Structure

Physi-Chem Properties

Molecular Weight:  622.19
Volume:  578.119
LogP:  1.405
LogD:  0.379
LogS:  -3.63
# Rotatable Bonds:  8
TPSA:  227.2
# H-Bond Aceptor:  15
# H-Bond Donor:  7
# Rings:  5
# Heavy Atoms:  15

MedChem Properties

QED Drug-Likeness Score:  0.163
Synthetic Accessibility Score:  4.661
Fsp3:  0.483
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.36
MDCK Permeability:  4.911590804113075e-05
Pgp-inhibitor:  0.005
Pgp-substrate:  0.998
Human Intestinal Absorption (HIA):  0.743
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.085
Plasma Protein Binding (PPB):  71.0078353881836%
Volume Distribution (VD):  0.622
Pgp-substrate:  15.843550682067871%

ADMET: Metabolism

CYP1A2-inhibitor:  0.044
CYP1A2-substrate:  0.875
CYP2C19-inhibitor:  0.04
CYP2C19-substrate:  0.271
CYP2C9-inhibitor:  0.01
CYP2C9-substrate:  0.332
CYP2D6-inhibitor:  0.028
CYP2D6-substrate:  0.179
CYP3A4-inhibitor:  0.024
CYP3A4-substrate:  0.017

ADMET: Excretion

Clearance (CL):  1.53
Half-life (T1/2):  0.342

ADMET: Toxicity

hERG Blockers:  0.518
Human Hepatotoxicity (H-HT):  0.081
Drug-inuced Liver Injury (DILI):  0.939
AMES Toxicity:  0.696
Rat Oral Acute Toxicity:  0.022
Maximum Recommended Daily Dose:  0.006
Skin Sensitization:  0.714
Carcinogencity:  0.11
Eye Corrosion:  0.003
Eye Irritation:  0.032
Respiratory Toxicity:  0.059

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

  Natural Product: NPC204693

Natural Product ID:  NPC204693
Common Name*:   Pectolinarin
IUPAC Name:   5-hydroxy-6-methoxy-2-(4-methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
Synonyms:   Pectolinarin
Standard InCHIKey:  DUXQKCCELUKXOE-CBBZIXHGSA-N
Standard InCHI:  InChI=1S/C29H34O15/c1-11-20(31)23(34)25(36)28(41-11)40-10-18-21(32)24(35)26(37)29(44-18)43-17-9-16-19(22(33)27(17)39-3)14(30)8-15(42-16)12-4-6-13(38-2)7-5-12/h4-9,11,18,20-21,23-26,28-29,31-37H,10H2,1-3H3/t11-,18+,20-,21+,23+,24-,25+,26+,28+,29+/m0/s1
SMILES:  C[C@H]1[C@@H]([C@H]([C@H]([C@H](OC[C@@H]2[C@H]([C@@H]([C@H]([C@H](Oc3cc4c(c(=O)cc(c5ccc(cc5)OC)o4)c(c3OC)O)O2)O)O)O)O1)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL445978
PubChem CID:   168849
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001111] Flavonoid glycosides
          • [CHEMONTID:0001583] Flavonoid O-glycosides
            • [CHEMONTID:0003533] Flavonoid-7-O-glycosides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO15289 Scoparia dulcis Species Plantaginaceae Eukaryota n.a. n.a. n.a. PMID[12880314]
NPO15289 Scoparia dulcis Species Plantaginaceae Eukaryota n.a. whole plant n.a. PMID[1294695]
NPO15289 Scoparia dulcis Species Plantaginaceae Eukaryota n.a. n.a. n.a. PMID[15104516]
NPO15289 Scoparia dulcis Species Plantaginaceae Eukaryota leaves and twigs Taiwan n.a. PMID[1659612]
NPO20096 Cirsium japonicum Species Asteraceae Eukaryota n.a. whole plant n.a. PMID[21899269]
NPO15289 Scoparia dulcis Species Plantaginaceae Eukaryota aerial parts Nanning, Guangxi Zhuang Autonomous Region, Peoples Republic of China 2012-OCT PMID[24955889]
NPO20096 Cirsium japonicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15289 Scoparia dulcis Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11697 Cirsium setosum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15289 Scoparia dulcis Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11697 Cirsium setosum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20096 Cirsium japonicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20096 Cirsium japonicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15289 Scoparia dulcis Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23706 Breea segeta n.a. n.a. n.a. n.a. n.a. n.a. Database[TM-MC]
NPO11697 Cirsium setosum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20096 Cirsium japonicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20096 Cirsium japonicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15289 Scoparia dulcis Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11697 Cirsium setosum Species Asteraceae 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
NPT171 Cell Line MRC5 Homo sapiens IC50 > 80300.0 nM PMID[476019]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 14120.0 nM PMID[476019]
NPT492 Cell Line Caco-2 Homo sapiens IC50 = 6180.0 nM PMID[476019]
NPT2287 Cell Line COR-L23 Homo sapiens IC50 = 5030.0 nM PMID[476019]
NPT369 Cell Line ACHN Homo sapiens IC50 = 17220.0 nM PMID[476019]
NPT1310 Individual Protein Xanthine dehydrogenase Bos taurus Inhibition = 11.5 % PMID[476020]
NPT2287 Cell Line COR-L23 Homo sapiens IC50 = 5000.0 nM PMID[476021]
NPT492 Cell Line Caco-2 Homo sapiens IC50 = 6200.0 nM PMID[476021]
NPT369 Cell Line ACHN Homo sapiens IC50 = 17200.0 nM PMID[476021]
NPT2282 Cell Line C32 Homo sapiens IC50 = 7200.0 nM PMID[476021]
NPT81 Cell Line A549 Homo sapiens IC50 = 38800.0 nM PMID[476021]
NPT1083 Cell Line A-375 Homo sapiens IC50 = 32900.0 nM PMID[476021]
NPT1618 Individual Protein Peroxisome proliferator-activated receptor gamma Mus musculus EC50 > 100000.0 nM PMID[476023]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 7170.0 nM PMID[476019]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 50800.0 nM PMID[476021]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 100000.0 nM PMID[476021]
NPT35 Others n.a. LogP = -0.7 n.a. PMID[476021]
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 39.1 % PMID[476022]
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 155.84 % PMID[476022]
NPT2 Others Unspecified IC50 = 37700.0 nM PMID[476024]

☑ 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 NPC204693 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
0.9815 High Similarity NPC259152
0.9815 High Similarity NPC3583
0.9814 High Similarity NPC475942
0.9814 High Similarity NPC201292
0.9814 High Similarity NPC469931
0.9814 High Similarity NPC186807
0.9814 High Similarity NPC45638
0.9814 High Similarity NPC209296
0.9814 High Similarity NPC195257
0.9814 High Similarity NPC93337
0.9814 High Similarity NPC58053
0.9814 High Similarity NPC105025
0.9814 High Similarity NPC226294
0.9758 High Similarity NPC126784
0.9758 High Similarity NPC241423
0.9758 High Similarity NPC473682
0.9758 High Similarity NPC110941
0.9758 High Similarity NPC473571
0.9758 High Similarity NPC470443
0.9758 High Similarity NPC470444
0.9756 High Similarity NPC169733
0.9755 High Similarity NPC239549
0.9755 High Similarity NPC51774
0.9755 High Similarity NPC236191
0.9753 High Similarity NPC22195
0.9753 High Similarity NPC183357
0.9753 High Similarity NPC21190
0.9752 High Similarity NPC146792
0.9752 High Similarity NPC45618
0.9752 High Similarity NPC58716
0.9695 High Similarity NPC102028
0.9695 High Similarity NPC142996
0.9693 High Similarity NPC267254
0.9693 High Similarity NPC476405
0.9693 High Similarity NPC301683
0.9693 High Similarity NPC205076
0.9693 High Similarity NPC211594
0.9693 High Similarity NPC117260
0.9693 High Similarity NPC172807
0.9693 High Similarity NPC307518
0.9693 High Similarity NPC48773
0.9693 High Similarity NPC475155
0.9693 High Similarity NPC254540
0.9691 High Similarity NPC95855
0.9691 High Similarity NPC472381
0.9691 High Similarity NPC210042
0.9691 High Similarity NPC86008
0.9691 High Similarity NPC472383
0.9691 High Similarity NPC112755
0.9691 High Similarity NPC170675
0.9691 High Similarity NPC471457
0.9689 High Similarity NPC210073
0.9689 High Similarity NPC115674
0.9689 High Similarity NPC99957
0.9689 High Similarity NPC181616
0.9641 High Similarity NPC470447
0.9641 High Similarity NPC470445
0.9641 High Similarity NPC470446
0.9641 High Similarity NPC470449
0.9641 High Similarity NPC473072
0.9636 High Similarity NPC65563
0.9636 High Similarity NPC470949
0.9636 High Similarity NPC8573
0.9634 High Similarity NPC21666
0.9634 High Similarity NPC42773
0.9634 High Similarity NPC208668
0.9634 High Similarity NPC169977
0.9634 High Similarity NPC45522
0.9634 High Similarity NPC24043
0.9634 High Similarity NPC101026
0.9632 High Similarity NPC293004
0.9632 High Similarity NPC245014
0.9632 High Similarity NPC177731
0.9632 High Similarity NPC471416
0.9632 High Similarity NPC79056
0.9632 High Similarity NPC231194
0.9632 High Similarity NPC51326
0.9632 High Similarity NPC105095
0.9632 High Similarity NPC282987
0.9632 High Similarity NPC44328
0.9632 High Similarity NPC105511
0.9632 High Similarity NPC84265
0.9632 High Similarity NPC44558
0.9632 High Similarity NPC34287
0.9632 High Similarity NPC224462
0.9632 High Similarity NPC474434
0.963 High Similarity NPC93099
0.9627 High Similarity NPC284277
0.9627 High Similarity NPC311830
0.9627 High Similarity NPC22832
0.9627 High Similarity NPC475366
0.9627 High Similarity NPC475497
0.9583 High Similarity NPC148710
0.9583 High Similarity NPC470451
0.9583 High Similarity NPC470455
0.9581 High Similarity NPC473071
0.9581 High Similarity NPC473073
0.9576 High Similarity NPC476472
0.9576 High Similarity NPC220173
0.9576 High Similarity NPC294815
0.9576 High Similarity NPC473327
0.9576 High Similarity NPC19108
0.9576 High Similarity NPC16194
0.9576 High Similarity NPC198199
0.9576 High Similarity NPC477848
0.9573 High Similarity NPC180918
0.9573 High Similarity NPC156977
0.9573 High Similarity NPC256760
0.9573 High Similarity NPC472386
0.9571 High Similarity NPC183036
0.9571 High Similarity NPC293629
0.9571 High Similarity NPC229687
0.9571 High Similarity NPC43587
0.9568 High Similarity NPC8856
0.9568 High Similarity NPC236934
0.9568 High Similarity NPC5778
0.9565 High Similarity NPC88023
0.9565 High Similarity NPC222936
0.9565 High Similarity NPC94777
0.9565 High Similarity NPC270335
0.9565 High Similarity NPC243930
0.9565 High Similarity NPC284960
0.9565 High Similarity NPC309025
0.9565 High Similarity NPC191306
0.9565 High Similarity NPC19709
0.9518 High Similarity NPC198324
0.9518 High Similarity NPC472991
0.9518 High Similarity NPC472992
0.9518 High Similarity NPC233994
0.9518 High Similarity NPC211532
0.9518 High Similarity NPC472385
0.9512 High Similarity NPC78734
0.9512 High Similarity NPC67105
0.9512 High Similarity NPC52353
0.9512 High Similarity NPC95866
0.9512 High Similarity NPC285197
0.9512 High Similarity NPC150767
0.9512 High Similarity NPC194483
0.9509 High Similarity NPC135345
0.9509 High Similarity NPC45400
0.9509 High Similarity NPC229729
0.9506 High Similarity NPC15358
0.9503 High Similarity NPC473043
0.9503 High Similarity NPC189142
0.9503 High Similarity NPC77660
0.9461 High Similarity NPC476622
0.9461 High Similarity NPC168584
0.9461 High Similarity NPC476619
0.9461 High Similarity NPC89052
0.9461 High Similarity NPC476621
0.9461 High Similarity NPC120952
0.9461 High Similarity NPC476623
0.9461 High Similarity NPC476618
0.9461 High Similarity NPC251417
0.9461 High Similarity NPC173837
0.9461 High Similarity NPC475261
0.9461 High Similarity NPC476620
0.9461 High Similarity NPC472387
0.9458 High Similarity NPC49344
0.9458 High Similarity NPC43211
0.9458 High Similarity NPC101191
0.9458 High Similarity NPC210094
0.9458 High Similarity NPC237435
0.9458 High Similarity NPC264735
0.9458 High Similarity NPC472607
0.9458 High Similarity NPC115760
0.9458 High Similarity NPC135277
0.9455 High Similarity NPC471725
0.9455 High Similarity NPC26230
0.9455 High Similarity NPC261254
0.9455 High Similarity NPC155877
0.9455 High Similarity NPC134532
0.9455 High Similarity NPC60735
0.9455 High Similarity NPC203259
0.9455 High Similarity NPC33054
0.9455 High Similarity NPC471748
0.9455 High Similarity NPC176740
0.9451 High Similarity NPC223747
0.9451 High Similarity NPC105283
0.9451 High Similarity NPC227508
0.9451 High Similarity NPC120099
0.9451 High Similarity NPC225434
0.9451 High Similarity NPC219904
0.9451 High Similarity NPC203050
0.9451 High Similarity NPC61791
0.9448 High Similarity NPC21100
0.9448 High Similarity NPC70441
0.9448 High Similarity NPC197285
0.9444 High Similarity NPC88043
0.9444 High Similarity NPC29830
0.9444 High Similarity NPC168822
0.9441 High Similarity NPC182045
0.9408 High Similarity NPC36138
0.9405 High Similarity NPC192539
0.9405 High Similarity NPC473895
0.9401 High Similarity NPC255799
0.9401 High Similarity NPC89127
0.9401 High Similarity NPC472384
0.9401 High Similarity NPC268533
0.9401 High Similarity NPC472380

  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 NPC204693 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
0.9814 High Similarity NPD7054 Approved
0.9753 High Similarity NPD7472 Approved
0.9632 High Similarity NPD7074 Phase 3
0.9515 High Similarity NPD7251 Discontinued
0.9458 High Similarity NPD7808 Phase 3
0.9458 High Similarity NPD4338 Clinical (unspecified phase)
0.9455 High Similarity NPD6797 Phase 2
0.9273 High Similarity NPD3818 Discontinued
0.9068 High Similarity NPD2801 Approved
0.9036 High Similarity NPD6167 Clinical (unspecified phase)
0.9036 High Similarity NPD6168 Clinical (unspecified phase)
0.9036 High Similarity NPD6166 Phase 2
0.9018 High Similarity NPD4381 Clinical (unspecified phase)
0.8988 High Similarity NPD7804 Clinical (unspecified phase)
0.8889 High Similarity NPD1934 Approved
0.872 High Similarity NPD2393 Clinical (unspecified phase)
0.8554 High Similarity NPD3817 Phase 2
0.8509 High Similarity NPD1511 Approved
0.8503 High Similarity NPD4868 Clinical (unspecified phase)
0.8503 High Similarity NPD3882 Suspended
0.8462 Intermediate Similarity NPD5494 Approved
0.8424 Intermediate Similarity NPD4380 Phase 2
0.8405 Intermediate Similarity NPD1512 Approved
0.8343 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD5402 Approved
0.8303 Intermediate Similarity NPD1653 Approved
0.8295 Intermediate Similarity NPD6559 Discontinued
0.8235 Intermediate Similarity NPD7075 Discontinued
0.8187 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8171 Intermediate Similarity NPD7228 Approved
0.8125 Intermediate Similarity NPD5844 Phase 1
0.809 Intermediate Similarity NPD7685 Pre-registration
0.8077 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.8059 Intermediate Similarity NPD1465 Phase 2
0.8059 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8025 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8025 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8012 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8012 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8011 Intermediate Similarity NPD7473 Discontinued
0.8 Intermediate Similarity NPD6801 Discontinued
0.8 Intermediate Similarity NPD8312 Approved
0.8 Intermediate Similarity NPD8313 Approved
0.7989 Intermediate Similarity NPD6959 Discontinued
0.7975 Intermediate Similarity NPD1549 Phase 2
0.7966 Intermediate Similarity NPD3751 Discontinued
0.7953 Intermediate Similarity NPD7819 Suspended
0.7943 Intermediate Similarity NPD6232 Discontinued
0.7943 Intermediate Similarity NPD3787 Discontinued
0.7917 Intermediate Similarity NPD5403 Approved
0.7853 Intermediate Similarity NPD2796 Approved
0.7844 Intermediate Similarity NPD6799 Approved
0.7836 Intermediate Similarity NPD7411 Suspended
0.7814 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7811 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7805 Intermediate Similarity NPD7266 Discontinued
0.7798 Intermediate Similarity NPD5401 Approved
0.7798 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7791 Intermediate Similarity NPD1510 Phase 2
0.7789 Intermediate Similarity NPD6777 Approved
0.7789 Intermediate Similarity NPD6776 Approved
0.7789 Intermediate Similarity NPD6780 Approved
0.7789 Intermediate Similarity NPD6782 Approved
0.7789 Intermediate Similarity NPD6781 Approved
0.7789 Intermediate Similarity NPD6779 Approved
0.7789 Intermediate Similarity NPD6778 Approved
0.7784 Intermediate Similarity NPD7199 Phase 2
0.7771 Intermediate Similarity NPD6234 Discontinued
0.776 Intermediate Similarity NPD7435 Discontinued
0.776 Intermediate Similarity NPD7696 Phase 3
0.776 Intermediate Similarity NPD7697 Approved
0.776 Intermediate Similarity NPD7698 Approved
0.7755 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7755 Intermediate Similarity NPD7783 Phase 2
0.7744 Intermediate Similarity NPD8151 Discontinued
0.7692 Intermediate Similarity NPD7701 Phase 2
0.7692 Intermediate Similarity NPD7240 Approved
0.7688 Intermediate Similarity NPD37 Approved
0.7684 Intermediate Similarity NPD1247 Approved
0.7665 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7657 Intermediate Similarity NPD4965 Approved
0.7657 Intermediate Similarity NPD4966 Approved
0.7657 Intermediate Similarity NPD4967 Phase 2
0.7654 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7654 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7654 Intermediate Similarity NPD1613 Approved
0.7644 Intermediate Similarity NPD8455 Phase 2
0.7641 Intermediate Similarity NPD7584 Approved
0.7629 Intermediate Similarity NPD7871 Phase 2
0.7629 Intermediate Similarity NPD7870 Phase 2
0.7617 Intermediate Similarity NPD6823 Phase 2
0.7598 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7592 Intermediate Similarity NPD7700 Phase 2
0.7592 Intermediate Similarity NPD7699 Phase 2
0.7572 Intermediate Similarity NPD6599 Discontinued
0.7546 Intermediate Similarity NPD943 Approved
0.7546 Intermediate Similarity NPD1240 Approved
0.7545 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7526 Intermediate Similarity NPD6534 Approved
0.7526 Intermediate Similarity NPD6535 Approved
0.7525 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7525 Intermediate Similarity NPD7874 Approved
0.7515 Intermediate Similarity NPD6190 Approved
0.75 Intermediate Similarity NPD230 Phase 1
0.75 Intermediate Similarity NPD1933 Approved
0.75 Intermediate Similarity NPD3926 Phase 2
0.7487 Intermediate Similarity NPD7801 Approved
0.7472 Intermediate Similarity NPD919 Approved
0.7469 Intermediate Similarity NPD3027 Phase 3
0.7458 Intermediate Similarity NPD7768 Phase 2
0.7456 Intermediate Similarity NPD3750 Approved
0.7455 Intermediate Similarity NPD1607 Approved
0.7425 Intermediate Similarity NPD2935 Discontinued
0.7423 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7416 Intermediate Similarity NPD3749 Approved
0.7407 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD447 Suspended
0.7386 Intermediate Similarity NPD6844 Discontinued
0.7371 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7353 Intermediate Similarity NPD4628 Phase 3
0.7346 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD1551 Phase 2
0.731 Intermediate Similarity NPD7680 Approved
0.7302 Intermediate Similarity NPD8150 Discontinued
0.7292 Intermediate Similarity NPD6213 Phase 3
0.7292 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7292 Intermediate Similarity NPD6212 Phase 3
0.7283 Intermediate Similarity NPD2534 Approved
0.7283 Intermediate Similarity NPD2532 Approved
0.7283 Intermediate Similarity NPD2533 Approved
0.7273 Intermediate Similarity NPD8320 Phase 1
0.7273 Intermediate Similarity NPD8319 Approved
0.7268 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD7585 Approved
0.7216 Intermediate Similarity NPD7458 Discontinued
0.7211 Intermediate Similarity NPD8434 Phase 2
0.72 Intermediate Similarity NPD7583 Approved
0.72 Intermediate Similarity NPD920 Approved
0.7193 Intermediate Similarity NPD6674 Discontinued
0.7193 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD2800 Approved
0.7166 Intermediate Similarity NPD5953 Discontinued
0.7163 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD3748 Approved
0.7151 Intermediate Similarity NPD7286 Phase 2
0.7134 Intermediate Similarity NPD9494 Approved
0.7119 Intermediate Similarity NPD3226 Approved
0.7118 Intermediate Similarity NPD6100 Approved
0.7118 Intermediate Similarity NPD6099 Approved
0.7111 Intermediate Similarity NPD5353 Approved
0.7091 Intermediate Similarity NPD6832 Phase 2
0.709 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD1091 Approved
0.7077 Intermediate Similarity NPD4360 Phase 2
0.7077 Intermediate Similarity NPD4363 Phase 3
0.7059 Intermediate Similarity NPD7033 Discontinued
0.7041 Intermediate Similarity NPD6651 Approved
0.7029 Intermediate Similarity NPD7390 Discontinued
0.7014 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD2313 Discontinued
0.7 Intermediate Similarity NPD7549 Discontinued
0.6995 Remote Similarity NPD8058 Clinical (unspecified phase)
0.6995 Remote Similarity NPD8059 Phase 3
0.6994 Remote Similarity NPD1652 Phase 2
0.6994 Remote Similarity NPD1243 Approved
0.6994 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6989 Remote Similarity NPD7784 Clinical (unspecified phase)
0.6988 Remote Similarity NPD4908 Phase 1
0.698 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6977 Remote Similarity NPD2346 Discontinued
0.6977 Remote Similarity NPD2344 Approved
0.6971 Remote Similarity NPD643 Clinical (unspecified phase)
0.697 Remote Similarity NPD2798 Approved
0.6964 Remote Similarity NPD6233 Phase 2
0.6959 Remote Similarity NPD2799 Discontinued
0.6954 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6944 Remote Similarity NPD6385 Approved
0.6944 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6944 Remote Similarity NPD6386 Approved
0.6935 Remote Similarity NPD5242 Approved
0.6927 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6919 Remote Similarity NPD8127 Discontinued
0.6915 Remote Similarity NPD5006 Approved
0.6915 Remote Similarity NPD5005 Approved
0.6909 Remote Similarity NPD1203 Approved
0.6907 Remote Similarity NPD6841 Approved
0.6907 Remote Similarity NPD6842 Approved
0.6907 Remote Similarity NPD6843 Phase 3
0.6905 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6901 Remote Similarity NPD7097 Phase 1
0.6893 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6882 Remote Similarity NPD5124 Phase 1
0.6882 Remote Similarity NPD5710 Approved
0.6882 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6882 Remote Similarity NPD5711 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