Structure

Physi-Chem Properties

Molecular Weight:  740.22
Volume:  673.908
LogP:  0.406
LogD:  -0.245
LogS:  -2.729
# Rotatable Bonds:  9
TPSA:  297.12
# H-Bond Aceptor:  19
# H-Bond Donor:  10
# Rings:  6
# Heavy Atoms:  19

MedChem Properties

QED Drug-Likeness Score:  0.104
Synthetic Accessibility Score:  5.211
Fsp3:  0.545
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.435
MDCK Permeability:  9.460082947043702e-05
Pgp-inhibitor:  0.003
Pgp-substrate:  0.999
Human Intestinal Absorption (HIA):  0.972
20% Bioavailability (F20%):  0.012
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.156
Plasma Protein Binding (PPB):  73.55980682373047%
Volume Distribution (VD):  0.492
Pgp-substrate:  12.751924514770508%

ADMET: Metabolism

CYP1A2-inhibitor:  0.035
CYP1A2-substrate:  0.053
CYP2C19-inhibitor:  0.042
CYP2C19-substrate:  0.066
CYP2C9-inhibitor:  0.002
CYP2C9-substrate:  0.082
CYP2D6-inhibitor:  0.022
CYP2D6-substrate:  0.149
CYP3A4-inhibitor:  0.018
CYP3A4-substrate:  0.004

ADMET: Excretion

Clearance (CL):  0.914
Half-life (T1/2):  0.626

ADMET: Toxicity

hERG Blockers:  0.438
Human Hepatotoxicity (H-HT):  0.049
Drug-inuced Liver Injury (DILI):  0.954
AMES Toxicity:  0.59
Rat Oral Acute Toxicity:  0.018
Maximum Recommended Daily Dose:  0.002
Skin Sensitization:  0.626
Carcinogencity:  0.13
Eye Corrosion:  0.003
Eye Irritation:  0.046
Respiratory Toxicity:  0.029

Download Data

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

  Natural Product: NPC475382

Natural Product ID:  NPC475382
Common Name*:   Acacetin 7-O-Alpha-L-Rhamnopyranosyl-(1->6)-[Alpha-L-Rhamnopyranosyl](1->2)-Beta-D-Glucopyranoside
IUPAC Name:   7-[(2R,3R,4S,5R,6R)-6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]oxy-5-hydroxy-2-(4-methoxyphenyl)chromen-4-one
Synonyms:  
Standard InCHIKey:  LPFFEQMPQWBGLC-CAMRQUDDSA-N
Standard InCHI:  InChI=1S/C33H40O19/c1-11-21(37)23(39)26(42)30(46-11)50-29-25(41)22(38)19(10-34)49-33(29)52-32-28(44)24(40)27(43)31(51-32)47-14-7-15(35)20-16(36)9-17(48-18(20)8-14)12-3-5-13(45-2)6-4-12/h3-9,11,19,21-35,37-44H,10H2,1-2H3/t11-,19+,21-,22+,23+,24-,25-,26+,27+,28+,29+,30-,31+,32-,33-/m0/s1
SMILES:  CC1C(C(C(C(O1)OC2C(C(C(OC2OC3C(C(C(C(O3)OC4=CC(=C5C(=C4)OC(=CC5=O)C6=CC=C(C=C6)OC)O)O)O)O)CO)O)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL504601
PubChem CID:   44575350
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
NPO11577 Buddleja officinalis Species Scrophulariaceae Eukaryota flowers bought from a drugstore in Beijing n.a. PMID[10514305]
NPO11577 Buddleja officinalis Species Scrophulariaceae Eukaryota flower buds n.a. n.a. PMID[14738377]
NPO11577 Buddleja officinalis Species Scrophulariaceae Eukaryota flowers n.a. n.a. PMID[21524582]
NPO11577 Buddleja officinalis Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11577 Buddleja officinalis Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11577 Buddleja officinalis Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11577 Buddleja officinalis Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11577 Buddleja officinalis Species Scrophulariaceae 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
NPT183 Individual Protein Arachidonate 5-lipoxygenase Rattus norvegicus Inhibition = 0.0 % PMID[515870]
NPT2 Others Unspecified Inhibition = 0.0 % PMID[515870]

☑ 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 NPC475382 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
0.9935 High Similarity NPC473644
0.9935 High Similarity NPC311850
0.9871 High Similarity NPC287889
0.9871 High Similarity NPC135358
0.9808 High Similarity NPC477613
0.9808 High Similarity NPC221342
0.9808 High Similarity NPC186816
0.9808 High Similarity NPC142142
0.9808 High Similarity NPC298666
0.9808 High Similarity NPC68592
0.9808 High Similarity NPC476470
0.9808 High Similarity NPC12013
0.9808 High Similarity NPC11432
0.9808 High Similarity NPC262222
0.9808 High Similarity NPC32641
0.9808 High Similarity NPC203145
0.9808 High Similarity NPC189564
0.9808 High Similarity NPC256188
0.9804 High Similarity NPC473634
0.9804 High Similarity NPC22062
0.9804 High Similarity NPC138811
0.9744 High Similarity NPC292929
0.9744 High Similarity NPC289667
0.9744 High Similarity NPC76831
0.9742 High Similarity NPC298171
0.9742 High Similarity NPC244875
0.974 High Similarity NPC142860
0.974 High Similarity NPC97285
0.974 High Similarity NPC246469
0.974 High Similarity NPC473623
0.974 High Similarity NPC271270
0.9739 High Similarity NPC473512
0.9739 High Similarity NPC44931
0.9739 High Similarity NPC129827
0.9739 High Similarity NPC65003
0.9677 High Similarity NPC101636
0.9673 High Similarity NPC473657
0.9673 High Similarity NPC295613
0.9615 High Similarity NPC240306
0.9615 High Similarity NPC190450
0.9613 High Similarity NPC136761
0.9613 High Similarity NPC187379
0.9608 High Similarity NPC95090
0.9608 High Similarity NPC27408
0.9557 High Similarity NPC64425
0.9554 High Similarity NPC124155
0.9554 High Similarity NPC257566
0.9551 High Similarity NPC135846
0.9551 High Similarity NPC276377
0.9551 High Similarity NPC163242
0.9551 High Similarity NPC303913
0.9551 High Similarity NPC215710
0.9551 High Similarity NPC473438
0.9551 High Similarity NPC170052
0.9551 High Similarity NPC265885
0.9551 High Similarity NPC64305
0.9551 High Similarity NPC249281
0.9551 High Similarity NPC476215
0.9551 High Similarity NPC246943
0.9551 High Similarity NPC116458
0.9551 High Similarity NPC253788
0.9551 High Similarity NPC181465
0.9551 High Similarity NPC139320
0.9551 High Similarity NPC173582
0.9551 High Similarity NPC297987
0.9545 High Similarity NPC206378
0.9542 High Similarity NPC83283
0.9542 High Similarity NPC29763
0.9542 High Similarity NPC143851
0.9542 High Similarity NPC210003
0.9542 High Similarity NPC39360
0.95 High Similarity NPC209550
0.95 High Similarity NPC138990
0.95 High Similarity NPC175429
0.95 High Similarity NPC277532
0.949 High Similarity NPC44947
0.9487 High Similarity NPC304741
0.9487 High Similarity NPC471079
0.9487 High Similarity NPC470405
0.9484 High Similarity NPC108831
0.9484 High Similarity NPC182634
0.9484 High Similarity NPC60966
0.9481 High Similarity NPC26195
0.9481 High Similarity NPC72649
0.9481 High Similarity NPC39351
0.9481 High Similarity NPC97052
0.9481 High Similarity NPC169248
0.9444 High Similarity NPC198199
0.9441 High Similarity NPC288152
0.9441 High Similarity NPC137871
0.9441 High Similarity NPC474522
0.9441 High Similarity NPC470714
0.9441 High Similarity NPC470715
0.9441 High Similarity NPC257011
0.9441 High Similarity NPC470716
0.9441 High Similarity NPC180918
0.9441 High Similarity NPC9002
0.9437 High Similarity NPC5319
0.9434 High Similarity NPC70441
0.9427 High Similarity NPC47923
0.9423 High Similarity NPC73511
0.9423 High Similarity NPC41121
0.9423 High Similarity NPC320283
0.9423 High Similarity NPC472459
0.9423 High Similarity NPC111929
0.9419 High Similarity NPC170475
0.9419 High Similarity NPC203500
0.9419 High Similarity NPC323593
0.9419 High Similarity NPC307938
0.9416 High Similarity NPC106625
0.9387 High Similarity NPC14187
0.9387 High Similarity NPC122467
0.9387 High Similarity NPC202908
0.9387 High Similarity NPC292019
0.9387 High Similarity NPC231787
0.9387 High Similarity NPC48984
0.9379 High Similarity NPC470712
0.9379 High Similarity NPC199079
0.9379 High Similarity NPC164704
0.9379 High Similarity NPC210808
0.9363 High Similarity NPC153342
0.9359 High Similarity NPC135391
0.9359 High Similarity NPC161749
0.9359 High Similarity NPC77672
0.9359 High Similarity NPC122809
0.9359 High Similarity NPC197896
0.9359 High Similarity NPC197304
0.9359 High Similarity NPC78263
0.9359 High Similarity NPC54802
0.9359 High Similarity NPC313163
0.9359 High Similarity NPC258035
0.9359 High Similarity NPC133671
0.9359 High Similarity NPC156457
0.9355 High Similarity NPC99233
0.9351 High Similarity NPC259182
0.9351 High Similarity NPC121001
0.9351 High Similarity NPC88484
0.9351 High Similarity NPC259767
0.9346 High Similarity NPC191154
0.9329 High Similarity NPC89052
0.9329 High Similarity NPC120952
0.9329 High Similarity NPC251417
0.9317 High Similarity NPC209296
0.9317 High Similarity NPC86008
0.9317 High Similarity NPC195257
0.9317 High Similarity NPC105283
0.9317 High Similarity NPC293629
0.9317 High Similarity NPC43587
0.9313 High Similarity NPC473278
0.9313 High Similarity NPC115674
0.9313 High Similarity NPC8856
0.9313 High Similarity NPC210073
0.9313 High Similarity NPC260504
0.9313 High Similarity NPC89809
0.9304 High Similarity NPC224530
0.9304 High Similarity NPC216496
0.9304 High Similarity NPC477629
0.9304 High Similarity NPC472994
0.9304 High Similarity NPC470125
0.9304 High Similarity NPC195685
0.9304 High Similarity NPC270675
0.9304 High Similarity NPC48093
0.9304 High Similarity NPC85707
0.9304 High Similarity NPC477628
0.9304 High Similarity NPC259957
0.9304 High Similarity NPC210961
0.9304 High Similarity NPC129217
0.9304 High Similarity NPC159579
0.9299 High Similarity NPC308265
0.9295 High Similarity NPC127406
0.9295 High Similarity NPC261866
0.9295 High Similarity NPC45165
0.9286 High Similarity NPC134819
0.9273 High Similarity NPC192539
0.9268 High Similarity NPC255799
0.9268 High Similarity NPC219043
0.9264 High Similarity NPC25724
0.9259 High Similarity NPC177731
0.9259 High Similarity NPC44328
0.9259 High Similarity NPC76047
0.9259 High Similarity NPC188815
0.9259 High Similarity NPC79056
0.9259 High Similarity NPC105095
0.9259 High Similarity NPC67105
0.925 High Similarity NPC15358
0.925 High Similarity NPC475497
0.925 High Similarity NPC475366
0.925 High Similarity NPC139060
0.925 High Similarity NPC284277
0.9245 High Similarity NPC472876
0.9245 High Similarity NPC150164
0.9245 High Similarity NPC131745
0.9245 High Similarity NPC27942
0.9245 High Similarity NPC259834
0.9241 High Similarity NPC200708
0.9241 High Similarity NPC472320
0.9241 High Similarity NPC271479
0.9236 High Similarity NPC23817
0.9236 High Similarity NPC6985
0.9236 High Similarity NPC43638

  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 NPC475382 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
0.9437 High Similarity NPD7804 Clinical (unspecified phase)
0.9379 High Similarity NPD7472 Approved
0.9359 High Similarity NPD4381 Clinical (unspecified phase)
0.9325 High Similarity NPD7808 Phase 3
0.9317 High Similarity NPD7054 Approved
0.9264 High Similarity NPD7251 Discontinued
0.9259 High Similarity NPD7074 Phase 3
0.9202 High Similarity NPD6797 Phase 2
0.8734 High Similarity NPD4380 Phase 2
0.8675 High Similarity NPD3818 Discontinued
0.8639 High Similarity NPD4338 Clinical (unspecified phase)
0.8554 High Similarity NPD6168 Clinical (unspecified phase)
0.8554 High Similarity NPD6166 Phase 2
0.8554 High Similarity NPD6167 Clinical (unspecified phase)
0.8528 High Similarity NPD7075 Discontinued
0.8442 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8442 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8405 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8395 Intermediate Similarity NPD1934 Approved
0.8395 Intermediate Similarity NPD6801 Discontinued
0.8387 Intermediate Similarity NPD1549 Phase 2
0.8363 Intermediate Similarity NPD6559 Discontinued
0.8344 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8344 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8313 Intermediate Similarity NPD5403 Approved
0.8302 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8239 Intermediate Similarity NPD6799 Approved
0.8232 Intermediate Similarity NPD2801 Approved
0.8221 Intermediate Similarity NPD7411 Suspended
0.8187 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8187 Intermediate Similarity NPD5401 Approved
0.8182 Intermediate Similarity NPD3817 Phase 2
0.8161 Intermediate Similarity NPD8313 Approved
0.8161 Intermediate Similarity NPD8312 Approved
0.8141 Intermediate Similarity NPD2796 Approved
0.8125 Intermediate Similarity NPD1511 Approved
0.8121 Intermediate Similarity NPD7819 Suspended
0.8121 Intermediate Similarity NPD8455 Phase 2
0.8092 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8077 Intermediate Similarity NPD1510 Phase 2
0.8072 Intermediate Similarity NPD5402 Approved
0.8047 Intermediate Similarity NPD6959 Discontinued
0.8045 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8025 Intermediate Similarity NPD1512 Approved
0.8024 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8012 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7939 Intermediate Similarity NPD6599 Discontinued
0.7935 Intermediate Similarity NPD1240 Approved
0.7917 Intermediate Similarity NPD3882 Suspended
0.7872 Intermediate Similarity NPD7584 Approved
0.7834 Intermediate Similarity NPD1607 Approved
0.7826 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7811 Intermediate Similarity NPD7768 Phase 2
0.7806 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7789 Intermediate Similarity NPD8151 Discontinued
0.7778 Intermediate Similarity NPD5494 Approved
0.7716 Intermediate Similarity NPD3750 Approved
0.7714 Intermediate Similarity NPD3751 Discontinued
0.7708 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7708 Intermediate Similarity NPD7783 Phase 2
0.7688 Intermediate Similarity NPD3787 Discontinued
0.7676 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.764 Intermediate Similarity NPD7685 Pre-registration
0.7619 Intermediate Similarity NPD7698 Approved
0.7619 Intermediate Similarity NPD7697 Approved
0.7619 Intermediate Similarity NPD7696 Phase 3
0.7614 Intermediate Similarity NPD7228 Approved
0.7607 Intermediate Similarity NPD4628 Phase 3
0.7605 Intermediate Similarity NPD1653 Approved
0.7593 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7578 Intermediate Similarity NPD1551 Phase 2
0.7571 Intermediate Similarity NPD5844 Phase 1
0.7558 Intermediate Similarity NPD3749 Approved
0.7557 Intermediate Similarity NPD7473 Discontinued
0.7553 Intermediate Similarity NPD6777 Approved
0.7553 Intermediate Similarity NPD6776 Approved
0.7553 Intermediate Similarity NPD6780 Approved
0.7553 Intermediate Similarity NPD6778 Approved
0.7553 Intermediate Similarity NPD6779 Approved
0.7553 Intermediate Similarity NPD6781 Approved
0.7553 Intermediate Similarity NPD6782 Approved
0.7552 Intermediate Similarity NPD7701 Phase 2
0.7546 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7526 Intermediate Similarity NPD7435 Discontinued
0.7487 Intermediate Similarity NPD7870 Phase 2
0.7487 Intermediate Similarity NPD7871 Phase 2
0.7486 Intermediate Similarity NPD6232 Discontinued
0.7485 Intermediate Similarity NPD1465 Phase 2
0.7461 Intermediate Similarity NPD7585 Approved
0.7456 Intermediate Similarity NPD7458 Discontinued
0.7452 Intermediate Similarity NPD6832 Phase 2
0.7451 Intermediate Similarity NPD1091 Approved
0.7447 Intermediate Similarity NPD7699 Phase 2
0.7447 Intermediate Similarity NPD7700 Phase 2
0.7446 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7438 Intermediate Similarity NPD1933 Approved
0.7429 Intermediate Similarity NPD7199 Phase 2
0.7423 Intermediate Similarity NPD7266 Discontinued
0.7409 Intermediate Similarity NPD7583 Approved
0.7407 Intermediate Similarity NPD3748 Approved
0.7407 Intermediate Similarity NPD7033 Discontinued
0.7401 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD8319 Approved
0.7396 Intermediate Similarity NPD8320 Phase 1
0.7391 Intermediate Similarity NPD6651 Approved
0.7385 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7385 Intermediate Similarity NPD7874 Approved
0.7382 Intermediate Similarity NPD6823 Phase 2
0.7374 Intermediate Similarity NPD7286 Phase 2
0.7348 Intermediate Similarity NPD7240 Approved
0.7347 Intermediate Similarity NPD7801 Approved
0.7337 Intermediate Similarity NPD920 Approved
0.7333 Intermediate Similarity NPD2800 Approved
0.7333 Intermediate Similarity NPD1652 Phase 2
0.7308 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7293 Intermediate Similarity NPD5953 Discontinued
0.7287 Intermediate Similarity NPD4363 Phase 3
0.7287 Intermediate Similarity NPD6535 Approved
0.7287 Intermediate Similarity NPD6534 Approved
0.7287 Intermediate Similarity NPD4360 Phase 2
0.7283 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD1613 Approved
0.7267 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7261 Intermediate Similarity NPD1203 Approved
0.7256 Intermediate Similarity NPD2935 Discontinued
0.7247 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7243 Intermediate Similarity NPD8434 Phase 2
0.7233 Intermediate Similarity NPD4908 Phase 1
0.7229 Intermediate Similarity NPD1243 Approved
0.7226 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7225 Intermediate Similarity NPD37 Approved
0.7222 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD5124 Phase 1
0.7219 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD2533 Approved
0.7219 Intermediate Similarity NPD2532 Approved
0.7219 Intermediate Similarity NPD2534 Approved
0.7216 Intermediate Similarity NPD6234 Discontinued
0.7215 Intermediate Similarity NPD2798 Approved
0.7202 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD4966 Approved
0.72 Intermediate Similarity NPD4965 Approved
0.72 Intermediate Similarity NPD4967 Phase 2
0.719 Intermediate Similarity NPD1548 Phase 1
0.7168 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD6100 Approved
0.7152 Intermediate Similarity NPD6099 Approved
0.7151 Intermediate Similarity NPD8150 Discontinued
0.7143 Intermediate Similarity NPD2313 Discontinued
0.7143 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD3268 Approved
0.7143 Intermediate Similarity NPD6798 Discontinued
0.7134 Intermediate Similarity NPD7097 Phase 1
0.7126 Intermediate Similarity NPD6844 Discontinued
0.7119 Intermediate Similarity NPD919 Approved
0.7118 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD422 Phase 1
0.7108 Intermediate Similarity NPD2344 Approved
0.7099 Intermediate Similarity NPD6233 Phase 2
0.7091 Intermediate Similarity NPD2799 Discontinued
0.7089 Intermediate Similarity NPD3225 Approved
0.707 Intermediate Similarity NPD9717 Approved
0.7059 Intermediate Similarity NPD7390 Discontinued
0.7056 Intermediate Similarity NPD3926 Phase 2
0.7055 Intermediate Similarity NPD943 Approved
0.7053 Intermediate Similarity NPD6213 Phase 3
0.7053 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7053 Intermediate Similarity NPD6212 Phase 3
0.7052 Intermediate Similarity NPD3226 Approved
0.7044 Intermediate Similarity NPD2797 Approved
0.7039 Intermediate Similarity NPD1247 Approved
0.7024 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7012 Intermediate Similarity NPD230 Phase 1
0.7012 Intermediate Similarity NPD6355 Discontinued
0.7006 Intermediate Similarity NPD1610 Phase 2
0.6982 Remote Similarity NPD6398 Clinical (unspecified phase)
0.698 Remote Similarity NPD7930 Approved
0.6975 Remote Similarity NPD3027 Phase 3
0.6957 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6941 Remote Similarity NPD6190 Approved
0.6941 Remote Similarity NPD2309 Approved
0.6923 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6923 Remote Similarity NPD2654 Approved
0.6919 Remote Similarity NPD4662 Approved
0.6919 Remote Similarity NPD4661 Approved
0.6909 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6909 Remote Similarity NPD447 Suspended
0.6905 Remote Similarity NPD2346 Discontinued
0.6904 Remote Similarity NPD7680 Approved
0.6891 Remote Similarity NPD4362 Clinical (unspecified phase)
0.6891 Remote Similarity NPD4361 Phase 2
0.6886 Remote Similarity NPD4308 Phase 3
0.6872 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6864 Remote Similarity NPD2424 Discontinued
0.686 Remote Similarity NPD7212 Phase 2
0.686 Remote Similarity NPD7213 Phase 3
0.6859 Remote Similarity NPD9545 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