Structure

Physi-Chem Properties

Molecular Weight:  406.18
Volume:  432.873
LogP:  6.247
LogD:  3.84
LogS:  -4.264
# Rotatable Bonds:  6
TPSA:  87.74
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.316
Synthetic Accessibility Score:  2.816
Fsp3:  0.28
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:  -4.772
MDCK Permeability:  1.7085825675167143e-05
Pgp-inhibitor:  0.708
Pgp-substrate:  0.006
Human Intestinal Absorption (HIA):  0.019
20% Bioavailability (F20%):  0.037
30% Bioavailability (F30%):  0.825

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.013
Plasma Protein Binding (PPB):  95.80303192138672%
Volume Distribution (VD):  0.604
Pgp-substrate:  3.1079282760620117%

ADMET: Metabolism

CYP1A2-inhibitor:  0.343
CYP1A2-substrate:  0.199
CYP2C19-inhibitor:  0.835
CYP2C19-substrate:  0.068
CYP2C9-inhibitor:  0.846
CYP2C9-substrate:  0.921
CYP2D6-inhibitor:  0.03
CYP2D6-substrate:  0.176
CYP3A4-inhibitor:  0.119
CYP3A4-substrate:  0.098

ADMET: Excretion

Clearance (CL):  10.0
Half-life (T1/2):  0.141

ADMET: Toxicity

hERG Blockers:  0.011
Human Hepatotoxicity (H-HT):  0.835
Drug-inuced Liver Injury (DILI):  0.972
AMES Toxicity:  0.086
Rat Oral Acute Toxicity:  0.323
Maximum Recommended Daily Dose:  0.048
Skin Sensitization:  0.446
Carcinogencity:  0.261
Eye Corrosion:  0.003
Eye Irritation:  0.04
Respiratory Toxicity:  0.38

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

  Natural Product: NPC196137

Natural Product ID:  NPC196137
Common Name*:   Isomammeisin
IUPAC Name:   5,7-dihydroxy-8-(3-methylbutanoyl)-6-(3-methylbut-2-enyl)-4-phenylchromen-2-one
Synonyms:   Isomammeisin
Standard InCHIKey:  SBHOAZQBEGVQLJ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C25H26O5/c1-14(2)10-11-17-23(28)21-18(16-8-6-5-7-9-16)13-20(27)30-25(21)22(24(17)29)19(26)12-15(3)4/h5-10,13,15,28-29H,11-12H2,1-4H3
SMILES:  CC(=CCc1c(c2c(cc(=O)oc2c(C(=O)CC(C)C)c1O)c1ccccc1)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL511810
PubChem CID:   5748555
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0001614] Neoflavonoids
        • [CHEMONTID:0003650] Prenylated neoflavonoids

*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
NPO33501 marila pluricostata Species Calophyllaceae Eukaryota leaves n.a. n.a. PMID[15787438]
NPO4756 Mesua elegans Species Calophyllaceae Eukaryota n.a. n.a. n.a. PMID[20943395]
NPO21645 Mammea americana Species Calophyllaceae Eukaryota n.a. n.a. n.a. PMID[21214226]
NPO21645 Mammea americana Species Calophyllaceae Eukaryota n.a. stem n.a. PMID[21214226]
NPO21645 Mammea americana Species Calophyllaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO21645 Mammea americana Species Calophyllaceae Eukaryota n.a. n.a. Database[FooDB]
NPO21645 Mammea americana Species Calophyllaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21645 Mammea americana Species Calophyllaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13839 Mammea harmandii Species Calophyllaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21645 Mammea americana Species Calophyllaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4756 Mesua elegans Species Calophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21645 Mammea americana Species Calophyllaceae 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
NPT83 Cell Line MCF7 Homo sapiens GI50 = 0.7 ug.mL-1 PMID[452899]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 = 0.8 ug.mL-1 PMID[452899]
NPT395 Cell Line SF-268 Homo sapiens GI50 = 0.6 ug.mL-1 PMID[452899]
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus IC50 > 20000.0 nM PMID[452900]
NPT396 Cell Line T47D Homo sapiens IC50 = 1570.0 nM PMID[452901]
NPT306 Cell Line PC-3 Homo sapiens IC50 = 2180.0 nM PMID[452901]
NPT21802 PROTEIN FAMILY Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha Homo sapiens IC50 = 3230.0 nM PMID[452901]
NPT21802 PROTEIN FAMILY Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha Homo sapiens IC50 = 3730.0 nM PMID[452901]

☑ 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 NPC196137 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 NPC1886
0.9928 High Similarity NPC196459
0.9928 High Similarity NPC112791
0.9928 High Similarity NPC181388
0.9928 High Similarity NPC94794
0.9928 High Similarity NPC154217
0.9928 High Similarity NPC470322
0.9928 High Similarity NPC188632
0.9928 High Similarity NPC87609
0.9928 High Similarity NPC470296
0.9856 High Similarity NPC469935
0.9856 High Similarity NPC178627
0.9855 High Similarity NPC36181
0.9787 High Similarity NPC208303
0.9787 High Similarity NPC161864
0.9718 High Similarity NPC469932
0.9716 High Similarity NPC297886
0.9716 High Similarity NPC140120
0.9716 High Similarity NPC249942
0.965 High Similarity NPC474735
0.9648 High Similarity NPC469933
0.9645 High Similarity NPC57470
0.9638 High Similarity NPC473209
0.9583 High Similarity NPC290671
0.958 High Similarity NPC19238
0.9577 High Similarity NPC180477
0.9574 High Similarity NPC469953
0.9565 High Similarity NPC199458
0.9565 High Similarity NPC183639
0.95 High Similarity NPC282300
0.95 High Similarity NPC470555
0.9496 High Similarity NPC301217
0.9496 High Similarity NPC220062
0.9496 High Similarity NPC96565
0.9496 High Similarity NPC216978
0.9496 High Similarity NPC241975
0.9496 High Similarity NPC303633
0.9496 High Similarity NPC217186
0.9496 High Similarity NPC55018
0.9496 High Similarity NPC53181
0.9496 High Similarity NPC19476
0.9493 High Similarity NPC138047
0.9493 High Similarity NPC474624
0.9493 High Similarity NPC131782
0.9448 High Similarity NPC312549
0.9448 High Similarity NPC209142
0.9444 High Similarity NPC104236
0.9444 High Similarity NPC164205
0.9437 High Similarity NPC326500
0.9429 High Similarity NPC261227
0.9429 High Similarity NPC241100
0.9429 High Similarity NPC270883
0.9429 High Similarity NPC221173
0.9429 High Similarity NPC172986
0.9429 High Similarity NPC159275
0.9424 High Similarity NPC201395
0.9424 High Similarity NPC219584
0.9424 High Similarity NPC470083
0.9388 High Similarity NPC469934
0.9379 High Similarity NPC151973
0.9366 High Similarity NPC219915
0.9366 High Similarity NPC293053
0.9366 High Similarity NPC212932
0.9366 High Similarity NPC11700
0.9366 High Similarity NPC9117
0.9366 High Similarity NPC24821
0.9366 High Similarity NPC190637
0.9362 High Similarity NPC118840
0.9362 High Similarity NPC110969
0.9362 High Similarity NPC64908
0.9362 High Similarity NPC147688
0.9362 High Similarity NPC156590
0.9362 High Similarity NPC205006
0.9357 High Similarity NPC472343
0.9357 High Similarity NPC18260
0.9357 High Similarity NPC78913
0.9357 High Similarity NPC470986
0.9324 High Similarity NPC474738
0.9324 High Similarity NPC474609
0.9324 High Similarity NPC129053
0.9324 High Similarity NPC469936
0.9324 High Similarity NPC475797
0.9324 High Similarity NPC109967
0.9324 High Similarity NPC321372
0.9324 High Similarity NPC78554
0.9301 High Similarity NPC311741
0.9301 High Similarity NPC234629
0.9301 High Similarity NPC273538
0.9301 High Similarity NPC216538
0.9301 High Similarity NPC271288
0.9296 High Similarity NPC473042
0.9296 High Similarity NPC266725
0.9296 High Similarity NPC217083
0.9296 High Similarity NPC299080
0.9296 High Similarity NPC470556
0.9296 High Similarity NPC226636
0.9296 High Similarity NPC214236
0.9296 High Similarity NPC62840
0.9296 High Similarity NPC59739
0.9296 High Similarity NPC293852
0.9296 High Similarity NPC200694
0.9296 High Similarity NPC78803
0.9296 High Similarity NPC144499
0.9296 High Similarity NPC11561
0.9291 High Similarity NPC475680
0.9291 High Similarity NPC235239
0.9291 High Similarity NPC69769
0.9291 High Similarity NPC150522
0.9291 High Similarity NPC305355
0.9286 High Similarity NPC470669
0.9286 High Similarity NPC470668
0.9281 High Similarity NPC13408
0.9257 High Similarity NPC108937
0.9257 High Similarity NPC279218
0.9236 High Similarity NPC124729
0.9236 High Similarity NPC178343
0.9236 High Similarity NPC153758
0.9236 High Similarity NPC474161
0.9236 High Similarity NPC477955
0.9236 High Similarity NPC220418
0.9236 High Similarity NPC5820
0.9236 High Similarity NPC306488
0.9236 High Similarity NPC476088
0.9236 High Similarity NPC25844
0.9231 High Similarity NPC125894
0.9231 High Similarity NPC307895
0.9231 High Similarity NPC106985
0.9231 High Similarity NPC474939
0.9231 High Similarity NPC166138
0.9231 High Similarity NPC107177
0.9231 High Similarity NPC77794
0.9231 High Similarity NPC85162
0.9231 High Similarity NPC18585
0.9231 High Similarity NPC96216
0.9231 High Similarity NPC223812
0.9231 High Similarity NPC81697
0.9231 High Similarity NPC470909
0.9231 High Similarity NPC278249
0.9231 High Similarity NPC470553
0.9231 High Similarity NPC38219
0.9225 High Similarity NPC110038
0.9225 High Similarity NPC14871
0.9225 High Similarity NPC248372
0.9225 High Similarity NPC103362
0.922 High Similarity NPC283429
0.922 High Similarity NPC240305
0.9214 High Similarity NPC103001
0.9214 High Similarity NPC228661
0.9214 High Similarity NPC332594
0.9184 High Similarity NPC78835
0.9184 High Similarity NPC204561
0.9184 High Similarity NPC316960
0.9184 High Similarity NPC309512
0.9184 High Similarity NPC317715
0.9184 High Similarity NPC148945
0.9178 High Similarity NPC470461
0.9172 High Similarity NPC104406
0.9172 High Similarity NPC14001
0.9172 High Similarity NPC97716
0.9172 High Similarity NPC296998
0.9172 High Similarity NPC474108
0.9172 High Similarity NPC237635
0.9172 High Similarity NPC285748
0.9172 High Similarity NPC24673
0.9172 High Similarity NPC177995
0.9172 High Similarity NPC308200
0.9172 High Similarity NPC201731
0.9172 High Similarity NPC79469
0.9172 High Similarity NPC166757
0.9172 High Similarity NPC473077
0.9167 High Similarity NPC133060
0.9167 High Similarity NPC257236
0.9167 High Similarity NPC118059
0.9167 High Similarity NPC288910
0.9167 High Similarity NPC278175
0.9167 High Similarity NPC235217
0.9167 High Similarity NPC473014
0.9167 High Similarity NPC206212
0.9167 High Similarity NPC224714
0.9167 High Similarity NPC131568
0.9167 High Similarity NPC473015
0.9167 High Similarity NPC71184
0.9167 High Similarity NPC473013
0.9167 High Similarity NPC131579
0.9167 High Similarity NPC470554
0.9167 High Similarity NPC319752
0.9161 High Similarity NPC220998
0.9161 High Similarity NPC112829
0.9161 High Similarity NPC32739
0.9161 High Similarity NPC265040
0.9161 High Similarity NPC10937
0.9161 High Similarity NPC228504
0.9161 High Similarity NPC227579
0.9161 High Similarity NPC76338
0.9161 High Similarity NPC294432
0.9161 High Similarity NPC324436
0.9161 High Similarity NPC223500
0.9161 High Similarity NPC125855
0.9161 High Similarity NPC64915
0.9161 High Similarity NPC66515

  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 NPC196137 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
0.9301 High Similarity NPD4378 Clinical (unspecified phase)
0.9167 High Similarity NPD7410 Clinical (unspecified phase)
0.8926 High Similarity NPD7411 Suspended
0.8882 High Similarity NPD7075 Discontinued
0.8811 High Similarity NPD1550 Clinical (unspecified phase)
0.8811 High Similarity NPD1552 Clinical (unspecified phase)
0.8808 High Similarity NPD7096 Clinical (unspecified phase)
0.8808 High Similarity NPD7819 Suspended
0.8803 High Similarity NPD1510 Phase 2
0.8759 High Similarity NPD3750 Approved
0.875 High Similarity NPD1549 Phase 2
0.875 High Similarity NPD8443 Clinical (unspecified phase)
0.8742 High Similarity NPD6801 Discontinued
0.8741 High Similarity NPD2796 Approved
0.869 High Similarity NPD1243 Approved
0.8684 High Similarity NPD2393 Clinical (unspecified phase)
0.8652 High Similarity NPD1240 Approved
0.8621 High Similarity NPD970 Clinical (unspecified phase)
0.8609 High Similarity NPD4380 Phase 2
0.8581 High Similarity NPD1511 Approved
0.8581 High Similarity NPD6799 Approved
0.8571 High Similarity NPD7768 Phase 2
0.8562 High Similarity NPD7421 Clinical (unspecified phase)
0.8544 High Similarity NPD7852 Clinical (unspecified phase)
0.8542 High Similarity NPD2799 Discontinued
0.8531 High Similarity NPD1607 Approved
0.8516 High Similarity NPD3749 Approved
0.8511 High Similarity NPD2313 Discontinued
0.8467 Intermediate Similarity NPD1512 Approved
0.8442 Intermediate Similarity NPD2801 Approved
0.8435 Intermediate Similarity NPD2800 Approved
0.8414 Intermediate Similarity NPD3748 Approved
0.8411 Intermediate Similarity NPD920 Approved
0.8397 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8389 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.8387 Intermediate Similarity NPD3817 Phase 2
0.838 Intermediate Similarity NPD3268 Approved
0.838 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.8377 Intermediate Similarity NPD1934 Approved
0.8366 Intermediate Similarity NPD6599 Discontinued
0.8356 Intermediate Similarity NPD1551 Phase 2
0.8356 Intermediate Similarity NPD2935 Discontinued
0.8286 Intermediate Similarity NPD2797 Approved
0.8286 Intermediate Similarity NPD1203 Approved
0.8278 Intermediate Similarity NPD2532 Approved
0.8278 Intermediate Similarity NPD2534 Approved
0.8278 Intermediate Similarity NPD2533 Approved
0.8278 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.8276 Intermediate Similarity NPD6651 Approved
0.8272 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8261 Intermediate Similarity NPD7473 Discontinued
0.8187 Intermediate Similarity NPD6232 Discontinued
0.8182 Intermediate Similarity NPD3226 Approved
0.8171 Intermediate Similarity NPD5953 Discontinued
0.817 Intermediate Similarity NPD5403 Approved
0.8133 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.8129 Intermediate Similarity NPD422 Phase 1
0.8125 Intermediate Similarity NPD6959 Discontinued
0.8101 Intermediate Similarity NPD3882 Suspended
0.8082 Intermediate Similarity NPD5124 Phase 1
0.8082 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.8072 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.8071 Intermediate Similarity NPD9717 Approved
0.8054 Intermediate Similarity NPD2346 Discontinued
0.8049 Intermediate Similarity NPD7286 Phase 2
0.8041 Intermediate Similarity NPD4308 Phase 3
0.8039 Intermediate Similarity NPD5401 Approved
0.8028 Intermediate Similarity NPD3266 Approved
0.8028 Intermediate Similarity NPD3267 Approved
0.8013 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD919 Approved
0.7988 Intermediate Similarity NPD3818 Discontinued
0.7987 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7986 Intermediate Similarity NPD6832 Phase 2
0.7975 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7975 Intermediate Similarity NPD6166 Phase 2
0.7975 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7972 Intermediate Similarity NPD2798 Approved
0.7958 Intermediate Similarity NPD3225 Approved
0.795 Intermediate Similarity NPD5494 Approved
0.7939 Intermediate Similarity NPD5844 Phase 1
0.7939 Intermediate Similarity NPD7054 Approved
0.7933 Intermediate Similarity NPD2344 Approved
0.7925 Intermediate Similarity NPD5402 Approved
0.7919 Intermediate Similarity NPD7033 Discontinued
0.7904 Intermediate Similarity NPD6559 Discontinued
0.7895 Intermediate Similarity NPD4628 Phase 3
0.7892 Intermediate Similarity NPD7472 Approved
0.7892 Intermediate Similarity NPD7074 Phase 3
0.7877 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7867 Intermediate Similarity NPD6099 Approved
0.7867 Intermediate Similarity NPD6100 Approved
0.7857 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7844 Intermediate Similarity NPD6797 Phase 2
0.7817 Intermediate Similarity NPD1608 Approved
0.78 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7798 Intermediate Similarity NPD7251 Discontinued
0.777 Intermediate Similarity NPD4307 Phase 2
0.7755 Intermediate Similarity NPD1296 Phase 2
0.7751 Intermediate Similarity NPD7808 Phase 3
0.775 Intermediate Similarity NPD1465 Phase 2
0.774 Intermediate Similarity NPD4908 Phase 1
0.7736 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD2309 Approved
0.7702 Intermediate Similarity NPD4288 Approved
0.7651 Intermediate Similarity NPD943 Approved
0.7636 Intermediate Similarity NPD5711 Approved
0.7636 Intermediate Similarity NPD5710 Approved
0.7635 Intermediate Similarity NPD411 Approved
0.7632 Intermediate Similarity NPD5405 Approved
0.7632 Intermediate Similarity NPD5406 Approved
0.7632 Intermediate Similarity NPD5404 Approved
0.7632 Intermediate Similarity NPD5408 Approved
0.7628 Intermediate Similarity NPD7390 Discontinued
0.7627 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD1610 Phase 2
0.7614 Intermediate Similarity NPD4363 Phase 3
0.7614 Intermediate Similarity NPD4360 Phase 2
0.761 Intermediate Similarity NPD7458 Discontinued
0.7606 Intermediate Similarity NPD17 Approved
0.76 Intermediate Similarity NPD447 Suspended
0.76 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7595 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7589 Intermediate Similarity NPD1548 Phase 1
0.7586 Intermediate Similarity NPD4287 Approved
0.7582 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.758 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7571 Intermediate Similarity NPD4361 Phase 2
0.7571 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7562 Intermediate Similarity NPD6585 Discontinued
0.7548 Intermediate Similarity NPD7003 Approved
0.7534 Intermediate Similarity NPD1164 Approved
0.753 Intermediate Similarity NPD7229 Phase 3
0.7529 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7517 Intermediate Similarity NPD3764 Approved
0.7516 Intermediate Similarity NPD5890 Approved
0.7516 Intermediate Similarity NPD5889 Approved
0.75 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD1933 Approved
0.747 Intermediate Similarity NPD1247 Approved
0.7465 Intermediate Similarity NPD9545 Approved
0.745 Intermediate Similarity NPD4625 Phase 3
0.7447 Intermediate Similarity NPD9493 Approved
0.7421 Intermediate Similarity NPD5049 Phase 3
0.7405 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.74 Intermediate Similarity NPD6798 Discontinued
0.7383 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.7381 Intermediate Similarity NPD3926 Phase 2
0.7372 Intermediate Similarity NPD2654 Approved
0.7368 Intermediate Similarity NPD230 Phase 1
0.7368 Intermediate Similarity NPD6355 Discontinued
0.7365 Intermediate Similarity NPD1019 Discontinued
0.7365 Intermediate Similarity NPD7199 Phase 2
0.7355 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7355 Intermediate Similarity NPD6004 Phase 3
0.7355 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7355 Intermediate Similarity NPD6005 Phase 3
0.7355 Intermediate Similarity NPD6002 Phase 3
0.7329 Intermediate Similarity NPD1481 Phase 2
0.7312 Intermediate Similarity NPD6273 Approved
0.7303 Intermediate Similarity NPD4060 Phase 1
0.7303 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD8312 Approved
0.7299 Intermediate Similarity NPD8313 Approved
0.729 Intermediate Similarity NPD4476 Approved
0.729 Intermediate Similarity NPD4477 Approved
0.7286 Intermediate Similarity NPD5535 Approved
0.7279 Intermediate Similarity NPD4749 Approved
0.7278 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD2354 Approved
0.7267 Intermediate Similarity NPD1729 Discontinued
0.7267 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7261 Intermediate Similarity NPD1652 Phase 2
0.726 Intermediate Similarity NPD1535 Discovery
0.726 Intermediate Similarity NPD1201 Approved
0.7251 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7235 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.723 Intermediate Similarity NPD1283 Approved
0.7222 Intermediate Similarity NPD1894 Discontinued
0.7211 Intermediate Similarity NPD3972 Approved
0.72 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7191 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD6971 Discontinued
0.7181 Intermediate Similarity NPD1470 Approved
0.7175 Intermediate Similarity NPD8434 Phase 2
0.7169 Intermediate Similarity NPD2296 Approved
0.7166 Intermediate Similarity NPD7584 Approved
0.7152 Intermediate Similarity NPD2614 Approved
0.7152 Intermediate Similarity NPD37 Approved
0.7151 Intermediate Similarity NPD7177 Discontinued
0.7143 Intermediate Similarity NPD6234 Discontinued
0.7134 Intermediate Similarity NPD1471 Phase 3
0.7134 Intermediate Similarity NPD2355 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD2353 Approved
0.7134 Intermediate Similarity NPD6502 Phase 2
0.7126 Intermediate Similarity NPD4967 Phase 2
0.7126 Intermediate Similarity NPD4965 Approved
0.7126 Intermediate Similarity NPD4966 Approved
0.7125 Intermediate Similarity NPD6667 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