Structure

Physi-Chem Properties

Molecular Weight:  634.41
Volume:  653.712
LogP:  3.806
LogD:  3.9
LogS:  -4.13
# 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:  5.407
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:  -5.328
MDCK Permeability:  1.2601116395671852e-05
Pgp-inhibitor:  0.983
Pgp-substrate:  0.014
Human Intestinal Absorption (HIA):  0.062
20% Bioavailability (F20%):  0.028
30% Bioavailability (F30%):  0.668

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.039
Plasma Protein Binding (PPB):  89.70475769042969%
Volume Distribution (VD):  0.738
Pgp-substrate:  6.612666606903076%

ADMET: Metabolism

CYP1A2-inhibitor:  0.005
CYP1A2-substrate:  0.407
CYP2C19-inhibitor:  0.004
CYP2C19-substrate:  0.68
CYP2C9-inhibitor:  0.021
CYP2C9-substrate:  0.051
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.084
CYP3A4-inhibitor:  0.332
CYP3A4-substrate:  0.129

ADMET: Excretion

Clearance (CL):  1.577
Half-life (T1/2):  0.215

ADMET: Toxicity

hERG Blockers:  0.014
Human Hepatotoxicity (H-HT):  0.209
Drug-inuced Liver Injury (DILI):  0.017
AMES Toxicity:  0.023
Rat Oral Acute Toxicity:  0.634
Maximum Recommended Daily Dose:  0.963
Skin Sensitization:  0.096
Carcinogencity:  0.025
Eye Corrosion:  0.004
Eye Irritation:  0.013
Respiratory Toxicity:  0.98

Download Data

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

  Natural Product: NPC46388

Natural Product ID:  NPC46388
Common Name*:   Pomolic Acid-28-O-Beta-D-Glucopyranosyl Ester
IUPAC Name:   [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1R,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-1,10-dihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms:  
Standard InCHIKey:  RRIMLWHUVCZACL-HPUCWRFUSA-N
Standard InCHI:  InChI=1S/C36H58O9/c1-19-10-15-36(30(42)45-29-27(41)26(40)25(39)21(18-37)44-29)17-16-33(5)20(28(36)35(19,7)43)8-9-23-32(4)13-12-24(38)31(2,3)22(32)11-14-34(23,33)6/h8,19,21-29,37-41,43H,9-18H2,1-7H3/t19-,21-,22+,23-,24+,25-,26+,27-,28-,29+,32+,33-,34-,35-,36+/m1/s1
SMILES:  OC[C@H]1O[C@@H](OC(=O)[C@@]23CC[C@H]([C@@]([C@H]3C3=CC[C@H]4[C@@]([C@@]3(CC2)C)(C)CC[C@@H]2[C@]4(C)CC[C@@H](C2(C)C)O)(C)O)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2253394
PubChem CID:   76322845
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0002049] Terpene glycosides
          • [CHEMONTID:0001580] Triterpene glycosides
            • [CHEMONTID:0002358] Triterpene saponins

*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 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 Root n.a. n.a. Database[FooDB]
NPO26622 Taraxacum officinale Species Asteraceae Eukaryota n.a. n.a. Database[FooDB]
NPO26650 Terminalia chebula Species Combretaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26622 Taraxacum officinale Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26622 Taraxacum officinale Species Asteraceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO26622 Taraxacum officinale Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26650 Terminalia chebula Species Combretaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26650 Terminalia chebula Species Combretaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
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[TM-MC]
NPO26622 Taraxacum officinale Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
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]
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]
NPO26283 Streptomyces djakartensis 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]
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]
NPO26622 Taraxacum officinale 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]
NPO26048 Grateloupia elliptica Species Halymeniaceae 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 Inhibition = 27.0 % PMID[448771]

☑ 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 NPC46388 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 NPC37739
0.9904 High Similarity NPC271138
0.9904 High Similarity NPC47063
0.9904 High Similarity NPC138334
0.9904 High Similarity NPC189884
0.9904 High Similarity NPC204458
0.9904 High Similarity NPC269315
0.9903 High Similarity NPC191763
0.9808 High Similarity NPC116794
0.9808 High Similarity NPC128925
0.9808 High Similarity NPC256798
0.9806 High Similarity NPC274507
0.9717 High Similarity NPC160415
0.9717 High Similarity NPC58448
0.9712 High Similarity NPC108748
0.9712 High Similarity NPC473481
0.9712 High Similarity NPC235841
0.9712 High Similarity NPC211798
0.9712 High Similarity NPC297208
0.9712 High Similarity NPC30397
0.9709 High Similarity NPC306746
0.9709 High Similarity NPC204407
0.9709 High Similarity NPC237503
0.9709 High Similarity NPC57362
0.9709 High Similarity NPC167383
0.9626 High Similarity NPC68175
0.9623 High Similarity NPC475633
0.9615 High Similarity NPC476884
0.9615 High Similarity NPC270667
0.9615 High Similarity NPC279554
0.9615 High Similarity NPC199457
0.9615 High Similarity NPC476882
0.9615 High Similarity NPC29069
0.9615 High Similarity NPC68419
0.9615 High Similarity NPC474589
0.9615 High Similarity NPC102914
0.9615 High Similarity NPC174679
0.9615 High Similarity NPC164194
0.9615 High Similarity NPC127056
0.9615 High Similarity NPC59804
0.9615 High Similarity NPC56713
0.9615 High Similarity NPC476887
0.9615 High Similarity NPC136877
0.9615 High Similarity NPC108709
0.9615 High Similarity NPC476886
0.9615 High Similarity NPC475296
0.9615 High Similarity NPC476880
0.9615 High Similarity NPC7870
0.9615 High Similarity NPC476881
0.9615 High Similarity NPC476885
0.9615 High Similarity NPC110139
0.9615 High Similarity NPC476883
0.9615 High Similarity NPC75747
0.9615 High Similarity NPC90856
0.9612 High Similarity NPC28198
0.9612 High Similarity NPC284807
0.9612 High Similarity NPC177246
0.9612 High Similarity NPC476123
0.9537 High Similarity NPC36831
0.9533 High Similarity NPC471384
0.9533 High Similarity NPC161674
0.9528 High Similarity NPC124296
0.9528 High Similarity NPC258885
0.9524 High Similarity NPC31839
0.9524 High Similarity NPC164419
0.9524 High Similarity NPC179434
0.9519 High Similarity NPC127853
0.9519 High Similarity NPC137917
0.9515 High Similarity NPC473538
0.9515 High Similarity NPC283849
0.9444 High Similarity NPC136768
0.9444 High Similarity NPC148417
0.9444 High Similarity NPC110633
0.9434 High Similarity NPC104400
0.9434 High Similarity NPC109079
0.9434 High Similarity NPC10320
0.9434 High Similarity NPC79718
0.9434 High Similarity NPC276093
0.9434 High Similarity NPC292677
0.9434 High Similarity NPC471967
0.9434 High Similarity NPC139894
0.9434 High Similarity NPC475504
0.9434 High Similarity NPC473383
0.9434 High Similarity NPC102439
0.9434 High Similarity NPC101744
0.9434 High Similarity NPC473373
0.9434 High Similarity NPC104071
0.9434 High Similarity NPC48249
0.9434 High Similarity NPC80843
0.9434 High Similarity NPC139044
0.9434 High Similarity NPC257468
0.9434 High Similarity NPC324875
0.9434 High Similarity NPC475516
0.9434 High Similarity NPC1046
0.9434 High Similarity NPC471383
0.9434 High Similarity NPC469946
0.9429 High Similarity NPC242611
0.9429 High Similarity NPC269095
0.9429 High Similarity NPC78046
0.9429 High Similarity NPC220984
0.9423 High Similarity NPC285576
0.9417 High Similarity NPC475611
0.9364 High Similarity NPC268184
0.9352 High Similarity NPC291903
0.9352 High Similarity NPC37134
0.9346 High Similarity NPC46665
0.9346 High Similarity NPC133818
0.9346 High Similarity NPC96641
0.9346 High Similarity NPC73318
0.9346 High Similarity NPC241909
0.9346 High Similarity NPC295823
0.9346 High Similarity NPC475467
0.9346 High Similarity NPC309714
0.9346 High Similarity NPC251263
0.9346 High Similarity NPC475287
0.9346 High Similarity NPC473343
0.9346 High Similarity NPC323341
0.9346 High Similarity NPC151543
0.9346 High Similarity NPC166422
0.9346 High Similarity NPC174720
0.9346 High Similarity NPC473826
0.9346 High Similarity NPC475208
0.9346 High Similarity NPC155410
0.9346 High Similarity NPC238935
0.9346 High Similarity NPC192600
0.9346 High Similarity NPC114304
0.9346 High Similarity NPC219180
0.9346 High Similarity NPC114287
0.9346 High Similarity NPC150400
0.9346 High Similarity NPC163183
0.9346 High Similarity NPC134835
0.934 High Similarity NPC190837
0.9279 High Similarity NPC75417
0.9266 High Similarity NPC475119
0.9266 High Similarity NPC300419
0.9266 High Similarity NPC473824
0.9259 High Similarity NPC250247
0.9259 High Similarity NPC79643
0.9259 High Similarity NPC305981
0.9259 High Similarity NPC475486
0.9259 High Similarity NPC57484
0.9259 High Similarity NPC298034
0.9259 High Similarity NPC204414
0.9259 High Similarity NPC475140
0.9259 High Similarity NPC476068
0.9259 High Similarity NPC309907
0.9259 High Similarity NPC43550
0.9259 High Similarity NPC100639
0.9259 High Similarity NPC65105
0.9259 High Similarity NPC54636
0.9259 High Similarity NPC60557
0.9259 High Similarity NPC67857
0.9259 High Similarity NPC471550
0.9259 High Similarity NPC293330
0.9259 High Similarity NPC202828
0.9259 High Similarity NPC4328
0.9259 High Similarity NPC76972
0.9259 High Similarity NPC123199
0.9259 High Similarity NPC71065
0.9259 High Similarity NPC70809
0.9259 High Similarity NPC161717
0.9259 High Similarity NPC471385
0.9259 High Similarity NPC224381
0.9259 High Similarity NPC119592
0.9259 High Similarity NPC227551
0.9259 High Similarity NPC473714
0.9259 High Similarity NPC475160
0.9259 High Similarity NPC294453
0.9259 High Similarity NPC261506
0.9259 High Similarity NPC41061
0.9259 High Similarity NPC469782
0.9259 High Similarity NPC236638
0.9259 High Similarity NPC164389
0.9252 High Similarity NPC125923
0.9252 High Similarity NPC195132
0.9252 High Similarity NPC64106
0.9252 High Similarity NPC65590
0.9252 High Similarity NPC100383
0.9252 High Similarity NPC161434
0.9252 High Similarity NPC212968
0.9245 High Similarity NPC475501
0.9189 High Similarity NPC473645
0.9182 High Similarity NPC232237
0.9182 High Similarity NPC475899
0.9182 High Similarity NPC105800
0.9182 High Similarity NPC109588
0.9182 High Similarity NPC286347
0.9174 High Similarity NPC26626
0.9174 High Similarity NPC75287
0.9174 High Similarity NPC305267
0.9174 High Similarity NPC476992
0.9174 High Similarity NPC288205
0.9174 High Similarity NPC51465
0.9167 High Similarity NPC62696
0.9167 High Similarity NPC293038
0.9143 High Similarity NPC293512
0.9135 High Similarity NPC173583
0.9099 High Similarity NPC135849
0.9099 High Similarity NPC214484
0.9099 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 NPC46388 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
0.8972 High Similarity NPD8132 Clinical (unspecified phase)
0.8919 High Similarity NPD8295 Clinical (unspecified phase)
0.8783 High Similarity NPD8328 Phase 3
0.8319 Intermediate Similarity NPD8133 Approved
0.8108 Intermediate Similarity NPD6412 Phase 2
0.8037 Intermediate Similarity NPD7902 Approved
0.8036 Intermediate Similarity NPD6686 Approved
0.8017 Intermediate Similarity NPD7507 Approved
0.7983 Intermediate Similarity NPD8033 Approved
0.7925 Intermediate Similarity NPD7748 Approved
0.7899 Intermediate Similarity NPD8377 Approved
0.7899 Intermediate Similarity NPD8294 Approved
0.7833 Intermediate Similarity NPD8378 Approved
0.7833 Intermediate Similarity NPD8513 Phase 3
0.7833 Intermediate Similarity NPD8515 Approved
0.7833 Intermediate Similarity NPD8335 Approved
0.7833 Intermediate Similarity NPD8516 Approved
0.7833 Intermediate Similarity NPD8380 Approved
0.7833 Intermediate Similarity NPD8517 Approved
0.7833 Intermediate Similarity NPD8379 Approved
0.7833 Intermediate Similarity NPD8296 Approved
0.7823 Intermediate Similarity NPD7319 Approved
0.7757 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7757 Intermediate Similarity NPD7900 Approved
0.7742 Intermediate Similarity NPD7736 Approved
0.7736 Intermediate Similarity NPD7515 Phase 2
0.7731 Intermediate Similarity NPD7327 Approved
0.7731 Intermediate Similarity NPD7328 Approved
0.7667 Intermediate Similarity NPD7516 Approved
0.7541 Intermediate Similarity NPD7503 Approved
0.752 Intermediate Similarity NPD8293 Discontinued
0.7407 Intermediate Similarity NPD8034 Phase 2
0.7407 Intermediate Similarity NPD8035 Phase 2
0.7373 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.7339 Intermediate Similarity NPD6399 Phase 3
0.7339 Intermediate Similarity NPD6370 Approved
0.7311 Intermediate Similarity NPD8297 Approved
0.7311 Intermediate Similarity NPD6882 Approved
0.7265 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD7492 Approved
0.7213 Intermediate Similarity NPD7115 Discovery
0.7213 Intermediate Similarity NPD6009 Approved
0.7203 Intermediate Similarity NPD6372 Approved
0.7203 Intermediate Similarity NPD6373 Approved
0.7203 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7177 Intermediate Similarity NPD6059 Approved
0.7177 Intermediate Similarity NPD6319 Approved
0.7177 Intermediate Similarity NPD6054 Approved
0.7168 Intermediate Similarity NPD7638 Approved
0.7165 Intermediate Similarity NPD6616 Approved
0.7155 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7109 Intermediate Similarity NPD7078 Approved
0.7107 Intermediate Similarity NPD4632 Approved
0.7105 Intermediate Similarity NPD7639 Approved
0.7105 Intermediate Similarity NPD7640 Approved
0.7094 Intermediate Similarity NPD6675 Approved
0.7094 Intermediate Similarity NPD6402 Approved
0.7094 Intermediate Similarity NPD5739 Approved
0.7094 Intermediate Similarity NPD7128 Approved
0.7087 Intermediate Similarity NPD7645 Phase 2
0.7083 Intermediate Similarity NPD6649 Approved
0.7083 Intermediate Similarity NPD6650 Approved
0.7009 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7008 Intermediate Similarity NPD6067 Discontinued
0.6984 Remote Similarity NPD6015 Approved
0.6984 Remote Similarity NPD6016 Approved
0.6977 Remote Similarity NPD8074 Phase 3
0.6975 Remote Similarity NPD6899 Approved
0.6975 Remote Similarity NPD6881 Approved
0.6975 Remote Similarity NPD7320 Approved
0.6949 Remote Similarity NPD6008 Approved
0.6942 Remote Similarity NPD8130 Phase 1
0.6937 Remote Similarity NPD6411 Approved
0.6929 Remote Similarity NPD5988 Approved
0.6891 Remote Similarity NPD5701 Approved
0.6891 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6891 Remote Similarity NPD5697 Approved
0.687 Remote Similarity NPD4225 Approved
0.686 Remote Similarity NPD6883 Approved
0.686 Remote Similarity NPD7290 Approved
0.686 Remote Similarity NPD7102 Approved
0.6847 Remote Similarity NPD6698 Approved
0.6847 Remote Similarity NPD46 Approved
0.6803 Remote Similarity NPD6617 Approved
0.6803 Remote Similarity NPD6847 Approved
0.6803 Remote Similarity NPD6869 Approved
0.6789 Remote Similarity NPD3618 Phase 1
0.6783 Remote Similarity NPD6084 Phase 2
0.6783 Remote Similarity NPD6083 Phase 2
0.6777 Remote Similarity NPD6014 Approved
0.6777 Remote Similarity NPD6012 Approved
0.6777 Remote Similarity NPD6013 Approved
0.6759 Remote Similarity NPD4786 Approved
0.6757 Remote Similarity NPD6101 Approved
0.6757 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6744 Remote Similarity NPD7604 Phase 2
0.6729 Remote Similarity NPD3667 Approved
0.6727 Remote Similarity NPD3573 Approved
0.6726 Remote Similarity NPD8171 Discontinued
0.6724 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6719 Remote Similarity NPD6921 Approved
0.6719 Remote Similarity NPD5983 Phase 2
0.6694 Remote Similarity NPD6011 Approved
0.6667 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6033 Approved
0.6667 Remote Similarity NPD3670 Clinical (unspecified phase)
0.6667 Remote Similarity NPD3669 Approved
0.6641 Remote Similarity NPD6336 Discontinued
0.6638 Remote Similarity NPD4755 Approved
0.6637 Remote Similarity NPD7983 Approved
0.6607 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6607 Remote Similarity NPD5328 Approved
0.6585 Remote Similarity NPD4634 Approved
0.6581 Remote Similarity NPD5696 Approved
0.6579 Remote Similarity NPD5779 Approved
0.6579 Remote Similarity NPD4202 Approved
0.6579 Remote Similarity NPD5778 Approved
0.6555 Remote Similarity NPD7632 Discontinued
0.6542 Remote Similarity NPD7525 Registered
0.6525 Remote Similarity NPD5285 Approved
0.6525 Remote Similarity NPD5286 Approved
0.6525 Remote Similarity NPD4700 Approved
0.6525 Remote Similarity NPD4696 Approved
0.6491 Remote Similarity NPD6079 Approved
0.6486 Remote Similarity NPD7334 Approved
0.6486 Remote Similarity NPD5330 Approved
0.6486 Remote Similarity NPD7146 Approved
0.6486 Remote Similarity NPD7521 Approved
0.6486 Remote Similarity NPD6684 Approved
0.6486 Remote Similarity NPD6409 Approved
0.6481 Remote Similarity NPD1780 Approved
0.6481 Remote Similarity NPD1779 Approved
0.6471 Remote Similarity NPD5344 Discontinued
0.6471 Remote Similarity NPD8449 Approved
0.6466 Remote Similarity NPD5695 Phase 3
0.6466 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6457 Remote Similarity NPD6274 Approved
0.6457 Remote Similarity NPD6940 Discontinued
0.6439 Remote Similarity NPD8340 Approved
0.6439 Remote Similarity NPD8342 Approved
0.6439 Remote Similarity NPD8341 Approved
0.6439 Remote Similarity NPD8299 Approved
0.6434 Remote Similarity NPD7100 Approved
0.6434 Remote Similarity NPD7101 Approved
0.6423 Remote Similarity NPD8450 Suspended
0.6417 Remote Similarity NPD4633 Approved
0.6417 Remote Similarity NPD5224 Approved
0.6417 Remote Similarity NPD5211 Phase 2
0.6417 Remote Similarity NPD5225 Approved
0.6417 Remote Similarity NPD5226 Approved
0.641 Remote Similarity NPD4697 Phase 3
0.6406 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6393 Remote Similarity NPD4768 Approved
0.6393 Remote Similarity NPD4767 Approved
0.6391 Remote Similarity NPD8451 Approved
0.6372 Remote Similarity NPD5737 Approved
0.6372 Remote Similarity NPD6672 Approved
0.6372 Remote Similarity NPD6903 Approved
0.6364 Remote Similarity NPD5175 Approved
0.6364 Remote Similarity NPD5174 Approved
0.6357 Remote Similarity NPD6335 Approved
0.6357 Remote Similarity NPD7641 Discontinued
0.6355 Remote Similarity NPD6114 Approved
0.6355 Remote Similarity NPD6697 Approved
0.6355 Remote Similarity NPD6115 Approved
0.6355 Remote Similarity NPD6118 Approved
0.6349 Remote Similarity NPD6053 Discontinued
0.6345 Remote Similarity NPD7625 Phase 1
0.6343 Remote Similarity NPD8448 Approved
0.6341 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6336 Remote Similarity NPD6908 Approved
0.6336 Remote Similarity NPD6909 Approved
0.6333 Remote Similarity NPD5223 Approved
0.6324 Remote Similarity NPD8391 Approved
0.6324 Remote Similarity NPD8392 Approved
0.6324 Remote Similarity NPD8390 Approved
0.632 Remote Similarity NPD6371 Approved
0.6316 Remote Similarity NPD4753 Phase 2
0.6311 Remote Similarity NPD5141 Approved
0.6306 Remote Similarity NPD3666 Approved
0.6306 Remote Similarity NPD3133 Approved
0.6306 Remote Similarity NPD3668 Phase 3
0.6306 Remote Similarity NPD3665 Phase 1
0.629 Remote Similarity NPD4730 Approved
0.629 Remote Similarity NPD4729 Approved
0.6283 Remote Similarity NPD7524 Approved
0.6279 Remote Similarity NPD6317 Approved
0.6271 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6271 Remote Similarity NPD5222 Approved
0.6271 Remote Similarity NPD7839 Suspended
0.6271 Remote Similarity NPD5221 Approved
0.6262 Remote Similarity NPD6116 Phase 1
0.6261 Remote Similarity NPD7838 Discovery
0.6239 Remote Similarity NPD5282 Discontinued
0.6231 Remote Similarity NPD6314 Approved
0.6231 Remote Similarity NPD6313 Approved
0.623 Remote Similarity NPD4754 Approved
0.6218 Remote Similarity NPD5173 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