Structure

Physi-Chem Properties

Molecular Weight:  772.21
Volume:  691.488
LogP:  -0.976
LogD:  -0.639
LogS:  -3.815
# Rotatable Bonds:  9
TPSA:  348.58
# H-Bond Aceptor:  21
# H-Bond Donor:  13
# Rings:  6
# Heavy Atoms:  21

MedChem Properties

QED Drug-Likeness Score:  0.097
Synthetic Accessibility Score:  5.381
Fsp3:  0.545
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.637
MDCK Permeability:  0.0001198070531245321
Pgp-inhibitor:  0.0
Pgp-substrate:  0.998
Human Intestinal Absorption (HIA):  0.932
20% Bioavailability (F20%):  0.001
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.244
Plasma Protein Binding (PPB):  70.87443542480469%
Volume Distribution (VD):  0.593
Pgp-substrate:  17.9129695892334%

ADMET: Metabolism

CYP1A2-inhibitor:  0.069
CYP1A2-substrate:  0.011
CYP2C19-inhibitor:  0.01
CYP2C19-substrate:  0.058
CYP2C9-inhibitor:  0.0
CYP2C9-substrate:  0.069
CYP2D6-inhibitor:  0.012
CYP2D6-substrate:  0.106
CYP3A4-inhibitor:  0.007
CYP3A4-substrate:  0.001

ADMET: Excretion

Clearance (CL):  1.012
Half-life (T1/2):  0.691

ADMET: Toxicity

hERG Blockers:  0.375
Human Hepatotoxicity (H-HT):  0.069
Drug-inuced Liver Injury (DILI):  0.982
AMES Toxicity:  0.514
Rat Oral Acute Toxicity:  0.01
Maximum Recommended Daily Dose:  0.0
Skin Sensitization:  0.168
Carcinogencity:  0.032
Eye Corrosion:  0.003
Eye Irritation:  0.021
Respiratory Toxicity:  0.006

Download Data

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

  Natural Product: NPC251417

Natural Product ID:  NPC251417
Common Name*:   Moricandin
IUPAC Name:   5-hydroxy-2-[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
Synonyms:   moricandin
Standard InCHIKey:  CUNHEVJFIYAKHY-JFAQOVLHSA-N
Standard InCHI:  InChI=1S/C33H40O21/c1-9-19(38)23(42)26(45)31(48-9)49-11-5-13(37)18-15(6-11)50-29(30(22(18)41)54-33-28(47)25(44)21(40)17(8-35)53-33)10-2-3-14(12(36)4-10)51-32-27(46)24(43)20(39)16(7-34)52-32/h2-6,9,16-17,19-21,23-28,31-40,42-47H,7-8H2,1H3/t9-,16+,17+,19-,20+,21+,23+,24-,25-,26+,27+,28+,31-,32+,33-/m0/s1
SMILES:  C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)Oc1cc(c2c(c1)oc(c1ccc(c(c1)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)c(c2=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL442686
PubChem CID:   44575359
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
NPO14305 Moricandia arvensis Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[15844940]
NPO14305 Moricandia arvensis Species Brassicaceae 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
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 1.23 mM PMID[470192]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 48.1 ug.mL-1 PMID[470192]
NPT1 Others Radical scavenging activity Activity = 60.0 % PMID[470192]

☑ 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 NPC251417 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 NPC89052
0.9939 High Similarity NPC202908
0.9939 High Similarity NPC292019
0.9939 High Similarity NPC48984
0.9939 High Similarity NPC192539
0.9939 High Similarity NPC122467
0.9939 High Similarity NPC219043
0.9939 High Similarity NPC14187
0.9878 High Similarity NPC16194
0.9878 High Similarity NPC19108
0.9878 High Similarity NPC476472
0.9878 High Similarity NPC473327
0.9878 High Similarity NPC294815
0.9878 High Similarity NPC220173
0.9759 High Similarity NPC173837
0.9758 High Similarity NPC198199
0.9756 High Similarity NPC134532
0.9756 High Similarity NPC203259
0.9756 High Similarity NPC471748
0.9756 High Similarity NPC26230
0.9756 High Similarity NPC176740
0.9756 High Similarity NPC180918
0.9756 High Similarity NPC155877
0.9756 High Similarity NPC60735
0.9756 High Similarity NPC33054
0.9756 High Similarity NPC471725
0.9704 High Similarity NPC473554
0.9704 High Similarity NPC470719
0.9704 High Similarity NPC295625
0.9701 High Similarity NPC473571
0.9701 High Similarity NPC470443
0.9701 High Similarity NPC110941
0.9701 High Similarity NPC470444
0.9701 High Similarity NPC126784
0.9701 High Similarity NPC241423
0.9701 High Similarity NPC473682
0.9699 High Similarity NPC473862
0.9699 High Similarity NPC89127
0.9699 High Similarity NPC471669
0.9695 High Similarity NPC255157
0.9695 High Similarity NPC254855
0.9695 High Similarity NPC29958
0.9695 High Similarity NPC285197
0.9695 High Similarity NPC136042
0.9695 High Similarity NPC67326
0.9695 High Similarity NPC67105
0.9695 High Similarity NPC95866
0.9695 High Similarity NPC259896
0.9695 High Similarity NPC156869
0.9645 High Similarity NPC21359
0.9645 High Similarity NPC470451
0.9645 High Similarity NPC25946
0.9645 High Similarity NPC460984
0.9645 High Similarity NPC275977
0.9645 High Similarity NPC249560
0.9645 High Similarity NPC470720
0.9645 High Similarity NPC470455
0.9645 High Similarity NPC470717
0.9645 High Similarity NPC470713
0.9645 High Similarity NPC223860
0.9641 High Similarity NPC120952
0.9634 High Similarity NPC209296
0.9634 High Similarity NPC219904
0.9634 High Similarity NPC225434
0.9634 High Similarity NPC223747
0.9634 High Similarity NPC203050
0.9634 High Similarity NPC195257
0.9634 High Similarity NPC86008
0.9634 High Similarity NPC227508
0.9634 High Similarity NPC120099
0.9588 High Similarity NPC33083
0.9586 High Similarity NPC470718
0.9586 High Similarity NPC470445
0.9586 High Similarity NPC162394
0.9586 High Similarity NPC470449
0.9586 High Similarity NPC241781
0.9586 High Similarity NPC473072
0.9586 High Similarity NPC470447
0.9586 High Similarity NPC156785
0.9586 High Similarity NPC470446
0.9581 High Similarity NPC8573
0.9581 High Similarity NPC470949
0.9581 High Similarity NPC65563
0.9581 High Similarity NPC169733
0.9581 High Similarity NPC255799
0.9576 High Similarity NPC79056
0.9576 High Similarity NPC177731
0.9576 High Similarity NPC105095
0.9576 High Similarity NPC44328
0.9576 High Similarity NPC206123
0.9573 High Similarity NPC275454
0.9573 High Similarity NPC127546
0.9573 High Similarity NPC317489
0.9573 High Similarity NPC173637
0.9573 High Similarity NPC325555
0.9573 High Similarity NPC223424
0.9573 High Similarity NPC265530
0.9573 High Similarity NPC84362
0.9573 High Similarity NPC52550
0.9573 High Similarity NPC226304
0.9532 High Similarity NPC30011
0.9532 High Similarity NPC97817
0.9532 High Similarity NPC72554
0.9529 High Similarity NPC148710
0.9527 High Similarity NPC473071
0.9527 High Similarity NPC473073
0.9521 High Similarity NPC253685
0.9521 High Similarity NPC294629
0.9518 High Similarity NPC153755
0.9515 High Similarity NPC105283
0.9515 High Similarity NPC293629
0.9515 High Similarity NPC270578
0.9515 High Similarity NPC52382
0.9515 High Similarity NPC43587
0.9512 High Similarity NPC186816
0.9512 High Similarity NPC328940
0.9512 High Similarity NPC197285
0.9512 High Similarity NPC32641
0.9512 High Similarity NPC21100
0.9512 High Similarity NPC189564
0.9512 High Similarity NPC476470
0.9512 High Similarity NPC113968
0.9512 High Similarity NPC274618
0.9512 High Similarity NPC142142
0.9512 High Similarity NPC277174
0.9512 High Similarity NPC256188
0.9512 High Similarity NPC145038
0.9512 High Similarity NPC210073
0.9512 High Similarity NPC73855
0.9512 High Similarity NPC281131
0.9512 High Similarity NPC8856
0.9512 High Similarity NPC477613
0.9512 High Similarity NPC11432
0.9512 High Similarity NPC118284
0.9512 High Similarity NPC135599
0.9512 High Similarity NPC179950
0.9512 High Similarity NPC221342
0.9512 High Similarity NPC88789
0.9512 High Similarity NPC115674
0.9512 High Similarity NPC56077
0.9512 High Similarity NPC276222
0.9512 High Similarity NPC253662
0.9512 High Similarity NPC203145
0.9512 High Similarity NPC308404
0.9512 High Similarity NPC12013
0.9474 High Similarity NPC104910
0.9474 High Similarity NPC474093
0.9461 High Similarity NPC21666
0.9461 High Similarity NPC24043
0.9461 High Similarity NPC204693
0.9461 High Similarity NPC45522
0.9461 High Similarity NPC208668
0.9461 High Similarity NPC169977
0.9461 High Similarity NPC101026
0.9461 High Similarity NPC42773
0.9461 High Similarity NPC4390
0.9461 High Similarity NPC25724
0.9458 High Similarity NPC244776
0.9458 High Similarity NPC116864
0.9458 High Similarity NPC51326
0.9458 High Similarity NPC231194
0.9455 High Similarity NPC92565
0.9455 High Similarity NPC160156
0.9451 High Similarity NPC55786
0.9451 High Similarity NPC135358
0.9451 High Similarity NPC287889
0.9451 High Similarity NPC475366
0.9451 High Similarity NPC240431
0.9451 High Similarity NPC76831
0.9451 High Similarity NPC289667
0.9451 High Similarity NPC284277
0.9451 High Similarity NPC292929
0.9451 High Similarity NPC475497
0.9451 High Similarity NPC311830
0.9451 High Similarity NPC15358
0.9451 High Similarity NPC277205
0.9451 High Similarity NPC22832
0.9451 High Similarity NPC19388
0.9419 High Similarity NPC475179
0.9419 High Similarity NPC64755
0.9408 High Similarity NPC477895
0.9408 High Similarity NPC217520
0.9408 High Similarity NPC139571
0.9405 High Similarity NPC142996
0.9405 High Similarity NPC102028
0.9401 High Similarity NPC476405
0.9401 High Similarity NPC175107
0.9401 High Similarity NPC245452
0.9401 High Similarity NPC117260
0.9401 High Similarity NPC256760
0.9401 High Similarity NPC3583
0.9401 High Similarity NPC259152
0.9401 High Similarity NPC190003
0.9394 High Similarity NPC5778
0.9394 High Similarity NPC236934
0.939 High Similarity NPC222936
0.939 High Similarity NPC309025
0.939 High Similarity NPC19709
0.939 High Similarity NPC270335
0.939 High Similarity NPC191306

  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 NPC251417 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
0.9878 High Similarity NPD7808 Phase 3
0.9817 High Similarity NPD7251 Discontinued
0.9756 High Similarity NPD6797 Phase 2
0.9695 High Similarity NPD7472 Approved
0.9634 High Similarity NPD7054 Approved
0.9576 High Similarity NPD7074 Phase 3
0.929 High Similarity NPD4338 Clinical (unspecified phase)
0.9281 High Similarity NPD7804 Clinical (unspecified phase)
0.9102 High Similarity NPD6166 Phase 2
0.9102 High Similarity NPD6168 Clinical (unspecified phase)
0.9102 High Similarity NPD6167 Clinical (unspecified phase)
0.8994 High Similarity NPD3818 Discontinued
0.8855 High Similarity NPD4381 Clinical (unspecified phase)
0.8735 High Similarity NPD3817 Phase 2
0.8727 High Similarity NPD1934 Approved
0.8571 High Similarity NPD3882 Suspended
0.8563 High Similarity NPD2801 Approved
0.8563 High Similarity NPD2393 Clinical (unspecified phase)
0.8514 High Similarity NPD7993 Clinical (unspecified phase)
0.8476 Intermediate Similarity NPD1512 Approved
0.8412 Intermediate Similarity NPD7075 Discontinued
0.8354 Intermediate Similarity NPD1511 Approved
0.8274 Intermediate Similarity NPD4380 Phase 2
0.8246 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8235 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8187 Intermediate Similarity NPD5402 Approved
0.8176 Intermediate Similarity NPD6801 Discontinued
0.8156 Intermediate Similarity NPD6559 Discontinued
0.8152 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8095 Intermediate Similarity NPD5403 Approved
0.8084 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8024 Intermediate Similarity NPD6799 Approved
0.8 Intermediate Similarity NPD5494 Approved
0.7977 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7976 Intermediate Similarity NPD5401 Approved
0.7967 Intermediate Similarity NPD8313 Approved
0.7967 Intermediate Similarity NPD8312 Approved
0.7956 Intermediate Similarity NPD7685 Pre-registration
0.7941 Intermediate Similarity NPD1653 Approved
0.7933 Intermediate Similarity NPD3751 Discontinued
0.7933 Intermediate Similarity NPD7228 Approved
0.7919 Intermediate Similarity NPD7819 Suspended
0.791 Intermediate Similarity NPD3787 Discontinued
0.7879 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7879 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7853 Intermediate Similarity NPD6959 Discontinued
0.7831 Intermediate Similarity NPD1549 Phase 2
0.7816 Intermediate Similarity NPD1465 Phase 2
0.779 Intermediate Similarity NPD5844 Phase 1
0.7784 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD7473 Discontinued
0.7765 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7754 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7746 Intermediate Similarity NPD6599 Discontinued
0.7716 Intermediate Similarity NPD8151 Discontinued
0.7714 Intermediate Similarity NPD8455 Phase 2
0.7711 Intermediate Similarity NPD2796 Approved
0.7709 Intermediate Similarity NPD6232 Discontinued
0.7701 Intermediate Similarity NPD7411 Suspended
0.7674 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7665 Intermediate Similarity NPD7266 Discontinued
0.7661 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7654 Intermediate Similarity NPD7199 Phase 2
0.7651 Intermediate Similarity NPD1510 Phase 2
0.7641 Intermediate Similarity NPD7698 Approved
0.7641 Intermediate Similarity NPD7696 Phase 3
0.7641 Intermediate Similarity NPD7697 Approved
0.7641 Intermediate Similarity NPD7435 Discontinued
0.764 Intermediate Similarity NPD919 Approved
0.7624 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7577 Intermediate Similarity NPD6778 Approved
0.7577 Intermediate Similarity NPD6779 Approved
0.7577 Intermediate Similarity NPD6781 Approved
0.7577 Intermediate Similarity NPD6782 Approved
0.7577 Intermediate Similarity NPD6777 Approved
0.7577 Intermediate Similarity NPD6780 Approved
0.7577 Intermediate Similarity NPD6776 Approved
0.7576 Intermediate Similarity NPD7701 Phase 2
0.7568 Intermediate Similarity NPD7240 Approved
0.7556 Intermediate Similarity NPD1247 Approved
0.755 Intermediate Similarity NPD7783 Phase 2
0.755 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7542 Intermediate Similarity NPD6234 Discontinued
0.7525 Intermediate Similarity NPD7584 Approved
0.7515 Intermediate Similarity NPD1613 Approved
0.7515 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7513 Intermediate Similarity NPD8320 Phase 1
0.7513 Intermediate Similarity NPD8319 Approved
0.7513 Intermediate Similarity NPD7870 Phase 2
0.7513 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7513 Intermediate Similarity NPD7871 Phase 2
0.75 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7874 Approved
0.7485 Intermediate Similarity NPD6190 Approved
0.7474 Intermediate Similarity NPD7700 Phase 2
0.7474 Intermediate Similarity NPD7699 Phase 2
0.7473 Intermediate Similarity NPD3926 Phase 2
0.7458 Intermediate Similarity NPD37 Approved
0.743 Intermediate Similarity NPD4965 Approved
0.743 Intermediate Similarity NPD7768 Phase 2
0.743 Intermediate Similarity NPD4967 Phase 2
0.743 Intermediate Similarity NPD4966 Approved
0.7427 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7412 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.741 Intermediate Similarity NPD1240 Approved
0.7399 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7376 Intermediate Similarity NPD7801 Approved
0.7365 Intermediate Similarity NPD1933 Approved
0.7333 Intermediate Similarity NPD3027 Phase 3
0.7326 Intermediate Similarity NPD3750 Approved
0.7321 Intermediate Similarity NPD1607 Approved
0.732 Intermediate Similarity NPD6534 Approved
0.732 Intermediate Similarity NPD6535 Approved
0.7305 Intermediate Similarity NPD943 Approved
0.7289 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7277 Intermediate Similarity NPD8434 Phase 2
0.7277 Intermediate Similarity NPD8150 Discontinued
0.7273 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7262 Intermediate Similarity NPD230 Phase 1
0.7243 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7236 Intermediate Similarity NPD6823 Phase 2
0.7225 Intermediate Similarity NPD4628 Phase 3
0.7212 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD7680 Approved
0.7198 Intermediate Similarity NPD3749 Approved
0.7193 Intermediate Similarity NPD1551 Phase 2
0.7172 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD447 Suspended
0.7143 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7585 Approved
0.7136 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD7458 Discontinued
0.7094 Intermediate Similarity NPD7583 Approved
0.7093 Intermediate Similarity NPD2935 Discontinued
0.7075 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.7069 Intermediate Similarity NPD6674 Discontinued
0.7069 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD2533 Approved
0.7062 Intermediate Similarity NPD2532 Approved
0.7062 Intermediate Similarity NPD2534 Approved
0.7035 Intermediate Similarity NPD3748 Approved
0.6994 Remote Similarity NPD6099 Approved
0.6994 Remote Similarity NPD6100 Approved
0.6983 Remote Similarity NPD920 Approved
0.6982 Remote Similarity NPD6798 Discontinued
0.6979 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6978 Remote Similarity NPD6844 Discontinued
0.6971 Remote Similarity NPD2800 Approved
0.697 Remote Similarity NPD4360 Phase 2
0.697 Remote Similarity NPD4363 Phase 3
0.6966 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6964 Remote Similarity NPD6832 Phase 2
0.6963 Remote Similarity NPD5953 Discontinued
0.6959 Remote Similarity NPD6355 Discontinued
0.6951 Remote Similarity NPD1091 Approved
0.6947 Remote Similarity NPD7286 Phase 2
0.6941 Remote Similarity NPD6233 Phase 2
0.6936 Remote Similarity NPD7033 Discontinued
0.6919 Remote Similarity NPD6651 Approved
0.6919 Remote Similarity NPD6212 Phase 3
0.6919 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6919 Remote Similarity NPD6213 Phase 3
0.691 Remote Similarity NPD7390 Discontinued
0.6906 Remote Similarity NPD3226 Approved
0.6905 Remote Similarity NPD9494 Approved
0.6902 Remote Similarity NPD5353 Approved
0.6898 Remote Similarity NPD8127 Discontinued
0.6875 Remote Similarity NPD1652 Phase 2
0.6875 Remote Similarity NPD1243 Approved
0.6872 Remote Similarity NPD642 Clinical (unspecified phase)
0.6867 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6864 Remote Similarity NPD4908 Phase 1
0.6857 Remote Similarity NPD7930 Approved
0.6854 Remote Similarity NPD643 Clinical (unspecified phase)
0.6845 Remote Similarity NPD2798 Approved
0.6836 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6822 Remote Similarity NPD7907 Approved
0.6806 Remote Similarity NPD2163 Approved
0.6802 Remote Similarity NPD6841 Approved
0.6802 Remote Similarity NPD6843 Phase 3
0.6802 Remote Similarity NPD6842 Approved
0.6796 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6786 Remote Similarity NPD1203 Approved
0.6784 Remote Similarity NPD2313 Discontinued
0.6784 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6763 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6763 Remote Similarity NPD5124 Phase 1
0.6763 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6761 Remote Similarity NPD2344 Approved
0.6761 Remote Similarity NPD2346 Discontinued
0.6747 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6743 Remote Similarity NPD8059 Phase 3
0.6743 Remote Similarity NPD8058 Clinical (unspecified phase)
0.6743 Remote Similarity NPD2799 Discontinued
0.6739 Remote Similarity NPD6386 Approved
0.6739 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6739 Remote Similarity NPD6385 Approved
0.6737 Remote Similarity NPD5242 Approved
0.6735 Remote Similarity NPD7090 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