6935 Remote Similarity NPC471771
0.6935 Remote Similarity NPC290755
0.693 Remote Similarity NPC242728
0.6927 Remote Similarity NPC475409
0.6927 Remote Similarity NPC475564
0.6927 Remote Similarity NPC170302
0.6905 Remote Similarity NPC64140
0.6905 Remote Similarity NPC174122
0.6903 Remote Similarity NPC478007
0.6898 Remote Similarity NPC239762
0.6898 Remote Similarity NPC163392
0.6897 Remote Similarity NPC227778
0.6881 Remote Similarity NPC89831
0.6875 Remote Similarity NPC138083
0.6857 Remote Similarity NPC234069
0.6854 Remote Similarity NPC59827
0.6854 Remote Similarity NPC80514
0.6854 Remote Similarity NPC184933
0.6842 Remote Similarity NPC478008
0.6839 Remote Similarity NPC324081
0.6829 Remote Similarity NPC473546
0.6812 Remote Similarity NPC477637
0.681 Remote Similarity NPC96275
0.681 Remote Similarity NPC329731
0.6804 Remote Similarity NPC300443
0.6769 Remote Similarity NPC262166
0.6766 Remote Similarity NPC61004
0.6759 Remote Similarity NPC477527
0.6754 Remote Similarity NPC274268
0.6744 Remote Similarity NPC149962
0.6744 Remote Similarity NPC329295
0.6734 Remote Similarity NPC114806
0.6732 Remote Similarity NPC164608
0.6732 Remote Similarity NPC158277
0.6729 Remote Similarity NPC314083
0.672 Remote Similarity NPC48202
0.6719 Remote Similarity NPC81026
0.6716 Remote Similarity NPC328494
0.6714 Remote Similarity NPC235194
0.6713 Remote Similarity NPC144314
0.6701 Remote Similarity NPC476268
0.6701 Remote Similarity NPC2501
0.6684 Remote Similarity NPC122590
0.6683 Remote Similarity NPC32064
0.6683 Remote Similarity NPC24617
0.6682 Remote Similarity NPC50548
0.6682 Remote Similarity NPC276120
0.6667 Remote Similarity NPC266741
0.6653 Remote Similarity NPC319774
0.6651 Remote Similarity NPC123859
0.665 Remote Similarity NPC39431
0.665 Remote Similarity NPC302597
0.6649 Remote Similarity NPC91953
0.6649 Remote Similarity NPC168861
0.6639 Remote Similarity NPC314743
0.6633 Remote Similarity NPC56635
0.662 Remote Similarity NPC246591
0.6618 Remote Similarity NPC66490
0.6616 Remote Similarity NPC244509
0.66 Remote Similarity NPC244336
0.6599 Remote Similarity NPC56685
0.6598 Remote Similarity NPC135121
0.6597 Remote Similarity NPC197921
0.658 Remote Similarity NPC477217
0.658 Remote Similarity NPC201244
0.6562 Remote Similarity NPC469360
0.655 Remote Similarity NPC323336
0.655 Remote Similarity NPC197743
0.655 Remote Similarity NPC297145
0.655 Remote Similarity NPC326349
0.6545 Remote Similarity NPC214988
0.6528 Remote Similarity NPC52748
0.6526 Remote Similarity NPC127741

  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 NPC277306 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
0.7371 Intermediate Similarity NPD8303 Discontinued
0.7178 Intermediate Similarity NPD7959 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD8014 Clinical (unspecified phase)
0.7121 Intermediate Similarity NPD7484 Phase 3
0.7121 Intermediate Similarity NPD7485 Phase 3
0.7085 Intermediate Similarity NPD7608 Discontinued
0.7016 Intermediate Similarity NPD5348 Clinical (unspecified phase)
0.699 Remote Similarity NPD3465 Clinical (unspecified phase)
0.6939 Remote Similarity NPD8019 Approved
0.6939 Remote Similarity NPD4018 Clinical (unspecified phase)
0.6934 Remote Similarity NPD6312 Discontinued
0.6891 Remote Similarity NPD6689 Clinical (unspecified phase)
0.689 Remote Similarity NPD6089 Clinical (unspecified phase)
0.6884 Remote Similarity NPD8031 Discontinued
0.6875 Remote Similarity NPD6853 Approved
0.6875 Remote Similarity NPD6851 Approved
0.686 Remote Similarity NPD3936 Clinical (unspecified phase)
0.6853 Remote Similarity NPD7495 Discontinued
0.6769 Remote Similarity NPD7523 Phase 3
0.6753 Remote Similarity NPD6419 Discontinued
0.6712 Remote Similarity NPD8163 Clinical (unspecified phase)
0.6712 Remote Similarity NPD4971 Clinical (unspecified phase)
0.6712 Remote Similarity NPD8162 Phase 2
0.6684 Remote Similarity NPD7131 Phase 3
0.6683 Remote Similarity NPD6297 Approved
0.6667 Remote Similarity NPD5095 Phase 3
0.6667 Remote Similarity NPD3933 Discontinued
0.6667 Remote Similarity NPD5096 Phase 3
0.6651 Remote Similarity NPD3857 Clinical (unspecified phase)
0.6649 Remote Similarity NPD8076 Discontinued
0.6633 Remote Similarity NPD7118 Clinical (unspecified phase)
0.6615 Remote Similarity NPD6681 Discovery
0.66 Remote Similarity NPD5355 Approved
0.66 Remote Similarity NPD5356 Approved
0.6575 Remote Similarity NPD7811 Phase 3
0.6575 Remote Similarity NPD7810 Phase 3
0.655 Remote Similarity NPD2541 Clinical (unspecified phase)
0.6532 Remote Similarity NPD5152 Clinical (unspecified phase)
0.6473 Remote Similarity NPD6905 Phase 2
0.6465 Remote Similarity NPD4157 Discontinued
0.6465 Remote Similarity NPD6078 Clinical (unspecified phase)
0.6462 Remote Similarity NPD7132 Clinical (unspecified phase)
0.6455 Remote Similarity NPD5745 Approved
0.6425 Remote Similarity NPD2239 Approved
0.6425 Remote Similarity NPD2240 Approved
0.6425 Remote Similarity NPD3175 Clinical (unspecified phase)
0.6415 Remote Similarity NPD5192 Clinical (unspecified phase)
0.6413 Remote Similarity NPD6863 Phase 2
0.641 Remote Similarity NPD2976 Clinical (unspecified phase)
0.6402 Remote Similarity NPD5946 Clinical (unspecified phase)
0.64 Remote Similarity NPD6670 Clinical (unspecified phase)
0.6392 Remote Similarity NPD7978 Discontinued
0.6382 Remote Similarity NPD4186 Clinical (unspecified phase)
0.6349 Remote Similarity NPD3136 Phase 2
0.6349 Remote Similarity NPD5746 Approved
0.6333 Remote Similarity NPD3366 Approved
0.6332 Remote Similarity NPD3536 Discontinued
0.6324 Remote Similarity NPD7972 Discontinued
0.6323 Remote Similarity NPD3602 Clinical (unspecified phase)
0.6323 Remote Similarity NPD5542 Phase 2
0.6321 Remote Similarity NPD6901 Phase 3
0.63 Remote Similarity NPD4731 Phase 3
0.63 Remote Similarity NPD6390 Discontinued
0.6298 Remote Similarity NPD6107 Approved
0.6293 Remote Similarity NPD5967 Approved
0.6284 Remote Similarity NPD7617 Discontinued
0.6283 Remote Similarity NPD1423 Approved
0.6256 Remote Similarity NPD5200 Clinical (unspecified phase)
0.625 Remote Similarity NPD6237 Clinical (unspecified phase)
0.6244 Remote Similarity NPD1416 Approved
0.6232 Remote Similarity NPD8070 Approved
0.6231 Remote Similarity NPD5308 Clinical (unspecified phase)
0.6231 Remote Similarity NPD4588 Clinical (unspecified phase)
0.6229 Remote Similarity NPD7805 Phase 3
0.6227 Remote Similarity NPD5165 Clinical (unspecified phase)
0.6225 Remote Similarity NPD6677 Suspended
0.6221 Remote Similarity NPD6967 Phase 2
0.6216 Remote Similarity NPD3659 Discontinued
0.6198 Remote Similarity NPD2245 Discovery
0.6195 Remote Similarity NPD6510 Phase 1
0.6195 Remote Similarity NPD4227 Discontinued
0.6195 Remote Similarity NPD6511 Phase 1
0.6193 Remote Similarity NPD5341 Clinical (unspecified phase)
0.6186 Remote Similarity NPD4782 Clinical (unspecified phase)
0.6181 Remote Similarity NPD5309 Clinical (unspecified phase)
0.6175 Remote Similarity NPD6556 Clinical (unspecified phase)
0.6171 Remote Similarity NPD4413 Clinical (unspecified phase)
0.6168 Remote Similarity NPD5557 Phase 1
0.6167 Remote Similarity NPD5567 Approved
0.6162 Remote Similarity NPD2458 Approved
0.6162 Remote Similarity NPD2459 Approved
0.6162 Remote Similarity NPD2460 Phase 3
0.615 Remote Similarity NPD3909 Discontinued
0.615 Remote Similarity NPD8290 Clinical (unspecified phase)
0.6146 Remote Similarity NPD3056 Clinical (unspecified phase)
0.6143 Remote Similarity NPD5649 Clinical (unspecified phase)
0.6142 Remote Similarity NPD470 Approved
0.6142 Remote Similarity NPD469 Approved
0.6139 Remote Similarity NPD2186 Approved
0.6139 Remote Similarity NPD7303 Discontinued
0.6136 Remote Similarity NPD5910 Clinical (unspecified phase)
0.6135 Remote Similarity NPD2097 Approved
0.6134 Remote Similarity NPD4757 Clinical (unspecified phase)
0.6132 Remote Similarity NPD3451 Clinical (unspecified phase)
0.6131 Remote Similarity NPD1662 Clinical (unspecified phase)
0.6122 Remote Similarity NPD2661 Clinical (unspecified phase)
0.6117 Remote Similarity NPD3007 Approved
0.6117 Remote Similarity NPD2515 Approved
0.6114 Remote Similarity NPD4652 Approved
0.6111 Remote Similarity NPD7596 Clinical (unspecified phase)
0.6104 Remote Similarity NPD3591 Approved
0.6104 Remote Similarity NPD3592 Approved
0.6104 Remote Similarity NPD4917 Discontinued
0.6103 Remote Similarity NPD3052 Approved
0.6103 Remote Similarity NPD3054 Approved
0.6102 Remote Similarity NPD7963 Phase 3
0.6096 Remote Similarity NPD3804 Discontinued
0.6095 Remote Similarity NPD2904 Discontinued
0.6093 Remote Similarity NPD3885 Approved
0.6093 Remote Similarity NPD5484 Approved
0.6093 Remote Similarity NPD5485 Approved
0.6091 Remote Similarity NPD1725 Approved
0.6089 Remote Similarity NPD3985 Discontinued
0.6089 Remote Similarity NPD3157 Approved
0.6089 Remote Similarity NPD3158 Phase 1
0.6087 Remote Similarity NPD5772 Approved
0.6087 Remote Similarity NPD5773 Approved
0.6083 Remote Similarity NPD1381 Clinical (unspecified phase)
0.6081 Remote Similarity NPD3819 Phase 2
0.608 Remote Similarity NPD7792 Phase 1
0.608 Remote Similarity NPD6860 Clinical (unspecified phase)
0.6078 Remote Similarity NPD3686 Approved
0.6078 Remote Similarity NPD5267 Discontinued
0.6078 Remote Similarity NPD3687 Approved
0.6077 Remote Similarity NPD4064 Discontinued
0.6077 Remote Similarity NPD5219 Approved
0.6077 Remote Similarity NPD2098 Approved
0.6077 Remote Similarity NPD5218 Approved
0.6071 Remote Similarity NPD3964 Approved
0.6071 Remote Similarity NPD7667 Clinical (unspecified phase)
0.607 Remote Similarity NPD3281 Clinical (unspecified phase)
0.6068 Remote Similarity NPD4424 Discontinued
0.6068 Remote Similarity NPD2513 Approved
0.6063 Remote Similarity NPD6377 Clinical (unspecified phase)
0.6062 Remote Similarity NPD7565 Approved
0.6061 Remote Similarity NPD3656 Approved
0.6059 Remote Similarity NPD52 Approved
0.6059 Remote Similarity NPD7527 Clinical (unspecified phase)
0.6059 Remote Similarity NPD7613 Discontinued
0.6059 Remote Similarity NPD7526 Approved
0.6055 Remote Similarity NPD7280 Phase 3
0.6055 Remote Similarity NPD8064 Clinical (unspecified phase)
0.6055 Remote Similarity NPD7281 Phase 3
0.605 Remote Similarity NPD7066 Clinical (unspecified phase)
0.6049 Remote Similarity NPD6057 Approved
0.6049 Remote Similarity NPD6056 Approved
0.6048 Remote Similarity NPD8245 Clinical (unspecified phase)
0.6047 Remote Similarity NPD5312 Approved
0.6047 Remote Similarity NPD42 Phase 2
0.6047 Remote Similarity NPD5313 Approved
0.6047 Remote Similarity NPD6042 Phase 2
0.6045 Remote Similarity NPD3863 Clinical (unspecified phase)
0.6044 Remote Similarity NPD5652 Approved
0.6044 Remote Similarity NPD5650 Approved
0.6044 Remote Similarity NPD5651 Approved
0.6044 Remote Similarity NPD6034 Phase 2
0.6028 Remote Similarity NPD5605 Phase 2
0.6027 Remote Similarity NPD7669 Phase 3
0.6025 Remote Similarity NPD6796 Discontinued
0.6019 Remote Similarity NPD22 Approved
0.6019 Remote Similarity NPD7574 Phase 2
0.6019 Remote Similarity NPD3365 Discontinued
0.6019 Remote Similarity NPD2053 Approved
0.601 Remote Similarity NPD2874 Phase 2
0.601 Remote Similarity NPD3165 Approved
0.601 Remote Similarity NPD3167 Approved
0.601 Remote Similarity NPD1771 Clinical (unspecified phase)
0.601 Remote Similarity NPD6668 Clinical (unspecified phase)
0.601 Remote Similarity NPD3164 Approved
0.601 Remote Similarity NPD3166 Approved
0.6009 Remote Similarity NPD2166 Phase 3
0.6009 Remote Similarity NPD5137 Approved
0.6 Remote Similarity NPD4162 Approved
0.6 Remote Similarity NPD4521 Clinical (unspecified phase)
0.6 Remote Similarity NPD4124 Clinical (unspecified phase)
0.6 Remote Similarity NPD4487 Clinical (unspecified phase)
0.6 Remote Similarity NPD4791 Clinical (unspecified phase)
0.5992 Remote Similarity NPD8255 Phase 2
0.5991 Remote Similarity NPD2889 Approved
0.5991 Remote Similarity NPD8027 Approved
0.5991 Remote Similarity NPD2888 Approved
0.5991 Remote Similarity NPD2017 Approved
0.5991 Remote Similarity NPD2890 Approved
0.599 Remote Similarity NPD5295 Discontinued
0.599 Remote Similarity NPD3274 Phase 2
0.599 Remote Similarity NPD6072 Discontinued
0.599 Remote Similarity NPD454 Approved
0.5983 Remote Similarity NPD2498 Approved
0.5983 Remote Similarity NPD3106 Clinical (unspecified phase)
0.5982 Remote Similarity NPD5984 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