Structure

Physi-Chem Properties

Molecular Weight:  446.12
Volume:  421.653
LogP:  2.071
LogD:  1.501
LogS:  -4.067
# Rotatable Bonds:  5
TPSA:  159.05
# H-Bond Aceptor:  10
# H-Bond Donor:  5
# Rings:  4
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.37
Synthetic Accessibility Score:  3.731
Fsp3:  0.318
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.942
MDCK Permeability:  1.612555752217304e-05
Pgp-inhibitor:  0.016
Pgp-substrate:  0.958
Human Intestinal Absorption (HIA):  0.483
20% Bioavailability (F20%):  0.007
30% Bioavailability (F30%):  0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.054
Plasma Protein Binding (PPB):  84.88331604003906%
Volume Distribution (VD):  0.941
Pgp-substrate:  10.044079780578613%

ADMET: Metabolism

CYP1A2-inhibitor:  0.523
CYP1A2-substrate:  0.116
CYP2C19-inhibitor:  0.086
CYP2C19-substrate:  0.086
CYP2C9-inhibitor:  0.112
CYP2C9-substrate:  0.728
CYP2D6-inhibitor:  0.397
CYP2D6-substrate:  0.732
CYP3A4-inhibitor:  0.152
CYP3A4-substrate:  0.057

ADMET: Excretion

Clearance (CL):  2.36
Half-life (T1/2):  0.362

ADMET: Toxicity

hERG Blockers:  0.253
Human Hepatotoxicity (H-HT):  0.069
Drug-inuced Liver Injury (DILI):  0.883
AMES Toxicity:  0.764
Rat Oral Acute Toxicity:  0.025
Maximum Recommended Daily Dose:  0.029
Skin Sensitization:  0.716
Carcinogencity:  0.336
Eye Corrosion:  0.003
Eye Irritation:  0.073
Respiratory Toxicity:  0.068

Download Data

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

  Natural Product: NPC27408

Natural Product ID:  NPC27408
Common Name*:   Acacetin-7-O-Beta-D-Galactopyranoside
IUPAC Name:   5-hydroxy-2-(4-methoxyphenyl)-7-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Synonyms:  
Standard InCHIKey:  NLZCOTZRUWYPTP-WHCFWRGISA-N
Standard InCHI:  InChI=1S/C22H22O10/c1-29-11-4-2-10(3-5-11)15-8-14(25)18-13(24)6-12(7-16(18)31-15)30-22-21(28)20(27)19(26)17(9-23)32-22/h2-8,17,19-24,26-28H,9H2,1H3/t17-,19+,20+,21-,22-/m1/s1
SMILES:  OC[C@H]1O[C@@H](Oc2cc(O)c3c(c2)oc(cc3=O)c2ccc(cc2)OC)[C@@H]([C@H]([C@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL487994
PubChem CID:   5480899
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
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.1016/j.foodchem.2009.03.042]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.3136/fstr.15.499]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.5897/AJB10.140]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.5897/AJB2010.000-3252]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.5897/JMPR.9000078]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. flower n.a. PMID[12130858]
NPO1960 Lygodium japonicum Species Lygodiaceae Eukaryota n.a. n.a. n.a. PMID[18619266]
NPO5227 Lawsonia inermis Species Lythraceae Eukaryota leaves n.a. n.a. PMID[20634065]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers Tongxiang, China n.a. PMID[24621197]
NPO5227 Lawsonia inermis Species Lythraceae Eukaryota flower buds n.a. n.a. PMID[25987378]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[26099993]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota Flowers n.a. n.a. PMID[28156114]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. PMID[28248102]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[29400471]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota Aerial Parts n.a. n.a. PMID[30726671]
NPO21355 Elsholtzia ciliata Species Lamiaceae Eukaryota Aerial Parts n.a. n.a. PMID[32991171]
NPO30745 Chrysanthemum morifolium Species Asteraceae Eukaryota n.a. inflorescence n.a. PMID[8158164]
NPO30745 Chrysanthemum morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[8158164]
NPO1960 Lygodium japonicum Species Lygodiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14862 Tilia japonica Species Malvaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30745 Chrysanthemum morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5227 Lawsonia inermis Species Lythraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO918 Dahlia pinnata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21355 Elsholtzia ciliata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23814 Elsholtzia splendens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26697 Dracocephalum moldavicum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3392 Agastache rugosus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23814 Elsholtzia splendens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1960 Lygodium japonicum Species Lygodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3392 Agastache rugosus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO918 Dahlia pinnata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14862 Tilia japonica Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23795 Herba seu radix cirsii japonici n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5227 Lawsonia inermis Species Lythraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21355 Elsholtzia ciliata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25890 Herba cirsii japonici n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO26697 Dracocephalum moldavicum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19689 Radix cirsii japonici Species Lymnaeidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO30745 Chrysanthemum morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21355 Elsholtzia ciliata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26697 Dracocephalum moldavicum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1960 Lygodium japonicum Species Lygodiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21355 Elsholtzia ciliata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO23814 Elsholtzia splendens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14862 Tilia japonica Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26697 Dracocephalum moldavicum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO918 Dahlia pinnata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5227 Lawsonia inermis Species Lythraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21355 Elsholtzia ciliata Species Lamiaceae 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
NPT759 Cell Line H9 Homo sapiens IC50 = 37000.0 nM PMID[456095]
NPT27 Others Unspecified TI = 5.0 n.a. PMID[456095]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 = 8000.0 nM PMID[456095]

☑ 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 NPC27408 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 NPC95090
0.9932 High Similarity NPC143851
0.9932 High Similarity NPC83283
0.9932 High Similarity NPC210003
0.9932 High Similarity NPC39360
0.9932 High Similarity NPC29763
0.9866 High Similarity NPC60966
0.9866 High Similarity NPC182634
0.9866 High Similarity NPC44931
0.9866 High Similarity NPC473512
0.9866 High Similarity NPC65003
0.9866 High Similarity NPC108831
0.9866 High Similarity NPC129827
0.98 High Similarity NPC41121
0.98 High Similarity NPC73511
0.98 High Similarity NPC111929
0.98 High Similarity NPC472459
0.98 High Similarity NPC138811
0.98 High Similarity NPC473634
0.98 High Similarity NPC22062
0.98 High Similarity NPC320283
0.9799 High Similarity NPC323593
0.9799 High Similarity NPC206378
0.9799 High Similarity NPC203500
0.9799 High Similarity NPC307938
0.9797 High Similarity NPC106625
0.9735 High Similarity NPC187379
0.9735 High Similarity NPC473623
0.9733 High Similarity NPC77672
0.9733 High Similarity NPC122809
0.9733 High Similarity NPC161749
0.9733 High Similarity NPC197896
0.9733 High Similarity NPC156457
0.9733 High Similarity NPC258035
0.9733 High Similarity NPC54802
0.9733 High Similarity NPC133671
0.9733 High Similarity NPC78263
0.9733 High Similarity NPC313163
0.9733 High Similarity NPC135391
0.9733 High Similarity NPC197304
0.9732 High Similarity NPC26195
0.9732 High Similarity NPC39351
0.9732 High Similarity NPC99233
0.9732 High Similarity NPC169248
0.9732 High Similarity NPC72649
0.9732 High Similarity NPC97052
0.973 High Similarity NPC259767
0.973 High Similarity NPC88484
0.973 High Similarity NPC259182
0.973 High Similarity NPC121001
0.9728 High Similarity NPC191154
0.9671 High Similarity NPC276377
0.9671 High Similarity NPC473438
0.9671 High Similarity NPC476215
0.9671 High Similarity NPC249281
0.9671 High Similarity NPC265885
0.9671 High Similarity NPC259957
0.9671 High Similarity NPC163242
0.9671 High Similarity NPC129217
0.9671 High Similarity NPC101636
0.9671 High Similarity NPC216496
0.9671 High Similarity NPC224530
0.9671 High Similarity NPC116458
0.9671 High Similarity NPC48093
0.9671 High Similarity NPC246943
0.9671 High Similarity NPC139320
0.9671 High Similarity NPC253788
0.9671 High Similarity NPC159579
0.9671 High Similarity NPC181465
0.9671 High Similarity NPC215710
0.9671 High Similarity NPC303913
0.9671 High Similarity NPC173582
0.9671 High Similarity NPC85707
0.9667 High Similarity NPC127406
0.9667 High Similarity NPC170475
0.9667 High Similarity NPC473657
0.9667 High Similarity NPC261866
0.9667 High Similarity NPC45165
0.9667 High Similarity NPC295613
0.9662 High Similarity NPC134819
0.9608 High Similarity NPC240306
0.9608 High Similarity NPC475382
0.9608 High Similarity NPC44947
0.9608 High Similarity NPC27942
0.9608 High Similarity NPC150164
0.9608 High Similarity NPC131745
0.9608 High Similarity NPC298171
0.9605 High Similarity NPC470405
0.9605 High Similarity NPC471079
0.9605 High Similarity NPC246469
0.9605 High Similarity NPC153342
0.9605 High Similarity NPC142860
0.9605 High Similarity NPC271270
0.9605 High Similarity NPC304741
0.9605 High Similarity NPC97285
0.9605 High Similarity NPC136761
0.9603 High Similarity NPC23817
0.9603 High Similarity NPC6985
0.9603 High Similarity NPC43638
0.9592 High Similarity NPC199335
0.9545 High Similarity NPC257566
0.9545 High Similarity NPC183672
0.9545 High Similarity NPC121703
0.9545 High Similarity NPC179198
0.9545 High Similarity NPC88023
0.9545 High Similarity NPC473644
0.9545 High Similarity NPC124155
0.9545 High Similarity NPC243930
0.9545 High Similarity NPC66087
0.9545 High Similarity NPC309025
0.9545 High Similarity NPC311850
0.9545 High Similarity NPC19709
0.9545 High Similarity NPC278419
0.9542 High Similarity NPC477628
0.9542 High Similarity NPC282169
0.9542 High Similarity NPC195685
0.9542 High Similarity NPC135846
0.9542 High Similarity NPC470125
0.9542 High Similarity NPC297987
0.9542 High Similarity NPC270675
0.9542 High Similarity NPC210961
0.9542 High Similarity NPC477629
0.9542 High Similarity NPC47923
0.9542 High Similarity NPC64305
0.9542 High Similarity NPC472994
0.9542 High Similarity NPC170052
0.9539 High Similarity NPC104677
0.9539 High Similarity NPC308265
0.9539 High Similarity NPC43761
0.9536 High Similarity NPC149368
0.9536 High Similarity NPC265480
0.9533 High Similarity NPC211158
0.9533 High Similarity NPC87304
0.9533 High Similarity NPC78021
0.9533 High Similarity NPC268950
0.9533 High Similarity NPC108706
0.9524 High Similarity NPC23084
0.9484 High Similarity NPC311830
0.9484 High Similarity NPC287889
0.9484 High Similarity NPC22832
0.9484 High Similarity NPC72016
0.9484 High Similarity NPC139060
0.9484 High Similarity NPC135358
0.9481 High Similarity NPC189142
0.9481 High Similarity NPC473043
0.9481 High Similarity NPC77660
0.9481 High Similarity NPC259834
0.9481 High Similarity NPC190450
0.9477 High Similarity NPC271479
0.9477 High Similarity NPC200708
0.9477 High Similarity NPC472320
0.9474 High Similarity NPC288084
0.947 High Similarity NPC470603
0.947 High Similarity NPC470605
0.947 High Similarity NPC470604
0.9463 High Similarity NPC213723
0.9463 High Similarity NPC214454
0.9463 High Similarity NPC477240
0.9463 High Similarity NPC106025
0.9423 High Similarity NPC11432
0.9423 High Similarity NPC221342
0.9423 High Similarity NPC210073
0.9423 High Similarity NPC477613
0.9423 High Similarity NPC186816
0.9423 High Similarity NPC189564
0.9423 High Similarity NPC476470
0.9423 High Similarity NPC32641
0.9423 High Similarity NPC256188
0.9423 High Similarity NPC142142
0.9423 High Similarity NPC12013
0.9423 High Similarity NPC262222
0.9423 High Similarity NPC298666
0.9423 High Similarity NPC64425
0.9423 High Similarity NPC115674
0.9423 High Similarity NPC68592
0.9423 High Similarity NPC203145
0.9419 High Similarity NPC80068
0.9419 High Similarity NPC284960
0.9419 High Similarity NPC168822
0.9419 High Similarity NPC270335
0.9419 High Similarity NPC191306
0.9419 High Similarity NPC222936
0.9416 High Similarity NPC182045
0.94 High Similarity NPC190217
0.9392 High Similarity NPC218685
0.9363 High Similarity NPC52550
0.9363 High Similarity NPC84362
0.9363 High Similarity NPC229729
0.9363 High Similarity NPC223424
0.9363 High Similarity NPC173637
0.9363 High Similarity NPC127546
0.9363 High Similarity NPC317489
0.9359 High Similarity NPC205824
0.9359 High Similarity NPC76831
0.9359 High Similarity NPC292929
0.9359 High Similarity NPC289667
0.9359 High Similarity NPC19240
0.9359 High Similarity NPC85751
0.9359 High Similarity NPC129264
0.9359 High Similarity NPC277205

  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 NPC27408 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
0.9733 High Similarity NPD4381 Clinical (unspecified phase)
0.9304 High Similarity NPD7804 Clinical (unspecified phase)
0.9304 High Similarity NPD7054 Approved
0.9245 High Similarity NPD7472 Approved
0.9187 High Similarity NPD6797 Phase 2
0.913 High Similarity NPD7251 Discontinued
0.9125 High Similarity NPD7074 Phase 3
0.9079 High Similarity NPD4380 Phase 2
0.9074 High Similarity NPD7808 Phase 3
0.9 High Similarity NPD3818 Discontinued
0.8957 High Similarity NPD4338 Clinical (unspecified phase)
0.8784 High Similarity NPD1550 Clinical (unspecified phase)
0.8784 High Similarity NPD1552 Clinical (unspecified phase)
0.8734 High Similarity NPD7075 Discontinued
0.8725 High Similarity NPD1549 Phase 2
0.8718 High Similarity NPD6801 Discontinued
0.8718 High Similarity NPD1934 Approved
0.8667 High Similarity NPD6559 Discontinued
0.8662 High Similarity NPD2393 Clinical (unspecified phase)
0.8642 High Similarity NPD6166 Phase 2
0.8642 High Similarity NPD6167 Clinical (unspecified phase)
0.8642 High Similarity NPD6168 Clinical (unspecified phase)
0.8636 High Similarity NPD5403 Approved
0.8627 High Similarity NPD4378 Clinical (unspecified phase)
0.8562 High Similarity NPD6799 Approved
0.8544 High Similarity NPD7096 Clinical (unspecified phase)
0.8544 High Similarity NPD2801 Approved
0.8535 High Similarity NPD7411 Suspended
0.8506 High Similarity NPD5401 Approved
0.8506 High Similarity NPD7410 Clinical (unspecified phase)
0.8491 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8491 Intermediate Similarity NPD3817 Phase 2
0.8467 Intermediate Similarity NPD2796 Approved
0.8442 Intermediate Similarity NPD1511 Approved
0.84 Intermediate Similarity NPD1510 Phase 2
0.8375 Intermediate Similarity NPD5402 Approved
0.8333 Intermediate Similarity NPD1512 Approved
0.8323 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8255 Intermediate Similarity NPD1240 Approved
0.8239 Intermediate Similarity NPD6599 Discontinued
0.821 Intermediate Similarity NPD3882 Suspended
0.8199 Intermediate Similarity NPD7819 Suspended
0.8146 Intermediate Similarity NPD1607 Approved
0.8129 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.8121 Intermediate Similarity NPD6959 Discontinued
0.8084 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8033 Intermediate Similarity NPD7584 Approved
0.8013 Intermediate Similarity NPD3750 Approved
0.8011 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7953 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7952 Intermediate Similarity NPD5494 Approved
0.7919 Intermediate Similarity NPD8312 Approved
0.7919 Intermediate Similarity NPD8313 Approved
0.7898 Intermediate Similarity NPD4628 Phase 3
0.7888 Intermediate Similarity NPD1653 Approved
0.7885 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7882 Intermediate Similarity NPD3751 Discontinued
0.7879 Intermediate Similarity NPD7768 Phase 2
0.7871 Intermediate Similarity NPD1551 Phase 2
0.7866 Intermediate Similarity NPD8455 Phase 2
0.7857 Intermediate Similarity NPD3787 Discontinued
0.7836 Intermediate Similarity NPD5844 Phase 1
0.7834 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7831 Intermediate Similarity NPD3749 Approved
0.7755 Intermediate Similarity NPD1091 Approved
0.7751 Intermediate Similarity NPD6232 Discontinued
0.7735 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD1933 Approved
0.7719 Intermediate Similarity NPD7473 Discontinued
0.7716 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7705 Intermediate Similarity NPD6782 Approved
0.7705 Intermediate Similarity NPD6778 Approved
0.7705 Intermediate Similarity NPD6777 Approved
0.7705 Intermediate Similarity NPD6776 Approved
0.7705 Intermediate Similarity NPD6781 Approved
0.7705 Intermediate Similarity NPD6779 Approved
0.7705 Intermediate Similarity NPD6780 Approved
0.7701 Intermediate Similarity NPD7685 Pre-registration
0.7692 Intermediate Similarity NPD3748 Approved
0.7692 Intermediate Similarity NPD7199 Phase 2
0.7692 Intermediate Similarity NPD7033 Discontinued
0.7651 Intermediate Similarity NPD1465 Phase 2
0.7632 Intermediate Similarity NPD6832 Phase 2
0.761 Intermediate Similarity NPD2800 Approved
0.761 Intermediate Similarity NPD1652 Phase 2
0.7607 Intermediate Similarity NPD920 Approved
0.7606 Intermediate Similarity NPD7585 Approved
0.7581 Intermediate Similarity NPD7435 Discontinued
0.7572 Intermediate Similarity NPD7228 Approved
0.7566 Intermediate Similarity NPD8151 Discontinued
0.7564 Intermediate Similarity NPD6651 Approved
0.7557 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7553 Intermediate Similarity NPD7583 Approved
0.755 Intermediate Similarity NPD1203 Approved
0.7548 Intermediate Similarity NPD1613 Approved
0.7548 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7543 Intermediate Similarity NPD5953 Discontinued
0.7532 Intermediate Similarity NPD2935 Discontinued
0.7529 Intermediate Similarity NPD7286 Phase 2
0.7527 Intermediate Similarity NPD4360 Phase 2
0.7527 Intermediate Similarity NPD4363 Phase 3
0.7517 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD4908 Phase 1
0.7515 Intermediate Similarity NPD7458 Discontinued
0.75 Intermediate Similarity NPD2798 Approved
0.75 Intermediate Similarity NPD5124 Phase 1
0.75 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1243 Approved
0.7487 Intermediate Similarity NPD7697 Approved
0.7487 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7487 Intermediate Similarity NPD7696 Phase 3
0.7487 Intermediate Similarity NPD7783 Phase 2
0.7487 Intermediate Similarity NPD7698 Approved
0.7485 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD37 Approved
0.7485 Intermediate Similarity NPD2532 Approved
0.7485 Intermediate Similarity NPD2533 Approved
0.7485 Intermediate Similarity NPD2534 Approved
0.7484 Intermediate Similarity NPD7266 Discontinued
0.7483 Intermediate Similarity NPD1548 Phase 1
0.7471 Intermediate Similarity NPD6234 Discontinued
0.7469 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7457 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7456 Intermediate Similarity NPD4967 Phase 2
0.7456 Intermediate Similarity NPD4966 Approved
0.7456 Intermediate Similarity NPD4965 Approved
0.7447 Intermediate Similarity NPD7870 Phase 2
0.7447 Intermediate Similarity NPD7871 Phase 2
0.7433 Intermediate Similarity NPD6823 Phase 2
0.7432 Intermediate Similarity NPD6535 Approved
0.7432 Intermediate Similarity NPD6534 Approved
0.7423 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7421 Intermediate Similarity NPD7701 Phase 2
0.7419 Intermediate Similarity NPD3268 Approved
0.7419 Intermediate Similarity NPD2313 Discontinued
0.7419 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD6798 Discontinued
0.7403 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.74 Intermediate Similarity NPD422 Phase 1
0.7378 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7375 Intermediate Similarity NPD2344 Approved
0.7372 Intermediate Similarity NPD6233 Phase 2
0.7368 Intermediate Similarity NPD3225 Approved
0.7368 Intermediate Similarity NPD919 Approved
0.7358 Intermediate Similarity NPD2799 Discontinued
0.7351 Intermediate Similarity NPD9717 Approved
0.7344 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7344 Intermediate Similarity NPD7874 Approved
0.7333 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7325 Intermediate Similarity NPD943 Approved
0.7321 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD2797 Approved
0.7312 Intermediate Similarity NPD6100 Approved
0.7312 Intermediate Similarity NPD6099 Approved
0.7312 Intermediate Similarity NPD7699 Phase 2
0.7312 Intermediate Similarity NPD7700 Phase 2
0.7306 Intermediate Similarity NPD7801 Approved
0.7305 Intermediate Similarity NPD3226 Approved
0.7299 Intermediate Similarity NPD3926 Phase 2
0.729 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7285 Intermediate Similarity NPD1610 Phase 2
0.7283 Intermediate Similarity NPD1247 Approved
0.7278 Intermediate Similarity NPD6844 Discontinued
0.7278 Intermediate Similarity NPD230 Phase 1
0.7244 Intermediate Similarity NPD3027 Phase 3
0.7226 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD7390 Discontinued
0.7207 Intermediate Similarity NPD7240 Approved
0.7198 Intermediate Similarity NPD8434 Phase 2
0.7195 Intermediate Similarity NPD6190 Approved
0.7195 Intermediate Similarity NPD2309 Approved
0.7189 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7189 Intermediate Similarity NPD6213 Phase 3
0.7189 Intermediate Similarity NPD6212 Phase 3
0.7188 Intermediate Similarity NPD7097 Phase 1
0.7178 Intermediate Similarity NPD2654 Approved
0.7173 Intermediate Similarity NPD8320 Phase 1
0.7173 Intermediate Similarity NPD8319 Approved
0.717 Intermediate Similarity NPD6355 Discontinued
0.717 Intermediate Similarity NPD447 Suspended
0.717 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7169 Intermediate Similarity NPD4661 Approved
0.7169 Intermediate Similarity NPD4662 Approved
0.716 Intermediate Similarity NPD2346 Discontinued
0.7143 Intermediate Similarity NPD4308 Phase 3
0.7134 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD9545 Approved
0.7117 Intermediate Similarity NPD2424 Discontinued
0.7112 Intermediate Similarity NPD4361 Phase 2
0.7112 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7104 Intermediate Similarity NPD8150 Discontinued
0.7101 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD3266 Approved
0.7097 Intermediate Similarity NPD3267 Approved
0.7093 Intermediate Similarity NPD4288 Approved
0.7053 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7051 Intermediate Similarity NPD1019 Discontinued
0.7045 Intermediate Similarity NPD5710 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