Structure

Physi-Chem Properties

Molecular Weight:  634.41
Volume:  653.712
LogP:  3.88
LogD:  3.935
LogS:  -4.128
# Rotatable Bonds:  4
TPSA:  156.91
# H-Bond Aceptor:  9
# H-Bond Donor:  6
# Rings:  6
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.202
Synthetic Accessibility Score:  5.346
Fsp3:  0.917
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:  -5.293
MDCK Permeability:  9.34953277464956e-06
Pgp-inhibitor:  0.97
Pgp-substrate:  0.006
Human Intestinal Absorption (HIA):  0.047
20% Bioavailability (F20%):  0.011
30% Bioavailability (F30%):  0.317

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.037
Plasma Protein Binding (PPB):  90.15609741210938%
Volume Distribution (VD):  0.911
Pgp-substrate:  6.890422821044922%

ADMET: Metabolism

CYP1A2-inhibitor:  0.004
CYP1A2-substrate:  0.13
CYP2C19-inhibitor:  0.004
CYP2C19-substrate:  0.685
CYP2C9-inhibitor:  0.021
CYP2C9-substrate:  0.072
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.102
CYP3A4-inhibitor:  0.232
CYP3A4-substrate:  0.136

ADMET: Excretion

Clearance (CL):  1.873
Half-life (T1/2):  0.235

ADMET: Toxicity

hERG Blockers:  0.023
Human Hepatotoxicity (H-HT):  0.223
Drug-inuced Liver Injury (DILI):  0.015
AMES Toxicity:  0.039
Rat Oral Acute Toxicity:  0.355
Maximum Recommended Daily Dose:  0.945
Skin Sensitization:  0.053
Carcinogencity:  0.024
Eye Corrosion:  0.003
Eye Irritation:  0.012
Respiratory Toxicity:  0.959

Download Data

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

  Natural Product: NPC191763

Natural Product ID:  NPC191763
Common Name*:   Siaresinolic Acid-28-O-Beta-D-Glucopyranosyl Ester
IUPAC Name:   [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1S,4aR,6aR,6aS,6bR,8aR,10S,12aR,14bS)-1,10-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms:  
Standard InCHIKey:  BPRNBIVVHNFCPZ-SKCKXSBFSA-N
Standard InCHI:  InChI=1S/C36H58O9/c1-31(2)14-16-36(30(43)45-29-27(41)26(40)25(39)20(18-37)44-29)17-15-34(6)19(24(36)28(31)42)8-9-22-33(5)12-11-23(38)32(3,4)21(33)10-13-35(22,34)7/h8,20-29,37-42H,9-18H2,1-7H3/t20-,21+,22-,23+,24-,25-,26+,27-,28+,29+,33+,34-,35-,36+/m1/s1
SMILES:  CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O)[C@@H]2[C@@H]1O)C(=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2253398
PubChem CID:   76330022
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
NPO26650 Terminalia chebula Species Combretaceae Eukaryota n.a. n.a. n.a. PMID[11520216]
NPO26261 Streptomyces tendae Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[27642865]
NPO26622 Taraxacum officinale Species Asteraceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO26622 Taraxacum officinale Species Asteraceae Eukaryota n.a. n.a. Database[FooDB]
NPO26622 Taraxacum officinale Species Asteraceae Eukaryota n.a. n.a. Database[FooDB]
NPO26622 Taraxacum officinale Species Asteraceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO26622 Taraxacum officinale Species Asteraceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO26622 Taraxacum officinale Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26650 Terminalia chebula Species Combretaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26622 Taraxacum officinale Species Asteraceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO26650 Terminalia chebula Species Combretaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26622 Taraxacum officinale Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26622 Taraxacum officinale Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26650 Terminalia chebula Species Combretaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26650 Terminalia chebula Species Combretaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26622 Taraxacum officinale Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26650 Terminalia chebula Species Combretaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25649 Calliandra haematocephala Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25339 Trillium smallii Species Melanthiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26261 Streptomyces tendae Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO26345 Sideroxylon tomentosum Species Sapotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26283 Streptomyces djakartensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO25992 Lasallia papulosa Species Umbilicariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9182 Lychnophora passerina Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28950 Angelonia integerrima Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26622 Taraxacum officinale Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26048 Grateloupia elliptica Species Halymeniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4318 Aspergillus cristatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26399 Crepidiastrum lanceolatum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25765 Dryopteris aemula Species Dryopteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24698 Protium unifoliolatum Species Burseraceae 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
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus EC50 = 80.0 ug.mL-1 PMID[459577]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 7.6 % PMID[459577]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 25.3 % PMID[459577]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 65.7 % PMID[459577]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 84.5 % PMID[459577]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 89.2 % PMID[459577]

☑ 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 NPC191763 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
0.9903 High Similarity NPC256798
0.9903 High Similarity NPC116794
0.9903 High Similarity NPC46388
0.9903 High Similarity NPC37739
0.9903 High Similarity NPC128925
0.9902 High Similarity NPC274507
0.9808 High Similarity NPC138334
0.9808 High Similarity NPC204458
0.9808 High Similarity NPC271138
0.9808 High Similarity NPC189884
0.9808 High Similarity NPC269315
0.9808 High Similarity NPC47063
0.9806 High Similarity NPC211798
0.9806 High Similarity NPC30397
0.9806 High Similarity NPC473481
0.9806 High Similarity NPC235841
0.9806 High Similarity NPC297208
0.9806 High Similarity NPC108748
0.9804 High Similarity NPC306746
0.9804 High Similarity NPC167383
0.9804 High Similarity NPC237503
0.9804 High Similarity NPC57362
0.9804 High Similarity NPC204407
0.9714 High Similarity NPC475633
0.9709 High Similarity NPC475296
0.9709 High Similarity NPC476880
0.9709 High Similarity NPC174679
0.9709 High Similarity NPC199457
0.9709 High Similarity NPC59804
0.9709 High Similarity NPC110139
0.9709 High Similarity NPC136877
0.9709 High Similarity NPC56713
0.9709 High Similarity NPC476887
0.9709 High Similarity NPC476882
0.9709 High Similarity NPC474589
0.9709 High Similarity NPC102914
0.9709 High Similarity NPC7870
0.9709 High Similarity NPC476881
0.9709 High Similarity NPC476885
0.9709 High Similarity NPC164194
0.9709 High Similarity NPC476883
0.9709 High Similarity NPC75747
0.9709 High Similarity NPC90856
0.9709 High Similarity NPC127056
0.9709 High Similarity NPC270667
0.9709 High Similarity NPC279554
0.9709 High Similarity NPC476884
0.9709 High Similarity NPC29069
0.9709 High Similarity NPC68419
0.9709 High Similarity NPC108709
0.9709 High Similarity NPC476886
0.9706 High Similarity NPC177246
0.9706 High Similarity NPC476123
0.9706 High Similarity NPC284807
0.9706 High Similarity NPC28198
0.9623 High Similarity NPC160415
0.9623 High Similarity NPC471384
0.9623 High Similarity NPC58448
0.9623 High Similarity NPC161674
0.9619 High Similarity NPC258885
0.9619 High Similarity NPC124296
0.9615 High Similarity NPC164419
0.9615 High Similarity NPC31839
0.9615 High Similarity NPC179434
0.9612 High Similarity NPC137917
0.9612 High Similarity NPC127853
0.9608 High Similarity NPC473538
0.9608 High Similarity NPC283849
0.9533 High Similarity NPC68175
0.9533 High Similarity NPC136768
0.9533 High Similarity NPC148417
0.9533 High Similarity NPC110633
0.9524 High Similarity NPC139044
0.9524 High Similarity NPC473383
0.9524 High Similarity NPC139894
0.9524 High Similarity NPC475516
0.9524 High Similarity NPC102439
0.9524 High Similarity NPC276093
0.9524 High Similarity NPC104071
0.9524 High Similarity NPC324875
0.9524 High Similarity NPC104400
0.9524 High Similarity NPC292677
0.9524 High Similarity NPC257468
0.9524 High Similarity NPC469946
0.9524 High Similarity NPC101744
0.9524 High Similarity NPC473373
0.9524 High Similarity NPC1046
0.9524 High Similarity NPC471383
0.9524 High Similarity NPC48249
0.9524 High Similarity NPC80843
0.9524 High Similarity NPC109079
0.9524 High Similarity NPC475504
0.9524 High Similarity NPC10320
0.9524 High Similarity NPC79718
0.9524 High Similarity NPC471967
0.9519 High Similarity NPC78046
0.9519 High Similarity NPC220984
0.9519 High Similarity NPC269095
0.9519 High Similarity NPC242611
0.9515 High Similarity NPC285576
0.951 High Similarity NPC475611
0.9444 High Similarity NPC36831
0.9439 High Similarity NPC291903
0.9439 High Similarity NPC37134
0.9434 High Similarity NPC133818
0.9434 High Similarity NPC309714
0.9434 High Similarity NPC323341
0.9434 High Similarity NPC192600
0.9434 High Similarity NPC114304
0.9434 High Similarity NPC134835
0.9434 High Similarity NPC96641
0.9434 High Similarity NPC475208
0.9434 High Similarity NPC46665
0.9434 High Similarity NPC475467
0.9434 High Similarity NPC150400
0.9434 High Similarity NPC155410
0.9434 High Similarity NPC219180
0.9434 High Similarity NPC251263
0.9434 High Similarity NPC473826
0.9434 High Similarity NPC475287
0.9434 High Similarity NPC238935
0.9434 High Similarity NPC114287
0.9434 High Similarity NPC151543
0.9434 High Similarity NPC163183
0.9434 High Similarity NPC241909
0.9434 High Similarity NPC73318
0.9434 High Similarity NPC295823
0.9434 High Similarity NPC166422
0.9434 High Similarity NPC473343
0.9434 High Similarity NPC174720
0.9429 High Similarity NPC190837
0.9352 High Similarity NPC473824
0.9352 High Similarity NPC475119
0.9352 High Similarity NPC300419
0.9346 High Similarity NPC261506
0.9346 High Similarity NPC123199
0.9346 High Similarity NPC71065
0.9346 High Similarity NPC70809
0.9346 High Similarity NPC471385
0.9346 High Similarity NPC4328
0.9346 High Similarity NPC475160
0.9346 High Similarity NPC294453
0.9346 High Similarity NPC298034
0.9346 High Similarity NPC309907
0.9346 High Similarity NPC202828
0.9346 High Similarity NPC119592
0.9346 High Similarity NPC100639
0.9346 High Similarity NPC54636
0.9346 High Similarity NPC475140
0.9346 High Similarity NPC224381
0.9346 High Similarity NPC293330
0.9346 High Similarity NPC227551
0.9346 High Similarity NPC471550
0.9346 High Similarity NPC161717
0.9346 High Similarity NPC67857
0.9346 High Similarity NPC79643
0.9346 High Similarity NPC76972
0.9346 High Similarity NPC204414
0.9346 High Similarity NPC164389
0.9346 High Similarity NPC250247
0.9346 High Similarity NPC41061
0.9346 High Similarity NPC305981
0.9346 High Similarity NPC469782
0.9346 High Similarity NPC236638
0.9346 High Similarity NPC475486
0.9346 High Similarity NPC57484
0.9346 High Similarity NPC476068
0.9346 High Similarity NPC43550
0.9346 High Similarity NPC60557
0.9346 High Similarity NPC473714
0.9346 High Similarity NPC65105
0.934 High Similarity NPC212968
0.934 High Similarity NPC195132
0.934 High Similarity NPC100383
0.934 High Similarity NPC65590
0.934 High Similarity NPC64106
0.934 High Similarity NPC125923
0.934 High Similarity NPC161434
0.9273 High Similarity NPC268184
0.9266 High Similarity NPC286347
0.9266 High Similarity NPC109588
0.9266 High Similarity NPC232237
0.9266 High Similarity NPC105800
0.9259 High Similarity NPC75287
0.9259 High Similarity NPC288205
0.9259 High Similarity NPC305267
0.9259 High Similarity NPC26626
0.9259 High Similarity NPC51465
0.9259 High Similarity NPC476992
0.9252 High Similarity NPC62696
0.9252 High Similarity NPC293038
0.9231 High Similarity NPC293512
0.9223 High Similarity NPC173583
0.9189 High Similarity NPC75417
0.9182 High Similarity NPC309780
0.9182 High Similarity NPC208381
0.9182 High Similarity NPC469945
0.9182 High Similarity NPC157868
0.9182 High Similarity NPC6377
0.9182 High Similarity NPC475171

  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 NPC191763 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
0.9057 High Similarity NPD8132 Clinical (unspecified phase)
0.9 High Similarity NPD8295 Clinical (unspecified phase)
0.886 High Similarity NPD8328 Phase 3
0.823 Intermediate Similarity NPD8133 Approved
0.8182 Intermediate Similarity NPD6412 Phase 2
0.8113 Intermediate Similarity NPD7902 Approved
0.8108 Intermediate Similarity NPD6686 Approved
0.8 Intermediate Similarity NPD7748 Approved
0.7934 Intermediate Similarity NPD7507 Approved
0.7899 Intermediate Similarity NPD8033 Approved
0.783 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.783 Intermediate Similarity NPD7900 Approved
0.7815 Intermediate Similarity NPD8377 Approved
0.7815 Intermediate Similarity NPD8294 Approved
0.781 Intermediate Similarity NPD7515 Phase 2
0.775 Intermediate Similarity NPD8378 Approved
0.775 Intermediate Similarity NPD8516 Approved
0.775 Intermediate Similarity NPD8335 Approved
0.775 Intermediate Similarity NPD8515 Approved
0.775 Intermediate Similarity NPD8296 Approved
0.775 Intermediate Similarity NPD8380 Approved
0.775 Intermediate Similarity NPD8379 Approved
0.775 Intermediate Similarity NPD8513 Phase 3
0.775 Intermediate Similarity NPD8517 Approved
0.7742 Intermediate Similarity NPD7319 Approved
0.7661 Intermediate Similarity NPD7736 Approved
0.7647 Intermediate Similarity NPD7328 Approved
0.7647 Intermediate Similarity NPD7327 Approved
0.7583 Intermediate Similarity NPD7516 Approved
0.7477 Intermediate Similarity NPD8035 Phase 2
0.7477 Intermediate Similarity NPD8034 Phase 2
0.7459 Intermediate Similarity NPD7503 Approved
0.744 Intermediate Similarity NPD8293 Discontinued
0.7407 Intermediate Similarity NPD6399 Phase 3
0.7288 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.7258 Intermediate Similarity NPD6370 Approved
0.7232 Intermediate Similarity NPD7638 Approved
0.7227 Intermediate Similarity NPD6882 Approved
0.7227 Intermediate Similarity NPD8297 Approved
0.7217 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7168 Intermediate Similarity NPD7640 Approved
0.7168 Intermediate Similarity NPD7639 Approved
0.7157 Intermediate Similarity NPD7645 Phase 2
0.7143 Intermediate Similarity NPD7492 Approved
0.7131 Intermediate Similarity NPD6009 Approved
0.7131 Intermediate Similarity NPD7115 Discovery
0.7119 Intermediate Similarity NPD6373 Approved
0.7119 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7119 Intermediate Similarity NPD6372 Approved
0.7097 Intermediate Similarity NPD6054 Approved
0.7097 Intermediate Similarity NPD6319 Approved
0.7097 Intermediate Similarity NPD6059 Approved
0.7087 Intermediate Similarity NPD6616 Approved
0.7075 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD6067 Discontinued
0.7059 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7031 Intermediate Similarity NPD7078 Approved
0.7025 Intermediate Similarity NPD4632 Approved
0.7009 Intermediate Similarity NPD5739 Approved
0.7009 Intermediate Similarity NPD6675 Approved
0.7009 Intermediate Similarity NPD6402 Approved
0.7009 Intermediate Similarity NPD7128 Approved
0.7 Intermediate Similarity NPD6649 Approved
0.7 Intermediate Similarity NPD6650 Approved
0.7 Intermediate Similarity NPD6411 Approved
0.693 Remote Similarity NPD4225 Approved
0.6909 Remote Similarity NPD46 Approved
0.6909 Remote Similarity NPD6698 Approved
0.6905 Remote Similarity NPD6015 Approved
0.6905 Remote Similarity NPD6016 Approved
0.6899 Remote Similarity NPD8074 Phase 3
0.6891 Remote Similarity NPD6881 Approved
0.6891 Remote Similarity NPD6899 Approved
0.6891 Remote Similarity NPD7320 Approved
0.6864 Remote Similarity NPD6008 Approved
0.686 Remote Similarity NPD8130 Phase 1
0.6852 Remote Similarity NPD3618 Phase 1
0.685 Remote Similarity NPD5988 Approved
0.6822 Remote Similarity NPD4786 Approved
0.6818 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6818 Remote Similarity NPD6101 Approved
0.6807 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6807 Remote Similarity NPD5701 Approved
0.6807 Remote Similarity NPD5697 Approved
0.6792 Remote Similarity NPD3667 Approved
0.6786 Remote Similarity NPD8171 Discontinued
0.6777 Remote Similarity NPD7102 Approved
0.6777 Remote Similarity NPD6883 Approved
0.6777 Remote Similarity NPD7290 Approved
0.6727 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6721 Remote Similarity NPD6869 Approved
0.6721 Remote Similarity NPD6847 Approved
0.6721 Remote Similarity NPD6617 Approved
0.6696 Remote Similarity NPD6083 Phase 2
0.6696 Remote Similarity NPD6084 Phase 2
0.6696 Remote Similarity NPD7983 Approved
0.6694 Remote Similarity NPD6013 Approved
0.6694 Remote Similarity NPD6014 Approved
0.6694 Remote Similarity NPD6012 Approved
0.6667 Remote Similarity NPD7604 Phase 2
0.6667 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5328 Approved
0.6641 Remote Similarity NPD5983 Phase 2
0.6641 Remote Similarity NPD6921 Approved
0.6638 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6637 Remote Similarity NPD5779 Approved
0.6637 Remote Similarity NPD5778 Approved
0.6636 Remote Similarity NPD3573 Approved
0.6612 Remote Similarity NPD6011 Approved
0.661 Remote Similarity NPD7632 Discontinued
0.6591 Remote Similarity NPD6033 Approved
0.6585 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6574 Remote Similarity NPD3670 Clinical (unspecified phase)
0.6574 Remote Similarity NPD3669 Approved
0.6565 Remote Similarity NPD6336 Discontinued
0.6552 Remote Similarity NPD4755 Approved
0.6549 Remote Similarity NPD6079 Approved
0.6545 Remote Similarity NPD7334 Approved
0.6545 Remote Similarity NPD6409 Approved
0.6545 Remote Similarity NPD7521 Approved
0.6545 Remote Similarity NPD6684 Approved
0.6545 Remote Similarity NPD5330 Approved
0.6545 Remote Similarity NPD7146 Approved
0.6519 Remote Similarity NPD8449 Approved
0.6508 Remote Similarity NPD6940 Discontinued
0.6504 Remote Similarity NPD4634 Approved
0.6496 Remote Similarity NPD5696 Approved
0.6491 Remote Similarity NPD4202 Approved
0.6471 Remote Similarity NPD8450 Suspended
0.6466 Remote Similarity NPD4697 Phase 3
0.6449 Remote Similarity NPD7525 Registered
0.6441 Remote Similarity NPD5286 Approved
0.6441 Remote Similarity NPD4700 Approved
0.6441 Remote Similarity NPD4696 Approved
0.6441 Remote Similarity NPD5285 Approved
0.6429 Remote Similarity NPD5737 Approved
0.6429 Remote Similarity NPD6903 Approved
0.6429 Remote Similarity NPD6672 Approved
0.6415 Remote Similarity NPD6114 Approved
0.6415 Remote Similarity NPD6697 Approved
0.6415 Remote Similarity NPD6115 Approved
0.6415 Remote Similarity NPD6118 Approved
0.6406 Remote Similarity NPD7641 Discontinued
0.6389 Remote Similarity NPD1779 Approved
0.6389 Remote Similarity NPD1780 Approved
0.6387 Remote Similarity NPD5344 Discontinued
0.6379 Remote Similarity NPD5695 Phase 3
0.6379 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6378 Remote Similarity NPD6274 Approved
0.6364 Remote Similarity NPD8340 Approved
0.6364 Remote Similarity NPD8299 Approved
0.6364 Remote Similarity NPD8341 Approved
0.6364 Remote Similarity NPD3133 Approved
0.6364 Remote Similarity NPD3666 Approved
0.6364 Remote Similarity NPD3668 Phase 3
0.6364 Remote Similarity NPD3665 Phase 1
0.6364 Remote Similarity NPD8342 Approved
0.6357 Remote Similarity NPD7101 Approved
0.6357 Remote Similarity NPD7100 Approved
0.6333 Remote Similarity NPD5226 Approved
0.6333 Remote Similarity NPD4633 Approved
0.6333 Remote Similarity NPD5225 Approved
0.6333 Remote Similarity NPD5224 Approved
0.6333 Remote Similarity NPD5211 Phase 2
0.6328 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6325 Remote Similarity NPD5221 Approved
0.6325 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6325 Remote Similarity NPD5222 Approved
0.6325 Remote Similarity NPD7839 Suspended
0.6321 Remote Similarity NPD6116 Phase 1
0.6316 Remote Similarity NPD8451 Approved
0.6316 Remote Similarity NPD7838 Discovery
0.6311 Remote Similarity NPD4767 Approved
0.6311 Remote Similarity NPD4768 Approved
0.6281 Remote Similarity NPD5175 Approved
0.6281 Remote Similarity NPD5174 Approved
0.6279 Remote Similarity NPD6335 Approved
0.6276 Remote Similarity NPD7625 Phase 1
0.6271 Remote Similarity NPD5173 Approved
0.627 Remote Similarity NPD6053 Discontinued
0.6269 Remote Similarity NPD8448 Approved
0.6261 Remote Similarity NPD7637 Suspended
0.626 Remote Similarity NPD6909 Approved
0.626 Remote Similarity NPD6908 Approved
0.626 Remote Similarity NPD7899 Clinical (unspecified phase)
0.625 Remote Similarity NPD8391 Approved
0.625 Remote Similarity NPD5223 Approved
0.625 Remote Similarity NPD8392 Approved
0.625 Remote Similarity NPD8390 Approved
0.625 Remote Similarity NPD6868 Approved
0.624 Remote Similarity NPD6371 Approved
0.623 Remote Similarity NPD5141 Approved
0.6228 Remote Similarity NPD4753 Phase 2
0.6226 Remote Similarity NPD6117 Approved
0.6222 Remote Similarity NPD8337 Approved
0.6222 Remote Similarity NPD8336 Approved
0.621 Remote Similarity NPD4730 Approved
0.621 Remote Similarity NPD4729 Approved
0.6204 Remote Similarity NPD7260 Phase 2

  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