Structure

Physi-Chem Properties

Molecular Weight:  606.16
Volume:  558.187
LogP:  1.627
LogD:  0.704
LogS:  -5.05
# Rotatable Bonds:  8
TPSA:  235.04
# H-Bond Aceptor:  15
# H-Bond Donor:  7
# Rings:  5
# Heavy Atoms:  15

MedChem Properties

QED Drug-Likeness Score:  0.167
Synthetic Accessibility Score:  4.78
Fsp3:  0.429
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:  -6.384
MDCK Permeability:  3.636337351053953e-05
Pgp-inhibitor:  0.015
Pgp-substrate:  0.998
Human Intestinal Absorption (HIA):  0.557
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.046
Plasma Protein Binding (PPB):  81.55384063720703%
Volume Distribution (VD):  0.618
Pgp-substrate:  17.520532608032227%

ADMET: Metabolism

CYP1A2-inhibitor:  0.167
CYP1A2-substrate:  0.058
CYP2C19-inhibitor:  0.021
CYP2C19-substrate:  0.058
CYP2C9-inhibitor:  0.026
CYP2C9-substrate:  0.203
CYP2D6-inhibitor:  0.154
CYP2D6-substrate:  0.123
CYP3A4-inhibitor:  0.291
CYP3A4-substrate:  0.029

ADMET: Excretion

Clearance (CL):  1.403
Half-life (T1/2):  0.7

ADMET: Toxicity

hERG Blockers:  0.058
Human Hepatotoxicity (H-HT):  0.192
Drug-inuced Liver Injury (DILI):  0.981
AMES Toxicity:  0.789
Rat Oral Acute Toxicity:  0.036
Maximum Recommended Daily Dose:  0.013
Skin Sensitization:  0.225
Carcinogencity:  0.459
Eye Corrosion:  0.003
Eye Irritation:  0.034
Respiratory Toxicity:  0.027

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

  Natural Product: NPC72016

Natural Product ID:  NPC72016
Common Name*:   Kaempferol 3-O-(5-O-Acetyl-Alpha-D-Apiofuranosyl)-7-O-Alpha-L-Rhamnopyranoside
IUPAC Name:   [(3R,4S,5R)-3,4-dihydroxy-5-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-3-yl]oxyoxolan-3-yl]methyl acetate
Synonyms:  
Standard InCHIKey:  XOUMRQRJVFZBHB-BEAAOXLFSA-N
Standard InCHI:  InChI=1S/C28H30O15/c1-11-19(32)21(34)22(35)26(40-11)41-15-7-16(31)18-17(8-15)42-23(13-3-5-14(30)6-4-13)24(20(18)33)43-27-25(36)28(37,10-39-27)9-38-12(2)29/h3-8,11,19,21-22,25-27,30-32,34-37H,9-10H2,1-2H3/t11-,19-,21+,22+,25+,26-,27+,28-/m0/s1
SMILES:  CC(=O)OC[C@]1(O)CO[C@@H]([C@H]1O)Oc1c(oc2c(c1=O)c(O)cc(c2)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)c1ccc(cc1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1929025
PubChem CID:   25067894
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
NPO23510 Vicia faba Species Fabaceae Eukaryota flowers n.a. n.a. PMID[16180811]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[22014228]
NPO27656 Lotus edulis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[22014228]
NPO27656 Lotus edulis Species Fabaceae Eukaryota n.a. leaf n.a. PMID[22014228]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. leaf n.a. PMID[22014228]
NPO27656 Lotus edulis Species Fabaceae Eukaryota n.a. branch n.a. PMID[22014228]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. branch n.a. PMID[22014228]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO23510 Vicia faba Species Fabaceae Eukaryota Flower n.a. n.a. Database[FooDB]
NPO23510 Vicia faba Species Fabaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO23510 Vicia faba Species Fabaceae Eukaryota Oil n.a. n.a. Database[FooDB]
NPO23510 Vicia faba Species Fabaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO23510 Vicia faba Species Fabaceae Eukaryota Sprout Seedling n.a. n.a. Database[FooDB]
NPO23510 Vicia faba Species Fabaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27656 Lotus edulis 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
NPT143 Individual Protein DNA topoisomerase I Homo sapiens IC50 = 150000.0 nM PMID[537928]
NPT1044 Individual Protein DNA topoisomerase II alpha Homo sapiens Inhibition = 88.0 % PMID[537928]
NPT1044 Individual Protein DNA topoisomerase II alpha Homo sapiens Inhibition = 22.0 % PMID[537928]
NPT1044 Individual Protein DNA topoisomerase II alpha Homo sapiens IC50 = 240000.0 nM PMID[537928]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 350000.0 nM PMID[537928]
NPT165 Cell Line HeLa Homo sapiens IC50 = 350000.0 nM PMID[537928]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 410000.0 nM PMID[537928]
NPT2 Others Unspecified IC50 = 120000.0 nM PMID[537928]
NPT2 Others Unspecified Inhibition = 44.0 % PMID[537928]
NPT2 Others Unspecified Inhibition = 99.0 % PMID[537928]

☑ 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 NPC72016 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
0.9871 High Similarity NPC150164
0.9808 High Similarity NPC121703
0.9806 High Similarity NPC85707
0.9806 High Similarity NPC216496
0.9806 High Similarity NPC48093
0.9806 High Similarity NPC129217
0.9806 High Similarity NPC224530
0.9806 High Similarity NPC259957
0.9806 High Similarity NPC159579
0.9744 High Similarity NPC27942
0.9679 High Similarity NPC282169
0.9677 High Similarity NPC472459
0.9677 High Similarity NPC41121
0.9677 High Similarity NPC111929
0.9677 High Similarity NPC320283
0.9677 High Similarity NPC104677
0.9613 High Similarity NPC133671
0.9613 High Similarity NPC77672
0.9613 High Similarity NPC108831
0.9613 High Similarity NPC122809
0.9613 High Similarity NPC288084
0.9613 High Similarity NPC182634
0.9613 High Similarity NPC54802
0.9613 High Similarity NPC135391
0.9613 High Similarity NPC78263
0.9613 High Similarity NPC197304
0.956 High Similarity NPC64425
0.9554 High Similarity NPC215710
0.9554 High Similarity NPC473438
0.9554 High Similarity NPC265885
0.9554 High Similarity NPC163242
0.9554 High Similarity NPC249281
0.9554 High Similarity NPC476215
0.9554 High Similarity NPC246943
0.9554 High Similarity NPC116458
0.9554 High Similarity NPC253788
0.9554 High Similarity NPC181465
0.9554 High Similarity NPC139320
0.9554 High Similarity NPC276377
0.9554 High Similarity NPC173582
0.9548 High Similarity NPC307938
0.9548 High Similarity NPC323593
0.9548 High Similarity NPC203500
0.9503 High Similarity NPC277532
0.9503 High Similarity NPC138990
0.9503 High Similarity NPC209550
0.9503 High Similarity NPC175429
0.9497 High Similarity NPC139060
0.9497 High Similarity NPC19240
0.9497 High Similarity NPC129264
0.9497 High Similarity NPC85751
0.9497 High Similarity NPC205824
0.9494 High Similarity NPC240306
0.949 High Similarity NPC470405
0.949 High Similarity NPC153342
0.949 High Similarity NPC471079
0.949 High Similarity NPC187379
0.949 High Similarity NPC304741
0.9484 High Similarity NPC95090
0.9484 High Similarity NPC27408
0.9444 High Similarity NPC245452
0.9434 High Similarity NPC80068
0.9434 High Similarity NPC66087
0.9434 High Similarity NPC183672
0.9434 High Similarity NPC278419
0.9434 High Similarity NPC179198
0.943 High Similarity NPC297987
0.943 High Similarity NPC170052
0.943 High Similarity NPC135846
0.943 High Similarity NPC64305
0.943 High Similarity NPC470125
0.943 High Similarity NPC101636
0.9423 High Similarity NPC127406
0.9423 High Similarity NPC265480
0.9423 High Similarity NPC149368
0.9419 High Similarity NPC83283
0.9419 High Similarity NPC39360
0.9419 High Similarity NPC143851
0.9419 High Similarity NPC210003
0.9419 High Similarity NPC29763
0.9383 High Similarity NPC116864
0.9383 High Similarity NPC244776
0.9371 High Similarity NPC131745
0.9371 High Similarity NPC298171
0.9367 High Similarity NPC200708
0.9367 High Similarity NPC136761
0.9363 High Similarity NPC44931
0.9363 High Similarity NPC129827
0.9363 High Similarity NPC6985
0.9363 High Similarity NPC43638
0.9363 High Similarity NPC65003
0.9363 High Similarity NPC60966
0.9363 High Similarity NPC473512
0.9325 High Similarity NPC11847
0.9325 High Similarity NPC474522
0.9325 High Similarity NPC217822
0.9325 High Similarity NPC221288
0.9325 High Similarity NPC175107
0.9325 High Similarity NPC101399
0.9325 High Similarity NPC190003
0.9325 High Similarity NPC153755
0.9317 High Similarity NPC189564
0.9317 High Similarity NPC142142
0.9317 High Similarity NPC477613
0.9317 High Similarity NPC11432
0.9317 High Similarity NPC186816
0.9317 High Similarity NPC476470
0.9317 High Similarity NPC221342
0.9317 High Similarity NPC256188
0.9317 High Similarity NPC203145
0.9317 High Similarity NPC12013
0.9317 High Similarity NPC32641
0.9308 High Similarity NPC477629
0.9308 High Similarity NPC210961
0.9308 High Similarity NPC472994
0.9308 High Similarity NPC270675
0.9308 High Similarity NPC477628
0.9308 High Similarity NPC195685
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 NPC206378
0.9295 High Similarity NPC106625
0.9268 High Similarity NPC4390
0.9264 High Similarity NPC20505
0.9264 High Similarity NPC96605
0.9264 High Similarity NPC188815
0.9264 High Similarity NPC164704
0.9264 High Similarity NPC470712
0.9264 High Similarity NPC469344
0.9264 High Similarity NPC280642
0.9264 High Similarity NPC235260
0.9264 High Similarity NPC155763
0.9264 High Similarity NPC218161
0.9259 High Similarity NPC223424
0.9259 High Similarity NPC317489
0.9259 High Similarity NPC173637
0.9259 High Similarity NPC127546
0.9259 High Similarity NPC52550
0.9259 High Similarity NPC84362
0.9255 High Similarity NPC287889
0.9255 High Similarity NPC289667
0.9255 High Similarity NPC135358
0.9255 High Similarity NPC76831
0.9255 High Similarity NPC292929
0.925 High Similarity NPC259834
0.9245 High Similarity NPC473623
0.9241 High Similarity NPC197896
0.9241 High Similarity NPC313163
0.9241 High Similarity NPC161749
0.9241 High Similarity NPC156457
0.9241 High Similarity NPC258035
0.9236 High Similarity NPC97052
0.9236 High Similarity NPC169248
0.9236 High Similarity NPC39351
0.9236 High Similarity NPC72649
0.9236 High Similarity NPC26195
0.9236 High Similarity NPC99233
0.9231 High Similarity NPC259182
0.9231 High Similarity NPC88484
0.9231 High Similarity NPC121001
0.9231 High Similarity NPC259767
0.9226 High Similarity NPC106700
0.9226 High Similarity NPC191154
0.9212 High Similarity NPC264735
0.9207 High Similarity NPC470714
0.9207 High Similarity NPC470715
0.9207 High Similarity NPC470716
0.9202 High Similarity NPC203050
0.9202 High Similarity NPC120099
0.9202 High Similarity NPC223747
0.9202 High Similarity NPC476771
0.9202 High Similarity NPC138927
0.9202 High Similarity NPC225434
0.9202 High Similarity NPC5319
0.9202 High Similarity NPC219904
0.9198 High Similarity NPC276222
0.9198 High Similarity NPC56077
0.9198 High Similarity NPC281131
0.9198 High Similarity NPC73855
0.9198 High Similarity NPC298666
0.9198 High Similarity NPC67037
0.9198 High Similarity NPC328940
0.9198 High Similarity NPC255615
0.9198 High Similarity NPC68592
0.9198 High Similarity NPC262222
0.9198 High Similarity NPC308404
0.9198 High Similarity NPC253662
0.9198 High Similarity NPC113968
0.9198 High Similarity NPC274618
0.9198 High Similarity NPC135599
0.9198 High Similarity NPC118284
0.9198 High Similarity NPC88789
0.9198 High Similarity NPC179950
0.9198 High Similarity NPC277174
0.9198 High Similarity NPC145038
0.9187 High Similarity NPC303913
0.9182 High Similarity NPC470607

  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 NPC72016 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
0.9241 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
0.8882 High Similarity NPD7075 Discontinued
0.8868 High Similarity NPD6801 Discontinued
0.8855 High Similarity NPD7054 Approved
0.8802 High Similarity NPD7472 Approved
0.8795 High Similarity NPD3818 Discontinued
0.879 High Similarity NPD5403 Approved
0.8718 High Similarity NPD6799 Approved
0.8696 High Similarity NPD7096 Clinical (unspecified phase)
0.869 High Similarity NPD7074 Phase 3
0.8662 High Similarity NPD5401 Approved
0.8642 High Similarity NPD3817 Phase 2
0.8625 High Similarity NPD4380 Phase 2
0.8588 High Similarity NPD6559 Discontinued
0.8528 High Similarity NPD5402 Approved
0.8452 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8452 Intermediate Similarity NPD6166 Phase 2
0.8452 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8428 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8395 Intermediate Similarity NPD6599 Discontinued
0.8364 Intermediate Similarity NPD3882 Suspended
0.8344 Intermediate Similarity NPD7411 Suspended
0.8333 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8293 Intermediate Similarity NPD1934 Approved
0.828 Intermediate Similarity NPD1549 Phase 2
0.8258 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8242 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8199 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8148 Intermediate Similarity NPD1512 Approved
0.8144 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8133 Intermediate Similarity NPD2801 Approved
0.8084 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8038 Intermediate Similarity NPD2796 Approved
0.8025 Intermediate Similarity NPD1511 Approved
0.8024 Intermediate Similarity NPD7819 Suspended
0.8 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7988 Intermediate Similarity NPD3749 Approved
0.7975 Intermediate Similarity NPD1510 Phase 2
0.795 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7931 Intermediate Similarity NPD3751 Discontinued
0.7919 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7907 Intermediate Similarity NPD3787 Discontinued
0.788 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7861 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.784 Intermediate Similarity NPD3750 Approved
0.7834 Intermediate Similarity NPD1240 Approved
0.7821 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7819 Intermediate Similarity NPD7435 Discontinued
0.7791 Intermediate Similarity NPD5494 Approved
0.7789 Intermediate Similarity NPD7584 Approved
0.7771 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7765 Intermediate Similarity NPD8312 Approved
0.7765 Intermediate Similarity NPD8313 Approved
0.7753 Intermediate Similarity NPD7685 Pre-registration
0.775 Intermediate Similarity NPD7033 Discontinued
0.7746 Intermediate Similarity NPD7199 Phase 2
0.7746 Intermediate Similarity NPD6959 Discontinued
0.7736 Intermediate Similarity NPD1607 Approved
0.7733 Intermediate Similarity NPD919 Approved
0.773 Intermediate Similarity NPD4628 Phase 3
0.7725 Intermediate Similarity NPD1653 Approved
0.7719 Intermediate Similarity NPD7768 Phase 2
0.7716 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7706 Intermediate Similarity NPD8455 Phase 2
0.7702 Intermediate Similarity NPD1551 Phase 2
0.7684 Intermediate Similarity NPD5844 Phase 1
0.768 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7669 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7665 Intermediate Similarity NPD920 Approved
0.766 Intermediate Similarity NPD6776 Approved
0.766 Intermediate Similarity NPD6782 Approved
0.766 Intermediate Similarity NPD6781 Approved
0.766 Intermediate Similarity NPD6778 Approved
0.766 Intermediate Similarity NPD6779 Approved
0.766 Intermediate Similarity NPD6780 Approved
0.766 Intermediate Similarity NPD6777 Approved
0.7627 Intermediate Similarity NPD7228 Approved
0.7614 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD6232 Discontinued
0.7595 Intermediate Similarity NPD6798 Discontinued
0.7577 Intermediate Similarity NPD7874 Approved
0.7577 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7571 Intermediate Similarity NPD7473 Discontinued
0.7565 Intermediate Similarity NPD7585 Approved
0.7562 Intermediate Similarity NPD1933 Approved
0.7561 Intermediate Similarity NPD1243 Approved
0.7547 Intermediate Similarity NPD6233 Phase 2
0.7545 Intermediate Similarity NPD2534 Approved
0.7545 Intermediate Similarity NPD2532 Approved
0.7545 Intermediate Similarity NPD2533 Approved
0.7545 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7544 Intermediate Similarity NPD37 Approved
0.7541 Intermediate Similarity NPD8434 Phase 2
0.7531 Intermediate Similarity NPD3748 Approved
0.753 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD6234 Discontinued
0.7514 Intermediate Similarity NPD4966 Approved
0.7514 Intermediate Similarity NPD4967 Phase 2
0.7514 Intermediate Similarity NPD4965 Approved
0.7513 Intermediate Similarity NPD7583 Approved
0.75 Intermediate Similarity NPD1465 Phase 2
0.7485 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.747 Intermediate Similarity NPD6190 Approved
0.7468 Intermediate Similarity NPD6832 Phase 2
0.7455 Intermediate Similarity NPD2800 Approved
0.7455 Intermediate Similarity NPD1652 Phase 2
0.7453 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD5124 Phase 1
0.7453 Intermediate Similarity NPD6355 Discontinued
0.7449 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7449 Intermediate Similarity NPD7783 Phase 2
0.7448 Intermediate Similarity NPD7696 Phase 3
0.7448 Intermediate Similarity NPD7697 Approved
0.7448 Intermediate Similarity NPD7698 Approved
0.7443 Intermediate Similarity NPD1247 Approved
0.7436 Intermediate Similarity NPD8151 Discontinued
0.7418 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7409 Intermediate Similarity NPD7871 Phase 2
0.7409 Intermediate Similarity NPD8319 Approved
0.7409 Intermediate Similarity NPD8320 Phase 1
0.7409 Intermediate Similarity NPD7870 Phase 2
0.7403 Intermediate Similarity NPD5953 Discontinued
0.7394 Intermediate Similarity NPD6535 Approved
0.7394 Intermediate Similarity NPD6534 Approved
0.7389 Intermediate Similarity NPD7286 Phase 2
0.7389 Intermediate Similarity NPD1203 Approved
0.7385 Intermediate Similarity NPD7701 Phase 2
0.7378 Intermediate Similarity NPD2935 Discontinued
0.7368 Intermediate Similarity NPD7458 Discontinued
0.736 Intermediate Similarity NPD3926 Phase 2
0.7355 Intermediate Similarity NPD1091 Approved
0.7337 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD7266 Discontinued
0.7277 Intermediate Similarity NPD7700 Phase 2
0.7277 Intermediate Similarity NPD7699 Phase 2
0.7273 Intermediate Similarity NPD7801 Approved
0.7273 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7268 Intermediate Similarity NPD7240 Approved
0.7267 Intermediate Similarity NPD2313 Discontinued
0.7267 Intermediate Similarity NPD3268 Approved
0.7262 Intermediate Similarity NPD2354 Approved
0.7262 Intermediate Similarity NPD3887 Approved
0.7258 Intermediate Similarity NPD8150 Discontinued
0.7244 Intermediate Similarity NPD422 Phase 1
0.7229 Intermediate Similarity NPD2344 Approved
0.7222 Intermediate Similarity NPD4062 Phase 3
0.7216 Intermediate Similarity NPD6823 Phase 2
0.7215 Intermediate Similarity NPD3225 Approved
0.7212 Intermediate Similarity NPD2799 Discontinued
0.7211 Intermediate Similarity NPD4360 Phase 2
0.7211 Intermediate Similarity NPD4363 Phase 3
0.7206 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD9717 Approved
0.7195 Intermediate Similarity NPD6651 Approved
0.7184 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7178 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7178 Intermediate Similarity NPD1613 Approved
0.717 Intermediate Similarity NPD2797 Approved
0.7168 Intermediate Similarity NPD3226 Approved
0.7164 Intermediate Similarity NPD7930 Approved
0.7152 Intermediate Similarity NPD7097 Phase 1
0.7143 Intermediate Similarity NPD4908 Phase 1
0.7134 Intermediate Similarity NPD230 Phase 1
0.7134 Intermediate Similarity NPD4340 Discontinued
0.7134 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7127 Intermediate Similarity NPD2403 Approved
0.7125 Intermediate Similarity NPD2798 Approved
0.7111 Intermediate Similarity NPD5710 Approved
0.7111 Intermediate Similarity NPD5711 Approved
0.7108 Intermediate Similarity NPD4308 Phase 3
0.7101 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD1548 Phase 1
0.7093 Intermediate Similarity NPD5049 Phase 3
0.709 Intermediate Similarity NPD4287 Approved
0.7066 Intermediate Similarity NPD6100 Approved
0.7066 Intermediate Similarity NPD6099 Approved
0.7059 Intermediate Similarity NPD2309 Approved
0.7055 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7049 Intermediate Similarity NPD7799 Discontinued
0.7041 Intermediate Similarity NPD2654 Approved
0.703 Intermediate Similarity NPD447 Suspended
0.703 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7024 Intermediate Similarity NPD2353 Approved
0.7024 Intermediate Similarity NPD2346 Discontinued
0.7024 Intermediate Similarity NPD2355 Clinical (unspecified phase)
0.6995 Remote Similarity NPD4362 Clinical (unspecified phase)
0.6995 Remote Similarity NPD4361 Phase 2
0.6987 Remote Similarity NPD9545 Approved
0.6982 Remote Similarity NPD2424 Discontinued
0.6971 Remote Similarity NPD5808 Clinical (unspecified phase)
0.697 Remote Similarity NPD7966 Clinical (unspecified phase)
0.697 Remote Similarity NPD943 Approved
0.697 Remote Similarity NPD4060 Phase 1
0.6966 Remote Similarity NPD4288 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