Structure

Physi-Chem Properties

Molecular Weight:  671.38
Volume:  693.917
LogP:  4.518
LogD:  2.513
LogS:  -4.457
# Rotatable Bonds:  6
TPSA:  148.62
# H-Bond Aceptor:  12
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  12

MedChem Properties

QED Drug-Likeness Score:  0.355
Synthetic Accessibility Score:  5.181
Fsp3:  0.667
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:  -5.081
MDCK Permeability:  6.296828360063955e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.073
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.033
30% Bioavailability (F30%):  0.761

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.016
Plasma Protein Binding (PPB):  94.79134368896484%
Volume Distribution (VD):  0.691
Pgp-substrate:  1.6390446424484253%

ADMET: Metabolism

CYP1A2-inhibitor:  0.003
CYP1A2-substrate:  0.067
CYP2C19-inhibitor:  0.334
CYP2C19-substrate:  0.745
CYP2C9-inhibitor:  0.372
CYP2C9-substrate:  0.349
CYP2D6-inhibitor:  0.035
CYP2D6-substrate:  0.153
CYP3A4-inhibitor:  0.924
CYP3A4-substrate:  0.883

ADMET: Excretion

Clearance (CL):  5.195
Half-life (T1/2):  0.157

ADMET: Toxicity

hERG Blockers:  0.008
Human Hepatotoxicity (H-HT):  0.979
Drug-inuced Liver Injury (DILI):  0.948
AMES Toxicity:  0.01
Rat Oral Acute Toxicity:  0.735
Maximum Recommended Daily Dose:  0.29
Skin Sensitization:  0.039
Carcinogencity:  0.034
Eye Corrosion:  0.003
Eye Irritation:  0.005
Respiratory Toxicity:  0.008

Download Data

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

  Natural Product: NPC145113

Natural Product ID:  NPC145113
Common Name*:   Palmyramide A
IUPAC Name:   (3S,6S,10R,13S,16R,19S)-3-benzyl-6,9,9,17-tetramethyl-13,16-di(propan-2-yl)-10-propyl-4,7,11-trioxa-1,14,17-triazabicyclo[17.3.0]docosane-2,5,8,12,15,18-hexone
Synonyms:  
Standard InCHIKey:  QXWOTWUQMDHDCF-UEPNLWJJSA-N
Standard InCHI:  InChI=1S/C36H53N3O9/c1-10-15-27-36(7,8)35(45)46-23(6)33(43)47-26(20-24-16-12-11-13-17-24)32(42)39-19-14-18-25(39)31(41)38(9)29(22(4)5)30(40)37-28(21(2)3)34(44)48-27/h11-13,16-17,21-23,25-29H,10,14-15,18-20H2,1-9H3,(H,37,40)/t23-,25-,26-,27+,28-,29+/m0/s1
SMILES:  CCC[C@H]1OC(=O)[C@@H](N=C(O)[C@@H](C(C)C)N(C)C(=O)[C@H]2N(C(=O)[C@@H](OC(=O)[C@@H](OC(=O)C1(C)C)C)Cc1ccccc1)CCC2)C(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1076535
PubChem CID:   45380200
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
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10514329]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10654420]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10691708]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. palauan n.a. PMID[10691729]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10843570]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10924172]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10978206]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11076571]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11076573]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11076574]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11277744]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11389621]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11430000]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11473443]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11922791]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[12762816]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Papua New Guinea n.a. PMID[12828459]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[14575437]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[1517734]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Papua New Guinea n.a. PMID[16643028]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[17125217]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[17441769]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[18444683]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Singapore n.a. PMID[19093843]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[19489598]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. eastern Caribbean n.a. PMID[19739598]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[19839606]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[20030365]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. panamanian n.a. PMID[20158242]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Floridian n.a. PMID[20166701]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[20936843]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[21138309]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[2128518]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[21341718]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[21539315]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[21806011]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[21999614]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[22035372]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[29792428]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[3924698]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Caribbean n.a. PMID[7623050]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Caribbean n.a. PMID[8699186]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[9584405]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[9599278]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[9599279]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[9784156]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae 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
NPT397 Cell Line NCI-H460 Homo sapiens IC50 = 39700.0 nM PMID[457024]
NPT2 Others Unspecified IC50 = 17200.0 nM PMID[457024]

☑ 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 NPC145113 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
0.9161 High Similarity NPC162104
0.9149 High Similarity NPC329761
0.9149 High Similarity NPC225648
0.9143 High Similarity NPC5620
0.8929 High Similarity NPC263493
0.8929 High Similarity NPC269398
0.8889 High Similarity NPC129666
0.8865 High Similarity NPC161069
0.8857 High Similarity NPC268841
0.8857 High Similarity NPC46098
0.8857 High Similarity NPC307357
0.8714 High Similarity NPC68865
0.869 High Similarity NPC471821
0.869 High Similarity NPC471820
0.8652 High Similarity NPC178662
0.8652 High Similarity NPC98424
0.8652 High Similarity NPC470884
0.8652 High Similarity NPC92784
0.8652 High Similarity NPC476133
0.8621 High Similarity NPC138775
0.8611 High Similarity NPC209509
0.86 High Similarity NPC297145
0.86 High Similarity NPC197743
0.8582 High Similarity NPC127741
0.8582 High Similarity NPC471265
0.8582 High Similarity NPC471264
0.8472 Intermediate Similarity NPC176226
0.8472 Intermediate Similarity NPC139326
0.8435 Intermediate Similarity NPC240848
0.8414 Intermediate Similarity NPC476978
0.8378 Intermediate Similarity NPC2501
0.8345 Intermediate Similarity NPC197682
0.831 Intermediate Similarity NPC248283
0.8299 Intermediate Similarity NPC262077
0.8288 Intermediate Similarity NPC52748
0.8276 Intermediate Similarity NPC168113
0.8243 Intermediate Similarity NPC135121
0.8231 Intermediate Similarity NPC477217
0.8231 Intermediate Similarity NPC316008
0.8231 Intermediate Similarity NPC313867
0.8231 Intermediate Similarity NPC201244
0.8212 Intermediate Similarity NPC122590
0.8207 Intermediate Similarity NPC476259
0.8207 Intermediate Similarity NPC239762
0.8207 Intermediate Similarity NPC163392
0.8176 Intermediate Similarity NPC314358
0.8163 Intermediate Similarity NPC315283
0.8163 Intermediate Similarity NPC314388
0.8067 Intermediate Similarity NPC105717
0.8042 Intermediate Similarity NPC246079
0.8037 Intermediate Similarity NPC475421
0.8027 Intermediate Similarity NPC469427
0.8027 Intermediate Similarity NPC469426
0.8014 Intermediate Similarity NPC319766
0.8 Intermediate Similarity NPC196091
0.7972 Intermediate Similarity NPC130309
0.7963 Intermediate Similarity NPC318930
0.7963 Intermediate Similarity NPC317362
0.7892 Intermediate Similarity NPC167763
0.7892 Intermediate Similarity NPC470903
0.7892 Intermediate Similarity NPC470112
0.7887 Intermediate Similarity NPC239990
0.7887 Intermediate Similarity NPC71933
0.7887 Intermediate Similarity NPC89923
0.7887 Intermediate Similarity NPC105114
0.7887 Intermediate Similarity NPC152850
0.7862 Intermediate Similarity NPC287401
0.7857 Intermediate Similarity NPC6975
0.7857 Intermediate Similarity NPC286551
0.7857 Intermediate Similarity NPC46427
0.7853 Intermediate Similarity NPC26108
0.7853 Intermediate Similarity NPC317725
0.7853 Intermediate Similarity NPC326407
0.7832 Intermediate Similarity NPC473322
0.7817 Intermediate Similarity NPC136453
0.781 Intermediate Similarity NPC169328
0.7798 Intermediate Similarity NPC299806
0.7786 Intermediate Similarity NPC252878
0.777 Intermediate Similarity NPC200964
0.7754 Intermediate Similarity NPC310467
0.775 Intermediate Similarity NPC472923
0.7748 Intermediate Similarity NPC315266
0.7727 Intermediate Similarity NPC475168
0.7727 Intermediate Similarity NPC7817
0.7724 Intermediate Similarity NPC157311
0.7714 Intermediate Similarity NPC202521
0.7688 Intermediate Similarity NPC471052
0.7688 Intermediate Similarity NPC471053
0.7688 Intermediate Similarity NPC471051
0.7683 Intermediate Similarity NPC137627
0.7671 Intermediate Similarity NPC8761
0.7671 Intermediate Similarity NPC44805
0.7643 Intermediate Similarity NPC476990
0.764 Intermediate Similarity NPC63931
0.7628 Intermediate Similarity NPC473341
0.7626 Intermediate Similarity NPC237420
0.7603 Intermediate Similarity NPC255447
0.758 Intermediate Similarity NPC470902
0.7562 Intermediate Similarity NPC471527
0.7561 Intermediate Similarity NPC475123
0.7561 Intermediate Similarity NPC473693
0.7561 Intermediate Similarity NPC475204
0.7561 Intermediate Similarity NPC471568
0.7518 Intermediate Similarity NPC478015
0.7518 Intermediate Similarity NPC478016
0.7518 Intermediate Similarity NPC45777
0.7518 Intermediate Similarity NPC478014
0.7518 Intermediate Similarity NPC477061
0.75 Intermediate Similarity NPC62104
0.75 Intermediate Similarity NPC470546
0.75 Intermediate Similarity NPC101719
0.75 Intermediate Similarity NPC1390
0.7468 Intermediate Similarity NPC81026
0.7439 Intermediate Similarity NPC473502
0.7436 Intermediate Similarity NPC283783
0.7431 Intermediate Similarity NPC222466
0.7429 Intermediate Similarity NPC470545
0.7425 Intermediate Similarity NPC477462
0.7417 Intermediate Similarity NPC132636
0.7415 Intermediate Similarity NPC69496
0.7413 Intermediate Similarity NPC169485
0.7413 Intermediate Similarity NPC84281
0.7413 Intermediate Similarity NPC317474
0.7413 Intermediate Similarity NPC213126
0.7413 Intermediate Similarity NPC291027
0.7405 Intermediate Similarity NPC262166
0.7403 Intermediate Similarity NPC322878
0.7403 Intermediate Similarity NPC266741
0.7394 Intermediate Similarity NPC80150
0.7394 Intermediate Similarity NPC186617
0.7394 Intermediate Similarity NPC190663
0.7383 Intermediate Similarity NPC245836
0.7383 Intermediate Similarity NPC233910
0.7379 Intermediate Similarity NPC47667
0.7365 Intermediate Similarity NPC306804
0.7361 Intermediate Similarity NPC175726
0.7361 Intermediate Similarity NPC474082
0.7357 Intermediate Similarity NPC470544
0.7357 Intermediate Similarity NPC239357
0.7351 Intermediate Similarity NPC43755
0.7342 Intermediate Similarity NPC233702
0.7333 Intermediate Similarity NPC107938
0.7333 Intermediate Similarity NPC294516
0.7321 Intermediate Similarity NPC473354
0.7321 Intermediate Similarity NPC159767
0.7321 Intermediate Similarity NPC471165
0.7321 Intermediate Similarity NPC279871
0.7321 Intermediate Similarity NPC155506
0.7317 Intermediate Similarity NPC210377
0.7317 Intermediate Similarity NPC22883
0.7317 Intermediate Similarity NPC5719
0.7317 Intermediate Similarity NPC217804
0.7305 Intermediate Similarity NPC89831
0.7297 Intermediate Similarity NPC300315
0.7297 Intermediate Similarity NPC200589
0.7292 Intermediate Similarity NPC160493
0.7273 Intermediate Similarity NPC15068
0.7266 Intermediate Similarity NPC35850
0.7266 Intermediate Similarity NPC276949
0.7262 Intermediate Similarity NPC273755
0.726 Intermediate Similarity NPC474847
0.725 Intermediate Similarity NPC39431
0.7246 Intermediate Similarity NPC40234
0.7246 Intermediate Similarity NPC46009
0.7239 Intermediate Similarity NPC469901
0.7234 Intermediate Similarity NPC315276
0.7234 Intermediate Similarity NPC285926
0.7234 Intermediate Similarity NPC14672
0.723 Intermediate Similarity NPC469666
0.7229 Intermediate Similarity NPC63040
0.7225 Intermediate Similarity NPC471050
0.7225 Intermediate Similarity NPC471048
0.7225 Intermediate Similarity NPC471049
0.7222 Intermediate Similarity NPC71684
0.7219 Intermediate Similarity NPC476227
0.7214 Intermediate Similarity NPC33742
0.7211 Intermediate Similarity NPC65310
0.7202 Intermediate Similarity NPC230611
0.72 Intermediate Similarity NPC4910
0.7197 Intermediate Similarity NPC16188
0.7195 Intermediate Similarity NPC73655
0.7193 Intermediate Similarity NPC269750
0.7193 Intermediate Similarity NPC194671
0.7192 Intermediate Similarity NPC476241
0.7192 Intermediate Similarity NPC476260
0.7184 Intermediate Similarity NPC315542
0.7176 Intermediate Similarity NPC50016
0.717 Intermediate Similarity NPC473491
0.716 Intermediate Similarity NPC248670
0.7153 Intermediate Similarity NPC476183
0.7143 Intermediate Similarity NPC476125
0.7143 Intermediate Similarity NPC476179
0.7126 Intermediate Similarity NPC209463
0.7126 Intermediate Similarity NPC294951
0.7125 Intermediate Similarity NPC300443
0.7118 Intermediate Similarity NPC473402
0.7117 Intermediate Similarity NPC324850
0.7114 Intermediate Similarity NPC111428
0.711 Intermediate Similarity NPC476321
0.7103 Intermediate Similarity NPC476184

  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 NPC145113 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
0.8322 Intermediate Similarity NPD8172 Phase 2
0.8322 Intermediate Similarity NPD8173 Phase 2
0.8252 Intermediate Similarity NPD7113 Clinical (unspecified phase)
0.7986 Intermediate Similarity NPD2584 Suspended
0.7931 Intermediate Similarity NPD8416 Discontinued
0.7832 Intermediate Similarity NPD4177 Approved
0.7832 Intermediate Similarity NPD4175 Approved
0.7703 Intermediate Similarity NPD6073 Approved
0.7703 Intermediate Similarity NPD5725 Approved
0.7692 Intermediate Similarity NPD2585 Clinical (unspecified phase)
0.7651 Intermediate Similarity NPD6852 Discontinued
0.7635 Intermediate Similarity NPD8643 Discontinued
0.7619 Intermediate Similarity NPD5747 Discontinued
0.7595 Intermediate Similarity NPD8417 Discontinued
0.7566 Intermediate Similarity NPD2436 Approved
0.7566 Intermediate Similarity NPD2437 Approved
0.75 Intermediate Similarity NPD7634 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD4152 Approved
0.7483 Intermediate Similarity NPD3071 Approved
0.7483 Intermediate Similarity NPD3072 Approved
0.7483 Intermediate Similarity NPD3073 Approved
0.7453 Intermediate Similarity NPD4557 Approved
0.745 Intermediate Similarity NPD4153 Approved
0.7419 Intermediate Similarity NPD8323 Discontinued
0.7415 Intermediate Similarity NPD4125 Approved
0.7415 Intermediate Similarity NPD2613 Approved
0.7413 Intermediate Similarity NPD4216 Approved
0.7413 Intermediate Similarity NPD2610 Approved
0.7413 Intermediate Similarity NPD3132 Approved
0.7413 Intermediate Similarity NPD3131 Approved
0.7413 Intermediate Similarity NPD2612 Approved
0.7413 Intermediate Similarity NPD4218 Approved
0.7413 Intermediate Similarity NPD2609 Approved
0.7413 Intermediate Similarity NPD4762 Approved
0.7413 Intermediate Similarity NPD4215 Approved
0.7413 Intermediate Similarity NPD4706 Clinical (unspecified phase)
0.7413 Intermediate Similarity NPD2608 Approved
0.7413 Intermediate Similarity NPD2611 Approved
0.7413 Intermediate Similarity NPD4217 Approved
0.7413 Intermediate Similarity NPD4761 Approved
0.7403 Intermediate Similarity NPD6860 Clinical (unspecified phase)
0.7397 Intermediate Similarity NPD3608 Clinical (unspecified phase)
0.7383 Intermediate Similarity NPD3087 Approved
0.7383 Intermediate Similarity NPD2573 Approved
0.7383 Intermediate Similarity NPD2572 Clinical (unspecified phase)
0.7383 Intermediate Similarity NPD4745 Approved
0.7383 Intermediate Similarity NPD3088 Approved
0.7383 Intermediate Similarity NPD3614 Approved
0.7383 Intermediate Similarity NPD3090 Approved
0.7383 Intermediate Similarity NPD3616 Approved
0.7383 Intermediate Similarity NPD3089 Approved
0.7383 Intermediate Similarity NPD3615 Approved
0.7383 Intermediate Similarity NPD2574 Discontinued
0.7383 Intermediate Similarity NPD2566 Approved
0.7383 Intermediate Similarity NPD4746 Phase 3
0.7383 Intermediate Similarity NPD2570 Approved
0.7383 Intermediate Similarity NPD2571 Approved
0.7365 Intermediate Similarity NPD4738 Phase 2
0.7297 Intermediate Similarity NPD5263 Approved
0.7297 Intermediate Similarity NPD4676 Approved
0.7285 Intermediate Similarity NPD4685 Phase 3
0.7285 Intermediate Similarity NPD4684 Phase 3
0.7285 Intermediate Similarity NPD4686 Approved
0.7279 Intermediate Similarity NPD5339 Clinical (unspecified phase)
0.7255 Intermediate Similarity NPD3480 Approved
0.7248 Intermediate Similarity NPD2050 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD2047 Approved
0.7248 Intermediate Similarity NPD2051 Approved
0.7248 Intermediate Similarity NPD2049 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD2046 Approved
0.7248 Intermediate Similarity NPD2045 Approved
0.7248 Intermediate Similarity NPD4794 Discontinued
0.7248 Intermediate Similarity NPD21 Approved
0.7248 Intermediate Similarity NPD2048 Approved
0.7248 Intermediate Similarity NPD2043 Approved
0.7248 Intermediate Similarity NPD2044 Approved
0.7248 Intermediate Similarity NPD6919 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD2575 Approved
0.7233 Intermediate Similarity NPD7613 Discontinued
0.723 Intermediate Similarity NPD3663 Approved
0.723 Intermediate Similarity NPD3662 Phase 3
0.723 Intermediate Similarity NPD3664 Approved
0.723 Intermediate Similarity NPD3661 Approved
0.7222 Intermediate Similarity NPD7749 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD7118 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD8265 Approved
0.7219 Intermediate Similarity NPD6623 Phase 3
0.7211 Intermediate Similarity NPD2625 Approved
0.7211 Intermediate Similarity NPD2627 Approved
0.7211 Intermediate Similarity NPD2160 Approved
0.7211 Intermediate Similarity NPD2628 Approved
0.7211 Intermediate Similarity NPD2626 Approved
0.7211 Intermediate Similarity NPD2159 Approved
0.72 Intermediate Similarity NPD4619 Approved
0.72 Intermediate Similarity NPD1329 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD1330 Phase 2
0.72 Intermediate Similarity NPD4621 Approved
0.7179 Intermediate Similarity NPD5264 Approved
0.7179 Intermediate Similarity NPD5265 Approved
0.7143 Intermediate Similarity NPD4647 Approved
0.7143 Intermediate Similarity NPD4646 Approved
0.7143 Intermediate Similarity NPD4648 Approved
0.7143 Intermediate Similarity NPD8315 Phase 1
0.7143 Intermediate Similarity NPD2652 Approved
0.7143 Intermediate Similarity NPD2650 Approved
0.7134 Intermediate Similarity NPD6676 Phase 2
0.7125 Intermediate Similarity NPD5229 Approved
0.7125 Intermediate Similarity NPD5230 Approved
0.7124 Intermediate Similarity NPD4782 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD6119 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD6681 Discovery
0.7114 Intermediate Similarity NPD3626 Phase 3
0.7114 Intermediate Similarity NPD3040 Approved
0.7114 Intermediate Similarity NPD5204 Approved
0.7113 Intermediate Similarity NPD5291 Approved
0.7113 Intermediate Similarity NPD5292 Approved
0.7105 Intermediate Similarity NPD5296 Approved
0.7105 Intermediate Similarity NPD5323 Approved
0.7097 Intermediate Similarity NPD7512 Approved
0.7097 Intermediate Similarity NPD7511 Approved
0.7091 Intermediate Similarity NPD7080 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD5299 Approved
0.7075 Intermediate Similarity NPD4677 Discontinued
0.7067 Intermediate Similarity NPD7979 Clinical (unspecified phase)
0.7066 Intermediate Similarity NPD8303 Discontinued
0.7051 Intermediate Similarity NPD2022 Approved
0.7051 Intermediate Similarity NPD2088 Approved
0.7051 Intermediate Similarity NPD2087 Approved
0.7051 Intermediate Similarity NPD8076 Discontinued
0.703 Intermediate Similarity NPD7599 Phase 2
0.7027 Intermediate Similarity NPD3125 Approved
0.7025 Intermediate Similarity NPD5298 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6088 Approved
0.7 Intermediate Similarity NPD5759 Approved
0.6988 Remote Similarity NPD7600 Phase 2
0.6978 Remote Similarity NPD4234 Approved
0.6978 Remote Similarity NPD4233 Approved
0.6968 Remote Similarity NPD6294 Approved
0.6968 Remote Similarity NPD6295 Approved
0.6954 Remote Similarity NPD5202 Clinical (unspecified phase)
0.6939 Remote Similarity NPD4806 Approved
0.6939 Remote Similarity NPD4807 Approved
0.6933 Remote Similarity NPD3588 Discontinued
0.6933 Remote Similarity NPD3604 Clinical (unspecified phase)
0.6928 Remote Similarity NPD3561 Clinical (unspecified phase)
0.6923 Remote Similarity NPD4508 Discontinued
0.6903 Remote Similarity NPD7510 Approved
0.6897 Remote Similarity NPD2218 Phase 2
0.6897 Remote Similarity NPD2217 Approved
0.6894 Remote Similarity NPD6631 Clinical (unspecified phase)
0.6883 Remote Similarity NPD4791 Clinical (unspecified phase)
0.686 Remote Similarity NPD8126 Clinical (unspecified phase)
0.686 Remote Similarity NPD8124 Phase 3
0.6859 Remote Similarity NPD4126 Approved
0.6859 Remote Similarity NPD6901 Phase 3
0.6849 Remote Similarity NPD4504 Clinical (unspecified phase)
0.6848 Remote Similarity NPD7267 Clinical (unspecified phase)
0.6845 Remote Similarity NPD8351 Phase 2
0.6842 Remote Similarity NPD4617 Approved
0.6842 Remote Similarity NPD4620 Approved
0.6842 Remote Similarity NPD5201 Approved
0.6842 Remote Similarity NPD5203 Approved
0.6816 Remote Similarity NPD8103 Clinical (unspecified phase)
0.6815 Remote Similarity NPD3648 Clinical (unspecified phase)
0.6815 Remote Similarity NPD7728 Clinical (unspecified phase)
0.6807 Remote Similarity NPD7105 Phase 1
0.6806 Remote Similarity NPD1348 Approved
0.679 Remote Similarity NPD3987 Approved
0.679 Remote Similarity NPD5613 Approved
0.679 Remote Similarity NPD5614 Approved
0.679 Remote Similarity NPD3988 Approved
0.679 Remote Similarity NPD7892 Clinical (unspecified phase)
0.6781 Remote Similarity NPD6345 Approved
0.6781 Remote Similarity NPD6343 Approved
0.6774 Remote Similarity NPD6311 Approved
0.6774 Remote Similarity NPD5120 Approved
0.6774 Remote Similarity NPD6310 Approved
0.6774 Remote Similarity NPD5121 Approved
0.6774 Remote Similarity NPD5119 Approved
0.6774 Remote Similarity NPD6309 Approved
0.6772 Remote Similarity NPD4173 Approved
0.6772 Remote Similarity NPD6897 Clinical (unspecified phase)
0.6772 Remote Similarity NPD4172 Approved
0.6768 Remote Similarity NPD7131 Phase 3
0.6763 Remote Similarity NPD7965 Phase 2
0.6763 Remote Similarity NPD7964 Clinical (unspecified phase)
0.6759 Remote Similarity NPD4574 Approved
0.6759 Remote Similarity NPD4576 Approved
0.6757 Remote Similarity NPD4136 Approved
0.6757 Remote Similarity NPD4135 Approved
0.6757 Remote Similarity NPD4106 Approved
0.6753 Remote Similarity NPD2078 Clinical (unspecified phase)
0.6753 Remote Similarity NPD3632 Clinical (unspecified phase)
0.6748 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6712 Remote Similarity NPD5990 Approved
0.6712 Remote Similarity NPD5991 Approved
0.6711 Remote Similarity NPD4151 Approved
0.6711 Remote Similarity NPD5338 Clinical (unspecified phase)
0.6708 Remote Similarity NPD1968 Approved
0.6708 Remote Similarity NPD1967 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