Structure

Physi-Chem Properties

Molecular Weight:  756.21
Volume:  682.698
LogP:  -0.636
LogD:  -0.432
LogS:  -2.581
# Rotatable Bonds:  9
TPSA:  328.35
# H-Bond Aceptor:  20
# H-Bond Donor:  12
# Rings:  6
# Heavy Atoms:  20

MedChem Properties

QED Drug-Likeness Score:  0.1
Synthetic Accessibility Score:  5.313
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:  -6.613
MDCK Permeability:  5.0993268814636394e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.998
Human Intestinal Absorption (HIA):  0.967
20% Bioavailability (F20%):  0.014
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.136
Plasma Protein Binding (PPB):  79.31900024414062%
Volume Distribution (VD):  0.569
Pgp-substrate:  16.453662872314453%

ADMET: Metabolism

CYP1A2-inhibitor:  0.035
CYP1A2-substrate:  0.018
CYP2C19-inhibitor:  0.025
CYP2C19-substrate:  0.051
CYP2C9-inhibitor:  0.002
CYP2C9-substrate:  0.056
CYP2D6-inhibitor:  0.018
CYP2D6-substrate:  0.104
CYP3A4-inhibitor:  0.021
CYP3A4-substrate:  0.001

ADMET: Excretion

Clearance (CL):  0.859
Half-life (T1/2):  0.755

ADMET: Toxicity

hERG Blockers:  0.449
Human Hepatotoxicity (H-HT):  0.092
Drug-inuced Liver Injury (DILI):  0.985
AMES Toxicity:  0.759
Rat Oral Acute Toxicity:  0.026
Maximum Recommended Daily Dose:  0.0
Skin Sensitization:  0.743
Carcinogencity:  0.084
Eye Corrosion:  0.003
Eye Irritation:  0.039
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: NPC287889

Natural Product ID:  NPC287889
Common Name*:   Evolvoside C
IUPAC Name:   2-[4-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxyphenyl]-3,5,7-trihydroxychromen-4-one
Synonyms:   Evolvoside C
Standard InCHIKey:  QUQJMJUDBLDSLV-ZBXXLHPFSA-N
Standard InCHI:  InChI=1S/C33H40O20/c1-10-19(37)25(43)30(53-32-28(46)23(41)20(38)16(8-34)51-32)33(48-10)47-9-17-21(39)24(42)27(45)31(52-17)49-13-4-2-11(3-5-13)29-26(44)22(40)18-14(36)6-12(35)7-15(18)50-29/h2-7,10,16-17,19-21,23-25,27-28,30-39,41-46H,8-9H2,1H3/t10-,16+,17+,19-,20+,21+,23-,24-,25+,27+,28+,30+,31+,32-,33+/m0/s1
SMILES:  OC[C@H]1O[C@@H](O[C@H]2[C@H](OC[C@H]3O[C@@H](Oc4ccc(cc4)c4oc5cc(O)cc(c5c(=O)c4O)O)[C@@H]([C@H]([C@@H]3O)O)O)O[C@H]([C@@H]([C@H]2O)O)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2336776
PubChem CID:   71524785
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001111] Flavonoid glycosides
          • [CHEMONTID:0001583] Flavonoid 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
NPO22311 Evolvulus alsinoides Species Convolvulaceae Eukaryota n.a. whole plant n.a. PMID[17473466]
NPO22311 Evolvulus alsinoides Species Convolvulaceae Eukaryota n.a. n.a. n.a. PMID[23357036]
NPO22311 Evolvulus alsinoides Species Convolvulaceae Eukaryota n.a. n.a. n.a. PMID[24634069]
NPO22311 Evolvulus alsinoides Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22311 Evolvulus alsinoides Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22311 Evolvulus alsinoides Species Convolvulaceae 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
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 233.3 ng/ml PMID[497114]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 385.3 mg/dl PMID[497114]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 80.17 mg/dl PMID[497114]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 7.11 mg kg-1 PMID[497114]

☑ 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 NPC287889 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 NPC135358
0.9936 High Similarity NPC221342
0.9936 High Similarity NPC189564
0.9936 High Similarity NPC476470
0.9936 High Similarity NPC477613
0.9936 High Similarity NPC186816
0.9936 High Similarity NPC142142
0.9936 High Similarity NPC32641
0.9936 High Similarity NPC12013
0.9936 High Similarity NPC256188
0.9936 High Similarity NPC203145
0.9936 High Similarity NPC11432
0.9872 High Similarity NPC292929
0.9872 High Similarity NPC76831
0.9872 High Similarity NPC289667
0.9871 High Similarity NPC475382
0.9871 High Similarity NPC244875
0.9808 High Similarity NPC311850
0.9808 High Similarity NPC473644
0.9744 High Similarity NPC240306
0.9742 High Similarity NPC187379
0.9742 High Similarity NPC136761
0.9684 High Similarity NPC262222
0.9684 High Similarity NPC64425
0.9684 High Similarity NPC68592
0.9684 High Similarity NPC298666
0.9679 High Similarity NPC276377
0.9679 High Similarity NPC473438
0.9679 High Similarity NPC476215
0.9679 High Similarity NPC170052
0.9679 High Similarity NPC297987
0.9679 High Similarity NPC249281
0.9679 High Similarity NPC163242
0.9679 High Similarity NPC215710
0.9679 High Similarity NPC265885
0.9679 High Similarity NPC116458
0.9679 High Similarity NPC139320
0.9679 High Similarity NPC246943
0.9679 High Similarity NPC253788
0.9679 High Similarity NPC64305
0.9679 High Similarity NPC181465
0.9679 High Similarity NPC173582
0.9679 High Similarity NPC135846
0.9677 High Similarity NPC473634
0.9677 High Similarity NPC22062
0.9677 High Similarity NPC138811
0.9625 High Similarity NPC209550
0.9625 High Similarity NPC277532
0.9625 High Similarity NPC175429
0.9625 High Similarity NPC138990
0.9618 High Similarity NPC298171
0.9615 High Similarity NPC473623
0.9615 High Similarity NPC271270
0.9615 High Similarity NPC470405
0.9615 High Similarity NPC304741
0.9615 High Similarity NPC97285
0.9615 High Similarity NPC471079
0.9615 High Similarity NPC246469
0.9615 High Similarity NPC142860
0.9613 High Similarity NPC182634
0.9613 High Similarity NPC473512
0.9613 High Similarity NPC108831
0.9613 High Similarity NPC65003
0.9613 High Similarity NPC129827
0.9613 High Similarity NPC44931
0.9565 High Similarity NPC474522
0.9565 High Similarity NPC470714
0.9565 High Similarity NPC470716
0.9565 High Similarity NPC470715
0.9563 High Similarity NPC5319
0.9554 High Similarity NPC101636
0.9551 High Similarity NPC320283
0.9551 High Similarity NPC111929
0.9551 High Similarity NPC41121
0.9551 High Similarity NPC472459
0.9548 High Similarity NPC307938
0.9548 High Similarity NPC323593
0.9548 High Similarity NPC473657
0.9548 High Similarity NPC295613
0.9548 High Similarity NPC203500
0.9509 High Similarity NPC14187
0.9509 High Similarity NPC202908
0.9509 High Similarity NPC122467
0.9509 High Similarity NPC231787
0.9509 High Similarity NPC48984
0.9509 High Similarity NPC292019
0.9503 High Similarity NPC164704
0.9503 High Similarity NPC470712
0.9494 High Similarity NPC190450
0.949 High Similarity NPC153342
0.9487 High Similarity NPC54802
0.9487 High Similarity NPC78263
0.9487 High Similarity NPC197304
0.9487 High Similarity NPC77672
0.9487 High Similarity NPC135391
0.9487 High Similarity NPC133671
0.9484 High Similarity NPC95090
0.9484 High Similarity NPC27408
0.9451 High Similarity NPC251417
0.9451 High Similarity NPC89052
0.9434 High Similarity NPC257566
0.9434 High Similarity NPC124155
0.943 High Similarity NPC85707
0.943 High Similarity NPC216496
0.943 High Similarity NPC129217
0.943 High Similarity NPC224530
0.943 High Similarity NPC159579
0.943 High Similarity NPC259957
0.943 High Similarity NPC470125
0.943 High Similarity NPC48093
0.943 High Similarity NPC303913
0.9423 High Similarity NPC206378
0.9419 High Similarity NPC83283
0.9419 High Similarity NPC39360
0.9419 High Similarity NPC29763
0.9419 High Similarity NPC143851
0.9419 High Similarity NPC210003
0.9394 High Similarity NPC192539
0.939 High Similarity NPC219043
0.9383 High Similarity NPC67105
0.9383 High Similarity NPC188815
0.9375 High Similarity NPC139060
0.9371 High Similarity NPC27942
0.9371 High Similarity NPC259834
0.9371 High Similarity NPC44947
0.9371 High Similarity NPC131745
0.9371 High Similarity NPC150164
0.9363 High Similarity NPC6985
0.9363 High Similarity NPC60966
0.9359 High Similarity NPC26195
0.9359 High Similarity NPC169248
0.9359 High Similarity NPC39351
0.9359 High Similarity NPC72649
0.9359 High Similarity NPC97052
0.9329 High Similarity NPC19108
0.9329 High Similarity NPC198199
0.9329 High Similarity NPC473327
0.9329 High Similarity NPC476472
0.9329 High Similarity NPC16194
0.9329 High Similarity NPC220173
0.9329 High Similarity NPC294815
0.9325 High Similarity NPC257011
0.9325 High Similarity NPC11847
0.9325 High Similarity NPC471725
0.9325 High Similarity NPC203259
0.9325 High Similarity NPC288152
0.9325 High Similarity NPC471748
0.9325 High Similarity NPC137871
0.9325 High Similarity NPC221288
0.9325 High Similarity NPC101399
0.9325 High Similarity NPC180918
0.9325 High Similarity NPC217822
0.9325 High Similarity NPC176740
0.9325 High Similarity NPC33054
0.9325 High Similarity NPC134532
0.9325 High Similarity NPC155877
0.9325 High Similarity NPC9002
0.9321 High Similarity NPC227508
0.9317 High Similarity NPC70441
0.9313 High Similarity NPC66087
0.9313 High Similarity NPC121703
0.9313 High Similarity NPC179198
0.9313 High Similarity NPC278419
0.9313 High Similarity NPC183672
0.9313 High Similarity NPC80068
0.9308 High Similarity NPC473516
0.9308 High Similarity NPC47923
0.9308 High Similarity NPC282169
0.9304 High Similarity NPC73511
0.9304 High Similarity NPC104677
0.9299 High Similarity NPC170475
0.9295 High Similarity NPC106625
0.9273 High Similarity NPC473862
0.9273 High Similarity NPC89127
0.9273 High Similarity NPC471669
0.9264 High Similarity NPC136042
0.9264 High Similarity NPC280642
0.9264 High Similarity NPC67326
0.9264 High Similarity NPC92815
0.9264 High Similarity NPC199079
0.9264 High Similarity NPC254855
0.9264 High Similarity NPC469344
0.9264 High Similarity NPC255157
0.9264 High Similarity NPC285197
0.9264 High Similarity NPC259896
0.9264 High Similarity NPC210808
0.9264 High Similarity NPC96605
0.9264 High Similarity NPC156869
0.9264 High Similarity NPC95866
0.9264 High Similarity NPC218161
0.9264 High Similarity NPC29958
0.9259 High Similarity NPC275454
0.9255 High Similarity NPC205824
0.9255 High Similarity NPC85751
0.9255 High Similarity NPC129264
0.9255 High Similarity NPC72016
0.9255 High Similarity NPC19240
0.9245 High Similarity NPC321478
0.9241 High Similarity NPC288084
0.9241 High Similarity NPC197896

  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 NPC287889 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
0.9563 High Similarity NPD7804 Clinical (unspecified phase)
0.9448 High Similarity NPD7808 Phase 3
0.9387 High Similarity NPD7251 Discontinued
0.9325 High Similarity NPD6797 Phase 2
0.9264 High Similarity NPD7472 Approved
0.9241 High Similarity NPD4381 Clinical (unspecified phase)
0.9202 High Similarity NPD7054 Approved
0.9146 High Similarity NPD7074 Phase 3
0.8757 High Similarity NPD4338 Clinical (unspecified phase)
0.8675 High Similarity NPD6167 Clinical (unspecified phase)
0.8675 High Similarity NPD6168 Clinical (unspecified phase)
0.8675 High Similarity NPD6166 Phase 2
0.865 High Similarity NPD7075 Discontinued
0.8625 High Similarity NPD4380 Phase 2
0.8571 High Similarity NPD3818 Discontinued
0.8519 High Similarity NPD6801 Discontinued
0.8466 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8438 Intermediate Similarity NPD5403 Approved
0.8428 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8365 Intermediate Similarity NPD6799 Approved
0.8333 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8313 Intermediate Similarity NPD5401 Approved
0.8303 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8303 Intermediate Similarity NPD3817 Phase 2
0.8293 Intermediate Similarity NPD1934 Approved
0.828 Intermediate Similarity NPD1549 Phase 2
0.8266 Intermediate Similarity NPD6559 Discontinued
0.8242 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8208 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8193 Intermediate Similarity NPD5402 Approved
0.8156 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8148 Intermediate Similarity NPD1512 Approved
0.8133 Intermediate Similarity NPD2801 Approved
0.8121 Intermediate Similarity NPD7411 Suspended
0.8086 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8068 Intermediate Similarity NPD8312 Approved
0.8068 Intermediate Similarity NPD8313 Approved
0.8061 Intermediate Similarity NPD6599 Discontinued
0.8038 Intermediate Similarity NPD2796 Approved
0.8036 Intermediate Similarity NPD3882 Suspended
0.8025 Intermediate Similarity NPD1511 Approved
0.8024 Intermediate Similarity NPD8455 Phase 2
0.8024 Intermediate Similarity NPD7819 Suspended
0.7975 Intermediate Similarity NPD1510 Phase 2
0.7953 Intermediate Similarity NPD6959 Discontinued
0.7929 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7919 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7834 Intermediate Similarity NPD1240 Approved
0.7829 Intermediate Similarity NPD3751 Discontinued
0.7803 Intermediate Similarity NPD3787 Discontinued
0.7789 Intermediate Similarity NPD7584 Approved
0.7784 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7736 Intermediate Similarity NPD1607 Approved
0.773 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7725 Intermediate Similarity NPD7698 Approved
0.7725 Intermediate Similarity NPD7697 Approved
0.7725 Intermediate Similarity NPD7696 Phase 3
0.7719 Intermediate Similarity NPD7768 Phase 2
0.7708 Intermediate Similarity NPD8151 Discontinued
0.7707 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD5494 Approved
0.766 Intermediate Similarity NPD6776 Approved
0.766 Intermediate Similarity NPD6781 Approved
0.766 Intermediate Similarity NPD6780 Approved
0.766 Intermediate Similarity NPD6779 Approved
0.766 Intermediate Similarity NPD6778 Approved
0.766 Intermediate Similarity NPD6782 Approved
0.766 Intermediate Similarity NPD6777 Approved
0.7656 Intermediate Similarity NPD7701 Phase 2
0.7632 Intermediate Similarity NPD7435 Discontinued
0.7629 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7629 Intermediate Similarity NPD7783 Phase 2
0.7622 Intermediate Similarity NPD3750 Approved
0.7592 Intermediate Similarity NPD7871 Phase 2
0.7592 Intermediate Similarity NPD7870 Phase 2
0.7556 Intermediate Similarity NPD7685 Pre-registration
0.7553 Intermediate Similarity NPD7699 Phase 2
0.7553 Intermediate Similarity NPD7700 Phase 2
0.7528 Intermediate Similarity NPD7228 Approved
0.7515 Intermediate Similarity NPD1653 Approved
0.7515 Intermediate Similarity NPD4628 Phase 3
0.7514 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD8319 Approved
0.75 Intermediate Similarity NPD8320 Phase 1
0.75 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7487 Intermediate Similarity NPD7874 Approved
0.7487 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7486 Intermediate Similarity NPD5844 Phase 1
0.7485 Intermediate Similarity NPD1551 Phase 2
0.7472 Intermediate Similarity NPD7473 Discontinued
0.7471 Intermediate Similarity NPD3749 Approved
0.7455 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7449 Intermediate Similarity NPD7801 Approved
0.7401 Intermediate Similarity NPD6232 Discontinued
0.7399 Intermediate Similarity NPD1465 Phase 2
0.7394 Intermediate Similarity NPD6535 Approved
0.7394 Intermediate Similarity NPD6534 Approved
0.7391 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7385 Intermediate Similarity NPD7585 Approved
0.7368 Intermediate Similarity NPD7458 Discontinued
0.7366 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.736 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD6832 Phase 2
0.7355 Intermediate Similarity NPD1091 Approved
0.7353 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7351 Intermediate Similarity NPD8434 Phase 2
0.7346 Intermediate Similarity NPD1933 Approved
0.7345 Intermediate Similarity NPD7199 Phase 2
0.7333 Intermediate Similarity NPD7583 Approved
0.7333 Intermediate Similarity NPD7266 Discontinued
0.7317 Intermediate Similarity NPD3748 Approved
0.7317 Intermediate Similarity NPD7033 Discontinued
0.7306 Intermediate Similarity NPD6823 Phase 2
0.7301 Intermediate Similarity NPD6651 Approved
0.7293 Intermediate Similarity NPD7286 Phase 2
0.7268 Intermediate Similarity NPD7240 Approved
0.7267 Intermediate Similarity NPD6798 Discontinued
0.7258 Intermediate Similarity NPD8150 Discontinued
0.7251 Intermediate Similarity NPD920 Approved
0.7246 Intermediate Similarity NPD2800 Approved
0.7246 Intermediate Similarity NPD1652 Phase 2
0.7232 Intermediate Similarity NPD919 Approved
0.7228 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD6233 Phase 2
0.7213 Intermediate Similarity NPD5953 Discontinued
0.7211 Intermediate Similarity NPD4360 Phase 2
0.7211 Intermediate Similarity NPD4363 Phase 3
0.7178 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7178 Intermediate Similarity NPD1613 Approved
0.717 Intermediate Similarity NPD1203 Approved
0.7169 Intermediate Similarity NPD2935 Discontinued
0.7167 Intermediate Similarity NPD3926 Phase 2
0.7151 Intermediate Similarity NPD1247 Approved
0.7143 Intermediate Similarity NPD4908 Phase 1
0.7143 Intermediate Similarity NPD37 Approved
0.7143 Intermediate Similarity NPD1243 Approved
0.7135 Intermediate Similarity NPD2533 Approved
0.7135 Intermediate Similarity NPD2534 Approved
0.7135 Intermediate Similarity NPD6234 Discontinued
0.7135 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD2532 Approved
0.7134 Intermediate Similarity NPD6355 Discontinued
0.7134 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD5124 Phase 1
0.7134 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD2798 Approved
0.7122 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7119 Intermediate Similarity NPD4965 Approved
0.7119 Intermediate Similarity NPD4967 Phase 2
0.7119 Intermediate Similarity NPD4966 Approved
0.7118 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD1548 Phase 1
0.7086 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7066 Intermediate Similarity NPD6100 Approved
0.7066 Intermediate Similarity NPD6099 Approved
0.7059 Intermediate Similarity NPD6190 Approved
0.7055 Intermediate Similarity NPD3268 Approved
0.7055 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD2313 Discontinued
0.7048 Intermediate Similarity NPD7097 Phase 1
0.7045 Intermediate Similarity NPD6844 Discontinued
0.7035 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD422 Phase 1
0.7024 Intermediate Similarity NPD2344 Approved
0.7006 Intermediate Similarity NPD2799 Discontinued
0.7 Intermediate Similarity NPD3225 Approved
0.6981 Remote Similarity NPD9717 Approved
0.6979 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6979 Remote Similarity NPD6213 Phase 3
0.6979 Remote Similarity NPD6212 Phase 3
0.6977 Remote Similarity NPD7390 Discontinued
0.6971 Remote Similarity NPD3226 Approved
0.697 Remote Similarity NPD943 Approved
0.6957 Remote Similarity NPD2797 Approved
0.6933 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6928 Remote Similarity NPD230 Phase 1
0.6918 Remote Similarity NPD1610 Phase 2
0.6912 Remote Similarity NPD7930 Approved
0.6909 Remote Similarity NPD4062 Phase 3
0.6901 Remote Similarity NPD6398 Clinical (unspecified phase)
0.689 Remote Similarity NPD3027 Phase 3
0.6871 Remote Similarity NPD1530 Clinical (unspecified phase)
0.686 Remote Similarity NPD2354 Approved
0.686 Remote Similarity NPD3887 Approved
0.686 Remote Similarity NPD2309 Approved
0.6853 Remote Similarity NPD7501 Clinical (unspecified phase)
0.685 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6842 Remote Similarity NPD2654 Approved
0.6839 Remote Similarity NPD4662 Approved
0.6839 Remote Similarity NPD4661 Approved
0.6834 Remote Similarity NPD7680 Approved
0.6826 Remote Similarity NPD4340 Discontinued
0.6826 Remote Similarity NPD447 Suspended
0.6826 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6824 Remote Similarity NPD2346 Discontinued
0.6821 Remote Similarity NPD4361 Phase 2
0.6821 Remote Similarity NPD4362 Clinical (unspecified phase)
0.6805 Remote Similarity NPD651 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