Structure

Physi-Chem Properties

Molecular Weight:  230.09
Volume:  244.139
LogP:  3.391
LogD:  2.778
LogS:  -3.124
# Rotatable Bonds:  2
TPSA:  50.44
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.637
Synthetic Accessibility Score:  2.525
Fsp3:  0.214
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.698
MDCK Permeability:  2.214257801824715e-05
Pgp-inhibitor:  0.003
Pgp-substrate:  0.162
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.32
30% Bioavailability (F30%):  0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.031
Plasma Protein Binding (PPB):  91.77228546142578%
Volume Distribution (VD):  0.768
Pgp-substrate:  8.42446517944336%

ADMET: Metabolism

CYP1A2-inhibitor:  0.983
CYP1A2-substrate:  0.652
CYP2C19-inhibitor:  0.857
CYP2C19-substrate:  0.073
CYP2C9-inhibitor:  0.514
CYP2C9-substrate:  0.892
CYP2D6-inhibitor:  0.772
CYP2D6-substrate:  0.681
CYP3A4-inhibitor:  0.442
CYP3A4-substrate:  0.162

ADMET: Excretion

Clearance (CL):  15.606
Half-life (T1/2):  0.749

ADMET: Toxicity

hERG Blockers:  0.015
Human Hepatotoxicity (H-HT):  0.917
Drug-inuced Liver Injury (DILI):  0.757
AMES Toxicity:  0.298
Rat Oral Acute Toxicity:  0.196
Maximum Recommended Daily Dose:  0.048
Skin Sensitization:  0.43
Carcinogencity:  0.772
Eye Corrosion:  0.012
Eye Irritation:  0.255
Respiratory Toxicity:  0.789

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Similar NPs/Drugs  

  Natural Product: NPC244495

Natural Product ID:  NPC244495
Common Name*:   Osthenol
IUPAC Name:   7-hydroxy-8-(3-methylbut-2-enyl)chromen-2-one
Synonyms:   Osthenol
Standard InCHIKey:  RAKJVIPCCGXHHS-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C14H14O3/c1-9(2)3-6-11-12(15)7-4-10-5-8-13(16)17-14(10)11/h3-5,7-8,15H,6H2,1-2H3
SMILES:  CC(=CCc1c(ccc2ccc(=O)oc12)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL350475
PubChem CID:   5320318
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000145] Coumarins and derivatives
        • [CHEMONTID:0002908] Hydroxycoumarins
          • [CHEMONTID:0002909] 7-hydroxycoumarins

*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
NPO8680 Polypodium niponicum Species Polypodiaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0031-9422(00)80275-7]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. DOI[10.5012/bkcs.2003.24.11.1699]
NPO20244 Melicope semecarpifolia Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[11575945]
NPO18265 Citrus tamurana Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[11999424]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. PMID[12510838]
NPO24476.1 Phellodendron amurense var. wilsonii Varieties Rutaceae Eukaryota Leaves n.a. n.a. PMID[14510598]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. PMID[15646793]
NPO21056 Angelica keiskei Species Apiaceae Eukaryota exudates n.a. n.a. PMID[16441065]
NPO20244 Melicope semecarpifolia Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[18163582]
NPO21056 Angelica keiskei Species Apiaceae Eukaryota stems n.a. n.a. PMID[18558745]
NPO23546 Clausena lansium Species Rutaceae Eukaryota leaves n.a. n.a. PMID[19327990]
NPO30526 0topterygium incisum n.a. n.a. n.a. n.a. root n.a. PMID[20707067]
NPO30526 0topterygium incisum n.a. n.a. n.a. n.a. rhizome n.a. PMID[20707067]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[21625478]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. PMID[21657081]
NPO21056 Angelica keiskei Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[21824777]
NPO23546 Clausena lansium Species Rutaceae Eukaryota Stems n.a. n.a. PMID[22372931]
NPO23546 Clausena lansium Species Rutaceae Eukaryota Roots n.a. n.a. PMID[24798144]
NPO2392 Hansenia weberbaueriana Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[25333853]
NPO21056 Angelica keiskei Species Apiaceae Eukaryota stems n.a. n.a. PMID[25891102]
NPO23546 Clausena lansium Species Rutaceae Eukaryota Leaves n.a. n.a. PMID[26523463]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[27444348]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota Roots n.a. n.a. PMID[31464439]
NPO21056 Angelica keiskei Species Apiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO11785 Citrus hassaku Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23546 Clausena lansium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24178 Citrus rugulosa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20244 Melicope semecarpifolia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24476.1 Phellodendron amurense var. wilsonii Varieties Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12100 Citrus sulcata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21056 Angelica keiskei Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14773 Uncaria perrottetii Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8680 Polypodium niponicum Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30526 0topterygium incisum n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO18265 Citrus tamurana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18677 Anagallis arvensis Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23546 Clausena lansium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2392 Hansenia weberbaueriana Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21056 Angelica keiskei Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18265 Citrus tamurana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11785 Citrus hassaku Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24178 Citrus rugulosa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24476.1 Phellodendron amurense var. wilsonii Varieties Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20244 Melicope semecarpifolia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14773 Uncaria perrottetii Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12100 Citrus sulcata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8680 Polypodium niponicum Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23546 Clausena lansium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8680 Polypodium niponicum Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30526 0topterygium incisum n.a. n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2392 Hansenia weberbaueriana Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23546 Clausena lansium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12100 Citrus sulcata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8680 Polypodium niponicum Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18677 Anagallis arvensis Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20244 Melicope semecarpifolia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24178 Citrus rugulosa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14773 Uncaria perrottetii Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2629 Cystoseira caespitosa Species Sargassaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18265 Citrus tamurana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11785 Citrus hassaku Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21056 Angelica keiskei Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9366 Rosa transmorrisonensis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1117 Hypholoma capnoides Species Strophariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19014 Palythoa tuberculosa Species Sphenopidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24248.1 Lactarius deliciosus var. deterrimus Varieties Russulaceae 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
NPT30 Individual Protein Cyclooxygenase-1 Homo sapiens IC50 = 64000.0 nM PMID[464464]
NPT80 Cell Line Raji Homo sapiens Activity = 70.0 % PMID[464465]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 91833.26 nM PMID[464467]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 55462.57 nM PMID[464467]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 29376.5 nM PMID[464467]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 38370.72 nM PMID[464467]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 28248.8 nM PMID[464467]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 23988.33 nM PMID[464467]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 15275.66 nM PMID[464467]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 38194.43 nM PMID[464467]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 37583.74 nM PMID[464467]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 60117.37 nM PMID[464467]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 54827.7 nM PMID[464467]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 26915.35 nM PMID[464467]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 21877.62 nM PMID[464467]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 20892.96 nM PMID[464467]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 52966.34 nM PMID[464467]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 31622.78 nM PMID[464467]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 51880.0 nM PMID[464467]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 63679.55 nM PMID[464467]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[464467]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 47097.73 nM PMID[464467]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 48194.78 nM PMID[464467]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 75509.22 nM PMID[464467]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 20511.62 nM PMID[464467]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 92044.96 nM PMID[464467]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 26730.06 nM PMID[464467]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 37757.22 nM PMID[464467]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 51522.86 nM PMID[464467]
NPT168 Cell Line P388 Mus musculus GI50 n.a. 42657.95 nM PMID[464467]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 45708.82 nM PMID[464467]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 5834.45 nM PMID[464467]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 100000.0 nM PMID[464467]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 54450.27 nM PMID[464467]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 45814.19 nM PMID[464467]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 60117.37 nM PMID[464467]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 57411.65 nM PMID[464467]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 33651.16 nM PMID[464467]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 34914.03 nM PMID[464467]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 51641.64 nM PMID[464467]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 27925.44 nM PMID[464467]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[464467]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 44565.62 nM PMID[464467]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 73451.39 nM PMID[464467]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 61517.69 nM PMID[464467]
NPT552 Cell Line P388/ADR Mus musculus GI50 n.a. 50003.45 nM PMID[464467]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 68548.82 nM PMID[464467]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 45603.69 nM PMID[464467]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 31988.95 nM PMID[464467]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 33884.42 nM PMID[464467]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[464467]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 33036.95 nM PMID[464467]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 47643.1 nM PMID[464467]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[464467]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 49431.07 nM PMID[464467]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[464467]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 38547.84 nM PMID[464467]
NPT738 Cell Line SN12K1 Homo sapiens GI50 n.a. 59703.53 nM PMID[464467]
NPT732 Cell Line HOP-18 Homo sapiens GI50 n.a. 43551.19 nM PMID[464467]
NPT2794 Individual Protein Quinolone resistance protein norA Staphylococcus aureus MIC = 2.0 ug.mL-1 PMID[464469]
NPT2794 Individual Protein Quinolone resistance protein norA Staphylococcus aureus FC = 4.0 n.a. PMID[464469]
NPT2795 Individual Protein Fluoroquinolone resistance protein Staphylococcus aureus MIC = 256.0 ug.mL-1 PMID[464469]
NPT2795 Individual Protein Fluoroquinolone resistance protein Staphylococcus aureus FC = 0.0 n.a. PMID[464469]
NPT261 Individual Protein Monoamine oxidase A Homo sapiens Activity = 90.7 % PMID[464470]
NPT261 Individual Protein Monoamine oxidase A Homo sapiens Activity = 23.7 % PMID[464470]
NPT261 Individual Protein Monoamine oxidase A Homo sapiens Ki = 260.0 nM PMID[464470]
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus IC50 = 25300.0 nM PMID[464470]
NPT582 Individual Protein Monoamine oxidase B Homo sapiens IC50 > 60000.0 nM PMID[464470]
NPT261 Individual Protein Monoamine oxidase A Homo sapiens IC50 = 740.0 nM PMID[464470]
NPT582 Individual Protein Monoamine oxidase B Homo sapiens Activity = 84.7 % PMID[464470]
NPT261 Individual Protein Monoamine oxidase A Homo sapiens Activity = 9.9 % PMID[464470]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 90.4 % PMID[464463]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 23.2 % PMID[464463]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 13.7 % PMID[464463]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 89.8 % PMID[464463]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 84.8 % PMID[464463]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 79.2 % PMID[464463]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 87.0 % PMID[464463]
NPT2 Others Unspecified Activity = 0.0 % PMID[464465]
NPT2 Others Unspecified Activity = 30.1 % PMID[464465]
NPT2 Others Unspecified Activity = 69.8 % PMID[464465]
NPT2 Others Unspecified Activity = 90.6 % PMID[464465]
NPT2 Others Unspecified IC50 = 290.0 molar ratio PMID[464465]
NPT2 Others Unspecified Ratio = 2.0 n.a. PMID[464465]
NPT740 Individual Protein Beta-secretase 1 Homo sapiens IC50 > 500000.0 nM PMID[464466]
NPT740 Individual Protein Beta-secretase 1 Homo sapiens Inhibition = 39.4 % PMID[464466]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 2600.0 nM PMID[464468]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 10000.0 nM PMID[464468]
NPT2 Others Unspecified MIC = 32.0 ug.mL-1 PMID[464469]
NPT2 Others Unspecified FC = 0.0 n.a. PMID[464469]
NPT2 Others Unspecified MIC = 64.0 ug.mL-1 PMID[464469]
NPT2 Others Unspecified Ratio IC50 > 81.1 n.a. PMID[464470]

☑ 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 NPC244495 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 NPC93219
0.9833 High Similarity NPC243688
0.9661 High Similarity NPC52247
0.9496 High Similarity NPC187868
0.9492 High Similarity NPC247553
0.944 High Similarity NPC194277
0.9435 High Similarity NPC32463
0.9431 High Similarity NPC185066
0.9417 High Similarity NPC96286
0.9417 High Similarity NPC248429
0.9412 High Similarity NPC302107
0.9365 High Similarity NPC163557
0.9344 High Similarity NPC168259
0.9339 High Similarity NPC472518
0.9262 High Similarity NPC73413
0.9262 High Similarity NPC111347
0.9262 High Similarity NPC201667
0.9256 High Similarity NPC13007
0.9256 High Similarity NPC257188
0.9213 High Similarity NPC31849
0.918 High Similarity NPC273772
0.918 High Similarity NPC109675
0.9174 High Similarity NPC144418
0.916 High Similarity NPC152306
0.916 High Similarity NPC96705
0.916 High Similarity NPC265547
0.9141 High Similarity NPC326600
0.9141 High Similarity NPC50896
0.9141 High Similarity NPC204353
0.9141 High Similarity NPC131950
0.9113 High Similarity NPC188327
0.9113 High Similarity NPC234109
0.9106 High Similarity NPC291899
0.9106 High Similarity NPC27671
0.9083 High Similarity NPC281356
0.9083 High Similarity NPC298796
0.9048 High Similarity NPC168710
0.9048 High Similarity NPC474289
0.904 High Similarity NPC258567
0.904 High Similarity NPC224774
0.904 High Similarity NPC121740
0.9032 High Similarity NPC471827
0.9032 High Similarity NPC471828
0.9024 High Similarity NPC290605
0.9024 High Similarity NPC173350
0.9024 High Similarity NPC154176
0.9008 High Similarity NPC221046
0.9008 High Similarity NPC332594
0.9 High Similarity NPC26954
0.9 High Similarity NPC38099
0.8992 High Similarity NPC62366
0.8992 High Similarity NPC253574
0.8992 High Similarity NPC98179
0.8992 High Similarity NPC128633
0.8968 High Similarity NPC469453
0.8968 High Similarity NPC472519
0.8968 High Similarity NPC199204
0.896 High Similarity NPC471826
0.8934 High Similarity NPC235190
0.8934 High Similarity NPC163200
0.8934 High Similarity NPC180006
0.8931 High Similarity NPC225106
0.8931 High Similarity NPC281014
0.8931 High Similarity NPC294456
0.8931 High Similarity NPC212124
0.8931 High Similarity NPC184861
0.8923 High Similarity NPC33986
0.8906 High Similarity NPC37009
0.8906 High Similarity NPC66430
0.888 High Similarity NPC202594
0.888 High Similarity NPC232692
0.8872 High Similarity NPC183642
0.8872 High Similarity NPC310370
0.8871 High Similarity NPC315807
0.8864 High Similarity NPC279573
0.8864 High Similarity NPC151946
0.8855 High Similarity NPC78746
0.8855 High Similarity NPC224543
0.8855 High Similarity NPC188380
0.8846 High Similarity NPC224475
0.8846 High Similarity NPC213173
0.8846 High Similarity NPC180716
0.8828 High Similarity NPC80170
0.8828 High Similarity NPC113098
0.8819 High Similarity NPC157212
0.8788 High Similarity NPC232246
0.8788 High Similarity NPC153818
0.8788 High Similarity NPC155963
0.878 High Similarity NPC319378
0.8779 High Similarity NPC472525
0.8779 High Similarity NPC61499
0.8769 High Similarity NPC83535
0.876 High Similarity NPC263754
0.876 High Similarity NPC250727
0.876 High Similarity NPC272650
0.876 High Similarity NPC267336
0.876 High Similarity NPC183154
0.876 High Similarity NPC29734
0.8731 High Similarity NPC170812
0.8731 High Similarity NPC195357
0.8731 High Similarity NPC152771
0.8722 High Similarity NPC211110
0.872 High Similarity NPC50720
0.8702 High Similarity NPC92830
0.8692 High Similarity NPC281558
0.8692 High Similarity NPC307289
0.8692 High Similarity NPC14248
0.8692 High Similarity NPC175159
0.8692 High Similarity NPC19157
0.8676 High Similarity NPC471824
0.8657 High Similarity NPC71903
0.8657 High Similarity NPC312881
0.8647 High Similarity NPC474886
0.8644 High Similarity NPC141068
0.864 High Similarity NPC150214
0.8626 High Similarity NPC318400
0.8626 High Similarity NPC133956
0.8626 High Similarity NPC296624
0.8626 High Similarity NPC207002
0.8626 High Similarity NPC1220
0.8626 High Similarity NPC205797
0.8626 High Similarity NPC167111
0.8626 High Similarity NPC291551
0.8626 High Similarity NPC277021
0.8626 High Similarity NPC469449
0.8626 High Similarity NPC7526
0.8626 High Similarity NPC472524
0.8626 High Similarity NPC241165
0.8626 High Similarity NPC141822
0.8626 High Similarity NPC55147
0.8626 High Similarity NPC2363
0.8626 High Similarity NPC222036
0.8626 High Similarity NPC142563
0.8626 High Similarity NPC471910
0.8615 High Similarity NPC73738
0.8615 High Similarity NPC472517
0.8613 High Similarity NPC475719
0.8613 High Similarity NPC101255
0.8613 High Similarity NPC43716
0.8613 High Similarity NPC295696
0.8613 High Similarity NPC71739
0.8603 High Similarity NPC229916
0.8603 High Similarity NPC236419
0.8593 High Similarity NPC287286
0.8582 High Similarity NPC37428
0.8582 High Similarity NPC35501
0.8582 High Similarity NPC47040
0.8582 High Similarity NPC148738
0.8582 High Similarity NPC319870
0.8582 High Similarity NPC278600
0.8582 High Similarity NPC144512
0.8582 High Similarity NPC137262
0.8582 High Similarity NPC73078
0.8582 High Similarity NPC327612
0.8571 High Similarity NPC223616
0.8571 High Similarity NPC143725
0.8571 High Similarity NPC151113
0.8561 High Similarity NPC198381
0.8561 High Similarity NPC18804
0.8561 High Similarity NPC74655
0.8561 High Similarity NPC260265
0.8561 High Similarity NPC307412
0.8561 High Similarity NPC319859
0.8561 High Similarity NPC164269
0.8561 High Similarity NPC55149
0.8561 High Similarity NPC127888
0.8561 High Similarity NPC100986
0.8561 High Similarity NPC47163
0.8561 High Similarity NPC287182
0.8561 High Similarity NPC195343
0.8561 High Similarity NPC267412
0.8561 High Similarity NPC84894
0.8561 High Similarity NPC166672
0.855 High Similarity NPC137949
0.854 High Similarity NPC471763
0.8537 High Similarity NPC131118
0.8537 High Similarity NPC74821
0.8527 High Similarity NPC2401
0.8527 High Similarity NPC219923
0.8525 High Similarity NPC33717
0.8516 High Similarity NPC163248
0.8507 High Similarity NPC471068
0.8507 High Similarity NPC52086
0.8507 High Similarity NPC148835
0.8507 High Similarity NPC38874
0.8507 High Similarity NPC131198
0.8507 High Similarity NPC471069
0.8507 High Similarity NPC76336
0.8507 High Similarity NPC20511
0.8507 High Similarity NPC139548
0.8507 High Similarity NPC95162
0.8504 High Similarity NPC246648
0.8504 High Similarity NPC197351
0.8504 High Similarity NPC106914
0.8504 High Similarity NPC134195
0.8504 High Similarity NPC159132
0.8504 High Similarity NPC86502
0.8504 High Similarity NPC140521
0.85 High Similarity NPC199462
0.8496 Intermediate Similarity NPC471909

  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 NPC244495 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
0.9661 High Similarity NPD422 Phase 1
0.8626 High Similarity NPD5124 Phase 1
0.8626 High Similarity NPD5123 Clinical (unspecified phase)
0.8537 High Similarity NPD1548 Phase 1
0.8385 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.8268 Intermediate Similarity NPD1610 Phase 2
0.8261 Intermediate Similarity NPD3750 Approved
0.8258 Intermediate Similarity NPD1296 Phase 2
0.822 Intermediate Similarity NPD9697 Approved
0.8154 Intermediate Similarity NPD2797 Approved
0.812 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.812 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.8077 Intermediate Similarity NPD3225 Approved
0.8058 Intermediate Similarity NPD1652 Phase 2
0.8058 Intermediate Similarity NPD1243 Approved
0.8 Intermediate Similarity NPD1240 Approved
0.8 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.797 Intermediate Similarity NPD4908 Phase 1
0.7923 Intermediate Similarity NPD9717 Approved
0.791 Intermediate Similarity NPD4625 Phase 3
0.7902 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7902 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7899 Intermediate Similarity NPD3748 Approved
0.7883 Intermediate Similarity NPD1607 Approved
0.7879 Intermediate Similarity NPD1203 Approved
0.7863 Intermediate Similarity NPD4749 Approved
0.7857 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7857 Intermediate Similarity NPD1549 Phase 2
0.7852 Intermediate Similarity NPD3268 Approved
0.7842 Intermediate Similarity NPD1551 Phase 2
0.7836 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7829 Intermediate Similarity NPD4626 Approved
0.7823 Intermediate Similarity NPD7411 Suspended
0.7815 Intermediate Similarity NPD940 Approved
0.7815 Intermediate Similarity NPD846 Approved
0.7801 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7786 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7786 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.777 Intermediate Similarity NPD1510 Phase 2
0.7762 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7761 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.776 Intermediate Similarity NPD5535 Approved
0.774 Intermediate Similarity NPD1653 Approved
0.7733 Intermediate Similarity NPD7768 Phase 2
0.7682 Intermediate Similarity NPD7075 Discontinued
0.7671 Intermediate Similarity NPD920 Approved
0.7655 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7651 Intermediate Similarity NPD6801 Discontinued
0.7643 Intermediate Similarity NPD4308 Phase 3
0.7622 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7615 Intermediate Similarity NPD5691 Approved
0.7612 Intermediate Similarity NPD3266 Approved
0.7612 Intermediate Similarity NPD3267 Approved
0.7609 Intermediate Similarity NPD4060 Phase 1
0.7609 Intermediate Similarity NPD1613 Approved
0.7609 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD7819 Suspended
0.7591 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7589 Intermediate Similarity NPD2796 Approved
0.7589 Intermediate Similarity NPD2935 Discontinued
0.7586 Intermediate Similarity NPD6799 Approved
0.7561 Intermediate Similarity NPD3134 Approved
0.7538 Intermediate Similarity NPD9545 Approved
0.7519 Intermediate Similarity NPD1608 Approved
0.7518 Intermediate Similarity NPD2799 Discontinued
0.75 Intermediate Similarity NPD3496 Discontinued
0.75 Intermediate Similarity NPD1358 Approved
0.7467 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7466 Intermediate Similarity NPD1511 Approved
0.7464 Intermediate Similarity NPD2313 Discontinued
0.7451 Intermediate Similarity NPD3749 Approved
0.7444 Intermediate Similarity NPD1611 Approved
0.7444 Intermediate Similarity NPD1535 Discovery
0.7442 Intermediate Similarity NPD6671 Approved
0.7431 Intermediate Similarity NPD2800 Approved
0.7424 Intermediate Similarity NPD1778 Approved
0.7422 Intermediate Similarity NPD1241 Discontinued
0.74 Intermediate Similarity NPD6599 Discontinued
0.74 Intermediate Similarity NPD4380 Phase 2
0.7397 Intermediate Similarity NPD6667 Approved
0.7397 Intermediate Similarity NPD6666 Approved
0.7394 Intermediate Similarity NPD7033 Discontinued
0.7389 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7388 Intermediate Similarity NPD1481 Phase 2
0.7385 Intermediate Similarity NPD9493 Approved
0.7368 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD1512 Approved
0.736 Intermediate Similarity NPD290 Approved
0.7357 Intermediate Similarity NPD4307 Phase 2
0.7343 Intermediate Similarity NPD6099 Approved
0.7343 Intermediate Similarity NPD6100 Approved
0.7338 Intermediate Similarity NPD411 Approved
0.732 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD4288 Approved
0.7319 Intermediate Similarity NPD6832 Phase 2
0.7315 Intermediate Similarity NPD5403 Approved
0.7313 Intermediate Similarity NPD1091 Approved
0.7305 Intermediate Similarity NPD4340 Discontinued
0.7305 Intermediate Similarity NPD447 Suspended
0.7302 Intermediate Similarity NPD2684 Approved
0.7299 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD2533 Approved
0.7297 Intermediate Similarity NPD2534 Approved
0.7297 Intermediate Similarity NPD5401 Approved
0.7297 Intermediate Similarity NPD2532 Approved
0.7293 Intermediate Similarity NPD17 Approved
0.729 Intermediate Similarity NPD919 Approved
0.728 Intermediate Similarity NPD968 Approved
0.7273 Intermediate Similarity NPD1894 Discontinued
0.7273 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7266 Intermediate Similarity NPD3027 Phase 3
0.726 Intermediate Similarity NPD4628 Phase 3
0.7255 Intermediate Similarity NPD1465 Phase 2
0.725 Intermediate Similarity NPD5844 Phase 1
0.7246 Intermediate Similarity NPD2861 Phase 2
0.723 Intermediate Similarity NPD7212 Phase 2
0.723 Intermediate Similarity NPD7213 Phase 3
0.7226 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD3226 Approved
0.7214 Intermediate Similarity NPD6798 Discontinued
0.719 Intermediate Similarity NPD1934 Approved
0.7183 Intermediate Similarity NPD230 Phase 1
0.7181 Intermediate Similarity NPD7447 Phase 1
0.7174 Intermediate Similarity NPD1019 Discontinued
0.7172 Intermediate Similarity NPD6005 Phase 3
0.7172 Intermediate Similarity NPD6004 Phase 3
0.7172 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD6002 Phase 3
0.7172 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD5953 Discontinued
0.7154 Intermediate Similarity NPD1242 Phase 1
0.7153 Intermediate Similarity NPD8651 Approved
0.7153 Intermediate Similarity NPD1283 Approved
0.7153 Intermediate Similarity NPD6696 Suspended
0.7143 Intermediate Similarity NPD7286 Phase 2
0.7143 Intermediate Similarity NPD2801 Approved
0.7133 Intermediate Similarity NPD6651 Approved
0.7123 Intermediate Similarity NPD2424 Discontinued
0.7113 Intermediate Similarity NPD4140 Approved
0.7111 Intermediate Similarity NPD3847 Discontinued
0.7109 Intermediate Similarity NPD4750 Phase 3
0.7105 Intermediate Similarity NPD8158 Clinical (unspecified phase)
0.7103 Intermediate Similarity NPD4477 Approved
0.7103 Intermediate Similarity NPD4476 Approved
0.7101 Intermediate Similarity NPD1164 Approved
0.7101 Intermediate Similarity NPD987 Approved
0.7097 Intermediate Similarity NPD3817 Phase 2
0.7092 Intermediate Similarity NPD3764 Approved
0.708 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7077 Intermediate Similarity NPD7843 Approved
0.7077 Intermediate Similarity NPD821 Approved
0.7063 Intermediate Similarity NPD6355 Discontinued
0.7055 Intermediate Similarity NPD2344 Approved
0.7055 Intermediate Similarity NPD2346 Discontinued
0.7055 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7051 Intermediate Similarity NPD3882 Suspended
0.705 Intermediate Similarity NPD3690 Phase 2
0.705 Intermediate Similarity NPD3691 Phase 2
0.7044 Intermediate Similarity NPD6232 Discontinued
0.7037 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD7003 Approved
0.7021 Intermediate Similarity NPD7095 Approved
0.7012 Intermediate Similarity NPD6559 Discontinued
0.7 Intermediate Similarity NPD7837 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD228 Approved
0.6987 Remote Similarity NPD5402 Approved
0.6972 Remote Similarity NPD1048 Approved
0.697 Remote Similarity NPD7549 Discontinued
0.6967 Remote Similarity NPD2860 Approved
0.6967 Remote Similarity NPD2859 Approved
0.6967 Remote Similarity NPD1809 Phase 2
0.6966 Remote Similarity NPD7097 Phase 1
0.6957 Remote Similarity NPD6583 Phase 3
0.6957 Remote Similarity NPD6582 Phase 2
0.6953 Remote Similarity NPD9265 Clinical (unspecified phase)
0.695 Remote Similarity NPD2614 Approved
0.6944 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6942 Remote Similarity NPD845 Approved
0.6939 Remote Similarity NPD5763 Approved
0.6939 Remote Similarity NPD5762 Approved
0.6937 Remote Similarity NPD7229 Phase 3
0.6934 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6934 Remote Similarity NPD1281 Approved
0.6929 Remote Similarity NPD2798 Approved
0.6923 Remote Similarity NPD6233 Phase 2
0.6917 Remote Similarity NPD7157 Approved
0.6914 Remote Similarity NPD7473 Discontinued
0.6908 Remote Similarity NPD5049 Phase 3
0.6908 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6908 Remote Similarity NPD1940 Clinical (unspecified phase)
0.6901 Remote Similarity NPD5163 Phase 2
0.6899 Remote Similarity NPD6971 Discontinued
0.6899 Remote Similarity NPD9266 Approved
0.6899 Remote Similarity NPD74 Approved
0.6894 Remote Similarity NPD1398 Phase 1
0.6885 Remote Similarity NPD2933 Approved
0.6885 Remote Similarity NPD2934 Approved
0.6883 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6879 Remote Similarity NPD3018 Phase 2

  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