Structure

Physi-Chem Properties

Molecular Weight:  578.16
Volume:  534.737
LogP:  0.269
LogD:  0.203
LogS:  -3.808
# Rotatable Bonds:  6
TPSA:  228.97
# H-Bond Aceptor:  14
# H-Bond Donor:  8
# Rings:  5
# Heavy Atoms:  14

MedChem Properties

QED Drug-Likeness Score:  0.174
Synthetic Accessibility Score:  4.634
Fsp3:  0.444
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.536
MDCK Permeability:  2.5797420676099136e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.997
Human Intestinal Absorption (HIA):  0.89
20% Bioavailability (F20%):  0.012
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.057
Plasma Protein Binding (PPB):  89.6176528930664%
Volume Distribution (VD):  0.61
Pgp-substrate:  7.907190322875977%

ADMET: Metabolism

CYP1A2-inhibitor:  0.098
CYP1A2-substrate:  0.039
CYP2C19-inhibitor:  0.107
CYP2C19-substrate:  0.059
CYP2C9-inhibitor:  0.019
CYP2C9-substrate:  0.158
CYP2D6-inhibitor:  0.094
CYP2D6-substrate:  0.147
CYP3A4-inhibitor:  0.043
CYP3A4-substrate:  0.007

ADMET: Excretion

Clearance (CL):  1.343
Half-life (T1/2):  0.565

ADMET: Toxicity

hERG Blockers:  0.243
Human Hepatotoxicity (H-HT):  0.041
Drug-inuced Liver Injury (DILI):  0.811
AMES Toxicity:  0.647
Rat Oral Acute Toxicity:  0.059
Maximum Recommended Daily Dose:  0.008
Skin Sensitization:  0.93
Carcinogencity:  0.216
Eye Corrosion:  0.003
Eye Irritation:  0.231
Respiratory Toxicity:  0.043

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

  Natural Product: NPC303913

Natural Product ID:  NPC303913
Common Name*:   Sphaerobioside
IUPAC Name:   5-hydroxy-3-(4-hydroxyphenyl)-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:  
Standard InCHIKey:  XIQCIPHUIZGDLB-SEPMLUPWSA-N
Standard InCHI:  InChI=1S/C27H30O14/c1-10-19(30)22(33)24(35)26(39-10)38-9-17-21(32)23(34)25(36)27(41-17)40-13-6-15(29)18-16(7-13)37-8-14(20(18)31)11-2-4-12(28)5-3-11/h2-8,10,17,19,21-30,32-36H,9H2,1H3/t10-,17+,19-,21+,22+,23-,24+,25+,26+,27+/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](Oc3cc(c4c(c3)occ(c3ccc(cc3)O)c4=O)O)O2)O)O)O)O1)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2227762
PubChem CID:   76315025
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0002506] Isoflavonoids
        • [CHEMONTID:0000507] Isoflavonoid 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
NPO27553 Derris scandens Species Fabaceae Eukaryota n.a. stem n.a. DOI[10.1016/S0031-9422(99)00103-X]
NPO27553 Derris scandens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[19969457]
NPO27553 Derris scandens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[21314138]
NPO27553 Derris scandens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27553 Derris scandens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27553 Derris scandens Species Fabaceae 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
NPT1419 Organism Tribolium castaneum Tribolium castaneum LC50 = 0.2 ug.mL-1 PMID[475312]
NPT1419 Organism Tribolium castaneum Tribolium castaneum mortality = 100.0 % PMID[475312]
NPT2745 Organism Rhyzopertha dominica Rhyzopertha dominica LC50 = 0.27 ug.mL-1 PMID[475312]
NPT2745 Organism Rhyzopertha dominica Rhyzopertha dominica mortality = 100.0 % PMID[475312]
NPT778 Organism Sitophilus oryzae Sitophilus oryzae LC50 = 0.18 ug.mL-1 PMID[475312]
NPT778 Organism Sitophilus oryzae Sitophilus oryzae mortality = 100.0 % PMID[475312]
NPT2721 Organism Callosobruchus chinensis Callosobruchus chinensis LC50 = 0.21 ug.mL-1 PMID[475312]
NPT2721 Organism Callosobruchus chinensis Callosobruchus chinensis mortality = 100.0 % PMID[475312]
NPT2747 Organism Achaea janata Achaea janata Activity = 32.7 % PMID[475313]
NPT2747 Organism Achaea janata Achaea janata Activity = 7.5 % PMID[475313]
NPT2747 Organism Achaea janata Achaea janata Activity = 0.0 % PMID[475313]
NPT2747 Organism Achaea janata Achaea janata Activity = 9.5 % PMID[475313]
NPT2747 Organism Achaea janata Achaea janata mortality = 36.0 % PMID[475313]
NPT2747 Organism Achaea janata Achaea janata mortality = 41.2 % PMID[475313]
NPT2747 Organism Achaea janata Achaea janata Activity = 508.6 mg PMID[475313]
NPT2747 Organism Achaea janata Achaea janata Activity = 504.8 mg PMID[475313]
NPT2747 Organism Achaea janata Achaea janata TIME = 319.2 hr PMID[475313]
NPT2747 Organism Achaea janata Achaea janata TIME = 345.6 hr PMID[475313]
NPT2747 Organism Achaea janata Achaea janata mortality = 13.0 % PMID[475313]
NPT2747 Organism Achaea janata Achaea janata mortality = 31.8 % PMID[475313]
NPT2747 Organism Achaea janata Achaea janata TIME = 259.2 hr PMID[475313]
NPT2747 Organism Achaea janata Achaea janata TIME = 271.2 hr PMID[475313]
NPT2747 Organism Achaea janata Achaea janata LD50 = 3.87 microg/cm2 PMID[475313]
NPT2747 Organism Achaea janata Achaea janata Activity = 97.8 % PMID[475313]
NPT2747 Organism Achaea janata Achaea janata ED50 = 3.37 microg/cm2 PMID[475313]
NPT2747 Organism Achaea janata Achaea janata AFI = 96.2 % PMID[475313]

☑ 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 NPC303913 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
0.9868 High Similarity NPC73511
0.9805 High Similarity NPC44947
0.9803 High Similarity NPC197896
0.9803 High Similarity NPC473512
0.9803 High Similarity NPC156457
0.9803 High Similarity NPC258035
0.9803 High Similarity NPC44931
0.9803 High Similarity NPC313163
0.9803 High Similarity NPC129827
0.9803 High Similarity NPC161749
0.9803 High Similarity NPC65003
0.9742 High Similarity NPC257566
0.9742 High Similarity NPC124155
0.974 High Similarity NPC47923
0.9739 High Similarity NPC138811
0.9739 High Similarity NPC473634
0.9739 High Similarity NPC22062
0.9737 High Similarity NPC45165
0.9737 High Similarity NPC206378
0.9737 High Similarity NPC170475
0.9675 High Similarity NPC271270
0.9675 High Similarity NPC97285
0.9675 High Similarity NPC473623
0.9675 High Similarity NPC246469
0.9675 High Similarity NPC271479
0.9675 High Similarity NPC142860
0.9675 High Similarity NPC187379
0.9675 High Similarity NPC472320
0.9671 High Similarity NPC99233
0.9671 High Similarity NPC169248
0.9671 High Similarity NPC26195
0.9671 High Similarity NPC27408
0.9671 High Similarity NPC72649
0.9671 High Similarity NPC39351
0.9671 High Similarity NPC95090
0.9671 High Similarity NPC97052
0.9613 High Similarity NPC116458
0.9613 High Similarity NPC476215
0.9613 High Similarity NPC473438
0.9613 High Similarity NPC173582
0.9613 High Similarity NPC249281
0.9613 High Similarity NPC163242
0.9613 High Similarity NPC265885
0.9613 High Similarity NPC215710
0.9613 High Similarity NPC101636
0.9613 High Similarity NPC253788
0.9613 High Similarity NPC139320
0.9613 High Similarity NPC246943
0.9613 High Similarity NPC181465
0.9613 High Similarity NPC276377
0.961 High Similarity NPC308265
0.961 High Similarity NPC43761
0.9608 High Similarity NPC295613
0.9608 High Similarity NPC473657
0.9605 High Similarity NPC83283
0.9605 High Similarity NPC106625
0.9605 High Similarity NPC210003
0.9605 High Similarity NPC143851
0.9605 High Similarity NPC39360
0.9605 High Similarity NPC29763
0.956 High Similarity NPC231194
0.956 High Similarity NPC51326
0.9551 High Similarity NPC298171
0.9551 High Similarity NPC472876
0.9551 High Similarity NPC259834
0.9551 High Similarity NPC131745
0.9551 High Similarity NPC475382
0.9551 High Similarity NPC240306
0.9551 High Similarity NPC190450
0.9548 High Similarity NPC153342
0.9548 High Similarity NPC200708
0.9548 High Similarity NPC471079
0.9548 High Similarity NPC136761
0.9548 High Similarity NPC470405
0.9548 High Similarity NPC304741
0.9545 High Similarity NPC23817
0.9545 High Similarity NPC108831
0.9545 High Similarity NPC60966
0.9545 High Similarity NPC43638
0.9545 High Similarity NPC182634
0.9539 High Similarity NPC121001
0.9539 High Similarity NPC88484
0.9539 High Similarity NPC259767
0.9539 High Similarity NPC259182
0.9497 High Similarity NPC5319
0.9494 High Similarity NPC210073
0.9494 High Similarity NPC115674
0.9494 High Similarity NPC70441
0.949 High Similarity NPC311850
0.949 High Similarity NPC183672
0.949 High Similarity NPC179198
0.949 High Similarity NPC66087
0.949 High Similarity NPC473644
0.949 High Similarity NPC278419
0.9487 High Similarity NPC170052
0.9487 High Similarity NPC297987
0.9487 High Similarity NPC195685
0.9487 High Similarity NPC477629
0.9487 High Similarity NPC135846
0.9487 High Similarity NPC270675
0.9487 High Similarity NPC477628
0.9487 High Similarity NPC64305
0.9487 High Similarity NPC210961
0.9487 High Similarity NPC472994
0.9484 High Similarity NPC41121
0.9484 High Similarity NPC320283
0.9484 High Similarity NPC472459
0.9484 High Similarity NPC111929
0.9481 High Similarity NPC261866
0.9481 High Similarity NPC203500
0.9481 High Similarity NPC307938
0.9481 High Similarity NPC323593
0.9481 High Similarity NPC127406
0.9437 High Similarity NPC78734
0.9437 High Similarity NPC150767
0.9437 High Similarity NPC76047
0.9434 High Similarity NPC229729
0.943 High Similarity NPC287889
0.943 High Similarity NPC135358
0.943 High Similarity NPC139060
0.9419 High Similarity NPC77672
0.9419 High Similarity NPC122809
0.9419 High Similarity NPC135391
0.9419 High Similarity NPC197304
0.9419 High Similarity NPC6985
0.9419 High Similarity NPC54802
0.9419 High Similarity NPC78263
0.9419 High Similarity NPC133671
0.9416 High Similarity NPC470604
0.9416 High Similarity NPC470605
0.9416 High Similarity NPC470603
0.9408 High Similarity NPC213723
0.9408 High Similarity NPC191154
0.9379 High Similarity NPC256760
0.9375 High Similarity NPC209296
0.9375 High Similarity NPC195257
0.9375 High Similarity NPC229687
0.9375 High Similarity NPC43587
0.9375 High Similarity NPC293629
0.9371 High Similarity NPC221342
0.9371 High Similarity NPC476470
0.9371 High Similarity NPC477613
0.9371 High Similarity NPC142142
0.9371 High Similarity NPC11432
0.9371 High Similarity NPC5778
0.9371 High Similarity NPC203145
0.9371 High Similarity NPC236934
0.9371 High Similarity NPC186816
0.9371 High Similarity NPC262222
0.9371 High Similarity NPC189564
0.9371 High Similarity NPC68592
0.9371 High Similarity NPC256188
0.9371 High Similarity NPC64425
0.9371 High Similarity NPC8856
0.9371 High Similarity NPC298666
0.9371 High Similarity NPC32641
0.9371 High Similarity NPC12013
0.9367 High Similarity NPC168822
0.9367 High Similarity NPC19709
0.9367 High Similarity NPC29830
0.9367 High Similarity NPC309025
0.9367 High Similarity NPC88023
0.9367 High Similarity NPC80068
0.9367 High Similarity NPC243930
0.9363 High Similarity NPC224530
0.9363 High Similarity NPC216496
0.9363 High Similarity NPC470125
0.9363 High Similarity NPC48093
0.9363 High Similarity NPC85707
0.9363 High Similarity NPC259957
0.9363 High Similarity NPC129217
0.9363 High Similarity NPC159579
0.9355 High Similarity NPC265480
0.9355 High Similarity NPC149368
0.9351 High Similarity NPC268950
0.9351 High Similarity NPC109594
0.9351 High Similarity NPC326592
0.9351 High Similarity NPC112701
0.9351 High Similarity NPC87304
0.9351 High Similarity NPC211158
0.9351 High Similarity NPC108706
0.9351 High Similarity NPC78021
0.9346 High Similarity NPC134819
0.9346 High Similarity NPC190217
0.9321 High Similarity NPC208668
0.9317 High Similarity NPC210808
0.9317 High Similarity NPC95866
0.9317 High Similarity NPC105511
0.9317 High Similarity NPC44558
0.9317 High Similarity NPC44328
0.9317 High Similarity NPC218488
0.9317 High Similarity NPC79056
0.9317 High Similarity NPC199079
0.9317 High Similarity NPC177731
0.9317 High Similarity NPC67105
0.9317 High Similarity NPC105095
0.9313 High Similarity NPC45400
0.9308 High Similarity NPC129264
0.9308 High Similarity NPC19240
0.9308 High Similarity NPC292929

  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 NPC303913 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
0.9803 High Similarity NPD4381 Clinical (unspecified phase)
0.9497 High Similarity NPD7804 Clinical (unspecified phase)
0.9375 High Similarity NPD7054 Approved
0.9317 High Similarity NPD7074 Phase 3
0.9317 High Similarity NPD7472 Approved
0.9259 High Similarity NPD6797 Phase 2
0.9202 High Similarity NPD7251 Discontinued
0.9156 High Similarity NPD4380 Phase 2
0.9146 High Similarity NPD7808 Phase 3
0.9074 High Similarity NPD3818 Discontinued
0.8834 High Similarity NPD6168 Clinical (unspecified phase)
0.8834 High Similarity NPD6167 Clinical (unspecified phase)
0.8834 High Similarity NPD6166 Phase 2
0.8812 High Similarity NPD7075 Discontinued
0.8802 High Similarity NPD4338 Clinical (unspecified phase)
0.8743 High Similarity NPD6559 Discontinued
0.8684 High Similarity NPD1549 Phase 2
0.8679 High Similarity NPD1934 Approved
0.8679 High Similarity NPD6801 Discontinued
0.8625 High Similarity NPD7096 Clinical (unspecified phase)
0.8625 High Similarity NPD2393 Clinical (unspecified phase)
0.8618 High Similarity NPD1552 Clinical (unspecified phase)
0.8618 High Similarity NPD1550 Clinical (unspecified phase)
0.859 High Similarity NPD4378 Clinical (unspecified phase)
0.8553 High Similarity NPD2796 Approved
0.85 High Similarity NPD7411 Suspended
0.8487 Intermediate Similarity NPD1510 Phase 2
0.8481 Intermediate Similarity NPD5403 Approved
0.8471 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8457 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8408 Intermediate Similarity NPD6799 Approved
0.8405 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8395 Intermediate Similarity NPD2801 Approved
0.8354 Intermediate Similarity NPD5401 Approved
0.8344 Intermediate Similarity NPD3817 Phase 2
0.8344 Intermediate Similarity NPD5402 Approved
0.8313 Intermediate Similarity NPD6959 Discontinued
0.8291 Intermediate Similarity NPD1511 Approved
0.8282 Intermediate Similarity NPD7819 Suspended
0.8274 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8246 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8224 Intermediate Similarity NPD1240 Approved
0.821 Intermediate Similarity NPD6599 Discontinued
0.8208 Intermediate Similarity NPD8313 Approved
0.8208 Intermediate Similarity NPD8312 Approved
0.8192 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8187 Intermediate Similarity NPD1512 Approved
0.8182 Intermediate Similarity NPD3882 Suspended
0.8144 Intermediate Similarity NPD5494 Approved
0.8117 Intermediate Similarity NPD1607 Approved
0.8108 Intermediate Similarity NPD7584 Approved
0.8101 Intermediate Similarity NPD3750 Approved
0.8101 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.8061 Intermediate Similarity NPD8455 Phase 2
0.7987 Intermediate Similarity NPD4628 Phase 3
0.7965 Intermediate Similarity NPD3751 Discontinued
0.7964 Intermediate Similarity NPD7768 Phase 2
0.7919 Intermediate Similarity NPD5844 Phase 1
0.7917 Intermediate Similarity NPD3749 Approved
0.788 Intermediate Similarity NPD6778 Approved
0.788 Intermediate Similarity NPD6781 Approved
0.788 Intermediate Similarity NPD6777 Approved
0.788 Intermediate Similarity NPD6782 Approved
0.788 Intermediate Similarity NPD6779 Approved
0.788 Intermediate Similarity NPD6780 Approved
0.788 Intermediate Similarity NPD6776 Approved
0.7866 Intermediate Similarity NPD1653 Approved
0.7848 Intermediate Similarity NPD1551 Phase 2
0.7844 Intermediate Similarity NPD1465 Phase 2
0.7836 Intermediate Similarity NPD3787 Discontinued
0.7831 Intermediate Similarity NPD8151 Discontinued
0.7812 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7805 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7785 Intermediate Similarity NPD3748 Approved
0.7759 Intermediate Similarity NPD7228 Approved
0.7754 Intermediate Similarity NPD7698 Approved
0.7754 Intermediate Similarity NPD7435 Discontinued
0.7754 Intermediate Similarity NPD7697 Approved
0.7754 Intermediate Similarity NPD7696 Phase 3
0.775 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7742 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7733 Intermediate Similarity NPD6232 Discontinued
0.7717 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7711 Intermediate Similarity NPD7458 Discontinued
0.7701 Intermediate Similarity NPD7473 Discontinued
0.7697 Intermediate Similarity NPD920 Approved
0.7684 Intermediate Similarity NPD7585 Approved
0.7684 Intermediate Similarity NPD7701 Phase 2
0.7684 Intermediate Similarity NPD7685 Pre-registration
0.7674 Intermediate Similarity NPD7199 Phase 2
0.7656 Intermediate Similarity NPD7783 Phase 2
0.7656 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7632 Intermediate Similarity NPD7583 Approved
0.7627 Intermediate Similarity NPD5953 Discontinued
0.7625 Intermediate Similarity NPD2935 Discontinued
0.7619 Intermediate Similarity NPD7871 Phase 2
0.7619 Intermediate Similarity NPD7870 Phase 2
0.7609 Intermediate Similarity NPD6534 Approved
0.7609 Intermediate Similarity NPD6535 Approved
0.7606 Intermediate Similarity NPD6823 Phase 2
0.7597 Intermediate Similarity NPD2798 Approved
0.7595 Intermediate Similarity NPD1933 Approved
0.7593 Intermediate Similarity NPD1243 Approved
0.7593 Intermediate Similarity NPD2800 Approved
0.7582 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7581 Intermediate Similarity NPD7700 Phase 2
0.7581 Intermediate Similarity NPD7699 Phase 2
0.7578 Intermediate Similarity NPD7266 Discontinued
0.7576 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7562 Intermediate Similarity NPD7033 Discontinued
0.7561 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7542 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7532 Intermediate Similarity NPD1613 Approved
0.7532 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD2313 Discontinued
0.7514 Intermediate Similarity NPD4363 Phase 3
0.7514 Intermediate Similarity NPD4360 Phase 2
0.7514 Intermediate Similarity NPD7286 Phase 2
0.7513 Intermediate Similarity NPD7874 Approved
0.7513 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1091 Approved
0.75 Intermediate Similarity NPD6832 Phase 2
0.75 Intermediate Similarity NPD4908 Phase 1
0.7486 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7474 Intermediate Similarity NPD7801 Approved
0.7471 Intermediate Similarity NPD37 Approved
0.747 Intermediate Similarity NPD2534 Approved
0.747 Intermediate Similarity NPD2532 Approved
0.747 Intermediate Similarity NPD2533 Approved
0.7469 Intermediate Similarity NPD2344 Approved
0.7457 Intermediate Similarity NPD919 Approved
0.7457 Intermediate Similarity NPD6234 Discontinued
0.7453 Intermediate Similarity NPD2799 Discontinued
0.7442 Intermediate Similarity NPD4965 Approved
0.7442 Intermediate Similarity NPD4966 Approved
0.7442 Intermediate Similarity NPD4967 Phase 2
0.7438 Intermediate Similarity NPD6651 Approved
0.7435 Intermediate Similarity NPD8319 Approved
0.7435 Intermediate Similarity NPD8320 Phase 1
0.7421 Intermediate Similarity NPD943 Approved
0.7419 Intermediate Similarity NPD1203 Approved
0.7418 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.741 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7405 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD3226 Approved
0.7389 Intermediate Similarity NPD7240 Approved
0.7386 Intermediate Similarity NPD3926 Phase 2
0.7378 Intermediate Similarity NPD1652 Phase 2
0.7375 Intermediate Similarity NPD5124 Phase 1
0.7375 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7371 Intermediate Similarity NPD1247 Approved
0.7366 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7366 Intermediate Similarity NPD6213 Phase 3
0.7366 Intermediate Similarity NPD6212 Phase 3
0.7365 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7345 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD7390 Discontinued
0.7301 Intermediate Similarity NPD6100 Approved
0.7301 Intermediate Similarity NPD6099 Approved
0.7296 Intermediate Similarity NPD6798 Discontinued
0.7296 Intermediate Similarity NPD3268 Approved
0.7289 Intermediate Similarity NPD2309 Approved
0.7283 Intermediate Similarity NPD8150 Discontinued
0.7283 Intermediate Similarity NPD8434 Phase 2
0.7278 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD1610 Phase 2
0.7267 Intermediate Similarity NPD230 Phase 1
0.7267 Intermediate Similarity NPD6844 Discontinued
0.7256 Intermediate Similarity NPD2346 Discontinued
0.7239 Intermediate Similarity NPD4308 Phase 3
0.7237 Intermediate Similarity NPD1548 Phase 1
0.7233 Intermediate Similarity NPD3027 Phase 3
0.7229 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD9717 Approved
0.7215 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD2797 Approved
0.7193 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD6190 Approved
0.7184 Intermediate Similarity NPD4288 Approved
0.7178 Intermediate Similarity NPD7097 Phase 1
0.7161 Intermediate Similarity NPD422 Phase 1
0.716 Intermediate Similarity NPD447 Suspended
0.716 Intermediate Similarity NPD4662 Approved
0.716 Intermediate Similarity NPD6355 Discontinued
0.716 Intermediate Similarity NPD4661 Approved
0.716 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6233 Phase 2
0.7143 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD3225 Approved
0.7108 Intermediate Similarity NPD2424 Discontinued
0.7105 Intermediate Similarity NPD4361 Phase 2
0.7105 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7049 Intermediate Similarity NPD3823 Discontinued
0.7041 Intermediate Similarity NPD7211 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD5710 Approved
0.7039 Intermediate 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