Structure

Physi-Chem Properties

Molecular Weight:  719.35
Volume:  706.62
LogP:  1.549
LogD:  1.078
LogS:  -3.886
# Rotatable Bonds:  7
TPSA:  229.38
# H-Bond Aceptor:  14
# H-Bond Donor:  7
# Rings:  6
# Heavy Atoms:  14

MedChem Properties

QED Drug-Likeness Score:  0.195
Synthetic Accessibility Score:  6.093
Fsp3:  0.784
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:  -5.378
MDCK Permeability:  1.6628271623631008e-05
Pgp-inhibitor:  0.999
Pgp-substrate:  0.992
Human Intestinal Absorption (HIA):  0.814
20% Bioavailability (F20%):  0.989
30% Bioavailability (F30%):  0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.09
Plasma Protein Binding (PPB):  73.43052673339844%
Volume Distribution (VD):  0.668
Pgp-substrate:  18.534238815307617%

ADMET: Metabolism

CYP1A2-inhibitor:  0.004
CYP1A2-substrate:  0.253
CYP2C19-inhibitor:  0.015
CYP2C19-substrate:  0.678
CYP2C9-inhibitor:  0.013
CYP2C9-substrate:  0.088
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.056
CYP3A4-inhibitor:  0.723
CYP3A4-substrate:  0.658

ADMET: Excretion

Clearance (CL):  1.483
Half-life (T1/2):  0.592

ADMET: Toxicity

hERG Blockers:  0.041
Human Hepatotoxicity (H-HT):  0.172
Drug-inuced Liver Injury (DILI):  0.145
AMES Toxicity:  0.075
Rat Oral Acute Toxicity:  0.174
Maximum Recommended Daily Dose:  0.928
Skin Sensitization:  0.176
Carcinogencity:  0.101
Eye Corrosion:  0.003
Eye Irritation:  0.006
Respiratory Toxicity:  0.242

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

  Natural Product: NPC803

Natural Product ID:  NPC803
Common Name*:   (16Alpha,20R,24R)-24N,25-Carbamoyloxy-2,16,20-Trihydroxycucurbita-1,5-Diene-3,11,22-Trione 2-O-Beta-D-Glucopyranoside
IUPAC Name:   (8S,9R,10R,13R,14S,16R,17R)-17-[(2R)-4-[(4R)-5,5-dimethyl-2-oxo-1,3-oxazolidin-4-yl]-2-hydroxy-3-oxobutan-2-yl]-16-hydroxy-4,4,9,13,14-pentamethyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthrene-3,11-dione
Synonyms:  
Standard InCHIKey:  LSGLQIRVQKVXDL-QZWHHHJSSA-N
Standard InCHI:  InChI=1S/C37H53NO13/c1-32(2)16-9-10-21-34(5)13-18(40)28(37(8,48)23(41)12-22-33(3,4)51-31(47)38-22)35(34,6)14-24(42)36(21,7)17(16)11-19(29(32)46)49-30-27(45)26(44)25(43)20(15-39)50-30/h9,11,17-18,20-22,25-28,30,39-40,43-45,48H,10,12-15H2,1-8H3,(H,38,47)/t17-,18-,20-,21+,22-,25-,26+,27-,28+,30-,34+,35-,36+,37+/m1/s1
SMILES:  CC1(C)C2=CC[C@H]3[C@]4(C)C[C@H]([C@@H]([C@@]4(C)CC(=O)[C@@]3(C)[C@@H]2C=C(C1=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)[C@](C)(C(=O)C[C@@H]1C(C)(C)OC(=N1)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1923783
PubChem CID:   56655722
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0001013] Steroidal glycosides

*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
NPO30742 Machilus yaoshansis Species Lauraceae Eukaryota root Dayao Mountain, Guangxi, China 2007-DEC PMID[22044245]
NPO30742 Machilus yaoshansis Species Lauraceae Eukaryota n.a. root n.a. PMID[22044245]
NPO30742 Machilus yaoshansis Species Lauraceae Eukaryota Roots n.a. n.a. PMID[22779787]

☑ 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
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens IC50 = 4260.0 nM PMID[551927]
NPT179 Cell Line A2780 Homo sapiens IC50 > 10000.0 nM PMID[551927]
NPT180 Cell Line HCT-8 Homo sapiens IC50 > 10000.0 nM PMID[551927]
NPT181 Cell Line Bel-7402 Homo sapiens IC50 > 10000.0 nM PMID[551927]
NPT81 Cell Line A549 Homo sapiens IC50 > 10000.0 nM PMID[551927]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 10000.0 nM PMID[551927]

☑ 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 NPC803 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
0.8561 High Similarity NPC93368
0.8538 High Similarity NPC42675
0.8409 Intermediate Similarity NPC141196
0.8409 Intermediate Similarity NPC238005
0.8409 Intermediate Similarity NPC1980
0.8346 Intermediate Similarity NPC190846
0.8346 Intermediate Similarity NPC277191
0.8284 Intermediate Similarity NPC198714
0.8248 Intermediate Similarity NPC139585
0.8222 Intermediate Similarity NPC152091
0.8209 Intermediate Similarity NPC475194
0.8162 Intermediate Similarity NPC293623
0.8162 Intermediate Similarity NPC168899
0.8162 Intermediate Similarity NPC69273
0.806 Intermediate Similarity NPC216866
0.8043 Intermediate Similarity NPC213634
0.8043 Intermediate Similarity NPC241008
0.7972 Intermediate Similarity NPC302276
0.7972 Intermediate Similarity NPC180770
0.7862 Intermediate Similarity NPC162910
0.7786 Intermediate Similarity NPC201359
0.7755 Intermediate Similarity NPC298469
0.7744 Intermediate Similarity NPC31797
0.7727 Intermediate Similarity NPC477944
0.7704 Intermediate Similarity NPC319570
0.7664 Intermediate Similarity NPC475431
0.7635 Intermediate Similarity NPC141669
0.7635 Intermediate Similarity NPC193579
0.7622 Intermediate Similarity NPC477072
0.7609 Intermediate Similarity NPC476542
0.7584 Intermediate Similarity NPC214821
0.7584 Intermediate Similarity NPC298067
0.7554 Intermediate Similarity NPC7850
0.7554 Intermediate Similarity NPC6615
0.7536 Intermediate Similarity NPC28532
0.7517 Intermediate Similarity NPC284625
0.7517 Intermediate Similarity NPC69176
0.75 Intermediate Similarity NPC176005
0.75 Intermediate Similarity NPC27551
0.75 Intermediate Similarity NPC114961
0.75 Intermediate Similarity NPC36463
0.75 Intermediate Similarity NPC298005
0.7483 Intermediate Similarity NPC265908
0.7483 Intermediate Similarity NPC471855
0.7483 Intermediate Similarity NPC61717
0.7483 Intermediate Similarity NPC244380
0.7463 Intermediate Similarity NPC73455
0.7463 Intermediate Similarity NPC260665
0.7463 Intermediate Similarity NPC200944
0.7445 Intermediate Similarity NPC161738
0.7429 Intermediate Similarity NPC177820
0.7429 Intermediate Similarity NPC30188
0.7429 Intermediate Similarity NPC473505
0.7424 Intermediate Similarity NPC304495
0.7424 Intermediate Similarity NPC246205
0.7424 Intermediate Similarity NPC470257
0.741 Intermediate Similarity NPC131824
0.7407 Intermediate Similarity NPC471398
0.7391 Intermediate Similarity NPC471406
0.7388 Intermediate Similarity NPC130427
0.7376 Intermediate Similarity NPC174367
0.7376 Intermediate Similarity NPC104427
0.7376 Intermediate Similarity NPC47113
0.7361 Intermediate Similarity NPC475472
0.7357 Intermediate Similarity NPC228701
0.7343 Intermediate Similarity NPC471407
0.7338 Intermediate Similarity NPC476544
0.7338 Intermediate Similarity NPC476545
0.7338 Intermediate Similarity NPC278163
0.7338 Intermediate Similarity NPC182900
0.7338 Intermediate Similarity NPC202051
0.7338 Intermediate Similarity NPC476543
0.7338 Intermediate Similarity NPC187950
0.7338 Intermediate Similarity NPC249553
0.7324 Intermediate Similarity NPC2757
0.7324 Intermediate Similarity NPC292290
0.7319 Intermediate Similarity NPC473920
0.7319 Intermediate Similarity NPC279143
0.731 Intermediate Similarity NPC73829
0.731 Intermediate Similarity NPC119794
0.7305 Intermediate Similarity NPC469841
0.7305 Intermediate Similarity NPC469842
0.7286 Intermediate Similarity NPC94072
0.7286 Intermediate Similarity NPC305771
0.7286 Intermediate Similarity NPC469943
0.7286 Intermediate Similarity NPC15918
0.7286 Intermediate Similarity NPC169816
0.7279 Intermediate Similarity NPC477580
0.7279 Intermediate Similarity NPC74727
0.7279 Intermediate Similarity NPC474557
0.7279 Intermediate Similarity NPC145899
0.7273 Intermediate Similarity NPC58370
0.7273 Intermediate Similarity NPC43285
0.7273 Intermediate Similarity NPC311534
0.726 Intermediate Similarity NPC76999
0.7246 Intermediate Similarity NPC86020
0.7246 Intermediate Similarity NPC475632
0.7239 Intermediate Similarity NPC475317
0.7239 Intermediate Similarity NPC52241
0.7239 Intermediate Similarity NPC154856
0.7234 Intermediate Similarity NPC27363
0.7234 Intermediate Similarity NPC227397
0.7218 Intermediate Similarity NPC473288
0.7214 Intermediate Similarity NPC275675
0.7214 Intermediate Similarity NPC133506
0.7211 Intermediate Similarity NPC235772
0.7211 Intermediate Similarity NPC75318
0.7211 Intermediate Similarity NPC280941
0.7206 Intermediate Similarity NPC178981
0.7203 Intermediate Similarity NPC240070
0.7203 Intermediate Similarity NPC305496
0.7203 Intermediate Similarity NPC329784
0.72 Intermediate Similarity NPC210729
0.72 Intermediate Similarity NPC172365
0.72 Intermediate Similarity NPC82931
0.7197 Intermediate Similarity NPC162033
0.7197 Intermediate Similarity NPC210178
0.7197 Intermediate Similarity NPC63023
0.7197 Intermediate Similarity NPC95243
0.7194 Intermediate Similarity NPC127530
0.7194 Intermediate Similarity NPC258592
0.7194 Intermediate Similarity NPC178548
0.7192 Intermediate Similarity NPC475487
0.7183 Intermediate Similarity NPC130229
0.7181 Intermediate Similarity NPC243680
0.7181 Intermediate Similarity NPC200788
0.7171 Intermediate Similarity NPC475892
0.7164 Intermediate Similarity NPC118225
0.7153 Intermediate Similarity NPC165439
0.7143 Intermediate Similarity NPC475187
0.7134 Intermediate Similarity NPC265699
0.7133 Intermediate Similarity NPC469750
0.7133 Intermediate Similarity NPC250556
0.7132 Intermediate Similarity NPC474265
0.7132 Intermediate Similarity NPC210420
0.7123 Intermediate Similarity NPC473805
0.7123 Intermediate Similarity NPC155529
0.7123 Intermediate Similarity NPC473519
0.7121 Intermediate Similarity NPC100955
0.7121 Intermediate Similarity NPC223741
0.7121 Intermediate Similarity NPC121566
0.7111 Intermediate Similarity NPC163314
0.7111 Intermediate Similarity NPC129340
0.7105 Intermediate Similarity NPC475584
0.7105 Intermediate Similarity NPC475394
0.7105 Intermediate Similarity NPC475152
0.7103 Intermediate Similarity NPC276838
0.7103 Intermediate Similarity NPC54614
0.7103 Intermediate Similarity NPC232785
0.7103 Intermediate Similarity NPC140092
0.7103 Intermediate Similarity NPC188234
0.7103 Intermediate Similarity NPC329986
0.7103 Intermediate Similarity NPC125077
0.7103 Intermediate Similarity NPC309096
0.7095 Intermediate Similarity NPC171619
0.7095 Intermediate Similarity NPC158350
0.7092 Intermediate Similarity NPC258789
0.7092 Intermediate Similarity NPC241310
0.7092 Intermediate Similarity NPC47567
0.7092 Intermediate Similarity NPC194310
0.7092 Intermediate Similarity NPC258815
0.7092 Intermediate Similarity NPC169727
0.7092 Intermediate Similarity NPC131841
0.7092 Intermediate Similarity NPC412
0.709 Intermediate Similarity NPC272576
0.7089 Intermediate Similarity NPC174336
0.7089 Intermediate Similarity NPC113620
0.7089 Intermediate Similarity NPC187497
0.7089 Intermediate Similarity NPC100612
0.7089 Intermediate Similarity NPC475599
0.7083 Intermediate Similarity NPC471357
0.7083 Intermediate Similarity NPC146456
0.7083 Intermediate Similarity NPC117702
0.7083 Intermediate Similarity NPC471356
0.7083 Intermediate Similarity NPC469757
0.7083 Intermediate Similarity NPC179412
0.708 Intermediate Similarity NPC194100
0.7077 Intermediate Similarity NPC474720
0.7075 Intermediate Similarity NPC102015
0.7075 Intermediate Similarity NPC476221
0.7075 Intermediate Similarity NPC477709
0.7067 Intermediate Similarity NPC79250
0.7067 Intermediate Similarity NPC290746
0.7063 Intermediate Similarity NPC473255
0.7059 Intermediate Similarity NPC43775
0.7055 Intermediate Similarity NPC159338
0.7055 Intermediate Similarity NPC253456
0.7055 Intermediate Similarity NPC16569
0.7055 Intermediate Similarity NPC173347
0.7047 Intermediate Similarity NPC141215
0.7047 Intermediate Similarity NPC190065
0.7047 Intermediate Similarity NPC127656
0.7047 Intermediate Similarity NPC471089
0.7042 Intermediate Similarity NPC313528
0.7042 Intermediate Similarity NPC471965
0.7042 Intermediate Similarity NPC156789
0.7037 Intermediate Similarity NPC474725
0.7037 Intermediate Similarity NPC265655
0.7037 Intermediate Similarity NPC8431
0.7034 Intermediate Similarity NPC475636

  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 NPC803 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
0.741 Intermediate Similarity NPD6370 Approved
0.7405 Intermediate Similarity NPD6412 Phase 2
0.7394 Intermediate Similarity NPD8336 Approved
0.7394 Intermediate Similarity NPD8337 Approved
0.7394 Intermediate Similarity NPD7736 Approved
0.7292 Intermediate Similarity NPD6914 Discontinued
0.7266 Intermediate Similarity NPD6054 Approved
0.7203 Intermediate Similarity NPD8293 Discontinued
0.7181 Intermediate Similarity NPD6334 Approved
0.7181 Intermediate Similarity NPD6333 Approved
0.7163 Intermediate Similarity NPD8080 Discontinued
0.7143 Intermediate Similarity NPD6059 Approved
0.7133 Intermediate Similarity NPD7507 Approved
0.7092 Intermediate Similarity NPD6016 Approved
0.7092 Intermediate Similarity NPD6015 Approved
0.7063 Intermediate Similarity NPD7492 Approved
0.7042 Intermediate Similarity NPD5988 Approved
0.7014 Intermediate Similarity NPD6616 Approved
0.7007 Intermediate Similarity NPD8297 Approved
0.7007 Intermediate Similarity NPD6882 Approved
0.6993 Remote Similarity NPD8328 Phase 3
0.6986 Remote Similarity NPD7319 Approved
0.6972 Remote Similarity NPD6909 Approved
0.6972 Remote Similarity NPD6908 Approved
0.6972 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6966 Remote Similarity NPD7078 Approved
0.6959 Remote Similarity NPD8338 Approved
0.6929 Remote Similarity NPD6009 Approved
0.6901 Remote Similarity NPD6319 Approved
0.6875 Remote Similarity NPD7604 Phase 2
0.6812 Remote Similarity NPD6650 Approved
0.6812 Remote Similarity NPD6649 Approved
0.6788 Remote Similarity NPD6373 Approved
0.6788 Remote Similarity NPD6372 Approved
0.6736 Remote Similarity NPD7503 Approved
0.6733 Remote Similarity NPD8449 Approved
0.6715 Remote Similarity NPD6686 Approved
0.6715 Remote Similarity NPD6881 Approved
0.6715 Remote Similarity NPD7320 Approved
0.6715 Remote Similarity NPD6899 Approved
0.6714 Remote Similarity NPD4632 Approved
0.6691 Remote Similarity NPD6675 Approved
0.6691 Remote Similarity NPD7128 Approved
0.6691 Remote Similarity NPD6402 Approved
0.6691 Remote Similarity NPD8130 Phase 1
0.6691 Remote Similarity NPD5739 Approved
0.669 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6689 Remote Similarity NPD8450 Suspended
0.6689 Remote Similarity NPD6033 Approved
0.6667 Remote Similarity NPD7260 Phase 2
0.6667 Remote Similarity NPD8377 Approved
0.6667 Remote Similarity NPD8294 Approved
0.6643 Remote Similarity NPD7327 Approved
0.6643 Remote Similarity NPD7328 Approved
0.6643 Remote Similarity NPD7641 Discontinued
0.6642 Remote Similarity NPD5697 Approved
0.6623 Remote Similarity NPD6845 Suspended
0.6621 Remote Similarity NPD8296 Approved
0.6621 Remote Similarity NPD8378 Approved
0.6621 Remote Similarity NPD8033 Approved
0.6621 Remote Similarity NPD8380 Approved
0.6621 Remote Similarity NPD8335 Approved
0.6621 Remote Similarity NPD8379 Approved
0.6619 Remote Similarity NPD6883 Approved
0.6619 Remote Similarity NPD7290 Approved
0.6619 Remote Similarity NPD7102 Approved
0.6604 Remote Similarity NPD7625 Phase 1
0.6597 Remote Similarity NPD7516 Approved
0.6573 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6571 Remote Similarity NPD6847 Approved
0.6571 Remote Similarity NPD6617 Approved
0.6571 Remote Similarity NPD6869 Approved
0.6547 Remote Similarity NPD6012 Approved
0.6547 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6547 Remote Similarity NPD6013 Approved
0.6547 Remote Similarity NPD6014 Approved
0.6541 Remote Similarity NPD6083 Phase 2
0.6541 Remote Similarity NPD6084 Phase 2
0.6522 Remote Similarity NPD5701 Approved
0.6515 Remote Similarity NPD5695 Phase 3
0.6507 Remote Similarity NPD5983 Phase 2
0.65 Remote Similarity NPD4634 Approved
0.649 Remote Similarity NPD5956 Approved
0.6475 Remote Similarity NPD6011 Approved
0.6444 Remote Similarity NPD5286 Approved
0.6444 Remote Similarity NPD5285 Approved
0.6444 Remote Similarity NPD4696 Approved
0.6443 Remote Similarity NPD6336 Discontinued
0.6418 Remote Similarity NPD4755 Approved
0.6382 Remote Similarity NPD8392 Approved
0.6382 Remote Similarity NPD8390 Approved
0.6382 Remote Similarity NPD8391 Approved
0.6377 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6376 Remote Similarity NPD8299 Approved
0.6376 Remote Similarity NPD8342 Approved
0.6376 Remote Similarity NPD8340 Approved
0.6376 Remote Similarity NPD8341 Approved
0.637 Remote Similarity NPD5696 Approved
0.6364 Remote Similarity NPD8133 Approved
0.635 Remote Similarity NPD5226 Approved
0.635 Remote Similarity NPD4633 Approved
0.635 Remote Similarity NPD5224 Approved
0.635 Remote Similarity NPD5225 Approved
0.635 Remote Similarity NPD5211 Phase 2
0.6338 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6333 Remote Similarity NPD8451 Approved
0.6324 Remote Similarity NPD4700 Approved
0.6309 Remote Similarity NPD7642 Approved
0.6309 Remote Similarity NPD6067 Discontinued
0.6304 Remote Similarity NPD5174 Approved
0.6304 Remote Similarity NPD5175 Approved
0.6294 Remote Similarity NPD6053 Discontinued
0.6291 Remote Similarity NPD8448 Approved
0.6282 Remote Similarity NPD8387 Clinical (unspecified phase)
0.6277 Remote Similarity NPD5223 Approved
0.6276 Remote Similarity NPD6274 Approved
0.6269 Remote Similarity NPD4629 Approved
0.6269 Remote Similarity NPD5210 Approved
0.626 Remote Similarity NPD4753 Phase 2
0.6259 Remote Similarity NPD7101 Approved
0.6259 Remote Similarity NPD7100 Approved
0.6259 Remote Similarity NPD5141 Approved
0.6241 Remote Similarity NPD4729 Approved
0.6241 Remote Similarity NPD4730 Approved
0.6218 Remote Similarity NPD8415 Approved
0.6214 Remote Similarity NPD6008 Approved
0.6214 Remote Similarity NPD4768 Approved
0.6214 Remote Similarity NPD4767 Approved
0.62 Remote Similarity NPD7829 Approved
0.62 Remote Similarity NPD7122 Discontinued
0.62 Remote Similarity NPD7830 Approved
0.619 Remote Similarity NPD6335 Approved
0.618 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6174 Remote Similarity NPD6921 Approved
0.6154 Remote Similarity NPD5248 Approved
0.6154 Remote Similarity NPD8407 Phase 2
0.6154 Remote Similarity NPD5247 Approved
0.6154 Remote Similarity NPD5249 Phase 3
0.6154 Remote Similarity NPD5250 Approved
0.6154 Remote Similarity NPD5251 Approved
0.6127 Remote Similarity NPD5128 Approved
0.6127 Remote Similarity NPD8174 Phase 2
0.6122 Remote Similarity NPD6317 Approved
0.6087 Remote Similarity NPD8424 Clinical (unspecified phase)
0.6081 Remote Similarity NPD6313 Approved
0.6081 Remote Similarity NPD6314 Approved
0.6077 Remote Similarity NPD8368 Discontinued
0.6071 Remote Similarity NPD8275 Approved
0.6071 Remote Similarity NPD4754 Approved
0.6071 Remote Similarity NPD8276 Approved
0.6067 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6045 Remote Similarity NPD6050 Approved
0.6031 Remote Similarity NPD5690 Phase 2
0.6022 Remote Similarity NPD8435 Approved
0.6015 Remote Similarity NPD6904 Approved
0.6015 Remote Similarity NPD6673 Approved
0.6015 Remote Similarity NPD6080 Approved
0.6014 Remote Similarity NPD7115 Discovery
0.6 Remote Similarity NPD5215 Approved
0.6 Remote Similarity NPD8084 Approved
0.6 Remote Similarity NPD8085 Approved
0.6 Remote Similarity NPD5217 Approved
0.6 Remote Similarity NPD8138 Approved
0.6 Remote Similarity NPD8082 Approved
0.6 Remote Similarity NPD8086 Approved
0.6 Remote Similarity NPD5216 Approved
0.6 Remote Similarity NPD8139 Approved
0.6 Remote Similarity NPD8083 Approved
0.5986 Remote Similarity NPD8393 Approved
0.5985 Remote Similarity NPD5220 Clinical (unspecified phase)
0.5985 Remote Similarity NPD5221 Approved
0.5985 Remote Similarity NPD4697 Phase 3
0.5985 Remote Similarity NPD5222 Approved
0.5974 Remote Similarity NPD8074 Phase 3
0.597 Remote Similarity NPD5692 Phase 3
0.596 Remote Similarity NPD8516 Approved
0.596 Remote Similarity NPD8266 Approved
0.596 Remote Similarity NPD8269 Approved
0.596 Remote Similarity NPD8444 Approved
0.596 Remote Similarity NPD8515 Approved
0.596 Remote Similarity NPD8517 Approved
0.596 Remote Similarity NPD8267 Approved
0.596 Remote Similarity NPD8268 Approved
0.596 Remote Similarity NPD8513 Phase 3
0.5956 Remote Similarity NPD5282 Discontinued
0.5954 Remote Similarity NPD5329 Approved
0.5944 Remote Similarity NPD7799 Discontinued
0.5944 Remote Similarity NPD7899 Clinical (unspecified phase)
0.5942 Remote Similarity NPD5173 Approved
0.594 Remote Similarity NPD5737 Approved
0.594 Remote Similarity NPD6672 Approved
0.5936 Remote Similarity NPD8360 Approved
0.5936 Remote Similarity NPD8361 Approved
0.5933 Remote Similarity NPD4522 Approved
0.5931 Remote Similarity NPD6420 Discontinued
0.5931 Remote Similarity NPD5169 Approved
0.5931 Remote Similarity NPD6421 Discontinued
0.5931 Remote Similarity NPD5134 Clinical (unspecified phase)
0.5931 Remote Similarity NPD5135 Approved
0.5926 Remote Similarity NPD6079 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