Structure

Physi-Chem Properties

Molecular Weight:  1097.52
Volume:  1055.423
LogP:  -3.235
LogD:  0.811
LogS:  -0.042
# Rotatable Bonds:  24
TPSA:  544.33
# H-Bond Aceptor:  30
# H-Bond Donor:  22
# Rings:  2
# Heavy Atoms:  30

MedChem Properties

QED Drug-Likeness Score:  0.036
Synthetic Accessibility Score:  7.358
Fsp3:  0.638
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  2
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -3.409
MDCK Permeability:  0.000908884045202285
Pgp-inhibitor:  0.002
Pgp-substrate:  1.0
Human Intestinal Absorption (HIA):  1.0
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.675
Plasma Protein Binding (PPB):  29.121776580810547%
Volume Distribution (VD):  0.186
Pgp-substrate:  41.08509826660156%

ADMET: Metabolism

CYP1A2-inhibitor:  0.0
CYP1A2-substrate:  0.0
CYP2C19-inhibitor:  0.001
CYP2C19-substrate:  0.019
CYP2C9-inhibitor:  0.0
CYP2C9-substrate:  0.021
CYP2D6-inhibitor:  0.0
CYP2D6-substrate:  0.019
CYP3A4-inhibitor:  0.013
CYP3A4-substrate:  0.0

ADMET: Excretion

Clearance (CL):  0.898
Half-life (T1/2):  0.815

ADMET: Toxicity

hERG Blockers:  0.0
Human Hepatotoxicity (H-HT):  1.0
Drug-inuced Liver Injury (DILI):  0.966
AMES Toxicity:  0.005
Rat Oral Acute Toxicity:  0.0
Maximum Recommended Daily Dose:  0.0
Skin Sensitization:  0.889
Carcinogencity:  0.036
Eye Corrosion:  0.003
Eye Irritation:  0.033
Respiratory Toxicity:  0.883

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

  Natural Product: NPC64205

Natural Product ID:  NPC64205
Common Name*:   Rel-Burkholdine-1097
IUPAC Name:   (2S)-2-[(3S,6S,9S,15R,18R,21R,25R)-9,15-bis(2-amino-2-oxoethyl)-18-[(R)-hydroxy-(4-hydroxyphenyl)methyl]-6,21-bis(hydroxymethyl)-2,5,8,11,14,17,20,23-octaoxo-25-[(2R,3S,4S)-2,3,4-trihydroxypentadecyl]-1,4,7,10,13,16,19,22-octazacyclopentacos-3-yl]-2-hydroxyacetamide
Synonyms:   Rel-Burkholdine-1097
Standard InCHIKey:  HNWUONUNQVXJAB-AIKTYEFNSA-N
Standard InCHI:  InChI=1S/C47H75N11O19/c1-2-3-4-5-6-7-8-9-10-11-30(62)39(69)31(63)16-24-17-34(66)54-28(21-59)44(74)57-36(38(68)23-12-14-25(61)15-13-23)47(77)55-26(18-32(48)64)42(72)51-20-35(67)53-27(19-33(49)65)43(73)56-29(22-60)45(75)58-37(46(76)52-24)40(70)41(50)71/h12-15,24,26-31,36-40,59-63,68-70H,2-11,16-22H2,1H3,(H2,48,64)(H2,49,65)(H2,50,71)(H,51,72)(H,52,76)(H,53,67)(H,54,66)(H,55,77)(H,56,73)(H,57,74)(H,58,75)/t24-,26-,27+,28-,29+,30+,31-,36-,37+,38-,39+,40+/m1/s1
SMILES:  CCCCCCCCCCC[C@@H]([C@@H]([C@@H](C[C@@H]1CC(=N[C@H](CO)C(=N[C@@H](C(=N[C@H](CC(=N)O)C(=NCC(=N[C@H](C(=N[C@H](C(=N[C@H](C(=N1)O)[C@@H](C(=N)O)O)O)CO)O)CC(=N)O)O)O)O)[C@@H](c1ccc(cc1)O)O)O)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2146947
PubChem CID:   71461797
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0001813] Peptidomimetics
        • [CHEMONTID:0002010] Hybrid peptides

*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
NPO6674 Burkholderia ambifaria Species Burkholderiaceae Bacteria n.a. n.a. n.a. PMID[22988812]
NPO8059 Piper aduncum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[8158163]
NPO8059 Piper aduncum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8059 Piper aduncum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8059 Piper aduncum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO6674 Burkholderia ambifaria Species Burkholderiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO8059 Piper aduncum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6837 Fusarium bostrycoides Species Nectriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8458 Myrrha octodecimguttata Species Coccinellidae 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
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae MIC = 1.6 ug.mL-1 PMID[552959]
NPT20 Organism Candida albicans Candida albicans MIC = 12.5 ug.mL-1 PMID[552959]
NPT21 Organism Aspergillus niger Aspergillus niger MIC = 1.6 ug.mL-1 PMID[552959]
NPT27 Others Unspecified HC10 = 4.5 ug ml-1 PMID[552959]
NPT2 Others Unspecified Ratio = 0.4 n.a. PMID[552959]

☑ 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 NPC64205 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
0.9137 High Similarity NPC476744
0.9065 High Similarity NPC476743
0.8944 High Similarity NPC476741
0.8873 High Similarity NPC476742
0.8429 Intermediate Similarity NPC469360
0.8357 Intermediate Similarity NPC197921
0.8308 Intermediate Similarity NPC283760
0.8298 Intermediate Similarity NPC91953
0.8281 Intermediate Similarity NPC317254
0.8042 Intermediate Similarity NPC168861
0.8014 Intermediate Similarity NPC6570
0.7953 Intermediate Similarity NPC258056
0.7902 Intermediate Similarity NPC214988
0.7898 Intermediate Similarity NPC328494
0.7815 Intermediate Similarity NPC244509
0.7799 Intermediate Similarity NPC471165
0.7786 Intermediate Similarity NPC118202
0.7752 Intermediate Similarity NPC474149
0.7744 Intermediate Similarity NPC38458
0.7744 Intermediate Similarity NPC311737
0.774 Intermediate Similarity NPC326241
0.7721 Intermediate Similarity NPC474862
0.7717 Intermediate Similarity NPC231705
0.7674 Intermediate Similarity NPC290566
0.7674 Intermediate Similarity NPC145638
0.7669 Intermediate Similarity NPC82963
0.7662 Intermediate Similarity NPC244336
0.7656 Intermediate Similarity NPC142297
0.764 Intermediate Similarity NPC50016
0.7622 Intermediate Similarity NPC267237
0.7606 Intermediate Similarity NPC326966
0.7594 Intermediate Similarity NPC10286
0.7594 Intermediate Similarity NPC213
0.7582 Intermediate Similarity NPC476268
0.7574 Intermediate Similarity NPC169207
0.7574 Intermediate Similarity NPC115627
0.7574 Intermediate Similarity NPC118522
0.7552 Intermediate Similarity NPC208757
0.7534 Intermediate Similarity NPC322526
0.7534 Intermediate Similarity NPC471201
0.7516 Intermediate Similarity NPC273755
0.7516 Intermediate Similarity NPC248670
0.7484 Intermediate Similarity NPC323336
0.7484 Intermediate Similarity NPC326349
0.748 Intermediate Similarity NPC178902
0.7466 Intermediate Similarity NPC473052
0.7466 Intermediate Similarity NPC473055
0.7452 Intermediate Similarity NPC156348
0.7451 Intermediate Similarity NPC56685
0.7447 Intermediate Similarity NPC323775
0.7447 Intermediate Similarity NPC236347
0.7439 Intermediate Similarity NPC45037
0.7434 Intermediate Similarity NPC473491
0.7429 Intermediate Similarity NPC62101
0.7429 Intermediate Similarity NPC95733
0.7422 Intermediate Similarity NPC113326
0.7422 Intermediate Similarity NPC224610
0.7422 Intermediate Similarity NPC88267
0.7422 Intermediate Similarity NPC194390
0.7394 Intermediate Similarity NPC477839
0.7391 Intermediate Similarity NPC475123
0.7391 Intermediate Similarity NPC46009
0.7391 Intermediate Similarity NPC475204
0.7388 Intermediate Similarity NPC142599
0.7376 Intermediate Similarity NPC29477
0.7372 Intermediate Similarity NPC268572
0.7361 Intermediate Similarity NPC473724
0.7357 Intermediate Similarity NPC307020
0.7343 Intermediate Similarity NPC325651
0.7338 Intermediate Similarity NPC262166
0.7338 Intermediate Similarity NPC27581
0.7328 Intermediate Similarity NPC24101
0.7328 Intermediate Similarity NPC96224
0.7313 Intermediate Similarity NPC1986
0.7313 Intermediate Similarity NPC474544
0.7312 Intermediate Similarity NPC61004
0.731 Intermediate Similarity NPC244866
0.7301 Intermediate Similarity NPC306804
0.7297 Intermediate Similarity NPC204848
0.7297 Intermediate Similarity NPC14600
0.7297 Intermediate Similarity NPC312770
0.7297 Intermediate Similarity NPC41473
0.7297 Intermediate Similarity NPC160607
0.7285 Intermediate Similarity NPC63628
0.7285 Intermediate Similarity NPC178466
0.7278 Intermediate Similarity NPC476194
0.7273 Intermediate Similarity NPC295478
0.7273 Intermediate Similarity NPC296712
0.7266 Intermediate Similarity NPC284078
0.7261 Intermediate Similarity NPC56635
0.7256 Intermediate Similarity NPC26108
0.7255 Intermediate Similarity NPC245974
0.7254 Intermediate Similarity NPC278097
0.725 Intermediate Similarity NPC63931
0.7248 Intermediate Similarity NPC476989
0.7246 Intermediate Similarity NPC319950
0.7241 Intermediate Similarity NPC45191
0.7239 Intermediate Similarity NPC89831
0.7234 Intermediate Similarity NPC211218
0.7226 Intermediate Similarity NPC137096
0.7222 Intermediate Similarity NPC271808
0.7205 Intermediate Similarity NPC15506
0.7203 Intermediate Similarity NPC322366
0.72 Intermediate Similarity NPC83289
0.72 Intermediate Similarity NPC212850
0.72 Intermediate Similarity NPC189724
0.7197 Intermediate Similarity NPC153690
0.7192 Intermediate Similarity NPC97870
0.7192 Intermediate Similarity NPC328070
0.7192 Intermediate Similarity NPC307123
0.7192 Intermediate Similarity NPC247018
0.7178 Intermediate Similarity NPC40234
0.7174 Intermediate Similarity NPC122009
0.7165 Intermediate Similarity NPC107619
0.716 Intermediate Similarity NPC294516
0.716 Intermediate Similarity NPC209463
0.716 Intermediate Similarity NPC328649
0.716 Intermediate Similarity NPC107938
0.7159 Intermediate Similarity NPC477552
0.7159 Intermediate Similarity NPC477550
0.7152 Intermediate Similarity NPC158277
0.7152 Intermediate Similarity NPC207675
0.7152 Intermediate Similarity NPC476227
0.7152 Intermediate Similarity NPC473354
0.7152 Intermediate Similarity NPC212699
0.7143 Intermediate Similarity NPC285078
0.7143 Intermediate Similarity NPC6854
0.7143 Intermediate Similarity NPC477637
0.7143 Intermediate Similarity NPC313737
0.7143 Intermediate Similarity NPC132771
0.7134 Intermediate Similarity NPC230611
0.7133 Intermediate Similarity NPC299583
0.7126 Intermediate Similarity NPC269750
0.7126 Intermediate Similarity NPC194671
0.7125 Intermediate Similarity NPC241794
0.7124 Intermediate Similarity NPC247298
0.7123 Intermediate Similarity NPC275538
0.7123 Intermediate Similarity NPC326599
0.7123 Intermediate Similarity NPC329595
0.7115 Intermediate Similarity NPC114659
0.7115 Intermediate Similarity NPC139699
0.7105 Intermediate Similarity NPC266741
0.7103 Intermediate Similarity NPC478147
0.7101 Intermediate Similarity NPC283468
0.7097 Intermediate Similarity NPC277857
0.7097 Intermediate Similarity NPC115144
0.7093 Intermediate Similarity NPC102959
0.708 Intermediate Similarity NPC37302
0.7079 Intermediate Similarity NPC477551
0.7078 Intermediate Similarity NPC5462
0.7075 Intermediate Similarity NPC93882
0.7075 Intermediate Similarity NPC471953
0.7075 Intermediate Similarity NPC274732
0.7075 Intermediate Similarity NPC130595
0.7067 Intermediate Similarity NPC48202
0.7063 Intermediate Similarity NPC160931
0.7063 Intermediate Similarity NPC37205
0.7059 Intermediate Similarity NPC81026
0.7055 Intermediate Similarity NPC302597
0.7052 Intermediate Similarity NPC60516
0.7048 Intermediate Similarity NPC473402
0.7047 Intermediate Similarity NPC6913
0.7041 Intermediate Similarity NPC473404
0.7041 Intermediate Similarity NPC476321
0.7034 Intermediate Similarity NPC153990
0.7024 Intermediate Similarity NPC119652
0.7024 Intermediate Similarity NPC97526
0.7013 Intermediate Similarity NPC16188
0.7012 Intermediate Similarity NPC280022
0.7008 Intermediate Similarity NPC313650
0.7007 Intermediate Similarity NPC114102
0.7006 Intermediate Similarity NPC202198
0.7006 Intermediate Similarity NPC261934
0.7006 Intermediate Similarity NPC5194
0.7006 Intermediate Similarity NPC477115
0.7 Intermediate Similarity NPC43275
0.7 Intermediate Similarity NPC471526
0.6994 Remote Similarity NPC179250
0.6994 Remote Similarity NPC50380
0.6988 Remote Similarity NPC137627
0.6985 Remote Similarity NPC146422
0.6981 Remote Similarity NPC275027
0.698 Remote Similarity NPC218530
0.6977 Remote Similarity NPC125732
0.6974 Remote Similarity NPC477838
0.6974 Remote Similarity NPC477837
0.6972 Remote Similarity NPC142577
0.697 Remote Similarity NPC471568
0.697 Remote Similarity NPC473693
0.697 Remote Similarity NPC211551
0.6968 Remote Similarity NPC313414
0.6966 Remote Similarity NPC323662
0.6966 Remote Similarity NPC476353
0.6962 Remote Similarity NPC184161
0.6959 Remote Similarity NPC214869
0.6959 Remote Similarity NPC294951
0.6957 Remote Similarity NPC471203
0.6953 Remote Similarity NPC473501
0.6953 Remote Similarity NPC475439
0.695 Remote Similarity NPC17388

  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 NPC64205 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
0.8561 High Similarity NPD7978 Discontinued
0.7914 Intermediate Similarity NPD3136 Phase 2
0.7868 Intermediate Similarity NPD9622 Approved
0.7826 Intermediate Similarity NPD7451 Discontinued
0.7801 Intermediate Similarity NPD5729 Clinical (unspecified phase)
0.7744 Intermediate Similarity NPD317 Approved
0.7744 Intermediate Similarity NPD318 Approved
0.7676 Intermediate Similarity NPD1130 Approved
0.7676 Intermediate Similarity NPD1136 Approved
0.7676 Intermediate Similarity NPD1132 Approved
0.7674 Intermediate Similarity NPD9380 Clinical (unspecified phase)
0.7664 Intermediate Similarity NPD2561 Approved
0.7664 Intermediate Similarity NPD2562 Approved
0.7652 Intermediate Similarity NPD9614 Approved
0.7652 Intermediate Similarity NPD9618 Approved
0.7612 Intermediate Similarity NPD856 Approved
0.7612 Intermediate Similarity NPD16 Approved
0.7606 Intermediate Similarity NPD601 Approved
0.7606 Intermediate Similarity NPD598 Approved
0.7606 Intermediate Similarity NPD597 Approved
0.7586 Intermediate Similarity NPD3555 Approved
0.7586 Intermediate Similarity NPD3554 Approved
0.7586 Intermediate Similarity NPD3552 Approved
0.7586 Intermediate Similarity NPD3553 Approved
0.7574 Intermediate Similarity NPD9381 Approved
0.7574 Intermediate Similarity NPD9384 Approved
0.7517 Intermediate Similarity NPD2568 Approved
0.7517 Intermediate Similarity NPD5314 Approved
0.75 Intermediate Similarity NPD52 Approved
0.75 Intermediate Similarity NPD7526 Approved
0.75 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD7118 Clinical (unspecified phase)
0.7482 Intermediate Similarity NPD3676 Clinical (unspecified phase)
0.7447 Intermediate Similarity NPD9619 Approved
0.7447 Intermediate Similarity NPD9621 Approved
0.7447 Intermediate Similarity NPD9620 Approved
0.7431 Intermediate Similarity NPD839 Approved
0.7431 Intermediate Similarity NPD840 Approved
0.7397 Intermediate Similarity NPD823 Approved
0.7397 Intermediate Similarity NPD817 Approved
0.7379 Intermediate Similarity NPD3061 Approved
0.7379 Intermediate Similarity NPD3062 Approved
0.7379 Intermediate Similarity NPD3059 Approved
0.7376 Intermediate Similarity NPD1133 Approved
0.7376 Intermediate Similarity NPD1131 Approved
0.7376 Intermediate Similarity NPD1135 Approved
0.7376 Intermediate Similarity NPD4103 Phase 2
0.7376 Intermediate Similarity NPD1129 Approved
0.7376 Intermediate Similarity NPD4104 Clinical (unspecified phase)
0.7376 Intermediate Similarity NPD1134 Approved
0.7357 Intermediate Similarity NPD4659 Approved
0.7351 Intermediate Similarity NPD302 Approved
0.7338 Intermediate Similarity NPD7523 Phase 3
0.7324 Intermediate Similarity NPD602 Approved
0.7324 Intermediate Similarity NPD599 Approved
0.7297 Intermediate Similarity NPD6867 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD6866 Clinical (unspecified phase)
0.7287 Intermediate Similarity NPD9608 Approved
0.7287 Intermediate Similarity NPD9610 Approved
0.7278 Intermediate Similarity NPD5773 Approved
0.7278 Intermediate Similarity NPD5772 Approved
0.7255 Intermediate Similarity NPD6682 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD7450 Phase 2
0.7248 Intermediate Similarity NPD9570 Approved
0.7226 Intermediate Similarity NPD9613 Approved
0.7226 Intermediate Similarity NPD9615 Approved
0.7226 Intermediate Similarity NPD9616 Approved
0.7203 Intermediate Similarity NPD859 Approved
0.7203 Intermediate Similarity NPD858 Approved
0.7194 Intermediate Similarity NPD5238 Clinical (unspecified phase)
0.7192 Intermediate Similarity NPD1423 Approved
0.7192 Intermediate Similarity NPD6405 Approved
0.7192 Intermediate Similarity NPD6407 Approved
0.7174 Intermediate Similarity NPD316 Approved
0.7171 Intermediate Similarity NPD7066 Clinical (unspecified phase)
0.7171 Intermediate Similarity NPD3400 Discontinued
0.7152 Intermediate Similarity NPD6072 Discontinued
0.7107 Intermediate Similarity NPD8019 Approved
0.7103 Intermediate Similarity NPD600 Approved
0.7103 Intermediate Similarity NPD596 Approved
0.7075 Intermediate Similarity NPD2674 Phase 3
0.7047 Intermediate Similarity NPD3052 Approved
0.7047 Intermediate Similarity NPD3054 Approved
0.7039 Intermediate Similarity NPD7153 Discontinued
0.7021 Intermediate Similarity NPD3421 Phase 3
0.7014 Intermediate Similarity NPD3055 Approved
0.7014 Intermediate Similarity NPD3053 Approved
0.6987 Remote Similarity NPD5348 Clinical (unspecified phase)
0.6985 Remote Similarity NPD9379 Approved
0.6985 Remote Similarity NPD9377 Approved
0.6974 Remote Similarity NPD6809 Clinical (unspecified phase)
0.6959 Remote Similarity NPD829 Discontinued
0.6944 Remote Similarity NPD5311 Approved
0.6944 Remote Similarity NPD5310 Approved
0.6939 Remote Similarity NPD3180 Approved
0.6939 Remote Similarity NPD3179 Approved
0.6934 Remote Similarity NPD2229 Approved
0.6934 Remote Similarity NPD2234 Approved
0.6934 Remote Similarity NPD2228 Approved
0.6929 Remote Similarity NPD2218 Phase 2
0.6929 Remote Similarity NPD2217 Approved
0.6908 Remote Similarity NPD3175 Clinical (unspecified phase)
0.6899 Remote Similarity NPD9612 Approved
0.6899 Remote Similarity NPD9609 Approved
0.6899 Remote Similarity NPD9611 Approved
0.6894 Remote Similarity NPD7495 Discontinued
0.6892 Remote Similarity NPD3145 Approved
0.6892 Remote Similarity NPD3144 Approved
0.6883 Remote Similarity NPD3060 Approved
0.6879 Remote Similarity NPD3536 Discontinued
0.6867 Remote Similarity NPD555 Phase 2
0.6852 Remote Similarity NPD7972 Discontinued
0.6852 Remote Similarity NPD2977 Approved
0.6852 Remote Similarity NPD7089 Clinical (unspecified phase)
0.6852 Remote Similarity NPD2978 Approved
0.6846 Remote Similarity NPD259 Phase 1
0.6835 Remote Similarity NPD7303 Discontinued
0.6835 Remote Similarity NPD4186 Clinical (unspecified phase)
0.6821 Remote Similarity NPD1772 Clinical (unspecified phase)
0.6803 Remote Similarity NPD9569 Approved
0.6788 Remote Similarity NPD8303 Discontinued
0.6786 Remote Similarity NPD9568 Approved
0.6781 Remote Similarity NPD1818 Approved
0.6781 Remote Similarity NPD1819 Approved
0.6781 Remote Similarity NPD1817 Approved
0.6781 Remote Similarity NPD1820 Approved
0.6779 Remote Similarity NPD3056 Clinical (unspecified phase)
0.6772 Remote Similarity NPD4739 Approved
0.6772 Remote Similarity NPD3985 Discontinued
0.6767 Remote Similarity NPD310 Approved
0.6767 Remote Similarity NPD311 Approved
0.6767 Remote Similarity NPD315 Approved
0.6767 Remote Similarity NPD314 Approved
0.6767 Remote Similarity NPD10 Approved
0.6767 Remote Similarity NPD309 Approved
0.6753 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6742 Remote Similarity NPD855 Approved
0.6742 Remote Similarity NPD854 Approved
0.6741 Remote Similarity NPD6406 Approved
0.6736 Remote Similarity NPD5350 Clinical (unspecified phase)
0.6736 Remote Similarity NPD5351 Clinical (unspecified phase)
0.6733 Remote Similarity NPD7477 Discontinued
0.6712 Remote Similarity NPD9634 Clinical (unspecified phase)
0.6711 Remote Similarity NPD3167 Approved
0.6711 Remote Similarity NPD3165 Approved
0.6711 Remote Similarity NPD3166 Approved
0.6711 Remote Similarity NPD3164 Approved
0.6708 Remote Similarity NPD4005 Discontinued
0.6707 Remote Similarity NPD3558 Approved
0.6707 Remote Similarity NPD3560 Approved
0.6707 Remote Similarity NPD3557 Approved
0.6707 Remote Similarity NPD3556 Approved
0.6707 Remote Similarity NPD3559 Clinical (unspecified phase)
0.669 Remote Similarity NPD5303 Approved
0.669 Remote Similarity NPD2337 Clinical (unspecified phase)
0.669 Remote Similarity NPD5304 Approved
0.669 Remote Similarity NPD1759 Phase 1
0.6689 Remote Similarity NPD2238 Phase 2
0.6689 Remote Similarity NPD6346 Approved
0.6689 Remote Similarity NPD826 Approved
0.6689 Remote Similarity NPD825 Approved
0.6688 Remote Similarity NPD3692 Discontinued
0.6688 Remote Similarity NPD7274 Clinical (unspecified phase)
0.6688 Remote Similarity NPD2161 Phase 2
0.6686 Remote Similarity NPD7007 Discovery
0.6667 Remote Similarity NPD4123 Phase 3
0.6667 Remote Similarity NPD2459 Approved
0.6667 Remote Similarity NPD7608 Discontinued
0.6667 Remote Similarity NPD2460 Phase 3
0.6667 Remote Similarity NPD2579 Approved
0.6667 Remote Similarity NPD2458 Approved
0.6667 Remote Similarity NPD681 Clinical (unspecified phase)
0.6644 Remote Similarity NPD3685 Discontinued
0.6627 Remote Similarity NPD8070 Approved
0.6627 Remote Similarity NPD5137 Approved
0.6623 Remote Similarity NPD1753 Discontinued
0.6622 Remote Similarity NPD558 Phase 2
0.6622 Remote Similarity NPD2194 Approved
0.6622 Remote Similarity NPD258 Approved
0.6622 Remote Similarity NPD2195 Approved
0.6622 Remote Similarity NPD257 Approved
0.662 Remote Similarity NPD1758 Phase 1
0.6603 Remote Similarity NPD7596 Clinical (unspecified phase)
0.66 Remote Similarity NPD9536 Phase 1
0.66 Remote Similarity NPD9537 Phase 1
0.66 Remote Similarity NPD2372 Approved
0.6597 Remote Similarity NPD7342 Discontinued
0.6596 Remote Similarity NPD255 Approved
0.6596 Remote Similarity NPD256 Approved
0.6594 Remote Similarity NPD9280 Clinical (unspecified phase)
0.6582 Remote Similarity NPD8131 Suspended
0.6575 Remote Similarity NPD2235 Phase 2
0.6575 Remote Similarity NPD2231 Phase 2
0.6573 Remote Similarity NPD2226 Clinical (unspecified phase)
0.6568 Remote Similarity NPD4652 Approved
0.6564 Remote Similarity NPD4675 Approved
0.6564 Remote Similarity NPD4678 Approved
0.6562 Remote Similarity NPD3157 Approved
0.6562 Remote Similarity NPD6419 Discontinued

  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