Structure

Physi-Chem Properties

Molecular Weight:  684.13
Volume:  619.929
LogP:  1.096
LogD:  0.383
LogS:  -5.082
# Rotatable Bonds:  4
TPSA:  301.41
# H-Bond Aceptor:  17
# H-Bond Donor:  11
# Rings:  7
# Heavy Atoms:  17

MedChem Properties

QED Drug-Likeness Score:  0.091
Synthetic Accessibility Score:  5.229
Fsp3:  0.312
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:  -6.348
MDCK Permeability:  3.8038974707887974e-06
Pgp-inhibitor:  0.004
Pgp-substrate:  0.947
Human Intestinal Absorption (HIA):  0.99
20% Bioavailability (F20%):  0.599
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.003
Plasma Protein Binding (PPB):  86.1334457397461%
Volume Distribution (VD):  0.75
Pgp-substrate:  21.21649169921875%

ADMET: Metabolism

CYP1A2-inhibitor:  0.041
CYP1A2-substrate:  0.085
CYP2C19-inhibitor:  0.016
CYP2C19-substrate:  0.044
CYP2C9-inhibitor:  0.102
CYP2C9-substrate:  0.092
CYP2D6-inhibitor:  0.001
CYP2D6-substrate:  0.11
CYP3A4-inhibitor:  0.027
CYP3A4-substrate:  0.004

ADMET: Excretion

Clearance (CL):  1.457
Half-life (T1/2):  0.788

ADMET: Toxicity

hERG Blockers:  0.03
Human Hepatotoxicity (H-HT):  0.338
Drug-inuced Liver Injury (DILI):  0.987
AMES Toxicity:  0.524
Rat Oral Acute Toxicity:  0.015
Maximum Recommended Daily Dose:  0.118
Skin Sensitization:  0.454
Carcinogencity:  0.023
Eye Corrosion:  0.003
Eye Irritation:  0.266
Respiratory Toxicity:  0.014

Download Data

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

  Natural Product: NPC49690

Natural Product ID:  NPC49690
Common Name*:   Puniceaside B
IUPAC Name:   1,4,6,8-tetrahydroxy-2-[(5R,8S)-1,3,5-trihydroxy-9-oxo-8-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,6,7,8-tetrahydroxanthen-2-yl]xanthen-9-one
Synonyms:   Puniceaside B
Standard InCHIKey:  HECROWLXEXBVDW-DDFBWJSFSA-N
Standard InCHI:  InChI=1S/C32H28O17/c33-7-17-24(40)28(44)29(45)32(49-17)48-14-2-1-10(35)30-21(14)27(43)20-16(47-30)6-12(37)18(25(20)41)9-5-13(38)31-22(23(9)39)26(42)19-11(36)3-8(34)4-15(19)46-31/h3-6,10,14,17,24,28-29,32-41,44-45H,1-2,7H2/t10-,14+,17-,24-,28+,29-,32-/m1/s1
SMILES:  OC[C@H]1O[C@@H](O[C@H]2CC[C@H](c3c2c(=O)c2c(o3)cc(c(c2O)c2cc(O)c3c(c2O)c(=O)c2c(o3)cc(cc2O)O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1214705
PubChem CID:   49863991
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000123] Benzopyrans
        • [CHEMONTID:0003410] 1-benzopyrans
          • [CHEMONTID:0002817] Dibenzopyrans
            • [CHEMONTID:0000200] Xanthenes
              • [CHEMONTID:0000204] Xanthones

*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
NPO14238 Swertia punicea Species Gentianaceae Eukaryota n.a. n.a. n.a. DOI[10.1002/cbdv.200490123]
NPO14238 Swertia punicea Species Gentianaceae Eukaryota n.a. whole plant n.a. DOI[10.1021/jo00025a032]
NPO14238 Swertia punicea Species Gentianaceae Eukaryota n.a. n.a. n.a. DOI[10.1021/np50072a022]
NPO14238 Swertia punicea Species Gentianaceae Eukaryota n.a. n.a. n.a. PMID[20677781]
NPO14238 Swertia punicea Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14238 Swertia punicea Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14238 Swertia punicea Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14238 Swertia punicea Species Gentianaceae 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
NPT681 Cell Line PC-12 Rattus norvegicus Activity = 75.1 % PMID[497536]
NPT681 Cell Line PC-12 Rattus norvegicus Activity = 98.1 % PMID[497536]

☑ 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 NPC49690 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
0.9651 High Similarity NPC179947
0.9595 High Similarity NPC473618
0.9477 High Similarity NPC132111
0.9408 High Similarity NPC3583
0.9408 High Similarity NPC259152
0.936 High Similarity NPC324742
0.9357 High Similarity NPC255799
0.9353 High Similarity NPC25724
0.9349 High Similarity NPC218488
0.931 High Similarity NPC148710
0.9302 High Similarity NPC265380
0.9302 High Similarity NPC476618
0.9302 High Similarity NPC476620
0.9302 High Similarity NPC476623
0.9302 High Similarity NPC476622
0.9302 High Similarity NPC476619
0.9302 High Similarity NPC476621
0.9298 High Similarity NPC472607
0.9294 High Similarity NPC256760
0.929 High Similarity NPC471457
0.929 High Similarity NPC112755
0.929 High Similarity NPC170675
0.9257 High Similarity NPC111490
0.9257 High Similarity NPC261623
0.9249 High Similarity NPC185275
0.9244 High Similarity NPC472991
0.9244 High Similarity NPC8573
0.9244 High Similarity NPC472992
0.9244 High Similarity NPC169733
0.924 High Similarity NPC239549
0.924 High Similarity NPC204693
0.924 High Similarity NPC208668
0.924 High Similarity NPC51774
0.924 High Similarity NPC236191
0.9235 High Similarity NPC471416
0.9235 High Similarity NPC34287
0.9235 High Similarity NPC150767
0.9235 High Similarity NPC183357
0.9235 High Similarity NPC22195
0.9235 High Similarity NPC21190
0.9235 High Similarity NPC78734
0.9235 High Similarity NPC224462
0.9231 High Similarity NPC58716
0.9231 High Similarity NPC146792
0.9231 High Similarity NPC477502
0.9231 High Similarity NPC45618
0.9209 High Similarity NPC469652
0.9209 High Similarity NPC472721
0.9209 High Similarity NPC160543
0.9209 High Similarity NPC472724
0.9209 High Similarity NPC472720
0.9209 High Similarity NPC31208
0.9209 High Similarity NPC93065
0.92 High Similarity NPC318119
0.9191 High Similarity NPC168584
0.9191 High Similarity NPC472387
0.9186 High Similarity NPC102028
0.9186 High Similarity NPC142996
0.9181 High Similarity NPC180918
0.9181 High Similarity NPC307518
0.9181 High Similarity NPC301683
0.9181 High Similarity NPC48773
0.9181 High Similarity NPC267254
0.9181 High Similarity NPC156977
0.9181 High Similarity NPC205076
0.9176 High Similarity NPC469931
0.9176 High Similarity NPC45638
0.9176 High Similarity NPC186807
0.9176 High Similarity NPC475942
0.9176 High Similarity NPC201292
0.9176 High Similarity NPC105025
0.9176 High Similarity NPC93337
0.9176 High Similarity NPC472381
0.9176 High Similarity NPC86008
0.9176 High Similarity NPC95855
0.9176 High Similarity NPC472383
0.9176 High Similarity NPC226294
0.9176 High Similarity NPC183036
0.9176 High Similarity NPC58053
0.9176 High Similarity NPC210042
0.9172 High Similarity NPC8856
0.9172 High Similarity NPC99957
0.9172 High Similarity NPC181616
0.9162 High Similarity NPC477082
0.9157 High Similarity NPC264302
0.9157 High Similarity NPC321046
0.9153 High Similarity NPC290289
0.9153 High Similarity NPC158214
0.9153 High Similarity NPC240200
0.9153 High Similarity NPC477083
0.9153 High Similarity NPC223534
0.9153 High Similarity NPC477081
0.9148 High Similarity NPC469650
0.9143 High Similarity NPC476203
0.9143 High Similarity NPC321916
0.9138 High Similarity NPC241423
0.9138 High Similarity NPC110941
0.9138 High Similarity NPC473571
0.9138 High Similarity NPC473682
0.9138 High Similarity NPC470443
0.9138 High Similarity NPC470444
0.9138 High Similarity NPC126784
0.9133 High Similarity NPC470949
0.9133 High Similarity NPC65563
0.9123 High Similarity NPC105511
0.9123 High Similarity NPC245014
0.9123 High Similarity NPC282987
0.9123 High Similarity NPC44558
0.9123 High Similarity NPC231194
0.9123 High Similarity NPC52353
0.9123 High Similarity NPC474434
0.9123 High Similarity NPC51326
0.9123 High Similarity NPC285197
0.9123 High Similarity NPC84265
0.9118 High Similarity NPC93099
0.9118 High Similarity NPC275454
0.9118 High Similarity NPC45400
0.9101 High Similarity NPC187632
0.9096 High Similarity NPC64755
0.9096 High Similarity NPC260521
0.9096 High Similarity NPC469649
0.9091 High Similarity NPC470451
0.9091 High Similarity NPC231254
0.9091 High Similarity NPC470416
0.9091 High Similarity NPC470455
0.9086 High Similarity NPC473071
0.9086 High Similarity NPC473073
0.908 High Similarity NPC471789
0.908 High Similarity NPC475261
0.908 High Similarity NPC267549
0.9075 High Similarity NPC108202
0.9075 High Similarity NPC198199
0.9075 High Similarity NPC294629
0.907 High Similarity NPC476405
0.907 High Similarity NPC117260
0.907 High Similarity NPC211594
0.907 High Similarity NPC212038
0.907 High Similarity NPC271848
0.907 High Similarity NPC60735
0.907 High Similarity NPC26230
0.907 High Similarity NPC254540
0.907 High Similarity NPC475155
0.907 High Similarity NPC262580
0.907 High Similarity NPC472386
0.907 High Similarity NPC289396
0.907 High Similarity NPC67134
0.907 High Similarity NPC47140
0.907 High Similarity NPC172807
0.907 High Similarity NPC81332
0.9064 High Similarity NPC227508
0.9064 High Similarity NPC229687
0.9064 High Similarity NPC209296
0.9064 High Similarity NPC195257
0.9064 High Similarity NPC471287
0.9064 High Similarity NPC105283
0.9061 High Similarity NPC3474
0.9059 High Similarity NPC236934
0.9059 High Similarity NPC115674
0.9059 High Similarity NPC210073
0.9059 High Similarity NPC5778
0.9053 High Similarity NPC191306
0.9053 High Similarity NPC270335
0.9053 High Similarity NPC29830
0.9053 High Similarity NPC222936
0.9053 High Similarity NPC284960
0.9053 High Similarity NPC94777
0.905 High Similarity NPC40078
0.905 High Similarity NPC471091
0.905 High Similarity NPC97924
0.9034 High Similarity NPC470446
0.9034 High Similarity NPC470447
0.9034 High Similarity NPC470718
0.9034 High Similarity NPC470449
0.9034 High Similarity NPC473072
0.9034 High Similarity NPC470445
0.9034 High Similarity NPC36138
0.9029 High Similarity NPC212290
0.9029 High Similarity NPC473895
0.9023 High Similarity NPC257714
0.9023 High Similarity NPC268533
0.9023 High Similarity NPC297574
0.9023 High Similarity NPC79736
0.9023 High Similarity NPC67629
0.9023 High Similarity NPC219043
0.9017 High Similarity NPC24043
0.9017 High Similarity NPC45522
0.9017 High Similarity NPC175230
0.9017 High Similarity NPC472993
0.9017 High Similarity NPC172033
0.9017 High Similarity NPC21666
0.9017 High Similarity NPC42773
0.9017 High Similarity NPC169977
0.9017 High Similarity NPC101026
0.9017 High Similarity NPC88560
0.9012 High Similarity NPC259896
0.9012 High Similarity NPC149011
0.9012 High Similarity NPC156869
0.9012 High Similarity NPC67326
0.9012 High Similarity NPC254855
0.9012 High Similarity NPC79056

  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 NPC49690 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
0.9123 High Similarity NPD7472 Approved
0.9064 High Similarity NPD7054 Approved
0.9012 High Similarity NPD7074 Phase 3
0.8966 High Similarity NPD7808 Phase 3
0.8966 High Similarity NPD4338 Clinical (unspecified phase)
0.896 High Similarity NPD6797 Phase 2
0.8908 High Similarity NPD7251 Discontinued
0.8895 High Similarity NPD3818 Discontinued
0.8779 High Similarity NPD6167 Clinical (unspecified phase)
0.8779 High Similarity NPD6168 Clinical (unspecified phase)
0.8779 High Similarity NPD6166 Phase 2
0.8736 High Similarity NPD7804 Clinical (unspecified phase)
0.8647 High Similarity NPD4381 Clinical (unspecified phase)
0.8531 High Similarity NPD7993 Clinical (unspecified phase)
0.848 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8471 Intermediate Similarity NPD2801 Approved
0.8471 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8412 Intermediate Similarity NPD1934 Approved
0.8361 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD5494 Approved
0.8315 Intermediate Similarity NPD5844 Phase 1
0.8294 Intermediate Similarity NPD4380 Phase 2
0.8287 Intermediate Similarity NPD8313 Approved
0.8287 Intermediate Similarity NPD8312 Approved
0.8286 Intermediate Similarity NPD6959 Discontinued
0.8278 Intermediate Similarity NPD6559 Discontinued
0.8172 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8136 Intermediate Similarity NPD6232 Discontinued
0.8103 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8103 Intermediate Similarity NPD8151 Discontinued
0.8101 Intermediate Similarity NPD7473 Discontinued
0.8056 Intermediate Similarity NPD7228 Approved
0.8047 Intermediate Similarity NPD1511 Approved
0.8046 Intermediate Similarity NPD8455 Phase 2
0.8046 Intermediate Similarity NPD1465 Phase 2
0.8 Intermediate Similarity NPD3817 Phase 2
0.7956 Intermediate Similarity NPD3751 Discontinued
0.7955 Intermediate Similarity NPD3882 Suspended
0.7953 Intermediate Similarity NPD1512 Approved
0.7944 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7929 Intermediate Similarity NPD7783 Phase 2
0.7929 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.791 Intermediate Similarity NPD7075 Discontinued
0.7898 Intermediate Similarity NPD5402 Approved
0.7861 Intermediate Similarity NPD1653 Approved
0.7841 Intermediate Similarity NPD7819 Suspended
0.7833 Intermediate Similarity NPD3787 Discontinued
0.7829 Intermediate Similarity NPD7411 Suspended
0.7791 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7791 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7784 Intermediate Similarity NPD6777 Approved
0.7784 Intermediate Similarity NPD6776 Approved
0.7784 Intermediate Similarity NPD6780 Approved
0.7784 Intermediate Similarity NPD6782 Approved
0.7784 Intermediate Similarity NPD6781 Approved
0.7784 Intermediate Similarity NPD6801 Discontinued
0.7784 Intermediate Similarity NPD6779 Approved
0.7784 Intermediate Similarity NPD6778 Approved
0.7765 Intermediate Similarity NPD6234 Discontinued
0.7755 Intermediate Similarity NPD7697 Approved
0.7755 Intermediate Similarity NPD7698 Approved
0.7755 Intermediate Similarity NPD7696 Phase 3
0.774 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7716 Intermediate Similarity NPD7871 Phase 2
0.7716 Intermediate Similarity NPD7870 Phase 2
0.7713 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD7240 Approved
0.7688 Intermediate Similarity NPD7701 Phase 2
0.7688 Intermediate Similarity NPD7685 Pre-registration
0.7684 Intermediate Similarity NPD37 Approved
0.768 Intermediate Similarity NPD7199 Phase 2
0.7665 Intermediate Similarity NPD7435 Discontinued
0.7654 Intermediate Similarity NPD4965 Approved
0.7654 Intermediate Similarity NPD7768 Phase 2
0.7654 Intermediate Similarity NPD4967 Phase 2
0.7654 Intermediate Similarity NPD4966 Approved
0.7647 Intermediate Similarity NPD1549 Phase 2
0.76 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.759 Intermediate Similarity NPD7699 Phase 2
0.759 Intermediate Similarity NPD7700 Phase 2
0.7582 Intermediate Similarity NPD1247 Approved
0.7526 Intermediate Similarity NPD6534 Approved
0.7526 Intermediate Similarity NPD6535 Approved
0.7525 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7525 Intermediate Similarity NPD6823 Phase 2
0.7525 Intermediate Similarity NPD7874 Approved
0.7514 Intermediate Similarity NPD3749 Approved
0.75 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD5403 Approved
0.7488 Intermediate Similarity NPD7801 Approved
0.7471 Intermediate Similarity NPD1510 Phase 2
0.7427 Intermediate Similarity NPD2796 Approved
0.7405 Intermediate Similarity NPD3926 Phase 2
0.7396 Intermediate Similarity NPD8150 Discontinued
0.7386 Intermediate Similarity NPD5401 Approved
0.7377 Intermediate Similarity NPD919 Approved
0.7376 Intermediate Similarity NPD7584 Approved
0.7356 Intermediate Similarity NPD3750 Approved
0.7337 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD1613 Approved
0.733 Intermediate Similarity NPD6799 Approved
0.733 Intermediate Similarity NPD7390 Discontinued
0.733 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7313 Intermediate Similarity NPD7680 Approved
0.7299 Intermediate Similarity NPD2800 Approved
0.7296 Intermediate Similarity NPD6213 Phase 3
0.7296 Intermediate Similarity NPD6212 Phase 3
0.7296 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7288 Intermediate Similarity NPD2532 Approved
0.7288 Intermediate Similarity NPD2534 Approved
0.7288 Intermediate Similarity NPD2533 Approved
0.7286 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD6599 Discontinued
0.7277 Intermediate Similarity NPD8320 Phase 1
0.7277 Intermediate Similarity NPD8319 Approved
0.7273 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7251 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7235 Intermediate Similarity NPD943 Approved
0.7225 Intermediate Similarity NPD2935 Discontinued
0.7216 Intermediate Similarity NPD8434 Phase 2
0.7216 Intermediate Similarity NPD6190 Approved
0.72 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD6674 Discontinued
0.7191 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7191 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7184 Intermediate Similarity NPD7266 Discontinued
0.7164 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7159 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD1240 Approved
0.7127 Intermediate Similarity NPD3226 Approved
0.7127 Intermediate Similarity NPD7458 Discontinued
0.7127 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7111 Intermediate Similarity NPD920 Approved
0.7101 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7093 Intermediate Similarity NPD230 Phase 1
0.7069 Intermediate Similarity NPD3748 Approved
0.7062 Intermediate Similarity NPD4628 Phase 3
0.7059 Intermediate Similarity NPD3027 Phase 3
0.7052 Intermediate Similarity NPD1607 Approved
0.7023 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.701 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD1243 Approved
0.7005 Intermediate Similarity NPD7585 Approved
0.7005 Intermediate Similarity NPD8058 Clinical (unspecified phase)
0.7005 Intermediate Similarity NPD8059 Phase 3
0.7 Intermediate Similarity NPD4363 Phase 3
0.7 Intermediate Similarity NPD4360 Phase 2
0.6995 Remote Similarity NPD5953 Discontinued
0.6994 Remote Similarity NPD1933 Approved
0.699 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6983 Remote Similarity NPD643 Clinical (unspecified phase)
0.6971 Remote Similarity NPD1509 Clinical (unspecified phase)
0.6957 Remote Similarity NPD7583 Approved
0.6954 Remote Similarity NPD6651 Approved
0.6932 Remote Similarity NPD1551 Phase 2
0.6923 Remote Similarity NPD7549 Discontinued
0.6919 Remote Similarity NPD2313 Discontinued
0.6901 Remote Similarity NPD4908 Phase 1
0.6897 Remote Similarity NPD447 Suspended
0.6895 Remote Similarity NPD5711 Approved
0.6895 Remote Similarity NPD5710 Approved
0.6895 Remote Similarity NPD7229 Phase 3
0.6893 Remote Similarity NPD2344 Approved
0.6893 Remote Similarity NPD2346 Discontinued
0.6891 Remote Similarity NPD7286 Phase 2
0.6887 Remote Similarity NPD7930 Approved
0.6875 Remote Similarity NPD2799 Discontinued
0.6875 Remote Similarity NPD651 Clinical (unspecified phase)
0.6872 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6853 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6842 Remote Similarity NPD8127 Discontinued
0.6836 Remote Similarity NPD6099 Approved
0.6836 Remote Similarity NPD6100 Approved
0.6828 Remote Similarity NPD6844 Discontinued
0.6821 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6774 Remote Similarity NPD7907 Approved
0.6759 Remote Similarity NPD4111 Phase 1
0.6759 Remote Similarity NPD4665 Approved
0.6742 Remote Similarity NPD5405 Approved
0.6742 Remote Similarity NPD5408 Approved
0.6742 Remote Similarity NPD5406 Approved
0.6742 Remote Similarity NPD5404 Approved
0.674 Remote Similarity NPD2309 Approved
0.6716 Remote Similarity NPD4287 Approved
0.6705 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6705 Remote Similarity NPD5124 Phase 1
0.6699 Remote Similarity NPD8285 Discontinued
0.6686 Remote Similarity NPD1091 Approved
0.6686 Remote Similarity NPD2798 Approved
0.6686 Remote Similarity NPD6233 Phase 2
0.6685 Remote Similarity NPD8166 Discontinued
0.6685 Remote Similarity NPD7033 Discontinued
0.6684 Remote Similarity NPD5242 Approved
0.6684 Remote Similarity NPD7615 Clinical (unspecified phase)

  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