Structure

Physi-Chem Properties

Molecular Weight:  578.14
Volume:  555.862
LogP:  3.603
LogD:  2.561
LogS:  -4.418
# Rotatable Bonds:  8
TPSA:  196.35
# H-Bond Aceptor:  12
# H-Bond Donor:  6
# Rings:  5
# Heavy Atoms:  12

MedChem Properties

QED Drug-Likeness Score:  0.138
Synthetic Accessibility Score:  4.081
Fsp3:  0.2
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:  -6.134
MDCK Permeability:  1.7775337255443446e-05
Pgp-inhibitor:  0.004
Pgp-substrate:  0.915
Human Intestinal Absorption (HIA):  0.391
20% Bioavailability (F20%):  0.848
30% Bioavailability (F30%):  0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.012
Plasma Protein Binding (PPB):  100.83959197998047%
Volume Distribution (VD):  0.626
Pgp-substrate:  1.8221650123596191%

ADMET: Metabolism

CYP1A2-inhibitor:  0.681
CYP1A2-substrate:  0.036
CYP2C19-inhibitor:  0.453
CYP2C19-substrate:  0.052
CYP2C9-inhibitor:  0.644
CYP2C9-substrate:  0.914
CYP2D6-inhibitor:  0.803
CYP2D6-substrate:  0.449
CYP3A4-inhibitor:  0.559
CYP3A4-substrate:  0.089

ADMET: Excretion

Clearance (CL):  4.379
Half-life (T1/2):  0.667

ADMET: Toxicity

hERG Blockers:  0.217
Human Hepatotoxicity (H-HT):  0.145
Drug-inuced Liver Injury (DILI):  0.834
AMES Toxicity:  0.684
Rat Oral Acute Toxicity:  0.039
Maximum Recommended Daily Dose:  0.065
Skin Sensitization:  0.956
Carcinogencity:  0.516
Eye Corrosion:  0.003
Eye Irritation:  0.308
Respiratory Toxicity:  0.029

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

  Natural Product: NPC195685

Natural Product ID:  NPC195685
Common Name*:   Cosmosiin 6''-(Z)-P-Coumarate
IUPAC Name:   [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyoxan-2-yl]methyl (Z)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:  
Standard InCHIKey:  WPQRDUGBKUNFJW-SVZMWWRJSA-N
Standard InCHI:  InChI=1S/C30H26O12/c31-17-6-1-15(2-7-17)3-10-25(35)39-14-24-27(36)28(37)29(38)30(42-24)40-19-11-20(33)26-21(34)13-22(41-23(26)12-19)16-4-8-18(32)9-5-16/h1-13,24,27-33,36-38H,14H2/b10-3-/t24-,27-,28+,29-,30-/m1/s1
SMILES:  c1cc(ccc1/C=CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](Oc2cc(c3c(=O)cc(c4ccc(cc4)O)oc3c2)O)O1)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3597473
PubChem CID:   16109837
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
NPO2804 Calophyllum inophyllum Species Calophyllaceae Eukaryota n.a. n.a. n.a. PMID[15678383]
NPO2804 Calophyllum inophyllum Species Calophyllaceae Eukaryota n.a. n.a. n.a. PMID[16045947]
NPO8764 Laurencia decumbens Species Rhodomelaceae Eukaryota n.a. n.a. n.a. PMID[17711344]
NPO8653 Leuconostoc mesenteroides Species Leuconostocaceae Bacteria n.a. n.a. n.a. PMID[19025748]
NPO24671 Lycopodium japonicum Species Lycopodiaceae Eukaryota n.a. n.a. n.a. PMID[19245240]
NPO2804 Calophyllum inophyllum Species Calophyllaceae Eukaryota n.a. stem n.a. PMID[20188156]
NPO26700 Tinospora crispa Species Menispermaceae Eukaryota n.a. n.a. n.a. PMID[20356064]
NPO26700 Tinospora crispa Species Menispermaceae Eukaryota n.a. n.a. n.a. PMID[22283497]
NPO3123 Anthemis cretica Species Asteraceae Eukaryota n.a. aerial part n.a. PMID[22351977]
NPO26700 Tinospora crispa Species Menispermaceae Eukaryota leaf Putz City, Chiayi County, Taiwan 2009-Nov PMID[25999202]
NPO26700 Tinospora crispa Species Menispermaceae Eukaryota n.a. n.a. n.a. PMID[28742368]
NPO26700 Tinospora crispa Species Menispermaceae Eukaryota n.a. n.a. n.a. PMID[29397715]
NPO2804 Calophyllum inophyllum Species Calophyllaceae Eukaryota n.a. Malaysian n.a. PMID[7506311]
NPO24671 Lycopodium japonicum Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2804 Calophyllum inophyllum Species Calophyllaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28741 Afrocarpus gracilior Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3123 Anthemis cretica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24671 Lycopodium japonicum Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2804 Calophyllum inophyllum Species Calophyllaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24671 Lycopodium japonicum Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9567 Enicosanthum cupulare Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8653 Leuconostoc mesenteroides Species Leuconostocaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO2804 Calophyllum inophyllum Species Calophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10991 Maackia tashiroi Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8764 Laurencia decumbens Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2012 Turnera diffusa Species Passifloraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9136 Pseudocyclosorus subochthodes Species Thelypteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24671 Lycopodium japonicum Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26700 Tinospora crispa Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3123 Anthemis cretica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28741 Afrocarpus gracilior Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19826 Helicoverpa armigera Species 0ctuidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2495 Agave xylonacantha Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26103 Streptomyces bobili Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO6766 Antiphiona pinnatisecta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2 Others Unspecified IC50 = 10100.0 nM PMID[500624]
NPT35 Others n.a. Retention_time = 44.9 min PMID[500624]

☑ 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 NPC195685 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 NPC270675
1.0 High Similarity NPC477628
1.0 High Similarity NPC210961
1.0 High Similarity NPC472994
1.0 High Similarity NPC477629
0.987 High Similarity NPC80068
0.9806 High Similarity NPC19240
0.9806 High Similarity NPC129264
0.9806 High Similarity NPC85751
0.9806 High Similarity NPC205824
0.9806 High Similarity NPC139060
0.9805 High Similarity NPC472876
0.9744 High Similarity NPC473278
0.9744 High Similarity NPC260504
0.9744 High Similarity NPC89809
0.9613 High Similarity NPC470125
0.9613 High Similarity NPC101636
0.9605 High Similarity NPC210003
0.9605 High Similarity NPC143851
0.9605 High Similarity NPC83283
0.9605 High Similarity NPC39360
0.9605 High Similarity NPC29763
0.956 High Similarity NPC280642
0.956 High Similarity NPC96605
0.956 High Similarity NPC164704
0.956 High Similarity NPC218161
0.956 High Similarity NPC76047
0.956 High Similarity NPC188815
0.956 High Similarity NPC470712
0.9551 High Similarity NPC298171
0.9545 High Similarity NPC156457
0.9545 High Similarity NPC44931
0.9545 High Similarity NPC313163
0.9545 High Similarity NPC65003
0.9545 High Similarity NPC129827
0.9545 High Similarity NPC473512
0.9545 High Similarity NPC258035
0.9545 High Similarity NPC197896
0.9545 High Similarity NPC161749
0.9545 High Similarity NPC43638
0.9542 High Similarity NPC95090
0.9542 High Similarity NPC27408
0.9539 High Similarity NPC88484
0.9539 High Similarity NPC259767
0.95 High Similarity NPC11847
0.95 High Similarity NPC217822
0.95 High Similarity NPC470716
0.95 High Similarity NPC470714
0.95 High Similarity NPC221288
0.95 High Similarity NPC101399
0.95 High Similarity NPC474522
0.95 High Similarity NPC470715
0.9487 High Similarity NPC303913
0.9487 High Similarity NPC129217
0.9487 High Similarity NPC85707
0.9487 High Similarity NPC224530
0.9487 High Similarity NPC48093
0.9487 High Similarity NPC216496
0.9487 High Similarity NPC159579
0.9487 High Similarity NPC259957
0.9487 High Similarity NPC282169
0.9484 High Similarity NPC73511
0.9484 High Similarity NPC43761
0.9484 High Similarity NPC22062
0.9484 High Similarity NPC473634
0.9484 High Similarity NPC138811
0.9481 High Similarity NPC307938
0.9481 High Similarity NPC203500
0.9481 High Similarity NPC170475
0.9481 High Similarity NPC323593
0.9481 High Similarity NPC127406
0.9441 High Similarity NPC472993
0.9437 High Similarity NPC469344
0.9427 High Similarity NPC27942
0.9423 High Similarity NPC473623
0.9423 High Similarity NPC304741
0.9423 High Similarity NPC471079
0.9423 High Similarity NPC136761
0.9423 High Similarity NPC470405
0.9423 High Similarity NPC187379
0.9419 High Similarity NPC77672
0.9419 High Similarity NPC78263
0.9419 High Similarity NPC60966
0.9419 High Similarity NPC135391
0.9419 High Similarity NPC197304
0.9419 High Similarity NPC182634
0.9419 High Similarity NPC122809
0.9419 High Similarity NPC133671
0.9419 High Similarity NPC54802
0.9419 High Similarity NPC108831
0.9416 High Similarity NPC169248
0.9416 High Similarity NPC99233
0.9416 High Similarity NPC97052
0.9416 High Similarity NPC26195
0.9416 High Similarity NPC39351
0.9416 High Similarity NPC72649
0.9412 High Similarity NPC121001
0.9412 High Similarity NPC259182
0.9383 High Similarity NPC214621
0.9383 High Similarity NPC34267
0.9383 High Similarity NPC223426
0.9383 High Similarity NPC81042
0.9379 High Similarity NPC47140
0.9379 High Similarity NPC67134
0.9371 High Similarity NPC262222
0.9371 High Similarity NPC68592
0.9371 High Similarity NPC298666
0.9371 High Similarity NPC64425
0.9367 High Similarity NPC121703
0.9363 High Similarity NPC163242
0.9363 High Similarity NPC47923
0.9363 High Similarity NPC64305
0.9363 High Similarity NPC116458
0.9363 High Similarity NPC173582
0.9363 High Similarity NPC276377
0.9363 High Similarity NPC215710
0.9363 High Similarity NPC135846
0.9363 High Similarity NPC170052
0.9363 High Similarity NPC181465
0.9363 High Similarity NPC297987
0.9363 High Similarity NPC473438
0.9363 High Similarity NPC249281
0.9363 High Similarity NPC476215
0.9363 High Similarity NPC246943
0.9363 High Similarity NPC265885
0.9363 High Similarity NPC253788
0.9363 High Similarity NPC139320
0.9359 High Similarity NPC111929
0.9359 High Similarity NPC472459
0.9359 High Similarity NPC104677
0.9359 High Similarity NPC320283
0.9359 High Similarity NPC41121
0.9355 High Similarity NPC206378
0.9355 High Similarity NPC265480
0.9355 High Similarity NPC295613
0.9355 High Similarity NPC261866
0.9355 High Similarity NPC149368
0.9355 High Similarity NPC473657
0.9355 High Similarity NPC45165
0.9351 High Similarity NPC106625
0.9325 High Similarity NPC61904
0.9325 High Similarity NPC472992
0.9325 High Similarity NPC472991
0.9325 High Similarity NPC231787
0.9325 High Similarity NPC144097
0.9317 High Similarity NPC92815
0.9317 High Similarity NPC204937
0.9317 High Similarity NPC149011
0.9308 High Similarity NPC72016
0.9304 High Similarity NPC475382
0.9304 High Similarity NPC240306
0.9304 High Similarity NPC44947
0.9299 High Similarity NPC472320
0.9299 High Similarity NPC246469
0.9299 High Similarity NPC271479
0.9299 High Similarity NPC200708
0.9299 High Similarity NPC97285
0.9299 High Similarity NPC271270
0.9299 High Similarity NPC142860
0.9295 High Similarity NPC23817
0.9281 High Similarity NPC191154
0.9268 High Similarity NPC113836
0.9268 High Similarity NPC35167
0.9268 High Similarity NPC253521
0.9268 High Similarity NPC217520
0.9268 High Similarity NPC477895
0.9268 High Similarity NPC139571
0.9268 High Similarity NPC37668
0.9245 High Similarity NPC473644
0.9245 High Similarity NPC257566
0.9245 High Similarity NPC124155
0.9245 High Similarity NPC168822
0.9245 High Similarity NPC311850
0.9241 High Similarity NPC97812
0.9236 High Similarity NPC308265
0.9221 High Similarity NPC134819
0.9212 High Similarity NPC471030
0.9211 High Similarity NPC302989
0.9202 High Similarity NPC175230
0.9202 High Similarity NPC88560
0.9202 High Similarity NPC172033
0.9198 High Similarity NPC209550
0.9198 High Similarity NPC277532
0.9198 High Similarity NPC175429
0.9198 High Similarity NPC138990
0.9187 High Similarity NPC135358
0.9187 High Similarity NPC76831
0.9187 High Similarity NPC287889
0.9187 High Similarity NPC292929
0.9187 High Similarity NPC289667
0.9182 High Similarity NPC150164
0.9182 High Similarity NPC77660
0.9182 High Similarity NPC190450
0.9182 High Similarity NPC131745
0.9182 High Similarity NPC189142
0.9177 High Similarity NPC153342
0.9172 High Similarity NPC6985
0.9172 High Similarity NPC288084
0.9156 High Similarity NPC213723
0.9152 High Similarity NPC476622

  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 NPC195685 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
0.9545 High Similarity NPD4381 Clinical (unspecified phase)
0.9018 High Similarity NPD7804 Clinical (unspecified phase)
0.9018 High Similarity NPD7054 Approved
0.8963 High Similarity NPD7472 Approved
0.8916 High Similarity NPD4338 Clinical (unspecified phase)
0.891 High Similarity NPD4380 Phase 2
0.8909 High Similarity NPD6797 Phase 2
0.8855 High Similarity NPD7251 Discontinued
0.8848 High Similarity NPD7074 Phase 3
0.8841 High Similarity NPD3818 Discontinued
0.8802 High Similarity NPD7808 Phase 3
0.8734 High Similarity NPD7411 Suspended
0.8718 High Similarity NPD5403 Approved
0.8696 High Similarity NPD7075 Discontinued
0.8679 High Similarity NPD6801 Discontinued
0.8634 High Similarity NPD4868 Clinical (unspecified phase)
0.8631 High Similarity NPD6559 Discontinued
0.8606 High Similarity NPD6168 Clinical (unspecified phase)
0.8606 High Similarity NPD6167 Clinical (unspecified phase)
0.8606 High Similarity NPD6166 Phase 2
0.859 High Similarity NPD5401 Approved
0.8562 High Similarity NPD1549 Phase 2
0.8526 High Similarity NPD6799 Approved
0.8509 High Similarity NPD7096 Clinical (unspecified phase)
0.8497 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8497 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8471 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8457 Intermediate Similarity NPD5402 Approved
0.8383 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8353 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8344 Intermediate Similarity NPD3817 Phase 2
0.8344 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD1934 Approved
0.8314 Intermediate Similarity NPD8312 Approved
0.8314 Intermediate Similarity NPD8313 Approved
0.8282 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8247 Intermediate Similarity NPD1510 Phase 2
0.8239 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.821 Intermediate Similarity NPD6599 Discontinued
0.8194 Intermediate Similarity NPD2796 Approved
0.8192 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8176 Intermediate Similarity NPD1511 Approved
0.8171 Intermediate Similarity NPD8455 Phase 2
0.8171 Intermediate Similarity NPD7819 Suspended
0.8171 Intermediate Similarity NPD2801 Approved
0.8133 Intermediate Similarity NPD3749 Approved
0.8101 Intermediate Similarity NPD3750 Approved
0.8101 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.8095 Intermediate Similarity NPD6959 Discontinued
0.8075 Intermediate Similarity NPD1512 Approved
0.8072 Intermediate Similarity NPD7768 Phase 2
0.8038 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.8023 Intermediate Similarity NPD5844 Phase 1
0.7987 Intermediate Similarity NPD1240 Approved
0.7975 Intermediate Similarity NPD1653 Approved
0.7965 Intermediate Similarity NPD3751 Discontinued
0.7964 Intermediate Similarity NPD3882 Suspended
0.7962 Intermediate Similarity NPD1551 Phase 2
0.7914 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7912 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7885 Intermediate Similarity NPD1607 Approved
0.7875 Intermediate Similarity NPD4628 Phase 3
0.7857 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7836 Intermediate Similarity NPD6232 Discontinued
0.7836 Intermediate Similarity NPD3787 Discontinued
0.7831 Intermediate Similarity NPD8151 Discontinued
0.7819 Intermediate Similarity NPD7584 Approved
0.7803 Intermediate Similarity NPD7473 Discontinued
0.7785 Intermediate Similarity NPD3748 Approved
0.7778 Intermediate Similarity NPD7199 Phase 2
0.7754 Intermediate Similarity NPD7435 Discontinued
0.775 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7738 Intermediate Similarity NPD1465 Phase 2
0.7719 Intermediate Similarity NPD5494 Approved
0.7711 Intermediate Similarity NPD7458 Discontinued
0.7707 Intermediate Similarity NPD1933 Approved
0.7688 Intermediate Similarity NPD6776 Approved
0.7688 Intermediate Similarity NPD6782 Approved
0.7688 Intermediate Similarity NPD6779 Approved
0.7688 Intermediate Similarity NPD6781 Approved
0.7688 Intermediate Similarity NPD6778 Approved
0.7688 Intermediate Similarity NPD6777 Approved
0.7688 Intermediate Similarity NPD6780 Approved
0.7684 Intermediate Similarity NPD7685 Pre-registration
0.768 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7657 Intermediate Similarity NPD7228 Approved
0.7656 Intermediate Similarity NPD7783 Phase 2
0.7656 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD1203 Approved
0.7613 Intermediate Similarity NPD6832 Phase 2
0.7592 Intermediate Similarity NPD7585 Approved
0.759 Intermediate Similarity NPD920 Approved
0.7586 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7576 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7576 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7562 Intermediate Similarity NPD7033 Discontinued
0.7561 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7539 Intermediate Similarity NPD7583 Approved
0.7528 Intermediate Similarity NPD5953 Discontinued
0.7526 Intermediate Similarity NPD7870 Phase 2
0.7526 Intermediate Similarity NPD7871 Phase 2
0.7516 Intermediate Similarity NPD6798 Discontinued
0.7516 Intermediate Similarity NPD2935 Discontinued
0.7516 Intermediate Similarity NPD2313 Discontinued
0.7515 Intermediate Similarity NPD6143 Clinical (unspecified phase)
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 NPD1091 Approved
0.7485 Intermediate Similarity NPD1243 Approved
0.7485 Intermediate Similarity NPD1652 Phase 2
0.7474 Intermediate Similarity NPD7696 Phase 3
0.7474 Intermediate Similarity NPD7697 Approved
0.7474 Intermediate Similarity NPD7698 Approved
0.7471 Intermediate Similarity NPD37 Approved
0.7469 Intermediate Similarity NPD7266 Discontinued
0.7468 Intermediate Similarity NPD6233 Phase 2
0.7457 Intermediate Similarity NPD6234 Discontinued
0.7443 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7442 Intermediate Similarity NPD4966 Approved
0.7442 Intermediate Similarity NPD4965 Approved
0.7442 Intermediate Similarity NPD4967 Phase 2
0.7421 Intermediate Similarity NPD6823 Phase 2
0.7419 Intermediate Similarity NPD6534 Approved
0.7419 Intermediate Similarity NPD6535 Approved
0.7418 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7409 Intermediate Similarity NPD7701 Phase 2
0.7396 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD3226 Approved
0.7394 Intermediate Similarity NPD6190 Approved
0.7389 Intermediate Similarity NPD4908 Phase 1
0.7386 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7375 Intermediate Similarity NPD5124 Phase 1
0.7375 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD2533 Approved
0.7365 Intermediate Similarity NPD2534 Approved
0.7365 Intermediate Similarity NPD2532 Approved
0.7356 Intermediate Similarity NPD919 Approved
0.7355 Intermediate Similarity NPD3225 Approved
0.7346 Intermediate Similarity NPD2799 Discontinued
0.7344 Intermediate Similarity NPD8319 Approved
0.7344 Intermediate Similarity NPD8320 Phase 1
0.7338 Intermediate Similarity NPD9717 Approved
0.7312 Intermediate Similarity NPD1613 Approved
0.7312 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7302 Intermediate Similarity NPD7700 Phase 2
0.7302 Intermediate Similarity NPD7699 Phase 2
0.7296 Intermediate Similarity NPD3268 Approved
0.7296 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7296 Intermediate Similarity NPD7801 Approved
0.7293 Intermediate Similarity NPD7240 Approved
0.7284 Intermediate Similarity NPD7097 Phase 1
0.7283 Intermediate Similarity NPD8150 Discontinued
0.7273 Intermediate Similarity NPD2800 Approved
0.7273 Intermediate Similarity NPD422 Phase 1
0.7267 Intermediate Similarity NPD230 Phase 1
0.7261 Intermediate Similarity NPD2798 Approved
0.7256 Intermediate Similarity NPD2344 Approved
0.7253 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7237 Intermediate Similarity NPD1548 Phase 1
0.7234 Intermediate Similarity NPD4360 Phase 2
0.7234 Intermediate Similarity NPD4363 Phase 3
0.7228 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD6651 Approved
0.7209 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD943 Approved
0.7204 Intermediate Similarity NPD4287 Approved
0.7202 Intermediate Similarity NPD7390 Discontinued
0.7197 Intermediate Similarity NPD2797 Approved
0.7191 Intermediate Similarity NPD3926 Phase 2
0.7189 Intermediate Similarity NPD8434 Phase 2
0.7184 Intermediate Similarity NPD4288 Approved
0.7181 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7181 Intermediate Similarity NPD6212 Phase 3
0.7181 Intermediate Similarity NPD6213 Phase 3
0.716 Intermediate Similarity NPD447 Suspended
0.716 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD2346 Discontinued
0.7143 Intermediate Similarity NPD7440 Discontinued
0.7134 Intermediate Similarity NPD4308 Phase 3
0.7126 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7124 Intermediate Similarity NPD9545 Approved
0.7083 Intermediate Similarity NPD2309 Approved
0.7081 Intermediate Similarity NPD3764 Approved
0.7079 Intermediate Similarity NPD1247 Approved
0.7069 Intermediate Similarity NPD6844 Discontinued
0.7063 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD6355 Discontinued
0.7051 Intermediate Similarity NPD1610 Phase 2
0.7044 Intermediate Similarity NPD1019 Discontinued
0.7024 Intermediate Similarity NPD7003 Approved
0.7011 Intermediate Similarity NPD5889 Approved
0.7011 Intermediate Similarity NPD5890 Approved
0.7 Intermediate Similarity NPD7213 Phase 3
0.7 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD7212 Phase 2
0.6993 Remote Similarity NPD9493 Approved
0.6988 Remote Similarity NPD5406 Approved
0.6988 Remote Similarity NPD5404 Approved
0.6988 Remote Similarity NPD5405 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