Structure

Physi-Chem Properties

Molecular Weight:  594.14
Volume:  564.653
LogP:  2.954
LogD:  2.149
LogS:  -4.52
# Rotatable Bonds:  8
TPSA:  216.58
# H-Bond Aceptor:  13
# H-Bond Donor:  7
# Rings:  5
# Heavy Atoms:  13

MedChem Properties

QED Drug-Likeness Score:  0.12
Synthetic Accessibility Score:  4.151
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:  -6.205
MDCK Permeability:  1.2781440091202967e-05
Pgp-inhibitor:  0.01
Pgp-substrate:  0.469
Human Intestinal Absorption (HIA):  0.114
20% Bioavailability (F20%):  0.188
30% Bioavailability (F30%):  0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.014
Plasma Protein Binding (PPB):  99.96546936035156%
Volume Distribution (VD):  0.576
Pgp-substrate:  2.324453353881836%

ADMET: Metabolism

CYP1A2-inhibitor:  0.61
CYP1A2-substrate:  0.027
CYP2C19-inhibitor:  0.399
CYP2C19-substrate:  0.045
CYP2C9-inhibitor:  0.741
CYP2C9-substrate:  0.917
CYP2D6-inhibitor:  0.769
CYP2D6-substrate:  0.251
CYP3A4-inhibitor:  0.587
CYP3A4-substrate:  0.045

ADMET: Excretion

Clearance (CL):  4.67
Half-life (T1/2):  0.877

ADMET: Toxicity

hERG Blockers:  0.158
Human Hepatotoxicity (H-HT):  0.145
Drug-inuced Liver Injury (DILI):  0.976
AMES Toxicity:  0.766
Rat Oral Acute Toxicity:  0.137
Maximum Recommended Daily Dose:  0.03
Skin Sensitization:  0.944
Carcinogencity:  0.172
Eye Corrosion:  0.003
Eye Irritation:  0.535
Respiratory Toxicity:  0.013

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

  Natural Product: NPC85751

Natural Product ID:  NPC85751
Common Name*:   Kaempferol-3-Beta-D-(6-O-Cis-P-Coumaroyl)Glucopyranoside
IUPAC Name:   [(2R,3S,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (Z)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:  
Standard InCHIKey:  DVGGLGXQSFURLP-PYFXTMFGSA-N
Standard InCHI:  InChI=1S/C30H26O13/c31-16-6-1-14(2-7-16)3-10-22(35)40-13-21-24(36)26(38)27(39)30(42-21)43-29-25(37)23-19(34)11-18(33)12-20(23)41-28(29)15-4-8-17(32)9-5-15/h1-12,21,24,26-27,30-34,36,38-39H,13H2/b10-3-/t21-,24-,26+,27-,30+/m1/s1
SMILES:  O=C(OC[C@H]1O[C@@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O)/C=Cc1ccc(cc1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL499705
PubChem CID:   10175330
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001111] Flavonoid glycosides
          • [CHEMONTID:0001583] Flavonoid O-glycosides
            • [CHEMONTID:0003678] Flavonoid 3-O-p-coumaroyl 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
NPO10339 Fragaria x ananassa Species Rosaceae Eukaryota Fruit n.a. n.a. DOI[10.1016/S0963-9969(99)00095-2]
NPO19774 Rubus idaeus Species n.a. n.a. Fruit n.a. n.a. DOI[10.1016/S0963-9969(99)00095-2]
NPO10339 Fragaria x ananassa Species Rosaceae Eukaryota Leaves (mother plant) Suwon, Korea 2011-Sep DOI[10.7235/HORT.2013.12200]
NPO10339 Fragaria x ananassa Species Rosaceae Eukaryota Roots (runner plant) Suwon, Korea 2011-Sep DOI[10.7235/HORT.2013.12200]
NPO10339 Fragaria x ananassa Species Rosaceae Eukaryota Fruits Suwon, Korea 2012-Nov DOI[10.7235/HORT.2013.12200]
NPO10339 Fragaria x ananassa Species Rosaceae Eukaryota Leaves Suwon, Korea DOI[10.7235/HORT.2013.12200]
NPO10339 Fragaria x ananassa Species Rosaceae Eukaryota Runners Suwon, Korea 2011-Sep DOI[10.7235/HORT.2013.12200]
NPO10339 Fragaria x ananassa Species Rosaceae Eukaryota Leaves (runner plant) Suwon, Korea 2011-Sep DOI[10.7235/HORT.2013.12200]
NPO10339 Fragaria x ananassa Species Rosaceae Eukaryota Roots (mother plant) Suwon, Korea 2011-Sep DOI[10.7235/HORT.2013.12200]
NPO10339 Fragaria x ananassa Species Rosaceae Eukaryota n.a. n.a. n.a. PMID[1453178]
NPO10339 Fragaria x ananassa Species Rosaceae Eukaryota Fruits n.a. n.a. PMID[15568772]
NPO19774 Rubus idaeus Species n.a. n.a. n.a. n.a. n.a. PMID[21381697]
NPO19774 Rubus idaeus Species n.a. n.a. Fruits n.a. Database[FooDB]
NPO10339 Fragaria x ananassa Species Rosaceae Eukaryota n.a. n.a. Database[FooDB]
NPO19774 Rubus idaeus Species n.a. n.a. Fruit n.a. n.a. Database[FooDB]
NPO19774 Rubus idaeus Species n.a. n.a. Leaf n.a. n.a. Database[FooDB]
NPO19774 Rubus idaeus Species n.a. n.a. Seed n.a. n.a. Database[FooDB]
NPO19774 Rubus idaeus Species n.a. n.a. n.a. n.a. Database[FooDB]
NPO10339 Fragaria x ananassa Species Rosaceae Eukaryota Fruits n.a. Database[FooDB]
NPO23516 Potentilla discolor Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6625 Euphoria longan Species Scarabaeidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19774 Rubus idaeus Species n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO10339 Fragaria x ananassa Species Rosaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO19774 Rubus idaeus Species n.a. n.a. Fruits n.a. Database[Phenol-Explorer]
NPO19774 Rubus idaeus Species n.a. n.a. n.a. n.a. Database[Phenol-Explorer]
NPO23516 Potentilla discolor Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19774 Rubus idaeus Species n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO6625 Euphoria longan Species Scarabaeidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10339 Fragaria x ananassa Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10339 Fragaria x ananassa Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19774 Rubus idaeus Species n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO6625 Euphoria longan Species Scarabaeidae 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
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens IC50 = 700.0 nM PMID[558792]

☑ 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 NPC85751 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 NPC205824
1.0 High Similarity NPC19240
1.0 High Similarity NPC129264
0.9935 High Similarity NPC80068
0.9872 High Similarity NPC139060
0.9806 High Similarity NPC477628
0.9806 High Similarity NPC470125
0.9806 High Similarity NPC210961
0.9806 High Similarity NPC477629
0.9806 High Similarity NPC472994
0.9806 High Similarity NPC270675
0.9806 High Similarity NPC195685
0.9748 High Similarity NPC96605
0.9748 High Similarity NPC470712
0.9748 High Similarity NPC218161
0.9748 High Similarity NPC164704
0.9748 High Similarity NPC280642
0.9688 High Similarity NPC101399
0.9688 High Similarity NPC221288
0.9688 High Similarity NPC217822
0.9688 High Similarity NPC470714
0.9688 High Similarity NPC470715
0.9688 High Similarity NPC474522
0.9688 High Similarity NPC11847
0.9688 High Similarity NPC470716
0.9679 High Similarity NPC282169
0.9679 High Similarity NPC129217
0.9679 High Similarity NPC224530
0.9679 High Similarity NPC48093
0.9679 High Similarity NPC259957
0.9679 High Similarity NPC216496
0.9679 High Similarity NPC159579
0.9679 High Similarity NPC85707
0.9625 High Similarity NPC188815
0.9625 High Similarity NPC469344
0.9618 High Similarity NPC472876
0.9618 High Similarity NPC27942
0.9615 High Similarity NPC470405
0.9615 High Similarity NPC471079
0.9615 High Similarity NPC304741
0.9613 High Similarity NPC133671
0.9613 High Similarity NPC77672
0.9613 High Similarity NPC54802
0.9613 High Similarity NPC135391
0.9613 High Similarity NPC78263
0.9613 High Similarity NPC197304
0.9568 High Similarity NPC214621
0.9568 High Similarity NPC34267
0.9568 High Similarity NPC223426
0.9568 High Similarity NPC81042
0.956 High Similarity NPC64425
0.956 High Similarity NPC260504
0.956 High Similarity NPC473278
0.956 High Similarity NPC89809
0.9557 High Similarity NPC121703
0.9554 High Similarity NPC276377
0.9554 High Similarity NPC163242
0.9554 High Similarity NPC215710
0.9554 High Similarity NPC181465
0.9554 High Similarity NPC473438
0.9554 High Similarity NPC170052
0.9554 High Similarity NPC265885
0.9554 High Similarity NPC64305
0.9554 High Similarity NPC249281
0.9554 High Similarity NPC476215
0.9554 High Similarity NPC116458
0.9554 High Similarity NPC246943
0.9554 High Similarity NPC253788
0.9554 High Similarity NPC139320
0.9554 High Similarity NPC173582
0.9554 High Similarity NPC135846
0.9554 High Similarity NPC297987
0.9551 High Similarity NPC320283
0.9551 High Similarity NPC111929
0.9551 High Similarity NPC104677
0.9551 High Similarity NPC41121
0.9551 High Similarity NPC472459
0.9548 High Similarity NPC307938
0.9548 High Similarity NPC323593
0.9548 High Similarity NPC203500
0.9509 High Similarity NPC144097
0.9509 High Similarity NPC61904
0.9509 High Similarity NPC231787
0.9503 High Similarity NPC92815
0.9497 High Similarity NPC72016
0.9494 High Similarity NPC240306
0.949 High Similarity NPC187379
0.949 High Similarity NPC136761
0.9487 High Similarity NPC108831
0.9487 High Similarity NPC182634
0.9451 High Similarity NPC139571
0.9451 High Similarity NPC217520
0.9451 High Similarity NPC113836
0.9451 High Similarity NPC35167
0.9451 High Similarity NPC477895
0.9451 High Similarity NPC253521
0.9451 High Similarity NPC37668
0.943 High Similarity NPC101636
0.9419 High Similarity NPC83283
0.9419 High Similarity NPC143851
0.9419 High Similarity NPC39360
0.9419 High Similarity NPC210003
0.9419 High Similarity NPC29763
0.9383 High Similarity NPC175429
0.9383 High Similarity NPC277532
0.9383 High Similarity NPC209550
0.9383 High Similarity NPC76047
0.9383 High Similarity NPC138990
0.9375 High Similarity NPC76831
0.9375 High Similarity NPC292929
0.9375 High Similarity NPC289667
0.9371 High Similarity NPC150164
0.9371 High Similarity NPC298171
0.9367 High Similarity NPC153342
0.9363 High Similarity NPC129827
0.9363 High Similarity NPC65003
0.9363 High Similarity NPC44931
0.9363 High Similarity NPC313163
0.9363 High Similarity NPC156457
0.9363 High Similarity NPC258035
0.9363 High Similarity NPC473512
0.9363 High Similarity NPC43638
0.9363 High Similarity NPC161749
0.9363 High Similarity NPC288084
0.9363 High Similarity NPC197896
0.9359 High Similarity NPC95090
0.9359 High Similarity NPC27408
0.9355 High Similarity NPC259767
0.9355 High Similarity NPC88484
0.9333 High Similarity NPC258044
0.9333 High Similarity NPC293626
0.9333 High Similarity NPC267680
0.9333 High Similarity NPC217387
0.9333 High Similarity NPC196127
0.9317 High Similarity NPC203145
0.9317 High Similarity NPC142142
0.9317 High Similarity NPC477613
0.9317 High Similarity NPC186816
0.9317 High Similarity NPC11432
0.9317 High Similarity NPC476470
0.9317 High Similarity NPC221342
0.9317 High Similarity NPC256188
0.9317 High Similarity NPC189564
0.9317 High Similarity NPC12013
0.9317 High Similarity NPC32641
0.9313 High Similarity NPC66087
0.9313 High Similarity NPC179198
0.9313 High Similarity NPC278419
0.9308 High Similarity NPC303913
0.9304 High Similarity NPC138811
0.9304 High Similarity NPC22062
0.9304 High Similarity NPC73511
0.9304 High Similarity NPC43761
0.9304 High Similarity NPC473634
0.9299 High Similarity NPC127406
0.9299 High Similarity NPC170475
0.9281 High Similarity NPC241781
0.9281 High Similarity NPC97119
0.9281 High Similarity NPC470718
0.9281 High Similarity NPC135831
0.9281 High Similarity NPC156785
0.9281 High Similarity NPC162394
0.9281 High Similarity NPC36138
0.9281 High Similarity NPC297503
0.9273 High Similarity NPC296018
0.9273 High Similarity NPC154741
0.9268 High Similarity NPC472993
0.9264 High Similarity NPC20505
0.9264 High Similarity NPC116864
0.9264 High Similarity NPC244776
0.9264 High Similarity NPC235260
0.9264 High Similarity NPC155763
0.9255 High Similarity NPC287889
0.9255 High Similarity NPC135358
0.925 High Similarity NPC131745
0.9245 High Similarity NPC473623
0.9241 High Similarity NPC60966
0.9241 High Similarity NPC6985
0.9241 High Similarity NPC122809
0.9236 High Similarity NPC97052
0.9236 High Similarity NPC39351
0.9236 High Similarity NPC72649
0.9236 High Similarity NPC26195
0.9236 High Similarity NPC99233
0.9236 High Similarity NPC169248
0.9231 High Similarity NPC259182
0.9231 High Similarity NPC121001
0.9226 High Similarity NPC249560
0.9226 High Similarity NPC470713
0.9226 High Similarity NPC470717
0.9226 High Similarity NPC275977
0.9226 High Similarity NPC460984
0.9226 High Similarity NPC470416
0.9226 High Similarity NPC223860
0.9226 High Similarity NPC25946
0.9226 High Similarity NPC470720
0.9226 High Similarity NPC21359
0.9217 High Similarity NPC476773
0.9212 High Similarity NPC253685
0.9207 High Similarity NPC190003

  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 NPC85751 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
0.9363 High Similarity NPD4381 Clinical (unspecified phase)
0.9202 High Similarity NPD7804 Clinical (unspecified phase)
0.9096 High Similarity NPD4338 Clinical (unspecified phase)
0.9091 High Similarity NPD6797 Phase 2
0.9036 High Similarity NPD7251 Discontinued
0.8982 High Similarity NPD7808 Phase 3
0.891 High Similarity NPD5403 Approved
0.8882 High Similarity NPD7075 Discontinued
0.8868 High Similarity NPD6801 Discontinued
0.8855 High Similarity NPD7054 Approved
0.8802 High Similarity NPD7472 Approved
0.8782 High Similarity NPD5401 Approved
0.8742 High Similarity NPD4380 Phase 2
0.8718 High Similarity NPD6799 Approved
0.8696 High Similarity NPD7096 Clinical (unspecified phase)
0.869 High Similarity NPD7074 Phase 3
0.8683 High Similarity NPD3818 Discontinued
0.8675 High Similarity NPD6167 Clinical (unspecified phase)
0.8675 High Similarity NPD6168 Clinical (unspecified phase)
0.8675 High Similarity NPD6166 Phase 2
0.8642 High Similarity NPD5402 Approved
0.8571 High Similarity NPD7411 Suspended
0.8528 High Similarity NPD3817 Phase 2
0.848 Intermediate Similarity NPD6559 Discontinued
0.8476 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8421 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8397 Intermediate Similarity NPD1549 Phase 2
0.8395 Intermediate Similarity NPD6599 Discontinued
0.8362 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8313 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8313 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8235 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8193 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8182 Intermediate Similarity NPD1934 Approved
0.8171 Intermediate Similarity NPD8312 Approved
0.8171 Intermediate Similarity NPD8313 Approved
0.8148 Intermediate Similarity NPD1512 Approved
0.8144 Intermediate Similarity NPD3882 Suspended
0.814 Intermediate Similarity NPD3751 Discontinued
0.8133 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8089 Intermediate Similarity NPD1510 Phase 2
0.8077 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.8038 Intermediate Similarity NPD2796 Approved
0.8025 Intermediate Similarity NPD1511 Approved
0.8024 Intermediate Similarity NPD2801 Approved
0.8024 Intermediate Similarity NPD7819 Suspended
0.8024 Intermediate Similarity NPD8455 Phase 2
0.8012 Intermediate Similarity NPD3787 Discontinued
0.7988 Intermediate Similarity NPD3749 Approved
0.7953 Intermediate Similarity NPD6959 Discontinued
0.795 Intermediate Similarity NPD3750 Approved
0.795 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7929 Intermediate Similarity NPD7768 Phase 2
0.7914 Intermediate Similarity NPD7435 Discontinued
0.7888 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7886 Intermediate Similarity NPD5844 Phase 1
0.7834 Intermediate Similarity NPD1240 Approved
0.7831 Intermediate Similarity NPD1653 Approved
0.7812 Intermediate Similarity NPD1551 Phase 2
0.7771 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7759 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7754 Intermediate Similarity NPD6776 Approved
0.7754 Intermediate Similarity NPD6779 Approved
0.7754 Intermediate Similarity NPD6778 Approved
0.7754 Intermediate Similarity NPD6781 Approved
0.7754 Intermediate Similarity NPD6780 Approved
0.7754 Intermediate Similarity NPD6782 Approved
0.7754 Intermediate Similarity NPD6777 Approved
0.7736 Intermediate Similarity NPD1607 Approved
0.773 Intermediate Similarity NPD4628 Phase 3
0.7708 Intermediate Similarity NPD8151 Discontinued
0.7707 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7707 Intermediate Similarity NPD6798 Discontinued
0.7701 Intermediate Similarity NPD6232 Discontinued
0.7696 Intermediate Similarity NPD7584 Approved
0.767 Intermediate Similarity NPD7473 Discontinued
0.7668 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7668 Intermediate Similarity NPD7874 Approved
0.7658 Intermediate Similarity NPD6233 Phase 2
0.7644 Intermediate Similarity NPD7199 Phase 2
0.764 Intermediate Similarity NPD3748 Approved
0.7614 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7607 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7602 Intermediate Similarity NPD1465 Phase 2
0.7592 Intermediate Similarity NPD7871 Phase 2
0.7592 Intermediate Similarity NPD7870 Phase 2
0.7586 Intermediate Similarity NPD5494 Approved
0.7576 Intermediate Similarity NPD6190 Approved
0.7574 Intermediate Similarity NPD7458 Discontinued
0.7562 Intermediate Similarity NPD1933 Approved
0.7556 Intermediate Similarity NPD7685 Pre-registration
0.7554 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7539 Intermediate Similarity NPD7696 Phase 3
0.7539 Intermediate Similarity NPD7697 Approved
0.7539 Intermediate Similarity NPD7698 Approved
0.7538 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7538 Intermediate Similarity NPD7783 Phase 2
0.7529 Intermediate Similarity NPD919 Approved
0.7528 Intermediate Similarity NPD7228 Approved
0.75 Intermediate Similarity NPD1203 Approved
0.75 Intermediate Similarity NPD8320 Phase 1
0.75 Intermediate Similarity NPD8319 Approved
0.7487 Intermediate Similarity NPD6534 Approved
0.7487 Intermediate Similarity NPD6535 Approved
0.7486 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7474 Intermediate Similarity NPD7701 Phase 2
0.7474 Intermediate Similarity NPD7585 Approved
0.7468 Intermediate Similarity NPD6832 Phase 2
0.7456 Intermediate Similarity NPD920 Approved
0.744 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7425 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7423 Intermediate Similarity NPD7033 Discontinued
0.7423 Intermediate Similarity NPD7583 Approved
0.7403 Intermediate Similarity NPD5953 Discontinued
0.7389 Intermediate Similarity NPD7286 Phase 2
0.7381 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7378 Intermediate Similarity NPD2935 Discontinued
0.7376 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7375 Intermediate Similarity NPD2313 Discontinued
0.7368 Intermediate Similarity NPD7699 Phase 2
0.7368 Intermediate Similarity NPD7700 Phase 2
0.736 Intermediate Similarity NPD7801 Approved
0.7355 Intermediate Similarity NPD1091 Approved
0.7351 Intermediate Similarity NPD8150 Discontinued
0.7349 Intermediate Similarity NPD1243 Approved
0.7349 Intermediate Similarity NPD1652 Phase 2
0.7341 Intermediate Similarity NPD37 Approved
0.7333 Intermediate Similarity NPD7266 Discontinued
0.733 Intermediate Similarity NPD6234 Discontinued
0.7314 Intermediate Similarity NPD4965 Approved
0.7314 Intermediate Similarity NPD4966 Approved
0.7314 Intermediate Similarity NPD4967 Phase 2
0.7306 Intermediate Similarity NPD6823 Phase 2
0.7267 Intermediate Similarity NPD3226 Approved
0.7267 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7263 Intermediate Similarity NPD3926 Phase 2
0.7258 Intermediate Similarity NPD8434 Phase 2
0.725 Intermediate Similarity NPD4908 Phase 1
0.7247 Intermediate Similarity NPD1247 Approved
0.7244 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7239 Intermediate Similarity NPD6355 Discontinued
0.7239 Intermediate Similarity NPD5124 Phase 1
0.7239 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7235 Intermediate Similarity NPD2532 Approved
0.7235 Intermediate Similarity NPD2534 Approved
0.7235 Intermediate Similarity NPD2533 Approved
0.7215 Intermediate Similarity NPD3225 Approved
0.7212 Intermediate Similarity NPD2799 Discontinued
0.7197 Intermediate Similarity NPD9717 Approved
0.7178 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7178 Intermediate Similarity NPD1613 Approved
0.7174 Intermediate Similarity NPD7240 Approved
0.716 Intermediate Similarity NPD2354 Approved
0.716 Intermediate Similarity NPD3887 Approved
0.716 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD3268 Approved
0.7152 Intermediate Similarity NPD7097 Phase 1
0.7143 Intermediate Similarity NPD2800 Approved
0.7135 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD422 Phase 1
0.7134 Intermediate Similarity NPD230 Phase 1
0.7134 Intermediate Similarity NPD4340 Discontinued
0.7126 Intermediate Similarity NPD2344 Approved
0.7125 Intermediate Similarity NPD2798 Approved
0.712 Intermediate Similarity NPD4360 Phase 2
0.712 Intermediate Similarity NPD4363 Phase 3
0.7117 Intermediate Similarity NPD4062 Phase 3
0.7097 Intermediate Similarity NPD1548 Phase 1
0.7091 Intermediate Similarity NPD6651 Approved
0.709 Intermediate Similarity NPD4287 Approved
0.7086 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD7390 Discontinued
0.7073 Intermediate Similarity NPD943 Approved
0.7068 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7068 Intermediate Similarity NPD6213 Phase 3
0.7068 Intermediate Similarity NPD6212 Phase 3
0.7063 Intermediate Similarity NPD2797 Approved
0.7062 Intermediate Similarity NPD4288 Approved
0.703 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD447 Suspended
0.7024 Intermediate Similarity NPD2346 Discontinued
0.7018 Intermediate Similarity NPD7440 Discontinued
0.7006 Intermediate Similarity NPD4308 Phase 3
0.7 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.6994 Remote Similarity NPD5049 Phase 3
0.6987 Remote Similarity NPD9545 Approved
0.6959 Remote Similarity NPD2309 Approved
0.6951 Remote Similarity NPD3764 Approved
0.6949 Remote Similarity NPD6844 Discontinued
0.6935 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6933 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6923 Remote Similarity NPD2355 Clinical (unspecified phase)
0.6923 Remote Similarity NPD2353 Approved
0.6918 Remote Similarity NPD1610 Phase 2
0.6914 Remote Similarity NPD1019 Discontinued
0.6905 Remote Similarity NPD651 Clinical (unspecified phase)
0.6901 Remote Similarity NPD7003 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