Structure

Physi-Chem Properties

Molecular Weight:  610.44
Volume:  659.215
LogP:  6.482
LogD:  4.541
LogS:  -5.037
# Rotatable Bonds:  26
TPSA:  140.59
# H-Bond Aceptor:  8
# H-Bond Donor:  5
# Rings:  2
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.072
Synthetic Accessibility Score:  4.61
Fsp3:  0.857
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.168
MDCK Permeability:  1.9975121176685207e-05
Pgp-inhibitor:  0.198
Pgp-substrate:  0.999
Human Intestinal Absorption (HIA):  0.121
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.034
Plasma Protein Binding (PPB):  95.80899047851562%
Volume Distribution (VD):  1.263
Pgp-substrate:  3.0892741680145264%

ADMET: Metabolism

CYP1A2-inhibitor:  0.016
CYP1A2-substrate:  0.498
CYP2C19-inhibitor:  0.046
CYP2C19-substrate:  0.051
CYP2C9-inhibitor:  0.115
CYP2C9-substrate:  0.956
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.058
CYP3A4-inhibitor:  0.171
CYP3A4-substrate:  0.021

ADMET: Excretion

Clearance (CL):  11.127
Half-life (T1/2):  0.334

ADMET: Toxicity

hERG Blockers:  0.056
Human Hepatotoxicity (H-HT):  0.468
Drug-inuced Liver Injury (DILI):  0.019
AMES Toxicity:  0.038
Rat Oral Acute Toxicity:  0.021
Maximum Recommended Daily Dose:  0.956
Skin Sensitization:  0.945
Carcinogencity:  0.213
Eye Corrosion:  0.003
Eye Irritation:  0.015
Respiratory Toxicity:  0.929

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

  Natural Product: NPC130359

Natural Product ID:  NPC130359
Common Name*:   Montacin
IUPAC Name:   (2S)-2-methyl-4-[(2R,7S,18S)-2,7,18-trihydroxy-18-[(2S,5S)-5-[(1S)-1-hydroxyoctyl]oxolan-2-yl]-5-oxooctadecyl]-2H-furan-5-one
Synonyms:   Montacin
Standard InCHIKey:  LLIPLAYBUOQFER-RMJQFDBYSA-N
Standard InCHI:  InChI=1S/C35H62O8/c1-3-4-5-10-14-17-31(39)33-21-22-34(43-33)32(40)18-15-12-9-7-6-8-11-13-16-28(36)25-30(38)20-19-29(37)24-27-23-26(2)42-35(27)41/h23,26,28-29,31-34,36-37,39-40H,3-22,24-25H2,1-2H3/t26-,28-,29+,31-,32-,33-,34-/m0/s1
SMILES:  CCCCCCC[C@@H]([C@@H]1CC[C@H](O1)[C@H](CCCCCCCCCC[C@@H](CC(=O)CC[C@H](CC1=C[C@@H](OC1=O)C)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL500276
PubChem CID:   11238862
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0003909] Fatty Acyls
        • [CHEMONTID:0001334] Fatty alcohols
          • [CHEMONTID:0002518] Annonaceous acetogenins

*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
NPO13370 Annona montana Species Annonaceae Eukaryota n.a. trunk bark n.a. DOI[10.1039/P19820001205]
NPO13370 Annona montana Species Annonaceae Eukaryota n.a. root n.a. DOI[10.1039/P19820001205]
NPO13370 Annona montana Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[15568766]
NPO13370 Annona montana Species Annonaceae Eukaryota n.a. seed n.a. PMID[18687006]
NPO13370 Annona montana Species Annonaceae Eukaryota seeds n.a. n.a. PMID[18687006]
NPO13370 Annona montana Species Annonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13370 Annona montana Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13370 Annona montana Species Annonaceae 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
NPT310 Cell Line 1A9/ptx-10 Homo sapiens ED50 > 10.0 ug ml-1 PMID[508001]
NPT309 Cell Line 1A9 Homo sapiens ED50 > 10.0 ug ml-1 PMID[508001]
NPT306 Cell Line PC-3 Homo sapiens ED50 > 20.0 ug ml-1 PMID[508001]
NPT91 Cell Line KB Homo sapiens ED50 > 20.0 ug ml-1 PMID[508001]
NPT91 Cell Line KB Homo sapiens ED50 = 16.6 ug ml-1 PMID[508001]
NPT147 Cell Line SK-MEL-2 Homo sapiens ED50 = 11.2 ug ml-1 PMID[508001]
NPT180 Cell Line HCT-8 Homo sapiens ED50 = 16.5 ug ml-1 PMID[508001]
NPT83 Cell Line MCF7 Homo sapiens ED50 = 10.0 ug ml-1 PMID[508001]
NPT81 Cell Line A549 Homo sapiens ED50 = 12.9 ug ml-1 PMID[508001]
NPT309 Cell Line 1A9 Homo sapiens ED50 = 6.7 ug ml-1 PMID[508001]
NPT310 Cell Line 1A9/ptx-10 Homo sapiens ED50 = 7.9 ug ml-1 PMID[508001]
NPT81 Cell Line A549 Homo sapiens ED50 = 7.4 ug ml-1 PMID[508001]
NPT83 Cell Line MCF7 Homo sapiens ED50 = 5.5 ug ml-1 PMID[508001]
NPT180 Cell Line HCT-8 Homo sapiens ED50 = 12.3 ug ml-1 PMID[508001]
NPT147 Cell Line SK-MEL-2 Homo sapiens ED50 = 13.3 ug ml-1 PMID[508001]
NPT91 Cell Line KB Homo sapiens ED50 = 9.1 ug ml-1 PMID[508001]
NPT91 Cell Line KB Homo sapiens ED50 = 13.9 ug ml-1 PMID[508001]
NPT306 Cell Line PC-3 Homo sapiens ED50 = 14.2 ug ml-1 PMID[508001]
NPT310 Cell Line 1A9/ptx-10 Homo sapiens ED50 = 7.5 ug ml-1 PMID[508001]
NPT309 Cell Line 1A9 Homo sapiens ED50 = 4.5 ug ml-1 PMID[508001]
NPT310 Cell Line 1A9/ptx-10 Homo sapiens ED50 = 2.8 ug ml-1 PMID[508001]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 > 20.0 ug ml-1 PMID[508001]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 14.2 ug ml-1 PMID[508001]

☑ 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 NPC130359 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 NPC14901
0.9639 High Similarity NPC308412
0.9639 High Similarity NPC134807
0.9639 High Similarity NPC473687
0.9639 High Similarity NPC134865
0.9639 High Similarity NPC219498
0.9639 High Similarity NPC134885
0.9639 High Similarity NPC103523
0.9639 High Similarity NPC210218
0.9639 High Similarity NPC204686
0.9524 High Similarity NPC178215
0.9518 High Similarity NPC110710
0.9518 High Similarity NPC66346
0.9518 High Similarity NPC132496
0.9518 High Similarity NPC107986
0.9518 High Similarity NPC82795
0.9518 High Similarity NPC1083
0.9518 High Similarity NPC473478
0.9518 High Similarity NPC283085
0.9518 High Similarity NPC103284
0.9518 High Similarity NPC231009
0.9518 High Similarity NPC473669
0.9518 High Similarity NPC286338
0.9518 High Similarity NPC473651
0.9518 High Similarity NPC223871
0.9412 High Similarity NPC21208
0.9412 High Similarity NPC20339
0.9412 High Similarity NPC48338
0.9412 High Similarity NPC233551
0.9412 High Similarity NPC40376
0.9412 High Similarity NPC280621
0.9405 High Similarity NPC475581
0.9405 High Similarity NPC477015
0.9405 High Similarity NPC240695
0.9405 High Similarity NPC107717
0.9405 High Similarity NPC232555
0.9405 High Similarity NPC62118
0.9405 High Similarity NPC171174
0.9405 High Similarity NPC69082
0.9405 High Similarity NPC114694
0.9405 High Similarity NPC142117
0.9405 High Similarity NPC279267
0.9405 High Similarity NPC231096
0.9302 High Similarity NPC477011
0.9302 High Similarity NPC91067
0.9302 High Similarity NPC473504
0.9302 High Similarity NPC139418
0.9302 High Similarity NPC42598
0.9302 High Similarity NPC93794
0.9302 High Similarity NPC40066
0.9302 High Similarity NPC81778
0.9302 High Similarity NPC318963
0.9302 High Similarity NPC20621
0.9302 High Similarity NPC280612
0.9286 High Similarity NPC477014
0.9286 High Similarity NPC329838
0.9286 High Similarity NPC329615
0.9286 High Similarity NPC477013
0.9277 High Similarity NPC144415
0.9205 High Similarity NPC11456
0.9195 High Similarity NPC239517
0.9195 High Similarity NPC473904
0.9186 High Similarity NPC151403
0.9186 High Similarity NPC81045
0.9186 High Similarity NPC133730
0.9186 High Similarity NPC169511
0.9186 High Similarity NPC61257
0.9186 High Similarity NPC39754
0.9186 High Similarity NPC172821
0.9186 High Similarity NPC171135
0.9186 High Similarity NPC242364
0.9186 High Similarity NPC320569
0.9186 High Similarity NPC274446
0.9186 High Similarity NPC191929
0.9186 High Similarity NPC287164
0.9186 High Similarity NPC261952
0.9186 High Similarity NPC100454
0.9186 High Similarity NPC234077
0.9176 High Similarity NPC112685
0.9167 High Similarity NPC163093
0.9167 High Similarity NPC156804
0.9157 High Similarity NPC473780
0.9157 High Similarity NPC94875
0.9157 High Similarity NPC475159
0.9157 High Similarity NPC473529
0.9157 High Similarity NPC11332
0.9157 High Similarity NPC145914
0.9157 High Similarity NPC131002
0.9157 High Similarity NPC65930
0.9157 High Similarity NPC73310
0.9157 High Similarity NPC329829
0.9157 High Similarity NPC473712
0.9157 High Similarity NPC180363
0.908 High Similarity NPC477016
0.908 High Similarity NPC477017
0.907 High Similarity NPC258068
0.907 High Similarity NPC20533
0.907 High Similarity NPC477012
0.907 High Similarity NPC476583
0.9059 High Similarity NPC471567
0.9059 High Similarity NPC120398
0.9059 High Similarity NPC182383
0.9059 High Similarity NPC322529
0.9048 High Similarity NPC253801
0.8966 High Similarity NPC473905
0.8966 High Similarity NPC89001
0.8966 High Similarity NPC320458
0.8953 High Similarity NPC241360
0.8953 High Similarity NPC282815
0.8953 High Similarity NPC47937
0.8953 High Similarity NPC477010
0.8953 High Similarity NPC25703
0.8953 High Similarity NPC293136
0.8953 High Similarity NPC132940
0.8953 High Similarity NPC219652
0.8953 High Similarity NPC473840
0.8837 High Similarity NPC470400
0.8837 High Similarity NPC473671
0.8837 High Similarity NPC473156
0.8837 High Similarity NPC319036
0.8837 High Similarity NPC77871
0.8837 High Similarity NPC202055
0.8837 High Similarity NPC39279
0.8837 High Similarity NPC477018
0.8837 High Similarity NPC100921
0.8837 High Similarity NPC25764
0.8837 High Similarity NPC292809
0.8837 High Similarity NPC475268
0.8837 High Similarity NPC39167
0.8837 High Similarity NPC235809
0.8837 High Similarity NPC9678
0.8778 High Similarity NPC473561
0.8778 High Similarity NPC473723
0.8778 High Similarity NPC475173
0.8778 High Similarity NPC473663
0.8736 High Similarity NPC309211
0.8667 High Similarity NPC473707
0.8636 High Similarity NPC470401
0.8636 High Similarity NPC154097
0.8636 High Similarity NPC159750
0.8636 High Similarity NPC473995
0.8636 High Similarity NPC473649
0.837 Intermediate Similarity NPC473520
0.8315 Intermediate Similarity NPC469483
0.8256 Intermediate Similarity NPC47653
0.8182 Intermediate Similarity NPC286770
0.8182 Intermediate Similarity NPC284472
0.8182 Intermediate Similarity NPC229799
0.8172 Intermediate Similarity NPC273579
0.8172 Intermediate Similarity NPC295204
0.8172 Intermediate Similarity NPC162205
0.8172 Intermediate Similarity NPC288240
0.8152 Intermediate Similarity NPC474232
0.8125 Intermediate Similarity NPC161855
0.8068 Intermediate Similarity NPC475046
0.8068 Intermediate Similarity NPC310450
0.8068 Intermediate Similarity NPC474959
0.8068 Intermediate Similarity NPC11383
0.8065 Intermediate Similarity NPC30515
0.8023 Intermediate Similarity NPC221095
0.8023 Intermediate Similarity NPC279214
0.8 Intermediate Similarity NPC21469
0.8 Intermediate Similarity NPC471142
0.8 Intermediate Similarity NPC36954
0.798 Intermediate Similarity NPC472755
0.7979 Intermediate Similarity NPC469645
0.7979 Intermediate Similarity NPC469692
0.7979 Intermediate Similarity NPC476300
0.7979 Intermediate Similarity NPC81419
0.7979 Intermediate Similarity NPC179746
0.7978 Intermediate Similarity NPC475947
0.7957 Intermediate Similarity NPC51004
0.7957 Intermediate Similarity NPC473619
0.7938 Intermediate Similarity NPC471144
0.7935 Intermediate Similarity NPC475819
0.7921 Intermediate Similarity NPC26617
0.7917 Intermediate Similarity NPC477921
0.7917 Intermediate Similarity NPC473291
0.7912 Intermediate Similarity NPC469910
0.7907 Intermediate Similarity NPC176329
0.7907 Intermediate Similarity NPC49302
0.7907 Intermediate Similarity NPC125365
0.7907 Intermediate Similarity NPC474818
0.7907 Intermediate Similarity NPC51809
0.79 Intermediate Similarity NPC100487
0.79 Intermediate Similarity NPC203659
0.79 Intermediate Similarity NPC472756
0.7895 Intermediate Similarity NPC121825
0.7889 Intermediate Similarity NPC41856
0.7879 Intermediate Similarity NPC149371
0.7879 Intermediate Similarity NPC472754
0.7872 Intermediate Similarity NPC473321
0.7872 Intermediate Similarity NPC12172
0.7872 Intermediate Similarity NPC208886
0.7872 Intermediate Similarity NPC184463
0.7872 Intermediate Similarity NPC327760
0.7849 Intermediate Similarity NPC307411
0.7849 Intermediate Similarity NPC295312
0.7816 Intermediate Similarity NPC182292
0.7816 Intermediate Similarity NPC473471

  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 NPC130359 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
0.7921 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7766 Intermediate Similarity NPD46 Approved
0.7766 Intermediate Similarity NPD6698 Approved
0.75 Intermediate Similarity NPD7983 Approved
0.7396 Intermediate Similarity NPD7838 Discovery
0.7358 Intermediate Similarity NPD6371 Approved
0.7273 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7216 Intermediate Similarity NPD5785 Approved
0.7059 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.7053 Intermediate Similarity NPD5363 Approved
0.7009 Intermediate Similarity NPD6686 Approved
0.6893 Remote Similarity NPD4225 Approved
0.6818 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6737 Remote Similarity NPD4270 Approved
0.6737 Remote Similarity NPD4269 Approved
0.6702 Remote Similarity NPD4252 Approved
0.6701 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6633 Remote Similarity NPD5786 Approved
0.6632 Remote Similarity NPD5369 Approved
0.6581 Remote Similarity NPD8516 Approved
0.6581 Remote Similarity NPD8515 Approved
0.6581 Remote Similarity NPD8513 Phase 3
0.6581 Remote Similarity NPD8517 Approved
0.6566 Remote Similarity NPD4251 Approved
0.6566 Remote Similarity NPD4250 Approved
0.6559 Remote Similarity NPD4756 Discovery
0.6538 Remote Similarity NPD7839 Suspended
0.6531 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6522 Remote Similarity NPD7115 Discovery
0.6512 Remote Similarity NPD3197 Phase 1
0.6505 Remote Similarity NPD5282 Discontinued
0.6495 Remote Similarity NPD7154 Phase 3
0.6495 Remote Similarity NPD5362 Discontinued
0.6465 Remote Similarity NPD4249 Approved
0.6436 Remote Similarity NPD1695 Approved
0.6408 Remote Similarity NPD5778 Approved
0.6408 Remote Similarity NPD5779 Approved
0.6392 Remote Similarity NPD5209 Approved
0.6354 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6333 Remote Similarity NPD7642 Approved
0.6333 Remote Similarity NPD7829 Approved
0.6333 Remote Similarity NPD7830 Approved
0.6311 Remote Similarity NPD8074 Phase 3
0.6296 Remote Similarity NPD5344 Discontinued
0.6292 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6275 Remote Similarity NPD5370 Suspended
0.6224 Remote Similarity NPD6435 Approved
0.6224 Remote Similarity NPD4752 Clinical (unspecified phase)
0.621 Remote Similarity NPD7319 Approved
0.62 Remote Similarity NPD1694 Approved
0.6174 Remote Similarity NPD6053 Discontinued
0.6167 Remote Similarity NPD8444 Approved
0.6162 Remote Similarity NPD6110 Phase 1
0.6154 Remote Similarity NPD4810 Clinical (unspecified phase)
0.6146 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6146 Remote Similarity NPD4268 Approved
0.6146 Remote Similarity NPD4271 Approved
0.6124 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6111 Remote Similarity NPD7638 Approved
0.6102 Remote Similarity NPD7500 Approved
0.61 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6098 Remote Similarity NPD7507 Approved
0.6055 Remote Similarity NPD7640 Approved
0.6055 Remote Similarity NPD7639 Approved
0.6053 Remote Similarity NPD4061 Clinical (unspecified phase)
0.605 Remote Similarity NPD7641 Discontinued
0.6023 Remote Similarity NPD2664 Clinical (unspecified phase)
0.602 Remote Similarity NPD4819 Approved
0.602 Remote Similarity NPD5368 Approved
0.602 Remote Similarity NPD4822 Approved
0.602 Remote Similarity NPD4821 Approved
0.602 Remote Similarity NPD4820 Approved
0.6 Remote Similarity NPD7637 Suspended
0.6 Remote Similarity NPD5331 Approved
0.6 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6 Remote Similarity NPD3704 Approved
0.6 Remote Similarity NPD5332 Approved
0.6 Remote Similarity NPD8039 Approved
0.5977 Remote Similarity NPD4246 Clinical (unspecified phase)
0.5968 Remote Similarity NPD8451 Approved
0.5968 Remote Similarity NPD8273 Phase 1
0.5962 Remote Similarity NPD6101 Approved
0.5962 Remote Similarity NPD5764 Clinical (unspecified phase)
0.596 Remote Similarity NPD4790 Discontinued
0.595 Remote Similarity NPD6319 Approved
0.5948 Remote Similarity NPD7116 Clinical (unspecified phase)
0.5948 Remote Similarity NPD2204 Approved
0.5943 Remote Similarity NPD6399 Phase 3
0.5935 Remote Similarity NPD8328 Phase 3
0.592 Remote Similarity NPD8448 Approved
0.5909 Remote Similarity NPD6648 Approved
0.5902 Remote Similarity NPD8033 Approved
0.5897 Remote Similarity NPD8297 Approved
0.5889 Remote Similarity NPD2685 Clinical (unspecified phase)
0.5887 Remote Similarity NPD7492 Approved
0.5877 Remote Similarity NPD6412 Phase 2
0.5873 Remote Similarity NPD7736 Approved
0.5872 Remote Similarity NPD7902 Approved
0.5859 Remote Similarity NPD7260 Phase 2
0.5854 Remote Similarity NPD8080 Discontinued
0.5849 Remote Similarity NPD6411 Approved
0.584 Remote Similarity NPD6616 Approved
0.5833 Remote Similarity NPD3730 Approved
0.5833 Remote Similarity NPD3196 Approved
0.5833 Remote Similarity NPD4266 Approved
0.5833 Remote Similarity NPD3194 Approved
0.5833 Remote Similarity NPD3728 Approved
0.5833 Remote Similarity NPD3195 Phase 2
0.5826 Remote Similarity NPD5345 Clinical (unspecified phase)
0.5824 Remote Similarity NPD6108 Clinical (unspecified phase)
0.582 Remote Similarity NPD8294 Approved
0.582 Remote Similarity NPD6054 Approved
0.582 Remote Similarity NPD8377 Approved
0.5814 Remote Similarity NPD6845 Suspended
0.5794 Remote Similarity NPD7078 Approved
0.5794 Remote Similarity NPD8293 Discontinued
0.5785 Remote Similarity NPD7327 Approved
0.5785 Remote Similarity NPD7328 Approved
0.5781 Remote Similarity NPD8390 Approved
0.5781 Remote Similarity NPD8392 Approved
0.5781 Remote Similarity NPD8391 Approved
0.5772 Remote Similarity NPD8380 Approved
0.5772 Remote Similarity NPD8267 Approved
0.5772 Remote Similarity NPD8266 Approved
0.5772 Remote Similarity NPD8378 Approved
0.5772 Remote Similarity NPD8296 Approved
0.5772 Remote Similarity NPD8379 Approved
0.5772 Remote Similarity NPD8268 Approved
0.5772 Remote Similarity NPD8335 Approved
0.5772 Remote Similarity NPD8269 Approved
0.576 Remote Similarity NPD8341 Approved
0.576 Remote Similarity NPD8342 Approved
0.576 Remote Similarity NPD8340 Approved
0.576 Remote Similarity NPD8299 Approved
0.5747 Remote Similarity NPD6109 Phase 1
0.5747 Remote Similarity NPD69 Approved
0.5747 Remote Similarity NPD9119 Approved
0.5743 Remote Similarity NPD4800 Clinical (unspecified phase)
0.5741 Remote Similarity NPD7748 Approved
0.5739 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5738 Remote Similarity NPD7516 Approved
0.5726 Remote Similarity NPD2067 Discontinued
0.5726 Remote Similarity NPD6370 Approved
0.5726 Remote Similarity NPD6421 Discontinued
0.5714 Remote Similarity NPD4632 Approved
0.5714 Remote Similarity NPD3172 Approved
0.5702 Remote Similarity NPD7505 Discontinued
0.5702 Remote Similarity NPD8137 Clinical (unspecified phase)
0.5691 Remote Similarity NPD6059 Approved
0.5678 Remote Similarity NPD6650 Approved
0.5678 Remote Similarity NPD6649 Approved
0.5663 Remote Similarity NPD6927 Phase 3
0.5652 Remote Similarity NPD6008 Approved
0.5652 Remote Similarity NPD7331 Phase 2
0.5645 Remote Similarity NPD8274 Clinical (unspecified phase)
0.5645 Remote Similarity NPD6015 Approved
0.5645 Remote Similarity NPD6016 Approved
0.5641 Remote Similarity NPD8132 Clinical (unspecified phase)
0.5641 Remote Similarity NPD6372 Approved
0.5641 Remote Similarity NPD6373 Approved
0.5636 Remote Similarity NPD4792 Clinical (unspecified phase)
0.5632 Remote Similarity NPD9118 Approved
0.5614 Remote Similarity NPD6647 Phase 2
0.5606 Remote Similarity NPD8415 Approved
0.56 Remote Similarity NPD5988 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