Structure

Physi-Chem Properties

Molecular Weight:  708.37
Volume:  706.816
LogP:  0.967
LogD:  0.955
LogS:  -3.714
# Rotatable Bonds:  9
TPSA:  220.51
# H-Bond Aceptor:  13
# H-Bond Donor:  7
# Rings:  5
# Heavy Atoms:  13

MedChem Properties

QED Drug-Likeness Score:  0.174
Synthetic Accessibility Score:  6.104
Fsp3:  0.811
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:  -5.153
MDCK Permeability:  1.2000802598777227e-05
Pgp-inhibitor:  0.999
Pgp-substrate:  0.992
Human Intestinal Absorption (HIA):  0.882
20% Bioavailability (F20%):  0.353
30% Bioavailability (F30%):  0.916

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.139
Plasma Protein Binding (PPB):  59.28528594970703%
Volume Distribution (VD):  0.546
Pgp-substrate:  18.47601318359375%

ADMET: Metabolism

CYP1A2-inhibitor:  0.001
CYP1A2-substrate:  0.249
CYP2C19-inhibitor:  0.003
CYP2C19-substrate:  0.659
CYP2C9-inhibitor:  0.001
CYP2C9-substrate:  0.041
CYP2D6-inhibitor:  0.0
CYP2D6-substrate:  0.044
CYP3A4-inhibitor:  0.184
CYP3A4-substrate:  0.276

ADMET: Excretion

Clearance (CL):  2.03
Half-life (T1/2):  0.769

ADMET: Toxicity

hERG Blockers:  0.023
Human Hepatotoxicity (H-HT):  0.223
Drug-inuced Liver Injury (DILI):  0.034
AMES Toxicity:  0.104
Rat Oral Acute Toxicity:  0.883
Maximum Recommended Daily Dose:  0.913
Skin Sensitization:  0.044
Carcinogencity:  0.656
Eye Corrosion:  0.003
Eye Irritation:  0.007
Respiratory Toxicity:  0.925

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

  Natural Product: NPC238005

Natural Product ID:  NPC238005
Common Name*:   (16Alpha,20R,24S)-2,16,20,25-Tetrahydroxy-24-Methoxycucurbita-1,5-Diene-3,11,22-Trione 2-O-Beta-D-Glucopyranoside
IUPAC Name:   (8S,9R,10R,13R,14S,16R,17R)-17-[(2R,5S)-2,6-dihydroxy-5-methoxy-6-methyl-3-oxoheptan-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:  VFYMEDSYUASGPF-WLPFVFARSA-N
Standard InCHI:  InChI=1S/C37H56O13/c1-32(2)17-10-11-22-34(5)14-19(39)29(37(8,47)23(40)13-25(48-9)33(3,4)46)35(34,6)15-24(41)36(22,7)18(17)12-20(30(32)45)49-31-28(44)27(43)26(42)21(16-38)50-31/h10,12,18-19,21-22,25-29,31,38-39,42-44,46-47H,11,13-16H2,1-9H3/t18-,19-,21-,22+,25+,26-,27+,28-,29+,31-,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](C(C)(C)O)OC)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1923784
PubChem CID:   56833752
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0001013] Steroidal glycosides
          • [CHEMONTID:0002364] Steroidal saponins
            • [CHEMONTID:0001687] Cucurbitacin 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
NPT179 Cell Line A2780 Homo sapiens IC50 > 10000.0 nM PMID[518759]
NPT180 Cell Line HCT-8 Homo sapiens IC50 > 10000.0 nM PMID[518759]
NPT181 Cell Line Bel-7402 Homo sapiens IC50 > 10000.0 nM PMID[518759]
NPT81 Cell Line A549 Homo sapiens IC50 > 10000.0 nM PMID[518759]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 10000.0 nM PMID[518759]

☑ 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 NPC238005 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 NPC1980
1.0 High Similarity NPC141196
0.9826 High Similarity NPC198714
0.9823 High Similarity NPC42675
0.9565 High Similarity NPC216866
0.9487 High Similarity NPC93368
0.9407 High Similarity NPC152091
0.9402 High Similarity NPC277191
0.9402 High Similarity NPC190846
0.9174 High Similarity NPC213634
0.9138 High Similarity NPC319570
0.9076 High Similarity NPC475194
0.9008 High Similarity NPC69273
0.9008 High Similarity NPC168899
0.9008 High Similarity NPC293623
0.8917 High Similarity NPC7850
0.8917 High Similarity NPC6615
0.8879 High Similarity NPC31797
0.8862 High Similarity NPC241008
0.885 High Similarity NPC470257
0.876 High Similarity NPC30188
0.876 High Similarity NPC177820
0.8707 High Similarity NPC477944
0.8673 High Similarity NPC58370
0.8673 High Similarity NPC43285
0.8667 High Similarity NPC278163
0.8667 High Similarity NPC187950
0.8609 High Similarity NPC114961
0.8609 High Similarity NPC27551
0.8607 High Similarity NPC469841
0.8607 High Similarity NPC469842
0.8595 High Similarity NPC28532
0.8571 High Similarity NPC176005
0.8571 High Similarity NPC475632
0.8571 High Similarity NPC86020
0.8547 High Similarity NPC260665
0.8547 High Similarity NPC73455
0.8547 High Similarity NPC200944
0.8537 High Similarity NPC47113
0.8537 High Similarity NPC174367
0.8537 High Similarity NPC104427
0.8522 High Similarity NPC304495
0.8522 High Similarity NPC246205
0.85 High Similarity NPC178548
0.85 High Similarity NPC258592
0.8492 Intermediate Similarity NPC471855
0.8468 Intermediate Similarity NPC292290
0.8468 Intermediate Similarity NPC2757
0.8462 Intermediate Similarity NPC130427
0.8455 Intermediate Similarity NPC130229
0.8443 Intermediate Similarity NPC475431
0.843 Intermediate Similarity NPC475187
0.843 Intermediate Similarity NPC471406
0.8409 Intermediate Similarity NPC803
0.8374 Intermediate Similarity NPC476542
0.8361 Intermediate Similarity NPC241310
0.8361 Intermediate Similarity NPC131841
0.8361 Intermediate Similarity NPC169727
0.8361 Intermediate Similarity NPC47567
0.8361 Intermediate Similarity NPC412
0.8361 Intermediate Similarity NPC194310
0.8361 Intermediate Similarity NPC258789
0.8361 Intermediate Similarity NPC258815
0.8361 Intermediate Similarity NPC202051
0.8347 Intermediate Similarity NPC161738
0.8347 Intermediate Similarity NPC473920
0.8347 Intermediate Similarity NPC279143
0.8333 Intermediate Similarity NPC471407
0.8333 Intermediate Similarity NPC309096
0.8333 Intermediate Similarity NPC54614
0.832 Intermediate Similarity NPC305496
0.8319 Intermediate Similarity NPC116024
0.8319 Intermediate Similarity NPC74727
0.8319 Intermediate Similarity NPC471398
0.8319 Intermediate Similarity NPC474557
0.8306 Intermediate Similarity NPC473505
0.8293 Intermediate Similarity NPC471965
0.8293 Intermediate Similarity NPC156789
0.8293 Intermediate Similarity NPC131824
0.8291 Intermediate Similarity NPC52241
0.8291 Intermediate Similarity NPC154856
0.8291 Intermediate Similarity NPC475317
0.8281 Intermediate Similarity NPC475487
0.8279 Intermediate Similarity NPC476849
0.8276 Intermediate Similarity NPC473288
0.8268 Intermediate Similarity NPC173347
0.8261 Intermediate Similarity NPC210178
0.8261 Intermediate Similarity NPC162033
0.8254 Intermediate Similarity NPC245094
0.8254 Intermediate Similarity NPC295220
0.8254 Intermediate Similarity NPC311534
0.8254 Intermediate Similarity NPC475636
0.824 Intermediate Similarity NPC285091
0.8231 Intermediate Similarity NPC190065
0.8231 Intermediate Similarity NPC141215
0.8231 Intermediate Similarity NPC471089
0.8226 Intermediate Similarity NPC228701
0.8226 Intermediate Similarity NPC471961
0.8226 Intermediate Similarity NPC202666
0.8226 Intermediate Similarity NPC227397
0.8226 Intermediate Similarity NPC14617
0.8226 Intermediate Similarity NPC471964
0.8226 Intermediate Similarity NPC160084
0.8226 Intermediate Similarity NPC262199
0.8211 Intermediate Similarity NPC476545
0.8211 Intermediate Similarity NPC182900
0.8211 Intermediate Similarity NPC475182
0.8211 Intermediate Similarity NPC476544
0.8211 Intermediate Similarity NPC133506
0.8211 Intermediate Similarity NPC249553
0.8211 Intermediate Similarity NPC476543
0.8211 Intermediate Similarity NPC275675
0.8205 Intermediate Similarity NPC118225
0.8197 Intermediate Similarity NPC127530
0.8182 Intermediate Similarity NPC218970
0.8174 Intermediate Similarity NPC223741
0.8168 Intermediate Similarity NPC596
0.8168 Intermediate Similarity NPC140045
0.8168 Intermediate Similarity NPC295885
0.8167 Intermediate Similarity NPC165439
0.8167 Intermediate Similarity NPC477580
0.8167 Intermediate Similarity NPC473898
0.816 Intermediate Similarity NPC247315
0.816 Intermediate Similarity NPC473255
0.816 Intermediate Similarity NPC473474
0.816 Intermediate Similarity NPC471962
0.816 Intermediate Similarity NPC318135
0.816 Intermediate Similarity NPC471963
0.8154 Intermediate Similarity NPC262813
0.8151 Intermediate Similarity NPC474265
0.8151 Intermediate Similarity NPC210420
0.8145 Intermediate Similarity NPC305771
0.8145 Intermediate Similarity NPC15918
0.8145 Intermediate Similarity NPC94072
0.8145 Intermediate Similarity NPC169816
0.8145 Intermediate Similarity NPC313528
0.8142 Intermediate Similarity NPC474720
0.8136 Intermediate Similarity NPC129340
0.812 Intermediate Similarity NPC272576
0.8115 Intermediate Similarity NPC286347
0.8115 Intermediate Similarity NPC239293
0.8115 Intermediate Similarity NPC297179
0.8103 Intermediate Similarity NPC95243
0.8103 Intermediate Similarity NPC63023
0.8095 Intermediate Similarity NPC87662
0.8092 Intermediate Similarity NPC251998
0.8087 Intermediate Similarity NPC117185
0.8083 Intermediate Similarity NPC194100
0.8083 Intermediate Similarity NPC178981
0.8077 Intermediate Similarity NPC478069
0.8067 Intermediate Similarity NPC471243
0.8065 Intermediate Similarity NPC75417
0.8062 Intermediate Similarity NPC473519
0.8062 Intermediate Similarity NPC155529
0.8062 Intermediate Similarity NPC473805
0.8051 Intermediate Similarity NPC8431
0.8051 Intermediate Similarity NPC265655
0.8049 Intermediate Similarity NPC473884
0.8049 Intermediate Similarity NPC472949
0.8049 Intermediate Similarity NPC180550
0.8049 Intermediate Similarity NPC309780
0.8049 Intermediate Similarity NPC469945
0.8049 Intermediate Similarity NPC114441
0.8049 Intermediate Similarity NPC475171
0.8049 Intermediate Similarity NPC6377
0.8049 Intermediate Similarity NPC214484
0.8049 Intermediate Similarity NPC157868
0.8049 Intermediate Similarity NPC35405
0.8049 Intermediate Similarity NPC11551
0.8049 Intermediate Similarity NPC208381
0.8049 Intermediate Similarity NPC39211
0.8047 Intermediate Similarity NPC476966
0.8033 Intermediate Similarity NPC224121
0.8031 Intermediate Similarity NPC473265
0.8031 Intermediate Similarity NPC471357
0.8031 Intermediate Similarity NPC146456
0.8031 Intermediate Similarity NPC469757
0.8031 Intermediate Similarity NPC117702
0.8031 Intermediate Similarity NPC470882
0.8017 Intermediate Similarity NPC247069
0.8017 Intermediate Similarity NPC473882
0.8017 Intermediate Similarity NPC100955
0.8017 Intermediate Similarity NPC243354
0.8017 Intermediate Similarity NPC121566
0.8016 Intermediate Similarity NPC248202
0.8015 Intermediate Similarity NPC158350
0.8015 Intermediate Similarity NPC171619
0.8 Intermediate Similarity NPC275343
0.8 Intermediate Similarity NPC102015
0.8 Intermediate Similarity NPC249848
0.8 Intermediate Similarity NPC40775
0.8 Intermediate Similarity NPC235438
0.8 Intermediate Similarity NPC162574
0.8 Intermediate Similarity NPC170487
0.8 Intermediate Similarity NPC471244
0.8 Intermediate Similarity NPC107966
0.8 Intermediate Similarity NPC471245
0.7984 Intermediate Similarity NPC472257
0.7984 Intermediate Similarity NPC472076
0.7984 Intermediate Similarity NPC472075

  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 NPC238005 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
0.8595 High Similarity NPD6370 Approved
0.8548 High Similarity NPD7736 Approved
0.8509 High Similarity NPD6412 Phase 2
0.843 Intermediate Similarity NPD6054 Approved
0.832 Intermediate Similarity NPD8293 Discontinued
0.8279 Intermediate Similarity NPD6059 Approved
0.8226 Intermediate Similarity NPD8328 Phase 3
0.8211 Intermediate Similarity NPD6015 Approved
0.8211 Intermediate Similarity NPD6016 Approved
0.816 Intermediate Similarity NPD7492 Approved
0.8145 Intermediate Similarity NPD5988 Approved
0.813 Intermediate Similarity NPD6319 Approved
0.8095 Intermediate Similarity NPD6616 Approved
0.8031 Intermediate Similarity NPD7078 Approved
0.8 Intermediate Similarity NPD6882 Approved
0.8 Intermediate Similarity NPD8297 Approved
0.7907 Intermediate Similarity NPD7319 Approved
0.7886 Intermediate Similarity NPD6009 Approved
0.7812 Intermediate Similarity NPD7507 Approved
0.7769 Intermediate Similarity NPD6649 Approved
0.7769 Intermediate Similarity NPD6650 Approved
0.775 Intermediate Similarity NPD6372 Approved
0.775 Intermediate Similarity NPD6373 Approved
0.7742 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD6033 Approved
0.7686 Intermediate Similarity NPD4634 Approved
0.7667 Intermediate Similarity NPD6881 Approved
0.7667 Intermediate Similarity NPD6899 Approved
0.7647 Intermediate Similarity NPD6675 Approved
0.7647 Intermediate Similarity NPD5739 Approved
0.7647 Intermediate Similarity NPD6402 Approved
0.7647 Intermediate Similarity NPD7128 Approved
0.7642 Intermediate Similarity NPD4632 Approved
0.7638 Intermediate Similarity NPD7503 Approved
0.7623 Intermediate Similarity NPD8130 Phase 1
0.7583 Intermediate Similarity NPD5697 Approved
0.7541 Intermediate Similarity NPD7290 Approved
0.7541 Intermediate Similarity NPD6883 Approved
0.7541 Intermediate Similarity NPD7102 Approved
0.7521 Intermediate Similarity NPD6686 Approved
0.7521 Intermediate Similarity NPD7320 Approved
0.75 Intermediate Similarity NPD6083 Phase 2
0.75 Intermediate Similarity NPD6084 Phase 2
0.748 Intermediate Similarity NPD6847 Approved
0.748 Intermediate Similarity NPD6869 Approved
0.748 Intermediate Similarity NPD6617 Approved
0.7478 Intermediate Similarity NPD5695 Phase 3
0.7459 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7459 Intermediate Similarity NPD6014 Approved
0.7459 Intermediate Similarity NPD6012 Approved
0.7459 Intermediate Similarity NPD6013 Approved
0.7444 Intermediate Similarity NPD5956 Approved
0.7438 Intermediate Similarity NPD5701 Approved
0.7385 Intermediate Similarity NPD7604 Phase 2
0.7377 Intermediate Similarity NPD6011 Approved
0.7373 Intermediate Similarity NPD5286 Approved
0.7373 Intermediate Similarity NPD4696 Approved
0.7373 Intermediate Similarity NPD5285 Approved
0.7364 Intermediate Similarity NPD5983 Phase 2
0.735 Intermediate Similarity NPD4755 Approved
0.7288 Intermediate Similarity NPD5696 Approved
0.7287 Intermediate Similarity NPD8294 Approved
0.7287 Intermediate Similarity NPD8377 Approved
0.7273 Intermediate Similarity NPD6336 Discontinued
0.7266 Intermediate Similarity NPD7327 Approved
0.7266 Intermediate Similarity NPD7328 Approved
0.725 Intermediate Similarity NPD5225 Approved
0.725 Intermediate Similarity NPD5211 Phase 2
0.725 Intermediate Similarity NPD4633 Approved
0.725 Intermediate Similarity NPD5224 Approved
0.725 Intermediate Similarity NPD5226 Approved
0.7231 Intermediate Similarity NPD8378 Approved
0.7231 Intermediate Similarity NPD8380 Approved
0.7231 Intermediate Similarity NPD8335 Approved
0.7231 Intermediate Similarity NPD8033 Approved
0.7231 Intermediate Similarity NPD8379 Approved
0.7231 Intermediate Similarity NPD8296 Approved
0.7227 Intermediate Similarity NPD4700 Approved
0.7222 Intermediate Similarity NPD8133 Approved
0.7209 Intermediate Similarity NPD7516 Approved
0.72 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD4753 Phase 2
0.719 Intermediate Similarity NPD5174 Approved
0.719 Intermediate Similarity NPD5175 Approved
0.7179 Intermediate Similarity NPD4629 Approved
0.7179 Intermediate Similarity NPD5210 Approved
0.7167 Intermediate Similarity NPD5223 Approved
0.7131 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.7131 Intermediate Similarity NPD5141 Approved
0.7109 Intermediate Similarity NPD6274 Approved
0.7097 Intermediate Similarity NPD4729 Approved
0.7097 Intermediate Similarity NPD4730 Approved
0.7077 Intermediate Similarity NPD7101 Approved
0.7077 Intermediate Similarity NPD7100 Approved
0.7073 Intermediate Similarity NPD4767 Approved
0.7073 Intermediate Similarity NPD4768 Approved
0.7054 Intermediate Similarity NPD7115 Discovery
0.7008 Intermediate Similarity NPD6053 Discontinued
0.7 Intermediate Similarity NPD6335 Approved
0.6992 Remote Similarity NPD6067 Discontinued
0.6984 Remote Similarity NPD5248 Approved
0.6984 Remote Similarity NPD5250 Approved
0.6984 Remote Similarity NPD5247 Approved
0.6984 Remote Similarity NPD5251 Approved
0.6984 Remote Similarity NPD5249 Phase 3
0.697 Remote Similarity NPD8515 Approved
0.697 Remote Similarity NPD8513 Phase 3
0.697 Remote Similarity NPD8517 Approved
0.697 Remote Similarity NPD8516 Approved
0.696 Remote Similarity NPD5128 Approved
0.6949 Remote Similarity NPD5282 Discontinued
0.6947 Remote Similarity NPD4522 Approved
0.6935 Remote Similarity NPD6008 Approved
0.693 Remote Similarity NPD5690 Phase 2
0.6923 Remote Similarity NPD6317 Approved
0.6923 Remote Similarity NPD6050 Approved
0.6917 Remote Similarity NPD8080 Discontinued
0.6912 Remote Similarity NPD8337 Approved
0.6912 Remote Similarity NPD8336 Approved
0.6911 Remote Similarity NPD4754 Approved
0.6897 Remote Similarity NPD6080 Approved
0.6897 Remote Similarity NPD6673 Approved
0.6897 Remote Similarity NPD6904 Approved
0.688 Remote Similarity NPD7899 Clinical (unspecified phase)
0.687 Remote Similarity NPD6313 Approved
0.687 Remote Similarity NPD6314 Approved
0.6842 Remote Similarity NPD6909 Approved
0.6842 Remote Similarity NPD6908 Approved
0.6842 Remote Similarity NPD5329 Approved
0.6838 Remote Similarity NPD5692 Phase 3
0.6833 Remote Similarity NPD5222 Approved
0.6833 Remote Similarity NPD4697 Phase 3
0.6833 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6833 Remote Similarity NPD5221 Approved
0.6825 Remote Similarity NPD5345 Clinical (unspecified phase)
0.681 Remote Similarity NPD5737 Approved
0.681 Remote Similarity NPD6672 Approved
0.6797 Remote Similarity NPD5215 Approved
0.6797 Remote Similarity NPD5217 Approved
0.6797 Remote Similarity NPD5216 Approved
0.6783 Remote Similarity NPD4694 Approved
0.6783 Remote Similarity NPD5279 Phase 3
0.6783 Remote Similarity NPD5280 Approved
0.678 Remote Similarity NPD5694 Approved
0.678 Remote Similarity NPD5284 Approved
0.678 Remote Similarity NPD5281 Approved
0.678 Remote Similarity NPD6079 Approved
0.6777 Remote Similarity NPD5173 Approved
0.6763 Remote Similarity NPD7260 Phase 2
0.6754 Remote Similarity NPD3666 Approved
0.6754 Remote Similarity NPD3133 Approved
0.6754 Remote Similarity NPD4197 Approved
0.6754 Remote Similarity NPD3665 Phase 1
0.6752 Remote Similarity NPD5328 Approved
0.6723 Remote Similarity NPD4202 Approved
0.6723 Remote Similarity NPD6399 Phase 3
0.6719 Remote Similarity NPD6371 Approved
0.6719 Remote Similarity NPD5169 Approved
0.6719 Remote Similarity NPD5135 Approved
0.6719 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6716 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6716 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5127 Approved
0.6667 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6667 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6639 Remote Similarity NPD5693 Phase 1
0.6638 Remote Similarity NPD5330 Approved
0.6638 Remote Similarity NPD7146 Approved
0.6638 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6638 Remote Similarity NPD6098 Approved
0.6638 Remote Similarity NPD6684 Approved
0.6638 Remote Similarity NPD7521 Approved
0.6638 Remote Similarity NPD6409 Approved
0.6638 Remote Similarity NPD7334 Approved
0.6591 Remote Similarity NPD6868 Approved
0.6579 Remote Similarity NPD4221 Approved
0.6579 Remote Similarity NPD4223 Phase 3
0.6564 Remote Similarity NPD7799 Discontinued
0.6528 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6525 Remote Similarity NPD6903 Approved
0.6522 Remote Similarity NPD4788 Approved
0.6515 Remote Similarity NPD5167 Approved
0.6504 Remote Similarity NPD7902 Approved
0.65 Remote Similarity NPD6411 Approved
0.6496 Remote Similarity NPD3618 Phase 1
0.6483 Remote Similarity NPD6334 Approved
0.6483 Remote Similarity NPD6333 Approved
0.6479 Remote Similarity NPD6845 Suspended
0.6479 Remote Similarity NPD8338 Approved
0.6475 Remote Similarity NPD5654 Approved
0.6475 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6466 Remote Similarity NPD4786 Approved
0.6457 Remote Similarity NPD4056 Clinical (unspecified phase)
0.6457 Remote Similarity NPD4057 Clinical (unspecified phase)
0.6454 Remote Similarity NPD6914 Discontinued
0.6452 Remote Similarity NPD7638 Approved
0.6418 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6417 Remote Similarity NPD5207 Approved
0.64 Remote Similarity NPD7640 Approved
0.64 Remote Similarity NPD7639 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