Structure

Physi-Chem Properties

Molecular Weight:  472.36
Volume:  514.542
LogP:  5.501
LogD:  4.904
LogS:  -4.857
# Rotatable Bonds:  3
TPSA:  73.83
# H-Bond Aceptor:  4
# H-Bond Donor:  3
# Rings:  5
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.452
Synthetic Accessibility Score:  4.833
Fsp3:  0.867
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.063
MDCK Permeability:  2.8281740014790557e-05
Pgp-inhibitor:  0.099
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.022
30% Bioavailability (F30%):  0.894

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.082
Plasma Protein Binding (PPB):  94.66427612304688%
Volume Distribution (VD):  1.261
Pgp-substrate:  2.3453121185302734%

ADMET: Metabolism

CYP1A2-inhibitor:  0.03
CYP1A2-substrate:  0.778
CYP2C19-inhibitor:  0.076
CYP2C19-substrate:  0.93
CYP2C9-inhibitor:  0.176
CYP2C9-substrate:  0.956
CYP2D6-inhibitor:  0.014
CYP2D6-substrate:  0.86
CYP3A4-inhibitor:  0.12
CYP3A4-substrate:  0.352

ADMET: Excretion

Clearance (CL):  5.02
Half-life (T1/2):  0.123

ADMET: Toxicity

hERG Blockers:  0.034
Human Hepatotoxicity (H-HT):  0.23
Drug-inuced Liver Injury (DILI):  0.023
AMES Toxicity:  0.003
Rat Oral Acute Toxicity:  0.55
Maximum Recommended Daily Dose:  0.971
Skin Sensitization:  0.54
Carcinogencity:  0.014
Eye Corrosion:  0.003
Eye Irritation:  0.014
Respiratory Toxicity:  0.895

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

  Natural Product: NPC112009

Natural Product ID:  NPC112009
Common Name*:   Gypensapogenin E
IUPAC Name:   (2S)-2-(2-hydroxy-2-methylpropyl)-4-[(3S,5R,8R,9R,10R,13R,14R,17S)-3-hydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
Synonyms:   Gypensapogenin E
Standard InCHIKey:  QDAUOBHGLHSXJU-CFJKEVLMSA-N
Standard InCHI:  InChI=1S/C30H48O4/c1-26(2,33)17-18-16-20(25(32)34-18)19-10-14-29(6)21(19)8-9-23-28(5)13-12-24(31)27(3,4)22(28)11-15-30(23,29)7/h16,18-19,21-24,31,33H,8-15,17H2,1-7H3/t18-,19-,21-,22+,23-,24+,28+,29-,30-/m1/s1
SMILES:  O=C1O[C@H](C=C1[C@H]1CC[C@@]2([C@@H]1CC[C@H]1[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](C2(C)C)O)C)CC(O)(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2313421
PubChem CID:   71517216
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001553] Triterpenoids

*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
NPO12934 Gynostemma pentaphyllum Species Cucurbitaceae Eukaryota Stems n.a. n.a. PMID[20104880]
NPO12934 Gynostemma pentaphyllum Species Cucurbitaceae Eukaryota n.a. n.a. n.a. PMID[22342101]
NPO12934 Gynostemma pentaphyllum Species Cucurbitaceae Eukaryota aerial parts n.a. n.a. PMID[25895106]
NPO12934 Gynostemma pentaphyllum Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11990 Coleostephus myconis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO918 Dahlia pinnata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11990 Coleostephus myconis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO918 Dahlia pinnata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12934 Gynostemma pentaphyllum Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12934 Gynostemma pentaphyllum Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11990 Coleostephus myconis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12934 Gynostemma pentaphyllum Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16506 Synotis alata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO918 Dahlia pinnata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11990 Coleostephus myconis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4305 Pertusaria wulfenii Species Pertusariaceae 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
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens IC50 = 23000.0 nM PMID[501233]

☑ 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 NPC112009 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
0.9792 High Similarity NPC180204
0.9684 High Similarity NPC201406
0.9053 High Similarity NPC139692
0.9038 High Similarity NPC470063
0.8958 High Similarity NPC201725
0.8922 High Similarity NPC131665
0.8922 High Similarity NPC255387
0.8878 High Similarity NPC253826
0.8824 High Similarity NPC266570
0.8812 High Similarity NPC476237
0.8812 High Similarity NPC97487
0.8812 High Similarity NPC187302
0.8812 High Similarity NPC189588
0.8812 High Similarity NPC10232
0.8812 High Similarity NPC196471
0.88 High Similarity NPC222875
0.88 High Similarity NPC25177
0.88 High Similarity NPC295110
0.88 High Similarity NPC268829
0.88 High Similarity NPC471412
0.88 High Similarity NPC247701
0.8788 High Similarity NPC57079
0.8788 High Similarity NPC108368
0.8785 High Similarity NPC469794
0.8785 High Similarity NPC72772
0.8776 High Similarity NPC242848
0.8776 High Similarity NPC234993
0.8776 High Similarity NPC134072
0.8737 High Similarity NPC174342
0.8713 High Similarity NPC114540
0.8713 High Similarity NPC476081
0.8713 High Similarity NPC32577
0.8713 High Similarity NPC155332
0.87 High Similarity NPC117685
0.87 High Similarity NPC476299
0.87 High Similarity NPC474012
0.87 High Similarity NPC251680
0.87 High Similarity NPC476303
0.87 High Similarity NPC471413
0.8687 High Similarity NPC231751
0.8673 High Similarity NPC279974
0.8667 High Similarity NPC16270
0.8667 High Similarity NPC179642
0.866 High Similarity NPC472871
0.8646 High Similarity NPC302280
0.8641 High Similarity NPC189863
0.8641 High Similarity NPC119855
0.8641 High Similarity NPC220217
0.8627 High Similarity NPC160583
0.8627 High Similarity NPC120321
0.8627 High Similarity NPC36688
0.8627 High Similarity NPC297617
0.8627 High Similarity NPC176883
0.8611 High Similarity NPC196931
0.86 High Similarity NPC119036
0.86 High Similarity NPC98868
0.86 High Similarity NPC218107
0.8598 High Similarity NPC122056
0.8558 High Similarity NPC475294
0.8542 High Similarity NPC475921
0.8542 High Similarity NPC474704
0.8529 High Similarity NPC162973
0.8519 High Similarity NPC147912
0.8519 High Similarity NPC67259
0.8505 High Similarity NPC69291
0.85 High Similarity NPC175351
0.85 High Similarity NPC121402
0.85 High Similarity NPC132753
0.85 High Similarity NPC151681
0.85 High Similarity NPC224356
0.8485 Intermediate Similarity NPC476174
0.8476 Intermediate Similarity NPC472825
0.8469 Intermediate Similarity NPC38232
0.8469 Intermediate Similarity NPC470224
0.8469 Intermediate Similarity NPC472303
0.8469 Intermediate Similarity NPC476304
0.8468 Intermediate Similarity NPC470312
0.8462 Intermediate Similarity NPC34768
0.8462 Intermediate Similarity NPC186668
0.8454 Intermediate Similarity NPC126993
0.8454 Intermediate Similarity NPC78973
0.8454 Intermediate Similarity NPC471896
0.8447 Intermediate Similarity NPC329345
0.8447 Intermediate Similarity NPC472821
0.8447 Intermediate Similarity NPC476889
0.8447 Intermediate Similarity NPC475526
0.8447 Intermediate Similarity NPC478057
0.8447 Intermediate Similarity NPC72151
0.8447 Intermediate Similarity NPC473283
0.8447 Intermediate Similarity NPC222153
0.8438 Intermediate Similarity NPC104560
0.8431 Intermediate Similarity NPC235142
0.8431 Intermediate Similarity NPC282524
0.8431 Intermediate Similarity NPC115899
0.8426 Intermediate Similarity NPC73050
0.8421 Intermediate Similarity NPC131813
0.8416 Intermediate Similarity NPC252295
0.8411 Intermediate Similarity NPC474315
0.84 Intermediate Similarity NPC472363
0.84 Intermediate Similarity NPC472362
0.84 Intermediate Similarity NPC471039
0.84 Intermediate Similarity NPC195366
0.84 Intermediate Similarity NPC307164
0.84 Intermediate Similarity NPC114743
0.84 Intermediate Similarity NPC29952
0.84 Intermediate Similarity NPC250757
0.84 Intermediate Similarity NPC327788
0.84 Intermediate Similarity NPC154526
0.84 Intermediate Similarity NPC301534
0.8396 Intermediate Similarity NPC5475
0.8396 Intermediate Similarity NPC173905
0.8396 Intermediate Similarity NPC475030
0.8396 Intermediate Similarity NPC284828
0.8396 Intermediate Similarity NPC475065
0.8396 Intermediate Similarity NPC472216
0.8384 Intermediate Similarity NPC476186
0.8384 Intermediate Similarity NPC471720
0.8384 Intermediate Similarity NPC91010
0.8381 Intermediate Similarity NPC263729
0.8381 Intermediate Similarity NPC329048
0.8381 Intermediate Similarity NPC187435
0.8381 Intermediate Similarity NPC67321
0.8381 Intermediate Similarity NPC179380
0.8381 Intermediate Similarity NPC330011
0.8381 Intermediate Similarity NPC302788
0.8367 Intermediate Similarity NPC289479
0.8367 Intermediate Similarity NPC472814
0.8367 Intermediate Similarity NPC74296
0.8367 Intermediate Similarity NPC110923
0.8367 Intermediate Similarity NPC177037
0.8367 Intermediate Similarity NPC329842
0.8367 Intermediate Similarity NPC72845
0.8365 Intermediate Similarity NPC189616
0.8364 Intermediate Similarity NPC167606
0.8364 Intermediate Similarity NPC20302
0.8364 Intermediate Similarity NPC286528
0.8364 Intermediate Similarity NPC140055
0.8351 Intermediate Similarity NPC262858
0.8351 Intermediate Similarity NPC5509
0.8351 Intermediate Similarity NPC285982
0.8351 Intermediate Similarity NPC472240
0.835 Intermediate Similarity NPC22388
0.835 Intermediate Similarity NPC40918
0.835 Intermediate Similarity NPC165250
0.835 Intermediate Similarity NPC136289
0.835 Intermediate Similarity NPC476890
0.835 Intermediate Similarity NPC320447
0.8333 Intermediate Similarity NPC142361
0.8333 Intermediate Similarity NPC472826
0.8333 Intermediate Similarity NPC266955
0.8333 Intermediate Similarity NPC470906
0.8333 Intermediate Similarity NPC470074
0.8333 Intermediate Similarity NPC100267
0.8333 Intermediate Similarity NPC475524
0.8333 Intermediate Similarity NPC474684
0.8333 Intermediate Similarity NPC476274
0.8333 Intermediate Similarity NPC476767
0.8333 Intermediate Similarity NPC471041
0.8317 Intermediate Similarity NPC156546
0.8317 Intermediate Similarity NPC210337
0.8317 Intermediate Similarity NPC51499
0.8317 Intermediate Similarity NPC110937
0.8317 Intermediate Similarity NPC2049
0.8317 Intermediate Similarity NPC108078
0.8316 Intermediate Similarity NPC106416
0.8316 Intermediate Similarity NPC474013
0.8316 Intermediate Similarity NPC65661
0.8316 Intermediate Similarity NPC86316
0.8304 Intermediate Similarity NPC41123
0.8304 Intermediate Similarity NPC145074
0.8304 Intermediate Similarity NPC114939
0.8302 Intermediate Similarity NPC220155
0.8302 Intermediate Similarity NPC275539
0.8302 Intermediate Similarity NPC189075
0.8302 Intermediate Similarity NPC475418
0.8302 Intermediate Similarity NPC177064
0.8302 Intermediate Similarity NPC318363
0.8302 Intermediate Similarity NPC473482
0.8302 Intermediate Similarity NPC306265
0.83 Intermediate Similarity NPC33473
0.83 Intermediate Similarity NPC180950
0.83 Intermediate Similarity NPC276110
0.83 Intermediate Similarity NPC183012
0.83 Intermediate Similarity NPC84383
0.83 Intermediate Similarity NPC293052
0.8288 Intermediate Similarity NPC50774
0.8288 Intermediate Similarity NPC709
0.8288 Intermediate Similarity NPC146786
0.8288 Intermediate Similarity NPC257457
0.8288 Intermediate Similarity NPC311554
0.8286 Intermediate Similarity NPC60681
0.8286 Intermediate Similarity NPC472818
0.8286 Intermediate Similarity NPC173172
0.8286 Intermediate Similarity NPC475414
0.8283 Intermediate Similarity NPC205034
0.8283 Intermediate Similarity NPC294263
0.8283 Intermediate Similarity NPC162615
0.8283 Intermediate Similarity NPC115021
0.8283 Intermediate Similarity NPC152778
0.8269 Intermediate Similarity NPC171014

  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 NPC112009 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
0.8788 High Similarity NPD7638 Approved
0.87 High Similarity NPD7639 Approved
0.87 High Similarity NPD7640 Approved
0.8364 Intermediate Similarity NPD7115 Discovery
0.8302 Intermediate Similarity NPD7320 Approved
0.8302 Intermediate Similarity NPD6899 Approved
0.8302 Intermediate Similarity NPD6881 Approved
0.8286 Intermediate Similarity NPD6675 Approved
0.8286 Intermediate Similarity NPD7128 Approved
0.8286 Intermediate Similarity NPD6402 Approved
0.8286 Intermediate Similarity NPD5739 Approved
0.8208 Intermediate Similarity NPD5697 Approved
0.8148 Intermediate Similarity NPD6883 Approved
0.8148 Intermediate Similarity NPD7102 Approved
0.8148 Intermediate Similarity NPD7290 Approved
0.8137 Intermediate Similarity NPD6083 Phase 2
0.8137 Intermediate Similarity NPD6084 Phase 2
0.8103 Intermediate Similarity NPD7507 Approved
0.8073 Intermediate Similarity NPD6869 Approved
0.8073 Intermediate Similarity NPD6650 Approved
0.8073 Intermediate Similarity NPD6649 Approved
0.8073 Intermediate Similarity NPD6847 Approved
0.8073 Intermediate Similarity NPD8130 Phase 1
0.8073 Intermediate Similarity NPD6617 Approved
0.8056 Intermediate Similarity NPD6372 Approved
0.8056 Intermediate Similarity NPD6373 Approved
0.8056 Intermediate Similarity NPD6013 Approved
0.8056 Intermediate Similarity NPD6014 Approved
0.8056 Intermediate Similarity NPD6012 Approved
0.8037 Intermediate Similarity NPD5701 Approved
0.802 Intermediate Similarity NPD7748 Approved
0.8 Intermediate Similarity NPD6079 Approved
0.8 Intermediate Similarity NPD7515 Phase 2
0.8 Intermediate Similarity NPD6882 Approved
0.8 Intermediate Similarity NPD8297 Approved
0.8 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD7632 Discontinued
0.798 Intermediate Similarity NPD5328 Approved
0.7963 Intermediate Similarity NPD6011 Approved
0.7938 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7921 Intermediate Similarity NPD6399 Phase 3
0.7899 Intermediate Similarity NPD7319 Approved
0.7885 Intermediate Similarity NPD4225 Approved
0.7857 Intermediate Similarity NPD3618 Phase 1
0.783 Intermediate Similarity NPD5211 Phase 2
0.7822 Intermediate Similarity NPD8034 Phase 2
0.7822 Intermediate Similarity NPD8035 Phase 2
0.781 Intermediate Similarity NPD4696 Approved
0.781 Intermediate Similarity NPD5285 Approved
0.781 Intermediate Similarity NPD5286 Approved
0.7807 Intermediate Similarity NPD7328 Approved
0.7807 Intermediate Similarity NPD7327 Approved
0.7798 Intermediate Similarity NPD6686 Approved
0.7788 Intermediate Similarity NPD4755 Approved
0.7788 Intermediate Similarity NPD7902 Approved
0.7767 Intermediate Similarity NPD5695 Phase 3
0.7767 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7748 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7745 Intermediate Similarity NPD4202 Approved
0.7739 Intermediate Similarity NPD7516 Approved
0.7727 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7714 Intermediate Similarity NPD5696 Approved
0.77 Intermediate Similarity NPD6903 Approved
0.77 Intermediate Similarity NPD6672 Approved
0.77 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.77 Intermediate Similarity NPD5737 Approved
0.7692 Intermediate Similarity NPD5221 Approved
0.7692 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD5222 Approved
0.7685 Intermediate Similarity NPD5141 Approved
0.7677 Intermediate Similarity NPD6409 Approved
0.7677 Intermediate Similarity NPD5330 Approved
0.7677 Intermediate Similarity NPD7146 Approved
0.7677 Intermediate Similarity NPD7521 Approved
0.7677 Intermediate Similarity NPD7334 Approved
0.7677 Intermediate Similarity NPD6684 Approved
0.7672 Intermediate Similarity NPD8294 Approved
0.7672 Intermediate Similarity NPD8377 Approved
0.7664 Intermediate Similarity NPD5226 Approved
0.7664 Intermediate Similarity NPD5224 Approved
0.7664 Intermediate Similarity NPD5225 Approved
0.7664 Intermediate Similarity NPD4633 Approved
0.7653 Intermediate Similarity NPD4786 Approved
0.7647 Intermediate Similarity NPD5693 Phase 1
0.7642 Intermediate Similarity NPD4700 Approved
0.7632 Intermediate Similarity NPD6274 Approved
0.7624 Intermediate Similarity NPD4753 Phase 2
0.7619 Intermediate Similarity NPD5173 Approved
0.7607 Intermediate Similarity NPD8033 Approved
0.7607 Intermediate Similarity NPD8380 Approved
0.7607 Intermediate Similarity NPD8335 Approved
0.7607 Intermediate Similarity NPD8379 Approved
0.7607 Intermediate Similarity NPD8378 Approved
0.7607 Intermediate Similarity NPD8296 Approved
0.7604 Intermediate Similarity NPD7525 Registered
0.7593 Intermediate Similarity NPD5174 Approved
0.7593 Intermediate Similarity NPD5175 Approved
0.7586 Intermediate Similarity NPD7101 Approved
0.7586 Intermediate Similarity NPD7100 Approved
0.757 Intermediate Similarity NPD5223 Approved
0.7524 Intermediate Similarity NPD4697 Phase 3
0.7522 Intermediate Similarity NPD6053 Discontinued
0.75 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6335 Approved
0.75 Intermediate Similarity NPD7900 Approved
0.7478 Intermediate Similarity NPD6868 Approved
0.7475 Intermediate Similarity NPD3665 Phase 1
0.7475 Intermediate Similarity NPD3133 Approved
0.7475 Intermediate Similarity NPD3666 Approved
0.7456 Intermediate Similarity NPD4632 Approved
0.7455 Intermediate Similarity NPD6008 Approved
0.7451 Intermediate Similarity NPD6051 Approved
0.7451 Intermediate Similarity NPD6673 Approved
0.7451 Intermediate Similarity NPD6080 Approved
0.7451 Intermediate Similarity NPD6904 Approved
0.7449 Intermediate Similarity NPD3667 Approved
0.7429 Intermediate Similarity NPD5210 Approved
0.7429 Intermediate Similarity NPD4629 Approved
0.7417 Intermediate Similarity NPD7492 Approved
0.7414 Intermediate Similarity NPD6317 Approved
0.74 Intermediate Similarity NPD1694 Approved
0.7377 Intermediate Similarity NPD7736 Approved
0.7374 Intermediate Similarity NPD4788 Approved
0.7373 Intermediate Similarity NPD6319 Approved
0.7373 Intermediate Similarity NPD6054 Approved
0.7368 Intermediate Similarity NPD6117 Approved
0.7355 Intermediate Similarity NPD6616 Approved
0.735 Intermediate Similarity NPD6314 Approved
0.735 Intermediate Similarity NPD6313 Approved
0.7333 Intermediate Similarity NPD6001 Approved
0.7327 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD5128 Approved
0.7321 Intermediate Similarity NPD4730 Approved
0.7321 Intermediate Similarity NPD4729 Approved
0.7311 Intermediate Similarity NPD6291 Clinical (unspecified phase)
0.7311 Intermediate Similarity NPD6908 Approved
0.7311 Intermediate Similarity NPD6909 Approved
0.7297 Intermediate Similarity NPD4768 Approved
0.7297 Intermediate Similarity NPD4767 Approved
0.7295 Intermediate Similarity NPD7078 Approved
0.7292 Intermediate Similarity NPD6116 Phase 1
0.7273 Intermediate Similarity NPD4754 Approved
0.7273 Intermediate Similarity NPD4221 Approved
0.7273 Intermediate Similarity NPD4223 Phase 3
0.7265 Intermediate Similarity NPD6009 Approved
0.7255 Intermediate Similarity NPD3573 Approved
0.725 Intermediate Similarity NPD6370 Approved
0.7232 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.7228 Intermediate Similarity NPD5329 Approved
0.7227 Intermediate Similarity NPD6059 Approved
0.7216 Intermediate Similarity NPD6115 Approved
0.7216 Intermediate Similarity NPD6114 Approved
0.7216 Intermediate Similarity NPD6697 Approved
0.7216 Intermediate Similarity NPD6118 Approved
0.7212 Intermediate Similarity NPD5785 Approved
0.7193 Intermediate Similarity NPD5249 Phase 3
0.7193 Intermediate Similarity NPD5248 Approved
0.7193 Intermediate Similarity NPD5250 Approved
0.7193 Intermediate Similarity NPD5247 Approved
0.7193 Intermediate Similarity NPD5251 Approved
0.7193 Intermediate Similarity NPD4634 Approved
0.719 Intermediate Similarity NPD7604 Phase 2
0.7184 Intermediate Similarity NPD5208 Approved
0.7167 Intermediate Similarity NPD5983 Phase 2
0.7167 Intermediate Similarity NPD6015 Approved
0.7167 Intermediate Similarity NPD7503 Approved
0.7167 Intermediate Similarity NPD6016 Approved
0.7158 Intermediate Similarity NPD6113 Clinical (unspecified phase)
0.7157 Intermediate Similarity NPD6098 Approved
0.7157 Intermediate Similarity NPD5279 Phase 3
0.7155 Intermediate Similarity NPD8133 Approved
0.7154 Intermediate Similarity NPD8293 Discontinued
0.7143 Intermediate Similarity NPD7637 Suspended
0.7143 Intermediate Similarity NPD5281 Approved
0.7143 Intermediate Similarity NPD5284 Approved
0.7143 Intermediate Similarity NPD6050 Approved
0.713 Intermediate Similarity NPD5217 Approved
0.713 Intermediate Similarity NPD5216 Approved
0.713 Intermediate Similarity NPD5215 Approved
0.7129 Intermediate Similarity NPD4197 Approved
0.7107 Intermediate Similarity NPD5988 Approved
0.708 Intermediate Similarity NPD6412 Phase 2
0.7073 Intermediate Similarity NPD6336 Discontinued
0.7048 Intermediate Similarity NPD5207 Approved
0.7048 Intermediate Similarity NPD5692 Phase 3
0.7043 Intermediate Similarity NPD5135 Approved
0.7043 Intermediate Similarity NPD5169 Approved
0.7043 Intermediate Similarity NPD5134 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD5784 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD5362 Discontinued
0.7018 Intermediate Similarity NPD5168 Approved
0.699 Remote Similarity NPD4138 Approved
0.699 Remote Similarity NPD4693 Phase 3
0.699 Remote Similarity NPD5690 Phase 2
0.699 Remote Similarity NPD4688 Approved
0.699 Remote Similarity NPD4689 Approved
0.699 Remote Similarity NPD4690 Approved
0.699 Remote Similarity NPD5205 Approved
0.6983 Remote Similarity NPD5127 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