Structure

Physi-Chem Properties

Molecular Weight:  624.26
Volume:  638.049
LogP:  4.713
LogD:  3.805
LogS:  -5.462
# Rotatable Bonds:  8
TPSA:  120.36
# H-Bond Aceptor:  9
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.37
Synthetic Accessibility Score:  4.695
Fsp3:  0.441
Lipinski Rule-of-5:  Accepted
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:  -4.837
MDCK Permeability:  1.679192610026803e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.007
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.008
30% Bioavailability (F30%):  0.946

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.562
Plasma Protein Binding (PPB):  98.3327865600586%
Volume Distribution (VD):  0.419
Pgp-substrate:  0.9797205328941345%

ADMET: Metabolism

CYP1A2-inhibitor:  0.15
CYP1A2-substrate:  0.104
CYP2C19-inhibitor:  0.934
CYP2C19-substrate:  0.382
CYP2C9-inhibitor:  0.947
CYP2C9-substrate:  0.922
CYP2D6-inhibitor:  0.194
CYP2D6-substrate:  0.616
CYP3A4-inhibitor:  0.963
CYP3A4-substrate:  0.488

ADMET: Excretion

Clearance (CL):  6.218
Half-life (T1/2):  0.232

ADMET: Toxicity

hERG Blockers:  0.191
Human Hepatotoxicity (H-HT):  0.939
Drug-inuced Liver Injury (DILI):  0.901
AMES Toxicity:  0.033
Rat Oral Acute Toxicity:  0.722
Maximum Recommended Daily Dose:  0.904
Skin Sensitization:  0.917
Carcinogencity:  0.444
Eye Corrosion:  0.003
Eye Irritation:  0.008
Respiratory Toxicity:  0.031

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

  Natural Product: NPC269383

Natural Product ID:  NPC269383
Common Name*:   (E)-(3S,6R,10R,16R)-10-(3-Chloro-4-Methoxy-Benzyl)-3-Isobutyl-6-Methyl-16-((E)-3-Phenyl-Allyl)-1,4-Dioxa-8,11-Diaza-Cyclohexadec-13-Ene-2,5,9,12-Tetraone
IUPAC Name:   (3S,6R,10R,13E,16R)-10-[(3-chloro-4-methoxyphenyl)methyl]-6-methyl-3-(2-methylpropyl)-16-[(E)-3-phenylprop-2-enyl]-1,4-dioxa-8,11-diazacyclohexadec-13-ene-2,5,9,12-tetrone
Synonyms:  
Standard InCHIKey:  YMZVKVLSUBCSND-DWEOSBBHSA-N
Standard InCHI:  InChI=1S/C34H41ClN2O7/c1-22(2)18-30-34(41)43-26(13-8-12-24-10-6-5-7-11-24)14-9-15-31(38)37-28(32(39)36-21-23(3)33(40)44-30)20-25-16-17-29(42-4)27(35)19-25/h5-12,15-17,19,22-23,26,28,30H,13-14,18,20-21H2,1-4H3,(H,36,39)(H,37,38)/b12-8+,15-9+/t23-,26-,28-,30+/m1/s1
SMILES:  COc1ccc(cc1Cl)C[C@H]1N=C(O)/C=C/C[C@@H](C/C=C/c2ccccc2)OC(=O)[C@@H](OC(=O)[C@@H](CN=C1O)C)CC(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL266856
PubChem CID:   10508182
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
NPO18618 Neurolaena lobata Species Asteraceae Eukaryota n.a. aerial part n.a. DOI[10.1021/jo00416a020]
NPO3613 Eriobotrya deflexa Species Rosaceae Eukaryota n.a. n.a. n.a. PMID[11473413]
NPO4541 Capnella lacertiliensis Species Nephtheidae Eukaryota n.a. n.a. n.a. PMID[12608844]
NPO8945 Grevillea robusta Species Proteaceae Eukaryota leaves n.a. n.a. PMID[17243726]
NPO18618 Neurolaena lobata Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO18618 Neurolaena lobata Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[24476550]
NPO8305 Katsuwonus pelamis Species Scombridae Eukaryota n.a. n.a. Database[FooDB]
NPO8945 Grevillea robusta Species Proteaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3613 Eriobotrya deflexa Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12744 Ajuga nipponensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8945 Grevillea robusta Species Proteaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8945 Grevillea robusta Species Proteaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10879 Lasius meridionalis Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4198 Ungernia vvedenskyi Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12744 Ajuga nipponensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23436 Cladrastis sikokiana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8945 Grevillea robusta Species Proteaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8811 Cytisus prolifer Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1969 Streptomyces pilosus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO19804 Lycopodium saururus Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28833 Eleutherococcus sieboldianus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO834 Peperomia clusiifolia Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5335 0stoc sp Species 0stocaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO8623 Anneissia japonica Species Comatulidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9705 Meyerozyma guilliermondii Species Debaryomycetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18618 Neurolaena lobata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3613 Eriobotrya deflexa Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7788 Rana catesbeiana Species Ranidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19541 Smilax moranensis Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4541 Capnella lacertiliensis Species Nephtheidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1537 Vaccinium arctostaphylos Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8305 Katsuwonus pelamis Species Scombridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8426 Tinospora rumphii Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7240 Osteospermum oppositifolium Species Asteraceae 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
NPT319 Cell Line B16 Mus musculus IC50 > 10.0 nM PMID[516642]
NPT4526 Cell Line DA-3 cell line IC50 > 10.0 nM PMID[516642]
NPT91 Cell Line KB Homo sapiens IC50 > 10.0 nM PMID[516642]
NPT139 Cell Line HT-29 Homo sapiens IC50 > 10.0 nM PMID[516642]

☑ 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 NPC269383 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 NPC151030
0.9744 High Similarity NPC49315
0.9563 High Similarity NPC271958
0.9563 High Similarity NPC263507
0.9563 High Similarity NPC134413
0.9563 High Similarity NPC45112
0.9325 High Similarity NPC86678
0.9193 High Similarity NPC227778
0.8954 High Similarity NPC132771
0.8562 High Similarity NPC212699
0.8562 High Similarity NPC207675
0.7784 Intermediate Similarity NPC56635
0.764 Intermediate Similarity NPC86087
0.7532 Intermediate Similarity NPC470392
0.75 Intermediate Similarity NPC182475
0.75 Intermediate Similarity NPC6570
0.7471 Intermediate Similarity NPC473502
0.7433 Intermediate Similarity NPC473371
0.7409 Intermediate Similarity NPC194699
0.7409 Intermediate Similarity NPC219350
0.7386 Intermediate Similarity NPC196091
0.7358 Intermediate Similarity NPC45191
0.733 Intermediate Similarity NPC186617
0.7312 Intermediate Similarity NPC471953
0.7305 Intermediate Similarity NPC313414
0.7288 Intermediate Similarity NPC471568
0.7288 Intermediate Similarity NPC473693
0.7259 Intermediate Similarity NPC469442
0.7259 Intermediate Similarity NPC277306
0.725 Intermediate Similarity NPC326966
0.725 Intermediate Similarity NPC30390
0.7226 Intermediate Similarity NPC474862
0.7212 Intermediate Similarity NPC91953
0.7212 Intermediate Similarity NPC212850
0.7212 Intermediate Similarity NPC189724
0.7212 Intermediate Similarity NPC83289
0.7205 Intermediate Similarity NPC244866
0.7197 Intermediate Similarity NPC95733
0.7197 Intermediate Similarity NPC62101
0.7186 Intermediate Similarity NPC25539
0.717 Intermediate Similarity NPC296712
0.716 Intermediate Similarity NPC245974
0.7152 Intermediate Similarity NPC29477
0.7152 Intermediate Similarity NPC197921
0.7143 Intermediate Similarity NPC43275
0.7143 Intermediate Similarity NPC48909
0.7143 Intermediate Similarity NPC247298
0.7135 Intermediate Similarity NPC315542
0.7134 Intermediate Similarity NPC211218
0.7108 Intermediate Similarity NPC469360
0.7097 Intermediate Similarity NPC263835
0.7062 Intermediate Similarity NPC472923
0.7055 Intermediate Similarity NPC76453
0.7035 Intermediate Similarity NPC182119
0.7022 Intermediate Similarity NPC254700
0.7019 Intermediate Similarity NPC325651
0.701 Intermediate Similarity NPC469443
0.6988 Remote Similarity NPC312770
0.6988 Remote Similarity NPC41473
0.6988 Remote Similarity NPC204848
0.6988 Remote Similarity NPC14600
0.6988 Remote Similarity NPC160607
0.6982 Remote Similarity NPC63628
0.6982 Remote Similarity NPC178466
0.6971 Remote Similarity NPC305700
0.6971 Remote Similarity NPC18249
0.6971 Remote Similarity NPC197741
0.6971 Remote Similarity NPC140915
0.6971 Remote Similarity NPC10221
0.6971 Remote Similarity NPC187028
0.6957 Remote Similarity NPC475421
0.6946 Remote Similarity NPC299583
0.6933 Remote Similarity NPC114102
0.6932 Remote Similarity NPC287757
0.6932 Remote Similarity NPC319320
0.6895 Remote Similarity NPC51047
0.6894 Remote Similarity NPC301713
0.689 Remote Similarity NPC214869
0.6882 Remote Similarity NPC81026
0.6879 Remote Similarity NPC476183
0.6871 Remote Similarity NPC35961
0.6871 Remote Similarity NPC52029
0.6871 Remote Similarity NPC195749
0.6859 Remote Similarity NPC473378
0.6859 Remote Similarity NPC473407
0.6852 Remote Similarity NPC251571
0.6848 Remote Similarity NPC477115
0.6845 Remote Similarity NPC167763
0.6845 Remote Similarity NPC470112
0.6845 Remote Similarity NPC106688
0.6845 Remote Similarity NPC470903
0.6837 Remote Similarity NPC213529
0.6835 Remote Similarity NPC476184
0.6835 Remote Similarity NPC476281
0.6824 Remote Similarity NPC266741
0.6821 Remote Similarity NPC324081
0.6815 Remote Similarity NPC319950
0.6813 Remote Similarity NPC476241
0.6813 Remote Similarity NPC40234
0.6813 Remote Similarity NPC476260
0.681 Remote Similarity NPC478147
0.681 Remote Similarity NPC155838
0.6802 Remote Similarity NPC5462
0.68 Remote Similarity NPC220060
0.68 Remote Similarity NPC478189
0.6792 Remote Similarity NPC160493
0.6788 Remote Similarity NPC274732
0.6786 Remote Similarity NPC471201
0.678 Remote Similarity NPC282294
0.6774 Remote Similarity NPC317254
0.6772 Remote Similarity NPC299806
0.6772 Remote Similarity NPC474498
0.677 Remote Similarity NPC4974
0.677 Remote Similarity NPC476125
0.677 Remote Similarity NPC476179
0.6766 Remote Similarity NPC6913
0.6766 Remote Similarity NPC469444
0.6765 Remote Similarity NPC204546
0.6758 Remote Similarity NPC208280
0.675 Remote Similarity NPC476278
0.675 Remote Similarity NPC90577
0.6748 Remote Similarity NPC186898
0.6747 Remote Similarity NPC169766
0.6743 Remote Similarity NPC139699
0.6743 Remote Similarity NPC114659
0.6739 Remote Similarity NPC248670
0.6732 Remote Similarity NPC166837
0.6731 Remote Similarity NPC274268
0.673 Remote Similarity NPC83279
0.6727 Remote Similarity NPC275538
0.6725 Remote Similarity NPC222039
0.6725 Remote Similarity NPC100478
0.6724 Remote Similarity NPC277857
0.6724 Remote Similarity NPC115144
0.6722 Remote Similarity NPC472623
0.6709 Remote Similarity NPC256369
0.6706 Remote Similarity NPC477838
0.6706 Remote Similarity NPC477837
0.6705 Remote Similarity NPC9373
0.6705 Remote Similarity NPC39431
0.6703 Remote Similarity NPC209463
0.6703 Remote Similarity NPC476227
0.6703 Remote Similarity NPC473354
0.6703 Remote Similarity NPC471165
0.6703 Remote Similarity NPC26108
0.6703 Remote Similarity NPC107938
0.6703 Remote Similarity NPC294516
0.6703 Remote Similarity NPC164608
0.6702 Remote Similarity NPC232872
0.6701 Remote Similarity NPC328763
0.6688 Remote Similarity NPC38458
0.6688 Remote Similarity NPC311737
0.6687 Remote Similarity NPC307123
0.6687 Remote Similarity NPC97870
0.6687 Remote Similarity NPC247018
0.6687 Remote Similarity NPC476353
0.6687 Remote Similarity NPC27581
0.6687 Remote Similarity NPC142577
0.6686 Remote Similarity NPC153644
0.6685 Remote Similarity NPC89831
0.6684 Remote Similarity NPC470728
0.6667 Remote Similarity NPC303370
0.6667 Remote Similarity NPC326333
0.6667 Remote Similarity NPC190663
0.6667 Remote Similarity NPC469445
0.6667 Remote Similarity NPC47667
0.6667 Remote Similarity NPC246991
0.6667 Remote Similarity NPC50016
0.665 Remote Similarity NPC323662
0.6649 Remote Similarity NPC32064
0.6649 Remote Similarity NPC273755
0.6649 Remote Similarity NPC276120
0.6647 Remote Similarity NPC317741
0.6647 Remote Similarity NPC282087
0.6647 Remote Similarity NPC318984
0.6647 Remote Similarity NPC259800
0.6647 Remote Similarity NPC318028
0.6647 Remote Similarity NPC241086
0.6647 Remote Similarity NPC328137
0.6646 Remote Similarity NPC153990
0.6646 Remote Similarity NPC471315
0.6646 Remote Similarity NPC237420
0.6646 Remote Similarity NPC471314
0.6632 Remote Similarity NPC174122
0.6632 Remote Similarity NPC64140
0.6624 Remote Similarity NPC82963
0.6613 Remote Similarity NPC158277
0.6613 Remote Similarity NPC279871
0.6612 Remote Similarity NPC238430
0.6611 Remote Similarity NPC476194
0.6607 Remote Similarity NPC284855
0.6607 Remote Similarity NPC282477
0.6607 Remote Similarity NPC314743
0.6604 Remote Similarity NPC283760
0.6603 Remote Similarity NPC118202
0.6602 Remote Similarity NPC326027
0.6598 Remote Similarity NPC477526
0.6595 Remote Similarity NPC230611
0.6593 Remote Similarity NPC158900
0.6593 Remote Similarity NPC63931

  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 NPC269383 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
0.9563 High Similarity NPD7959 Clinical (unspecified phase)
0.9503 High Similarity NPD8014 Clinical (unspecified phase)
0.8061 Intermediate Similarity NPD4018 Clinical (unspecified phase)
0.8012 Intermediate Similarity NPD3465 Clinical (unspecified phase)
0.7679 Intermediate Similarity NPD3274 Phase 2
0.7568 Intermediate Similarity NPD6312 Discontinued
0.7485 Intermediate Similarity NPD7596 Clinical (unspecified phase)
0.7472 Intermediate Similarity NPD5095 Phase 3
0.7472 Intermediate Similarity NPD5096 Phase 3
0.7442 Intermediate Similarity NPD2379 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD3936 Clinical (unspecified phase)
0.7374 Intermediate Similarity NPD3933 Discontinued
0.7283 Intermediate Similarity NPD7972 Discontinued
0.7278 Intermediate Similarity NPD6390 Discontinued
0.7278 Intermediate Similarity NPD454 Approved
0.7273 Intermediate Similarity NPD5958 Discontinued
0.7273 Intermediate Similarity NPD3819 Phase 2
0.7273 Intermediate Similarity NPD4534 Discontinued
0.7243 Intermediate Similarity NPD3857 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD3536 Discontinued
0.7207 Intermediate Similarity NPD5822 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD5729 Clinical (unspecified phase)
0.7191 Intermediate Similarity NPD7608 Discontinued
0.7176 Intermediate Similarity NPD4186 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD1048 Approved
0.7135 Intermediate Similarity NPD7131 Phase 3
0.7134 Intermediate Similarity NPD3676 Clinical (unspecified phase)
0.7118 Intermediate Similarity NPD5348 Clinical (unspecified phase)
0.7093 Intermediate Similarity NPD2370 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD3136 Phase 2
0.7039 Intermediate Similarity NPD5649 Clinical (unspecified phase)
0.6989 Remote Similarity NPD7460 Discontinued
0.6941 Remote Similarity NPD3887 Approved
0.6932 Remote Similarity NPD7029 Discontinued
0.6923 Remote Similarity NPD2976 Clinical (unspecified phase)
0.6914 Remote Similarity NPD6502 Phase 2
0.6914 Remote Similarity NPD4972 Discontinued
0.6909 Remote Similarity NPD6355 Discontinued
0.6905 Remote Similarity NPD7978 Discontinued
0.6897 Remote Similarity NPD4003 Phase 3
0.6885 Remote Similarity NPD3366 Approved
0.6875 Remote Similarity NPD3098 Discontinued
0.6845 Remote Similarity NPD2239 Approved
0.6845 Remote Similarity NPD2240 Approved
0.6845 Remote Similarity NPD1501 Clinical (unspecified phase)
0.6842 Remote Similarity NPD2354 Approved
0.6836 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6829 Remote Similarity NPD6798 Discontinued
0.6798 Remote Similarity NPD5563 Clinical (unspecified phase)
0.6796 Remote Similarity NPD3365 Discontinued
0.6788 Remote Similarity NPD6233 Phase 2
0.6788 Remote Similarity NPD7477 Discontinued
0.6788 Remote Similarity NPD4062 Phase 3
0.6788 Remote Similarity NPD5745 Approved
0.6786 Remote Similarity NPD6866 Clinical (unspecified phase)
0.6786 Remote Similarity NPD6867 Clinical (unspecified phase)
0.6782 Remote Similarity NPD7527 Clinical (unspecified phase)
0.6782 Remote Similarity NPD52 Approved
0.6782 Remote Similarity NPD7526 Approved
0.678 Remote Similarity NPD958 Approved
0.678 Remote Similarity NPD4424 Discontinued
0.678 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6778 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6778 Remote Similarity NPD8031 Discontinued
0.6774 Remote Similarity NPD5557 Phase 1
0.6768 Remote Similarity NPD4971 Clinical (unspecified phase)
0.6768 Remote Similarity NPD5163 Phase 2
0.6765 Remote Similarity NPD2808 Discontinued
0.6758 Remote Similarity NPD5623 Approved
0.6757 Remote Similarity NPD3909 Discontinued
0.675 Remote Similarity NPD5108 Clinical (unspecified phase)
0.6746 Remote Similarity NPD6032 Approved
0.674 Remote Similarity NPD5709 Phase 3
0.673 Remote Similarity NPD3847 Discontinued
0.6724 Remote Similarity NPD4739 Approved
0.6721 Remote Similarity NPD7315 Approved
0.6707 Remote Similarity NPD1184 Approved
0.6707 Remote Similarity NPD2614 Approved
0.6706 Remote Similarity NPD2353 Approved
0.6706 Remote Similarity NPD2355 Clinical (unspecified phase)
0.6705 Remote Similarity NPD6666 Approved
0.6705 Remote Similarity NPD957 Approved
0.6705 Remote Similarity NPD6667 Approved
0.6704 Remote Similarity NPD5772 Approved
0.6704 Remote Similarity NPD5773 Approved
0.6703 Remote Similarity NPD6746 Phase 2
0.6703 Remote Similarity NPD4666 Phase 3
0.6687 Remote Similarity NPD1423 Approved
0.6686 Remote Similarity NPD6331 Phase 2
0.6686 Remote Similarity NPD6658 Clinical (unspecified phase)
0.6685 Remote Similarity NPD4064 Discontinued
0.6685 Remote Similarity NPD6677 Suspended
0.6667 Remote Similarity NPD7485 Phase 3
0.6667 Remote Similarity NPD196 Phase 1
0.6667 Remote Similarity NPD7484 Phase 3
0.6667 Remote Similarity NPD5746 Approved
0.6649 Remote Similarity NPD3823 Discontinued
0.6648 Remote Similarity NPD5356 Approved
0.6648 Remote Similarity NPD4433 Discontinued
0.6648 Remote Similarity NPD5355 Approved
0.6647 Remote Similarity NPD1519 Approved
0.6647 Remote Similarity NPD1537 Approved
0.6647 Remote Similarity NPD5837 Clinical (unspecified phase)
0.6647 Remote Similarity NPD1538 Phase 1
0.6629 Remote Similarity NPD4123 Phase 3
0.6629 Remote Similarity NPD7446 Clinical (unspecified phase)
0.6629 Remote Similarity NPD1714 Approved
0.6629 Remote Similarity NPD1715 Phase 1
0.6628 Remote Similarity NPD1416 Approved
0.6627 Remote Similarity NPD3374 Clinical (unspecified phase)
0.6627 Remote Similarity NPD1536 Approved
0.6612 Remote Similarity NPD7129 Suspended
0.6609 Remote Similarity NPD6815 Approved
0.6608 Remote Similarity NPD3656 Approved
0.6605 Remote Similarity NPD3685 Discontinued
0.6593 Remote Similarity NPD8070 Approved
0.6592 Remote Similarity NPD6072 Discontinued
0.6592 Remote Similarity NPD2541 Clinical (unspecified phase)
0.6584 Remote Similarity NPD6905 Phase 2
0.6576 Remote Similarity NPD2821 Approved
0.6573 Remote Similarity NPD3455 Phase 2
0.6573 Remote Similarity NPD6056 Approved
0.6573 Remote Similarity NPD6057 Approved
0.657 Remote Similarity NPD2030 Discontinued
0.657 Remote Similarity NPD2897 Discontinued
0.657 Remote Similarity NPD7153 Discontinued
0.6568 Remote Similarity NPD3052 Approved
0.6568 Remote Similarity NPD3054 Approved
0.6566 Remote Similarity NPD2598 Clinical (unspecified phase)
0.6566 Remote Similarity NPD7095 Approved
0.6566 Remote Similarity NPD1024 Discontinued
0.6562 Remote Similarity NPD2668 Approved
0.6562 Remote Similarity NPD2667 Approved
0.6556 Remote Similarity NPD7495 Discontinued
0.6556 Remote Similarity NPD8019 Approved
0.655 Remote Similarity NPD1522 Approved
0.655 Remote Similarity NPD1523 Approved
0.655 Remote Similarity NPD7450 Phase 2
0.655 Remote Similarity NPD1725 Approved
0.655 Remote Similarity NPD2161 Phase 2
0.6548 Remote Similarity NPD4060 Phase 1
0.6545 Remote Similarity NPD4993 Discontinued
0.6536 Remote Similarity NPD3579 Clinical (unspecified phase)
0.6534 Remote Similarity NPD3985 Discontinued
0.6533 Remote Similarity NPD7565 Approved
0.6532 Remote Similarity NPD2459 Approved
0.6532 Remote Similarity NPD2460 Phase 3
0.6532 Remote Similarity NPD2458 Approved
0.6532 Remote Similarity NPD4487 Clinical (unspecified phase)
0.6529 Remote Similarity NPD1521 Approved
0.6529 Remote Similarity NPD1520 Approved
0.6527 Remote Similarity NPD3056 Clinical (unspecified phase)
0.6524 Remote Similarity NPD5605 Phase 2
0.6524 Remote Similarity NPD987 Approved
0.6512 Remote Similarity NPD5865 Clinical (unspecified phase)
0.6503 Remote Similarity NPD1669 Approved
0.65 Remote Similarity NPD5542 Phase 2
0.65 Remote Similarity NPD6386 Approved
0.65 Remote Similarity NPD6385 Approved
0.6494 Remote Similarity NPD3400 Discontinued
0.6488 Remote Similarity NPD2674 Phase 3
0.6485 Remote Similarity NPD7451 Discontinued
0.6484 Remote Similarity NPD7318 Phase 3
0.6484 Remote Similarity NPD4874 Phase 2
0.6479 Remote Similarity NPD7548 Discontinued
0.6477 Remote Similarity NPD6682 Clinical (unspecified phase)
0.6474 Remote Similarity NPD6211 Clinical (unspecified phase)
0.6467 Remote Similarity NPD2372 Approved
0.6467 Remote Similarity NPD6315 Phase 2
0.6462 Remote Similarity NPD6981 Phase 2
0.6462 Remote Similarity NPD7805 Phase 3
0.6461 Remote Similarity NPD7523 Phase 3
0.6457 Remote Similarity NPD3973 Approved
0.6455 Remote Similarity NPD3965 Phase 1
0.6453 Remote Similarity NPD3175 Clinical (unspecified phase)
0.6453 Remote Similarity NPD4477 Approved
0.6453 Remote Similarity NPD4476 Approved
0.645 Remote Similarity NPD6346 Approved
0.645 Remote Similarity NPD7810 Phase 3
0.645 Remote Similarity NPD7811 Phase 3
0.6447 Remote Similarity NPD5984 Phase 2
0.6444 Remote Similarity NPD4678 Approved
0.6444 Remote Similarity NPD4675 Approved
0.6437 Remote Similarity NPD4237 Approved
0.6437 Remote Similarity NPD4236 Phase 3
0.6433 Remote Similarity NPD4538 Approved
0.6433 Remote Similarity NPD5688 Approved
0.6433 Remote Similarity NPD4536 Approved
0.6433 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6433 Remote Similarity NPD5689 Approved
0.6433 Remote Similarity NPD4978 Clinical (unspecified phase)
0.6429 Remote Similarity NPD3144 Approved
0.6429 Remote Similarity NPD3145 Approved
0.6429 Remote Similarity NPD7089 Clinical (unspecified phase)
0.6425 Remote Similarity NPD3687 Approved
0.6425 Remote Similarity NPD6556 Clinical (unspecified phase)
0.6425 Remote Similarity NPD3686 Approved
0.6406 Remote Similarity NPD2166 Phase 3
0.6404 Remote Similarity NPD5261 Clinical (unspecified phase)
0.6404 Remote Similarity NPD7613 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