Structure

Physi-Chem Properties

Molecular Weight:  686.29
Volume:  678.974
LogP:  3.558
LogD:  1.887
LogS:  -4.726
# Rotatable Bonds:  15
TPSA:  177.4
# H-Bond Aceptor:  13
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  13

MedChem Properties

QED Drug-Likeness Score:  0.111
Synthetic Accessibility Score:  6.349
Fsp3:  0.639
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:  -5.387
MDCK Permeability:  9.465526818530634e-05
Pgp-inhibitor:  0.877
Pgp-substrate:  0.389
Human Intestinal Absorption (HIA):  0.655
20% Bioavailability (F20%):  0.957
30% Bioavailability (F30%):  0.966

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.185
Plasma Protein Binding (PPB):  63.93415832519531%
Volume Distribution (VD):  1.552
Pgp-substrate:  20.362455368041992%

ADMET: Metabolism

CYP1A2-inhibitor:  0.008
CYP1A2-substrate:  0.048
CYP2C19-inhibitor:  0.088
CYP2C19-substrate:  0.279
CYP2C9-inhibitor:  0.443
CYP2C9-substrate:  0.003
CYP2D6-inhibitor:  0.021
CYP2D6-substrate:  0.027
CYP3A4-inhibitor:  0.898
CYP3A4-substrate:  0.557

ADMET: Excretion

Clearance (CL):  6.38
Half-life (T1/2):  0.702

ADMET: Toxicity

hERG Blockers:  0.492
Human Hepatotoxicity (H-HT):  0.826
Drug-inuced Liver Injury (DILI):  0.557
AMES Toxicity:  0.014
Rat Oral Acute Toxicity:  0.937
Maximum Recommended Daily Dose:  0.979
Skin Sensitization:  0.085
Carcinogencity:  0.104
Eye Corrosion:  0.003
Eye Irritation:  0.014
Respiratory Toxicity:  0.979

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

  Natural Product: NPC259943

Natural Product ID:  NPC259943
Common Name*:   Mombasol
IUPAC Name:   [(1aR,3R,3aR,4R,5R,6R,7aS)-6-[(2S,3R,4R)-2-(acetyloxymethyl)-3-(2-methoxy-2-oxoethyl)-2,4-dimethyl-7-oxo-3H-oxepin-4-yl]-5-formyloxy-3-(furan-3-yl)-3a-methyl-7-methylidene-1a,2,3,4,5,6-hexahydroindeno[1,7a-b]oxiren-4-yl] (2R,3R)-2-hydroxy-3-methylpentanoate
Synonyms:  
Standard InCHIKey:  YRFRXISQCYTJMQ-QMKHVEKRSA-N
Standard InCHI:  InChI=1S/C36H46O13/c1-9-19(2)29(41)32(42)47-31-30(46-18-37)28(20(3)36-25(48-36)14-23(35(31,36)7)22-11-13-44-16-22)33(5)12-10-26(39)49-34(6,17-45-21(4)38)24(33)15-27(40)43-8/h10-13,16,18-19,23-25,28-31,41H,3,9,14-15,17H2,1-2,4-8H3/t19-,23-,24-,25-,28-,29-,30-,31+,33+,34-,35-,36-/m1/s1
SMILES:  O=CO[C@@H]1[C@@H](C(=C)[C@@]23[C@]([C@H]1OC(=O)[C@@H]([C@@H](CC)C)O)(C)[C@H](C[C@H]3O2)c1cocc1)[C@@]1(C)C=CC(=O)O[C@]([C@@H]1CC(=O)OC)(C)COC(=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2229170
PubChem CID:   76325974
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000265] Carboxylic acids and derivatives
        • [CHEMONTID:0002995] Pentacarboxylic acids and derivatives

*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
NPO33254 munronia unifoliolata oliv Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[22500574]
NPO9173 Munronia henryi Species Meliaceae Eukaryota whole plants Wenshan, Yunnan Province, China 2012-Nov PMID[25798528]
NPO9173 Munronia henryi Species Meliaceae 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
NPT116 Cell Line HL-60 Homo sapiens IC50 > 10000.0 nM PMID[492494]
NPT659 Cell Line SMMC-7721 Homo sapiens IC50 > 10000.0 nM PMID[492494]
NPT81 Cell Line A549 Homo sapiens IC50 > 10000.0 nM PMID[492494]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 10000.0 nM PMID[492494]
NPT660 Cell Line SW480 Homo sapiens IC50 > 10000.0 nM PMID[492494]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 25.9 % PMID[492493]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 39.3 % PMID[492493]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 27.7 % PMID[492493]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 47.6 % PMID[492494]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 38.9 % PMID[492494]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 31.6 % PMID[492494]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 28.1 % PMID[492494]

☑ 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 NPC259943 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
0.9745 High Similarity NPC472650
0.9412 High Similarity NPC84063
0.9241 High Similarity NPC5741
0.9136 High Similarity NPC472659
0.9085 High Similarity NPC471632
0.8987 High Similarity NPC175964
0.8987 High Similarity NPC471169
0.8924 High Similarity NPC471175
0.8882 High Similarity NPC472668
0.8841 High Similarity NPC242334
0.8827 High Similarity NPC472669
0.8758 High Similarity NPC472671
0.8727 High Similarity NPC472673
0.8713 High Similarity NPC247563
0.8713 High Similarity NPC105395
0.8713 High Similarity NPC242068
0.8704 High Similarity NPC470789
0.8679 High Similarity NPC268905
0.865 High Similarity NPC471166
0.865 High Similarity NPC471167
0.8642 High Similarity NPC472779
0.8631 High Similarity NPC94763
0.8614 High Similarity NPC472766
0.8614 High Similarity NPC472652
0.8614 High Similarity NPC472765
0.8608 High Similarity NPC69647
0.8608 High Similarity NPC125182
0.858 High Similarity NPC475066
0.8563 High Similarity NPC470995
0.8554 High Similarity NPC472651
0.8554 High Similarity NPC472764
0.8545 High Similarity NPC271657
0.8538 High Similarity NPC470938
0.8537 High Similarity NPC290400
0.8537 High Similarity NPC470792
0.8537 High Similarity NPC96443
0.8528 High Similarity NPC475226
0.8521 High Similarity NPC236004
0.8512 High Similarity NPC159232
0.8512 High Similarity NPC285227
0.8509 High Similarity NPC302054
0.8509 High Similarity NPC253201
0.8503 High Similarity NPC271235
0.8494 Intermediate Similarity NPC472670
0.8494 Intermediate Similarity NPC307781
0.8485 Intermediate Similarity NPC472139
0.8485 Intermediate Similarity NPC471168
0.8481 Intermediate Similarity NPC255414
0.8476 Intermediate Similarity NPC472653
0.8471 Intermediate Similarity NPC469633
0.8466 Intermediate Similarity NPC214495
0.8466 Intermediate Similarity NPC470119
0.8462 Intermediate Similarity NPC469848
0.8447 Intermediate Similarity NPC472672
0.8443 Intermediate Similarity NPC472774
0.8443 Intermediate Similarity NPC472775
0.8443 Intermediate Similarity NPC476224
0.8424 Intermediate Similarity NPC472767
0.8424 Intermediate Similarity NPC18347
0.8424 Intermediate Similarity NPC149896
0.8424 Intermediate Similarity NPC117986
0.8421 Intermediate Similarity NPC478177
0.8415 Intermediate Similarity NPC474932
0.8415 Intermediate Similarity NPC475967
0.8412 Intermediate Similarity NPC469576
0.8412 Intermediate Similarity NPC471437
0.8393 Intermediate Similarity NPC327922
0.8393 Intermediate Similarity NPC160651
0.8393 Intermediate Similarity NPC471397
0.8391 Intermediate Similarity NPC186746
0.8383 Intermediate Similarity NPC149945
0.8383 Intermediate Similarity NPC478178
0.8383 Intermediate Similarity NPC23387
0.8373 Intermediate Similarity NPC302369
0.8373 Intermediate Similarity NPC39986
0.8373 Intermediate Similarity NPC134254
0.8354 Intermediate Similarity NPC470118
0.8354 Intermediate Similarity NPC5676
0.8354 Intermediate Similarity NPC187149
0.8354 Intermediate Similarity NPC197137
0.8354 Intermediate Similarity NPC45101
0.8354 Intermediate Similarity NPC299038
0.8333 Intermediate Similarity NPC476853
0.8333 Intermediate Similarity NPC182427
0.8333 Intermediate Similarity NPC173516
0.8333 Intermediate Similarity NPC29695
0.8333 Intermediate Similarity NPC478179
0.8333 Intermediate Similarity NPC476850
0.8333 Intermediate Similarity NPC472282
0.8333 Intermediate Similarity NPC476861
0.8323 Intermediate Similarity NPC476857
0.8323 Intermediate Similarity NPC476856
0.8323 Intermediate Similarity NPC476858
0.8323 Intermediate Similarity NPC476860
0.8314 Intermediate Similarity NPC470181
0.8313 Intermediate Similarity NPC200782
0.8293 Intermediate Similarity NPC126723
0.8282 Intermediate Similarity NPC98206
0.8282 Intermediate Similarity NPC237259
0.8282 Intermediate Similarity NPC34421
0.8274 Intermediate Similarity NPC472141
0.8274 Intermediate Similarity NPC470875
0.8274 Intermediate Similarity NPC214600
0.8272 Intermediate Similarity NPC18135
0.8263 Intermediate Similarity NPC472773
0.8263 Intermediate Similarity NPC234660
0.8263 Intermediate Similarity NPC165218
0.8263 Intermediate Similarity NPC469846
0.8263 Intermediate Similarity NPC51568
0.8261 Intermediate Similarity NPC472654
0.8256 Intermediate Similarity NPC262386
0.8253 Intermediate Similarity NPC335761
0.8242 Intermediate Similarity NPC36655
0.8242 Intermediate Similarity NPC261597
0.8242 Intermediate Similarity NPC472778
0.8242 Intermediate Similarity NPC472777
0.8242 Intermediate Similarity NPC472776
0.8235 Intermediate Similarity NPC82602
0.8232 Intermediate Similarity NPC214541
0.8232 Intermediate Similarity NPC155939
0.8232 Intermediate Similarity NPC44675
0.8232 Intermediate Similarity NPC296807
0.8232 Intermediate Similarity NPC141538
0.8232 Intermediate Similarity NPC92979
0.8221 Intermediate Similarity NPC308205
0.8221 Intermediate Similarity NPC322546
0.8221 Intermediate Similarity NPC33938
0.8214 Intermediate Similarity NPC276551
0.8214 Intermediate Similarity NPC123088
0.8214 Intermediate Similarity NPC469849
0.821 Intermediate Similarity NPC470997
0.8204 Intermediate Similarity NPC329938
0.8204 Intermediate Similarity NPC197596
0.8204 Intermediate Similarity NPC5079
0.8204 Intermediate Similarity NPC472771
0.8204 Intermediate Similarity NPC6326
0.8204 Intermediate Similarity NPC82851
0.8198 Intermediate Similarity NPC477824
0.8187 Intermediate Similarity NPC160818
0.8187 Intermediate Similarity NPC169299
0.8182 Intermediate Similarity NPC204663
0.8176 Intermediate Similarity NPC251865
0.8171 Intermediate Similarity NPC57998
0.8171 Intermediate Similarity NPC254588
0.8166 Intermediate Similarity NPC93172
0.8166 Intermediate Similarity NPC97574
0.8165 Intermediate Similarity NPC121158
0.8155 Intermediate Similarity NPC469338
0.8155 Intermediate Similarity NPC292389
0.8155 Intermediate Similarity NPC477405
0.8148 Intermediate Similarity NPC470790
0.8148 Intermediate Similarity NPC470791
0.8148 Intermediate Similarity NPC234494
0.8144 Intermediate Similarity NPC25255
0.8144 Intermediate Similarity NPC477402
0.8133 Intermediate Similarity NPC195131
0.8133 Intermediate Similarity NPC195954
0.8133 Intermediate Similarity NPC88007
0.8133 Intermediate Similarity NPC194499
0.8129 Intermediate Similarity NPC118086
0.8121 Intermediate Similarity NPC476262
0.8113 Intermediate Similarity NPC80635
0.8113 Intermediate Similarity NPC243577
0.8107 Intermediate Similarity NPC470940
0.8098 Intermediate Similarity NPC156189
0.8095 Intermediate Similarity NPC68848
0.8095 Intermediate Similarity NPC69028
0.8095 Intermediate Similarity NPC193798
0.8084 Intermediate Similarity NPC475295
0.8084 Intermediate Similarity NPC84349
0.8084 Intermediate Similarity NPC473473
0.8081 Intermediate Similarity NPC475237
0.8081 Intermediate Similarity NPC475641
0.8057 Intermediate Similarity NPC11062
0.8049 Intermediate Similarity NPC116717
0.8047 Intermediate Similarity NPC285567
0.8047 Intermediate Similarity NPC283209
0.8047 Intermediate Similarity NPC224394
0.8047 Intermediate Similarity NPC663
0.8038 Intermediate Similarity NPC67003
0.8037 Intermediate Similarity NPC470998
0.8025 Intermediate Similarity NPC471174
0.8025 Intermediate Similarity NPC216755
0.8025 Intermediate Similarity NPC221809
0.8024 Intermediate Similarity NPC469847
0.8024 Intermediate Similarity NPC472772
0.8024 Intermediate Similarity NPC249021
0.8024 Intermediate Similarity NPC286722
0.8024 Intermediate Similarity NPC167142
0.8024 Intermediate Similarity NPC173544
0.8012 Intermediate Similarity NPC100333
0.8012 Intermediate Similarity NPC264943
0.8 Intermediate Similarity NPC75906
0.8 Intermediate Similarity NPC261184
0.8 Intermediate Similarity NPC469503
0.8 Intermediate Similarity NPC246164
0.8 Intermediate Similarity NPC470996
0.8 Intermediate Similarity NPC470182
0.8 Intermediate Similarity NPC476201
0.7988 Intermediate Similarity NPC196846

  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 NPC259943 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
0.8121 Intermediate Similarity NPD5760 Phase 2
0.8121 Intermediate Similarity NPD5761 Phase 2
0.7921 Intermediate Similarity NPD8434 Phase 2
0.764 Intermediate Similarity NPD6764 Approved
0.764 Intermediate Similarity NPD6765 Approved
0.7473 Intermediate Similarity NPD6785 Approved
0.7473 Intermediate Similarity NPD6784 Approved
0.7377 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7253 Intermediate Similarity NPD7685 Pre-registration
0.7216 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD4628 Phase 3
0.7135 Intermediate Similarity NPD8127 Discontinued
0.7033 Intermediate Similarity NPD7799 Discontinued
0.7006 Intermediate Similarity NPD5763 Approved
0.7006 Intermediate Similarity NPD5762 Approved
0.7 Intermediate Similarity NPD7236 Approved
0.6977 Remote Similarity NPD6273 Approved
0.6914 Remote Similarity NPD6599 Discontinued
0.6912 Remote Similarity NPD8404 Phase 2
0.6911 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6904 Remote Similarity NPD7497 Discontinued
0.6897 Remote Similarity NPD7239 Suspended
0.6893 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6872 Remote Similarity NPD7075 Discontinued
0.6868 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6851 Remote Similarity NPD7199 Phase 2
0.6811 Remote Similarity NPD5844 Phase 1
0.6805 Remote Similarity NPD6004 Phase 3
0.6805 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6805 Remote Similarity NPD6005 Phase 3
0.6805 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6805 Remote Similarity NPD6002 Phase 3
0.6798 Remote Similarity NPD7819 Suspended
0.6742 Remote Similarity NPD6801 Discontinued
0.6738 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6722 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6707 Remote Similarity NPD6355 Discontinued
0.6702 Remote Similarity NPD6559 Discontinued
0.6667 Remote Similarity NPD5402 Approved
0.6667 Remote Similarity NPD3817 Phase 2
0.6667 Remote Similarity NPD6799 Approved
0.6667 Remote Similarity NPD6653 Approved
0.6632 Remote Similarity NPD8312 Approved
0.6632 Remote Similarity NPD8313 Approved
0.6631 Remote Similarity NPD7804 Clinical (unspecified phase)
0.663 Remote Similarity NPD4965 Approved
0.663 Remote Similarity NPD4966 Approved
0.663 Remote Similarity NPD4967 Phase 2
0.6629 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6615 Remote Similarity NPD8150 Discontinued
0.6614 Remote Similarity NPD8368 Discontinued
0.6597 Remote Similarity NPD8407 Phase 2
0.659 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6579 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6578 Remote Similarity NPD3818 Discontinued
0.6578 Remote Similarity NPD3751 Discontinued
0.6557 Remote Similarity NPD6234 Discontinued
0.6557 Remote Similarity NPD919 Approved
0.6556 Remote Similarity NPD37 Approved
0.6552 Remote Similarity NPD6190 Approved
0.6543 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6541 Remote Similarity NPD3787 Discontinued
0.6538 Remote Similarity NPD3882 Suspended
0.6538 Remote Similarity NPD7057 Phase 3
0.6538 Remote Similarity NPD7058 Phase 2
0.6534 Remote Similarity NPD2532 Approved
0.6534 Remote Similarity NPD2533 Approved
0.6534 Remote Similarity NPD2534 Approved
0.6524 Remote Similarity NPD7473 Discontinued
0.6522 Remote Similarity NPD5494 Approved
0.6512 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6503 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6497 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6492 Remote Similarity NPD7808 Phase 3
0.6489 Remote Similarity NPD7228 Approved
0.6486 Remote Similarity NPD1247 Approved
0.6485 Remote Similarity NPD5647 Approved
0.6485 Remote Similarity NPD7435 Discontinued
0.648 Remote Similarity NPD7458 Discontinued
0.6471 Remote Similarity NPD6166 Phase 2
0.6471 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6471 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6461 Remote Similarity NPD920 Approved
0.6461 Remote Similarity NPD5403 Approved
0.6452 Remote Similarity NPD6232 Discontinued
0.645 Remote Similarity NPD4140 Approved
0.6444 Remote Similarity NPD4380 Phase 2
0.6444 Remote Similarity NPD7028 Phase 2
0.6442 Remote Similarity NPD7507 Approved
0.6441 Remote Similarity NPD5401 Approved
0.644 Remote Similarity NPD7251 Discontinued
0.6437 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6429 Remote Similarity NPD8455 Phase 2
0.6429 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6424 Remote Similarity NPD7319 Approved
0.6421 Remote Similarity NPD7074 Phase 3
0.6412 Remote Similarity NPD5735 Approved
0.64 Remote Similarity NPD7982 Clinical (unspecified phase)
0.64 Remote Similarity NPD4109 Clinical (unspecified phase)
0.64 Remote Similarity NPD4110 Phase 3
0.6395 Remote Similarity NPD2799 Discontinued
0.6393 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6389 Remote Similarity NPD3226 Approved
0.6387 Remote Similarity NPD6797 Phase 2
0.6386 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6385 Remote Similarity NPD7907 Approved
0.6384 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6378 Remote Similarity NPD8361 Approved
0.6378 Remote Similarity NPD8360 Approved
0.6378 Remote Similarity NPD8435 Approved
0.6378 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6377 Remote Similarity NPD7874 Approved
0.6377 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6374 Remote Similarity NPD1934 Approved
0.6368 Remote Similarity NPD7054 Approved
0.6368 Remote Similarity NPD4111 Phase 1
0.6359 Remote Similarity NPD8424 Clinical (unspecified phase)
0.6354 Remote Similarity NPD7240 Approved
0.6348 Remote Similarity NPD642 Clinical (unspecified phase)
0.6348 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6341 Remote Similarity NPD7999 Approved
0.6339 Remote Similarity NPD1465 Phase 2
0.6339 Remote Similarity NPD2801 Approved
0.6337 Remote Similarity NPD6781 Approved
0.6337 Remote Similarity NPD6778 Approved
0.6337 Remote Similarity NPD6776 Approved
0.6337 Remote Similarity NPD6780 Approved
0.6337 Remote Similarity NPD6779 Approved
0.6337 Remote Similarity NPD6777 Approved
0.6337 Remote Similarity NPD6782 Approved
0.6335 Remote Similarity NPD7472 Approved
0.6331 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6326 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6325 Remote Similarity NPD6362 Approved
0.6324 Remote Similarity NPD7697 Approved
0.6324 Remote Similarity NPD7698 Approved
0.6324 Remote Similarity NPD7696 Phase 3
0.6319 Remote Similarity NPD7411 Suspended
0.6316 Remote Similarity NPD230 Phase 1
0.6301 Remote Similarity NPD7033 Discontinued
0.6298 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6294 Remote Similarity NPD6233 Phase 2
0.6294 Remote Similarity NPD8032 Phase 2
0.6293 Remote Similarity NPD7870 Phase 2
0.6293 Remote Similarity NPD7871 Phase 2
0.6291 Remote Similarity NPD4665 Approved
0.6286 Remote Similarity NPD970 Clinical (unspecified phase)
0.628 Remote Similarity NPD7701 Phase 2
0.6278 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6275 Remote Similarity NPD3057 Approved
0.6272 Remote Similarity NPD7095 Approved
0.627 Remote Similarity NPD7768 Phase 2
0.6268 Remote Similarity NPD7801 Approved
0.6264 Remote Similarity NPD1551 Phase 2
0.6264 Remote Similarity NPD6100 Approved
0.6264 Remote Similarity NPD6099 Approved
0.6257 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6256 Remote Similarity NPD7930 Approved
0.6256 Remote Similarity NPD4107 Approved
0.6243 Remote Similarity NPD3926 Phase 2
0.6242 Remote Similarity NPD1608 Approved
0.6237 Remote Similarity NPD3749 Approved
0.6236 Remote Similarity NPD643 Clinical (unspecified phase)
0.6235 Remote Similarity NPD6798 Discontinued
0.6229 Remote Similarity NPD2346 Discontinued
0.6229 Remote Similarity NPD1471 Phase 3
0.6221 Remote Similarity NPD447 Suspended
0.6215 Remote Similarity NPD3750 Approved
0.6215 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6214 Remote Similarity NPD8319 Approved
0.6214 Remote Similarity NPD8320 Phase 1
0.6211 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6199 Remote Similarity NPD6663 Approved
0.6195 Remote Similarity NPD3533 Approved
0.6195 Remote Similarity NPD2972 Approved
0.619 Remote Similarity NPD7782 Clinical (unspecified phase)
0.619 Remote Similarity NPD7229 Phase 3
0.619 Remote Similarity NPD7783 Phase 2
0.619 Remote Similarity NPD7315 Approved
0.6188 Remote Similarity NPD8485 Approved
0.6185 Remote Similarity NPD6353 Approved
0.618 Remote Similarity NPD3887 Approved
0.618 Remote Similarity NPD2354 Approved
0.6171 Remote Similarity NPD2796 Approved
0.6171 Remote Similarity NPD2935 Discontinued
0.6163 Remote Similarity NPD4060 Phase 1
0.6159 Remote Similarity NPD1778 Approved
0.6158 Remote Similarity NPD2800 Approved
0.6158 Remote Similarity NPD7699 Phase 2
0.6158 Remote Similarity NPD7700 Phase 2
0.6154 Remote Similarity NPD9494 Approved
0.6149 Remote Similarity NPD7097 Phase 1
0.6146 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6146 Remote Similarity NPD4482 Phase 3
0.614 Remote Similarity NPD7985 Registered
0.614 Remote Similarity NPD1699 Clinical (unspecified phase)
0.6138 Remote Similarity NPD6959 Discontinued
0.6133 Remote Similarity NPD1512 Approved
0.6129 Remote Similarity NPD5353 Approved
0.6124 Remote Similarity NPD8166 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