Structure

Physi-Chem Properties

Molecular Weight:  848.2
Volume:  779.496
LogP:  1.962
LogD:  1.557
LogS:  -5.409
# Rotatable Bonds:  18
TPSA:  305.85
# H-Bond Aceptor:  22
# H-Bond Donor:  4
# Rings:  5
# Heavy Atoms:  22

MedChem Properties

QED Drug-Likeness Score:  0.114
Synthetic Accessibility Score:  5.256
Fsp3:  0.447
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.647
MDCK Permeability:  0.0001264484308194369
Pgp-inhibitor:  0.112
Pgp-substrate:  0.389
Human Intestinal Absorption (HIA):  0.976
20% Bioavailability (F20%):  0.0
30% Bioavailability (F30%):  0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.045
Plasma Protein Binding (PPB):  75.8642807006836%
Volume Distribution (VD):  0.386
Pgp-substrate:  24.640518188476562%

ADMET: Metabolism

CYP1A2-inhibitor:  0.026
CYP1A2-substrate:  0.004
CYP2C19-inhibitor:  0.013
CYP2C19-substrate:  0.038
CYP2C9-inhibitor:  0.007
CYP2C9-substrate:  0.061
CYP2D6-inhibitor:  0.976
CYP2D6-substrate:  0.056
CYP3A4-inhibitor:  0.396
CYP3A4-substrate:  0.041

ADMET: Excretion

Clearance (CL):  1.314
Half-life (T1/2):  0.975

ADMET: Toxicity

hERG Blockers:  0.055
Human Hepatotoxicity (H-HT):  0.991
Drug-inuced Liver Injury (DILI):  0.994
AMES Toxicity:  0.283
Rat Oral Acute Toxicity:  0.031
Maximum Recommended Daily Dose:  0.011
Skin Sensitization:  0.096
Carcinogencity:  0.031
Eye Corrosion:  0.003
Eye Irritation:  0.044
Respiratory Toxicity:  0.021

Download Data

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

  Natural Product: NPC473862

Natural Product ID:  NPC473862
Common Name*:   Quercetin-3-O-(6-O-Alpha-L-Arabinopyranosyl)-Beta-D-Galactopyranoside Decaacetate
IUPAC Name:   [(3S,4S,5R,6R)-4,5-diacetyloxy-6-[[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxyoxan-2-yl]methoxy]oxan-3-yl] acetate
Synonyms:  
Standard InCHIKey:  NSIWKLPIFVEFJV-KYAOWRIJSA-N
Standard InCHI:  InChI=1S/C38H40O22/c1-14(39)52-26-12-50-37(35(56-18(5)43)32(26)54-16(3)41)51-13-27-31(53-15(2)40)34(55-17(4)42)36(57-19(6)44)38(59-27)60-33-29(49)28-24(48)10-21(45)11-25(28)58-30(33)20-7-8-22(46)23(47)9-20/h7-11,26-27,31-32,34-38,45-48H,12-13H2,1-6H3/t26-,27+,31-,32-,34-,35+,36+,37-,38-/m0/s1
SMILES:  CC(=O)OC1COC(C(C1OC(=O)C)OC(=O)C)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)O)OC(=O)C)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL453688
PubChem CID:   44584492
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001111] Flavonoid glycosides
          • [CHEMONTID:0001583] Flavonoid O-glycosides
            • [CHEMONTID:0003531] Flavonoid-3-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
NPO33118 Rhamnus Genus Rhamnaceae Eukaryota n.a. n.a. n.a. PMID[8350094]

☑ 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
NPT20967 CELL-LINE Platelet n.a. Activity = 78.3 % PMID[453542]
NPT20967 CELL-LINE Platelet n.a. Activity = 38.5 % PMID[453542]
NPT20967 CELL-LINE Platelet n.a. Activity = 87.7 % PMID[453542]

☑ 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 NPC473862 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
0.9878 High Similarity NPC471669
0.9878 High Similarity NPC89127
0.9818 High Similarity NPC173837
0.976 High Similarity NPC241781
0.976 High Similarity NPC156785
0.976 High Similarity NPC162394
0.9758 High Similarity NPC122467
0.9758 High Similarity NPC14187
0.9758 High Similarity NPC202908
0.9758 High Similarity NPC292019
0.9702 High Similarity NPC275977
0.9702 High Similarity NPC470455
0.9702 High Similarity NPC470713
0.9702 High Similarity NPC470451
0.9702 High Similarity NPC249560
0.9702 High Similarity NPC223860
0.9702 High Similarity NPC25946
0.9702 High Similarity NPC470720
0.9702 High Similarity NPC21359
0.9702 High Similarity NPC470717
0.9702 High Similarity NPC460984
0.9699 High Similarity NPC89052
0.9699 High Similarity NPC251417
0.9697 High Similarity NPC253685
0.9697 High Similarity NPC16194
0.9697 High Similarity NPC476472
0.9697 High Similarity NPC473327
0.9697 High Similarity NPC19108
0.9697 High Similarity NPC294815
0.9697 High Similarity NPC220173
0.9695 High Similarity NPC155877
0.9695 High Similarity NPC33054
0.9695 High Similarity NPC203259
0.9695 High Similarity NPC471748
0.9695 High Similarity NPC471725
0.9695 High Similarity NPC134532
0.9695 High Similarity NPC176740
0.9645 High Similarity NPC295625
0.9645 High Similarity NPC470719
0.9645 High Similarity NPC473554
0.9645 High Similarity NPC33083
0.9643 High Similarity NPC470449
0.9643 High Similarity NPC470447
0.9643 High Similarity NPC470718
0.9643 High Similarity NPC470445
0.9643 High Similarity NPC470446
0.9641 High Similarity NPC192539
0.9639 High Similarity NPC219043
0.9639 High Similarity NPC48984
0.9634 High Similarity NPC254855
0.9634 High Similarity NPC255157
0.9634 High Similarity NPC29958
0.9634 High Similarity NPC244776
0.9634 High Similarity NPC136042
0.9634 High Similarity NPC116864
0.9634 High Similarity NPC67105
0.9634 High Similarity NPC67326
0.9634 High Similarity NPC156869
0.9634 High Similarity NPC95866
0.9634 High Similarity NPC259896
0.9588 High Similarity NPC72554
0.9588 High Similarity NPC97817
0.9588 High Similarity NPC30011
0.9581 High Similarity NPC120952
0.9576 High Similarity NPC60735
0.9576 High Similarity NPC190003
0.9576 High Similarity NPC175107
0.9576 High Similarity NPC26230
0.9576 High Similarity NPC153755
0.9573 High Similarity NPC227508
0.9529 High Similarity NPC474093
0.9529 High Similarity NPC104910
0.9524 High Similarity NPC110941
0.9524 High Similarity NPC241423
0.9524 High Similarity NPC473682
0.9524 High Similarity NPC126784
0.9524 High Similarity NPC473571
0.9524 High Similarity NPC470444
0.9524 High Similarity NPC470443
0.9521 High Similarity NPC470949
0.9521 High Similarity NPC65563
0.9518 High Similarity NPC4390
0.9515 High Similarity NPC235260
0.9515 High Similarity NPC20505
0.9515 High Similarity NPC155763
0.9515 High Similarity NPC285197
0.9512 High Similarity NPC127546
0.9512 High Similarity NPC173637
0.9512 High Similarity NPC84362
0.9512 High Similarity NPC223424
0.9512 High Similarity NPC52550
0.9512 High Similarity NPC275454
0.9512 High Similarity NPC317489
0.9474 High Similarity NPC475179
0.9464 High Similarity NPC267680
0.9464 High Similarity NPC253521
0.9464 High Similarity NPC217387
0.9464 High Similarity NPC196127
0.9464 High Similarity NPC293626
0.9464 High Similarity NPC37668
0.9464 High Similarity NPC258044
0.9464 High Similarity NPC139571
0.9464 High Similarity NPC113836
0.9464 High Similarity NPC217520
0.9464 High Similarity NPC35167
0.9464 High Similarity NPC477895
0.9461 High Similarity NPC223426
0.9461 High Similarity NPC81042
0.9461 High Similarity NPC214621
0.9461 High Similarity NPC34267
0.9461 High Similarity NPC198199
0.9461 High Similarity NPC294629
0.9458 High Similarity NPC180918
0.9455 High Similarity NPC195257
0.9455 High Similarity NPC223747
0.9455 High Similarity NPC270578
0.9455 High Similarity NPC86008
0.9455 High Similarity NPC120099
0.9455 High Similarity NPC219904
0.9455 High Similarity NPC209296
0.9455 High Similarity NPC52382
0.9455 High Similarity NPC203050
0.9455 High Similarity NPC225434
0.9455 High Similarity NPC476180
0.9455 High Similarity NPC138927
0.9451 High Similarity NPC274618
0.9451 High Similarity NPC113968
0.9451 High Similarity NPC179950
0.9451 High Similarity NPC253662
0.9451 High Similarity NPC308404
0.9451 High Similarity NPC277174
0.9451 High Similarity NPC88789
0.9451 High Similarity NPC64425
0.9451 High Similarity NPC135599
0.9451 High Similarity NPC115674
0.9451 High Similarity NPC210073
0.9451 High Similarity NPC73855
0.9451 High Similarity NPC118284
0.9451 High Similarity NPC145038
0.9451 High Similarity NPC8856
0.9451 High Similarity NPC281131
0.9451 High Similarity NPC328940
0.9451 High Similarity NPC56077
0.9451 High Similarity NPC276222
0.9412 High Similarity NPC297503
0.9412 High Similarity NPC97119
0.9412 High Similarity NPC135831
0.9412 High Similarity NPC473072
0.9405 High Similarity NPC8573
0.9405 High Similarity NPC61904
0.9405 High Similarity NPC169733
0.9405 High Similarity NPC198324
0.9405 High Similarity NPC144097
0.9405 High Similarity NPC472385
0.9401 High Similarity NPC25724
0.9398 High Similarity NPC277532
0.9398 High Similarity NPC475434
0.9398 High Similarity NPC175429
0.9398 High Similarity NPC209550
0.9398 High Similarity NPC206123
0.9398 High Similarity NPC138990
0.9394 High Similarity NPC265530
0.9394 High Similarity NPC92565
0.9394 High Similarity NPC226304
0.9394 High Similarity NPC325555
0.9394 High Similarity NPC160156
0.939 High Similarity NPC55786
0.939 High Similarity NPC240431
0.939 High Similarity NPC277205
0.939 High Similarity NPC19388
0.936 High Similarity NPC64755
0.9357 High Similarity NPC148710
0.9357 High Similarity NPC470416
0.9353 High Similarity NPC473071
0.9353 High Similarity NPC473073
0.9345 High Similarity NPC237435
0.9345 High Similarity NPC101191
0.9345 High Similarity NPC477848
0.9345 High Similarity NPC49344
0.9345 High Similarity NPC210094
0.9345 High Similarity NPC264735
0.9345 High Similarity NPC115760
0.9345 High Similarity NPC43211
0.9345 High Similarity NPC135277
0.9341 High Similarity NPC474522
0.9341 High Similarity NPC245452
0.9337 High Similarity NPC105283
0.9337 High Similarity NPC43587
0.9333 High Similarity NPC32641
0.9333 High Similarity NPC21100
0.9333 High Similarity NPC477613
0.9333 High Similarity NPC203145
0.9333 High Similarity NPC189564
0.9333 High Similarity NPC142142
0.9333 High Similarity NPC197285
0.9333 High Similarity NPC256188
0.9333 High Similarity NPC475214
0.9333 High Similarity NPC476470
0.9333 High Similarity NPC221342
0.9333 High Similarity NPC12013

  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 NPC473862 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
0.9756 High Similarity NPD7251 Discontinued
0.9697 High Similarity NPD7808 Phase 3
0.9695 High Similarity NPD6797 Phase 2
0.9515 High Similarity NPD7472 Approved
0.9455 High Similarity NPD7054 Approved
0.9345 High Similarity NPD4338 Clinical (unspecified phase)
0.9281 High Similarity NPD7074 Phase 3
0.9222 High Similarity NPD7804 Clinical (unspecified phase)
0.8929 High Similarity NPD6167 Clinical (unspecified phase)
0.8929 High Similarity NPD6166 Phase 2
0.8929 High Similarity NPD6168 Clinical (unspecified phase)
0.8902 High Similarity NPD3817 Phase 2
0.8824 High Similarity NPD3818 Discontinued
0.8795 High Similarity NPD4381 Clinical (unspecified phase)
0.8683 High Similarity NPD7075 Discontinued
0.8671 High Similarity NPD7993 Clinical (unspecified phase)
0.8667 High Similarity NPD1934 Approved
0.8614 High Similarity NPD2393 Clinical (unspecified phase)
0.8528 High Similarity NPD1512 Approved
0.8512 High Similarity NPD4868 Clinical (unspecified phase)
0.8512 High Similarity NPD3882 Suspended
0.8503 High Similarity NPD7096 Clinical (unspecified phase)
0.8503 High Similarity NPD2801 Approved
0.8405 Intermediate Similarity NPD1511 Approved
0.8343 Intermediate Similarity NPD5402 Approved
0.8333 Intermediate Similarity NPD6801 Discontinued
0.8297 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8293 Intermediate Similarity NPD6799 Approved
0.8253 Intermediate Similarity NPD5403 Approved
0.8214 Intermediate Similarity NPD4380 Phase 2
0.8202 Intermediate Similarity NPD6559 Discontinued
0.8176 Intermediate Similarity NPD7819 Suspended
0.8133 Intermediate Similarity NPD5401 Approved
0.8133 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8111 Intermediate Similarity NPD8313 Approved
0.8111 Intermediate Similarity NPD8312 Approved
0.8023 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD6599 Discontinued
0.8 Intermediate Similarity NPD7685 Pre-registration
0.7988 Intermediate Similarity NPD1653 Approved
0.7978 Intermediate Similarity NPD7228 Approved
0.7965 Intermediate Similarity NPD1465 Phase 2
0.7953 Intermediate Similarity NPD7411 Suspended
0.7943 Intermediate Similarity NPD5494 Approved
0.7927 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7927 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7923 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7921 Intermediate Similarity NPD7473 Discontinued
0.791 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7898 Intermediate Similarity NPD6959 Discontinued
0.7892 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7879 Intermediate Similarity NPD1549 Phase 2
0.7877 Intermediate Similarity NPD3751 Discontinued
0.7865 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7861 Intermediate Similarity NPD8455 Phase 2
0.7853 Intermediate Similarity NPD6232 Discontinued
0.7853 Intermediate Similarity NPD3787 Discontinued
0.7846 Intermediate Similarity NPD8151 Discontinued
0.7833 Intermediate Similarity NPD5844 Phase 1
0.7824 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7818 Intermediate Similarity NPD7266 Discontinued
0.7784 Intermediate Similarity NPD919 Approved
0.7772 Intermediate Similarity NPD7435 Discontinued
0.7758 Intermediate Similarity NPD2796 Approved
0.7706 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7697 Intermediate Similarity NPD1510 Phase 2
0.7697 Intermediate Similarity NPD7199 Phase 2
0.7684 Intermediate Similarity NPD6234 Discontinued
0.767 Intermediate Similarity NPD7768 Phase 2
0.7665 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7644 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7633 Intermediate Similarity NPD6190 Approved
0.7626 Intermediate Similarity NPD7874 Approved
0.7626 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7609 Intermediate Similarity NPD7240 Approved
0.759 Intermediate Similarity NPD7698 Approved
0.759 Intermediate Similarity NPD7696 Phase 3
0.759 Intermediate Similarity NPD7697 Approved
0.7588 Intermediate Similarity NPD7783 Phase 2
0.7588 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7574 Intermediate Similarity NPD3750 Approved
0.7574 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7551 Intermediate Similarity NPD8320 Phase 1
0.7551 Intermediate Similarity NPD8319 Approved
0.7546 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7544 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7526 Intermediate Similarity NPD6778 Approved
0.7526 Intermediate Similarity NPD6776 Approved
0.7526 Intermediate Similarity NPD6782 Approved
0.7526 Intermediate Similarity NPD6777 Approved
0.7526 Intermediate Similarity NPD6779 Approved
0.7526 Intermediate Similarity NPD6781 Approved
0.7526 Intermediate Similarity NPD6780 Approved
0.7525 Intermediate Similarity NPD7701 Phase 2
0.7515 Intermediate Similarity NPD1933 Approved
0.7515 Intermediate Similarity NPD230 Phase 1
0.75 Intermediate Similarity NPD1247 Approved
0.75 Intermediate Similarity NPD37 Approved
0.7475 Intermediate Similarity NPD7584 Approved
0.7473 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7472 Intermediate Similarity NPD4965 Approved
0.7472 Intermediate Similarity NPD4966 Approved
0.7472 Intermediate Similarity NPD4967 Phase 2
0.7462 Intermediate Similarity NPD7870 Phase 2
0.7462 Intermediate Similarity NPD7871 Phase 2
0.7455 Intermediate Similarity NPD1613 Approved
0.7455 Intermediate Similarity NPD1240 Approved
0.7455 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD1551 Phase 2
0.743 Intermediate Similarity NPD3749 Approved
0.7423 Intermediate Similarity NPD7699 Phase 2
0.7423 Intermediate Similarity NPD7700 Phase 2
0.7418 Intermediate Similarity NPD3926 Phase 2
0.7407 Intermediate Similarity NPD8150 Discontinued
0.7407 Intermediate Similarity NPD8434 Phase 2
0.7368 Intermediate Similarity NPD4628 Phase 3
0.7365 Intermediate Similarity NPD1607 Approved
0.7349 Intermediate Similarity NPD943 Approved
0.7337 Intermediate Similarity NPD2935 Discontinued
0.733 Intermediate Similarity NPD7458 Discontinued
0.7327 Intermediate Similarity NPD7801 Approved
0.7317 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD447 Suspended
0.7299 Intermediate Similarity NPD2533 Approved
0.7299 Intermediate Similarity NPD2534 Approved
0.7299 Intermediate Similarity NPD2532 Approved
0.7278 Intermediate Similarity NPD3748 Approved
0.7268 Intermediate Similarity NPD6535 Approved
0.7268 Intermediate Similarity NPD6534 Approved
0.7264 Intermediate Similarity NPD7585 Approved
0.726 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7256 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7236 Intermediate Similarity NPD7680 Approved
0.7229 Intermediate Similarity NPD6798 Discontinued
0.7216 Intermediate Similarity NPD920 Approved
0.7214 Intermediate Similarity NPD7583 Approved
0.7212 Intermediate Similarity NPD6832 Phase 2
0.7208 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7202 Intermediate Similarity NPD6355 Discontinued
0.7186 Intermediate Similarity NPD6233 Phase 2
0.7186 Intermediate Similarity NPD6823 Phase 2
0.7181 Intermediate Similarity NPD5953 Discontinued
0.7176 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7169 Intermediate Similarity NPD3027 Phase 3
0.7166 Intermediate Similarity NPD7286 Phase 2
0.7135 Intermediate Similarity NPD3226 Approved
0.711 Intermediate Similarity NPD1243 Approved
0.7109 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.7102 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7102 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7085 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD7033 Discontinued
0.7069 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD6099 Approved
0.7035 Intermediate Similarity NPD6100 Approved
0.7033 Intermediate Similarity NPD5353 Approved
0.703 Intermediate Similarity NPD1203 Approved
0.7024 Intermediate Similarity NPD2313 Discontinued
0.7011 Intermediate Similarity NPD2800 Approved
0.7011 Intermediate Similarity NPD1652 Phase 2
0.7 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.6994 Remote Similarity NPD2346 Discontinued
0.6977 Remote Similarity NPD2799 Discontinued
0.6971 Remote Similarity NPD7930 Approved
0.6961 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6959 Remote Similarity NPD6651 Approved
0.6949 Remote Similarity NPD7390 Discontinued
0.6941 Remote Similarity NPD4060 Phase 1
0.6935 Remote Similarity NPD8127 Discontinued
0.6927 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6923 Remote Similarity NPD3268 Approved
0.6923 Remote Similarity NPD6844 Discontinued
0.6919 Remote Similarity NPD4360 Phase 2
0.6919 Remote Similarity NPD4363 Phase 3
0.6919 Remote Similarity NPD7097 Phase 1
0.6914 Remote Similarity NPD6674 Discontinued
0.6905 Remote Similarity NPD4908 Phase 1
0.6901 Remote Similarity NPD5124 Phase 1
0.6901 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6898 Remote Similarity NPD5711 Approved
0.6898 Remote Similarity NPD5710 Approved
0.689 Remote Similarity NPD1091 Approved
0.689 Remote Similarity NPD422 Phase 1
0.6886 Remote Similarity NPD2798 Approved
0.6882 Remote Similarity NPD4062 Phase 3
0.6875 Remote Similarity NPD8166 Discontinued
0.6869 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6869 Remote Similarity NPD6212 Phase 3
0.6869 Remote Similarity NPD6213 Phase 3
0.6868 Remote Similarity NPD6386 Approved
0.6868 Remote Similarity NPD6385 Approved
0.6867 Remote Similarity NPD3225 Approved
0.6864 Remote Similarity NPD7095 Approved
0.6862 Remote Similarity NPD5242 Approved
0.6856 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6851 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6848 Remote Similarity NPD9269 Phase 2
0.6848 Remote Similarity NPD9717 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