Structure

Physi-Chem Properties

Molecular Weight:  414.35
Volume:  470.926
LogP:  6.012
LogD:  5.396
LogS:  -5.661
# Rotatable Bonds:  5
TPSA:  40.46
# H-Bond Aceptor:  2
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.502
Synthetic Accessibility Score:  4.701
Fsp3:  0.857
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.695
MDCK Permeability:  1.642915594857186e-05
Pgp-inhibitor:  0.981
Pgp-substrate:  0.753
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.994
30% Bioavailability (F30%):  0.385

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.254
Plasma Protein Binding (PPB):  95.46034240722656%
Volume Distribution (VD):  1.078
Pgp-substrate:  2.0677945613861084%

ADMET: Metabolism

CYP1A2-inhibitor:  0.11
CYP1A2-substrate:  0.672
CYP2C19-inhibitor:  0.127
CYP2C19-substrate:  0.924
CYP2C9-inhibitor:  0.337
CYP2C9-substrate:  0.416
CYP2D6-inhibitor:  0.029
CYP2D6-substrate:  0.855
CYP3A4-inhibitor:  0.606
CYP3A4-substrate:  0.633

ADMET: Excretion

Clearance (CL):  7.219
Half-life (T1/2):  0.058

ADMET: Toxicity

hERG Blockers:  0.713
Human Hepatotoxicity (H-HT):  0.132
Drug-inuced Liver Injury (DILI):  0.75
AMES Toxicity:  0.01
Rat Oral Acute Toxicity:  0.191
Maximum Recommended Daily Dose:  0.874
Skin Sensitization:  0.582
Carcinogencity:  0.154
Eye Corrosion:  0.014
Eye Irritation:  0.232
Respiratory Toxicity:  0.511

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  Natural Product: NPC209411

Natural Product ID:  NPC209411
Common Name*:   Picropodophyllone
IUPAC Name:   (5aR,8aS,9R)-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-[2]benzofuro[5,6-f][1,3]benzodioxole-5,8-dione
Synonyms:  
Standard InCHIKey:  ISCQYPPCSYRZOT-MJXNMMHHSA-N
Standard InCHI:  InChI=1S/C22H20O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-19H,8-9H2,1-3H3/t13-,18+,19+/m0/s1
SMILES:  COc1cc(cc(c1OC)OC)[C@@H]1c2cc3c(cc2C(=O)[C@H]2COC(=O)[C@@H]12)OCO3
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL82303
PubChem CID:   3083574
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds
      • [CHEMONTID:0001510] Lignan lactones

*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
NPO21891 Panax notoginseng Species Araliaceae Eukaryota Flower buds n.a. n.a. PMID[12880307]
NPO17807 Dysosma versipellis Species Berberidaceae Eukaryota n.a. root n.a. PMID[17256902]
NPO17807 Dysosma versipellis Species Berberidaceae Eukaryota Roots Panan, Zhejiang Province, China 2004-MAY PMID[17256902]
NPO21891 Panax notoginseng Species Araliaceae Eukaryota Stems n.a. n.a. PMID[17663584]
NPO21891 Panax notoginseng Species Araliaceae Eukaryota Roots n.a. n.a. PMID[18186611]
NPO26380 Tacca plantaginea Species Taccaceae Eukaryota n.a. n.a. n.a. PMID[23031596]
NPO17807 Dysosma versipellis Species Berberidaceae Eukaryota n.a. n.a. n.a. PMID[25712646]
NPO11163 Methylobacterium organophilum Species Methylobacteriaceae Bacteria n.a. n.a. n.a. PMID[26032177]
NPO21891 Panax notoginseng Species Araliaceae Eukaryota Steamed Roots n.a. n.a. PMID[26200131]
NPO10903 Sinopodophyllum hexandrum Species Berberidaceae Eukaryota n.a. n.a. n.a. PMID[26359402]
NPO11163 Methylobacterium organophilum Species Methylobacteriaceae Bacteria n.a. n.a. n.a. PMID[3928379]
NPO7946 Navicula delognei Species Berkeleyaceae Eukaryota n.a. n.a. n.a. PMID[6512534]
NPO20275 Juniperus sabina Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23382 Podophyllum emodii Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17807 Dysosma versipellis Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26868 Diphylleia sinensis Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22413 Dysosma aurantiocaulis Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27244 Dysosma pleiantha Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26380 Tacca plantaginea Species Taccaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25340 Galega officinalis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25340 Galega officinalis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22208 Spiraea mongolica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7946 Navicula delognei Species Berkeleyaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23382 Podophyllum emodii Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27244 Dysosma pleiantha Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5627 Dysosma majoensis Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20275 Juniperus sabina Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26868 Diphylleia sinensis Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27647 Diphylleia cymosa Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26380 Tacca plantaginea Species Taccaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17807 Dysosma versipellis Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22413 Dysosma aurantiocaulis Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26868 Diphylleia sinensis Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22208 Spiraea mongolica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20275 Juniperus sabina Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26380 Tacca plantaginea Species Taccaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21891 Panax notoginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17807 Dysosma versipellis Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10903 Sinopodophyllum hexandrum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21891 Panax notoginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16081 Peltophorum dasyrhachis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23767 Aspropaxillus candidus Species Tricholomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18134 Heliobacterium modesticaldum Species Heliobacteriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO22413 Dysosma aurantiocaulis Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21763 Parmotrema subisidiosum Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3025 Schefflera capitata Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21288 Ficus rumphii Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25340 Galega officinalis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3675 Actinobole uliginosum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19243 Sarcophyton decaryi Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26179 Chrysosplenium tetrandrum Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22208 Spiraea mongolica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26710 Hypotrachyna rachista Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21892 Eisenibacter elegans Species Microscillaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO11163 Methylobacterium organophilum Species Methylobacteriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO4464 Senecio mexicanus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25651 Tecoma grandiflora Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21891 Panax notoginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27244 Dysosma pleiantha Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23074 Achillea grandifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11417 Gesneria cardinalis Species Crambidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26868 Diphylleia sinensis Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18381 Inula eupatorioides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7946 Navicula delognei Species Berkeleyaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27647 Diphylleia cymosa Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22783 Pteris arguta Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22726 Carthamus lanatus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20275 Juniperus sabina Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17807 Dysosma versipellis Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26380 Tacca plantaginea Species Taccaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13152 Chalcas paniculata n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO10903 Sinopodophyllum hexandrum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22266 Fagus taurica Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6893 Dimorphotheca sinuata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22026 Sibthorpia africana Species Plantaginaceae 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
NPT168 Cell Line P388 Mus musculus IC50 = 12000.0 nM PMID[506355]
NPT81 Cell Line A549 Homo sapiens IC50 = 12000.0 nM PMID[506355]
NPT139 Cell Line HT-29 Homo sapiens IC50 = 12000.0 nM PMID[506355]
NPT3885 Cell Line CV-1 Chlorocebus aethiops IC50 = 48000.0 nM PMID[506355]
NPT1769 Organism Mythimna separata Mythimna separata mortality = 27.6 % PMID[506356]
NPT1769 Organism Mythimna separata Mythimna separata mortality = 20.7 % PMID[506356]
NPT1769 Organism Mythimna separata Mythimna separata mortality = 16.7 % PMID[506356]

☑ 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 NPC209411 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 NPC239890
0.9427 High Similarity NPC61141
0.9167 High Similarity NPC234730
0.9145 High Similarity NPC80230
0.9145 High Similarity NPC304687
0.9145 High Similarity NPC101755
0.9145 High Similarity NPC104024
0.9145 High Similarity NPC65574
0.9114 High Similarity NPC474043
0.9103 High Similarity NPC273578
0.9091 High Similarity NPC149505
0.9062 High Similarity NPC76687
0.9045 High Similarity NPC254163
0.9038 High Similarity NPC308555
0.9032 High Similarity NPC210642
0.9032 High Similarity NPC13985
0.9026 High Similarity NPC177476
0.9026 High Similarity NPC262455
0.9024 High Similarity NPC178737
0.8994 High Similarity NPC325122
0.8987 High Similarity NPC473900
0.8974 High Similarity NPC104353
0.8961 High Similarity NPC40654
0.8961 High Similarity NPC262804
0.8947 High Similarity NPC475000
0.8882 High Similarity NPC191352
0.8882 High Similarity NPC258322
0.8875 High Similarity NPC125713
0.8868 High Similarity NPC301897
0.8834 High Similarity NPC477884
0.8831 High Similarity NPC193779
0.8831 High Similarity NPC213482
0.882 High Similarity NPC474770
0.882 High Similarity NPC78944
0.8816 High Similarity NPC40237
0.8816 High Similarity NPC151423
0.878 High Similarity NPC474042
0.878 High Similarity NPC174734
0.8774 High Similarity NPC24257
0.8774 High Similarity NPC153620
0.8766 High Similarity NPC474158
0.8758 High Similarity NPC137920
0.8758 High Similarity NPC86455
0.8758 High Similarity NPC125134
0.875 High Similarity NPC32373
0.875 High Similarity NPC115123
0.875 High Similarity NPC477380
0.875 High Similarity NPC239113
0.875 High Similarity NPC237946
0.8743 High Similarity NPC477881
0.8743 High Similarity NPC474568
0.8742 High Similarity NPC348849
0.8742 High Similarity NPC30009
0.8742 High Similarity NPC103197
0.8742 High Similarity NPC57211
0.8742 High Similarity NPC178195
0.8734 High Similarity NPC220577
0.8712 High Similarity NPC108767
0.8701 High Similarity NPC92693
0.8701 High Similarity NPC218841
0.8696 High Similarity NPC181168
0.8696 High Similarity NPC19947
0.8696 High Similarity NPC115281
0.8696 High Similarity NPC207584
0.8696 High Similarity NPC477885
0.8696 High Similarity NPC163527
0.8693 High Similarity NPC176586
0.8693 High Similarity NPC210354
0.8688 High Similarity NPC478238
0.8679 High Similarity NPC52623
0.8679 High Similarity NPC68882
0.8675 High Similarity NPC117911
0.8662 High Similarity NPC127827
0.8662 High Similarity NPC477698
0.8659 High Similarity NPC475865
0.865 High Similarity NPC15212
0.865 High Similarity NPC319749
0.8642 High Similarity NPC68619
0.8639 High Similarity NPC196771
0.8636 High Similarity NPC474288
0.8625 High Similarity NPC478213
0.8623 High Similarity NPC477883
0.8616 High Similarity NPC279061
0.8614 High Similarity NPC79322
0.8614 High Similarity NPC471180
0.8614 High Similarity NPC42230
0.8614 High Similarity NPC474948
0.8606 High Similarity NPC475738
0.8606 High Similarity NPC475953
0.8598 High Similarity NPC280778
0.859 High Similarity NPC296575
0.859 High Similarity NPC224687
0.859 High Similarity NPC87295
0.8589 High Similarity NPC119910
0.8589 High Similarity NPC218471
0.8589 High Similarity NPC96593
0.8589 High Similarity NPC239818
0.8589 High Similarity NPC268718
0.8589 High Similarity NPC150943
0.8589 High Similarity NPC91634
0.8588 High Similarity NPC477880
0.8588 High Similarity NPC477882
0.8581 High Similarity NPC191158
0.8581 High Similarity NPC177644
0.858 High Similarity NPC310206
0.858 High Similarity NPC146803
0.858 High Similarity NPC258644
0.858 High Similarity NPC19600
0.8562 High Similarity NPC245948
0.8562 High Similarity NPC148497
0.8562 High Similarity NPC153008
0.8553 High Similarity NPC62354
0.8553 High Similarity NPC164082
0.8553 High Similarity NPC477700
0.8553 High Similarity NPC303519
0.8553 High Similarity NPC32079
0.8544 High Similarity NPC476058
0.8537 High Similarity NPC152424
0.8537 High Similarity NPC288149
0.8537 High Similarity NPC115624
0.8537 High Similarity NPC100465
0.8528 High Similarity NPC113055
0.8526 High Similarity NPC229787
0.8519 High Similarity NPC474983
0.8519 High Similarity NPC155063
0.8509 High Similarity NPC54179
0.85 High Similarity NPC56184
0.85 High Similarity NPC118332
0.85 High Similarity NPC477699
0.8497 Intermediate Similarity NPC470962
0.8494 Intermediate Similarity NPC474647
0.8494 Intermediate Similarity NPC474301
0.8491 Intermediate Similarity NPC475722
0.8485 Intermediate Similarity NPC116838
0.8485 Intermediate Similarity NPC22130
0.8485 Intermediate Similarity NPC478199
0.8476 Intermediate Similarity NPC19554
0.8476 Intermediate Similarity NPC470637
0.8476 Intermediate Similarity NPC74749
0.8476 Intermediate Similarity NPC43971
0.8466 Intermediate Similarity NPC474990
0.8462 Intermediate Similarity NPC469506
0.8462 Intermediate Similarity NPC471181
0.8462 Intermediate Similarity NPC475964
0.8457 Intermediate Similarity NPC188962
0.8457 Intermediate Similarity NPC202249
0.8457 Intermediate Similarity NPC42871
0.8452 Intermediate Similarity NPC49487
0.8452 Intermediate Similarity NPC99613
0.8447 Intermediate Similarity NPC477960
0.8447 Intermediate Similarity NPC38469
0.8447 Intermediate Similarity NPC475116
0.8447 Intermediate Similarity NPC477962
0.8447 Intermediate Similarity NPC474514
0.8447 Intermediate Similarity NPC477961
0.8443 Intermediate Similarity NPC320471
0.8443 Intermediate Similarity NPC471923
0.8443 Intermediate Similarity NPC118162
0.8443 Intermediate Similarity NPC83049
0.8438 Intermediate Similarity NPC474660
0.8438 Intermediate Similarity NPC473466
0.8434 Intermediate Similarity NPC14294
0.8434 Intermediate Similarity NPC116759
0.843 Intermediate Similarity NPC212290
0.8428 Intermediate Similarity NPC174512
0.8428 Intermediate Similarity NPC477695
0.8428 Intermediate Similarity NPC293757
0.8428 Intermediate Similarity NPC24193
0.8428 Intermediate Similarity NPC474965
0.8428 Intermediate Similarity NPC668
0.8428 Intermediate Similarity NPC85141
0.8424 Intermediate Similarity NPC34376
0.8421 Intermediate Similarity NPC72796
0.8421 Intermediate Similarity NPC44245
0.8415 Intermediate Similarity NPC50430
0.8412 Intermediate Similarity NPC98776
0.8412 Intermediate Similarity NPC72455
0.8408 Intermediate Similarity NPC27106
0.8408 Intermediate Similarity NPC327052
0.8405 Intermediate Similarity NPC261484
0.84 Intermediate Similarity NPC475360
0.8395 Intermediate Similarity NPC136757
0.8395 Intermediate Similarity NPC287504
0.8395 Intermediate Similarity NPC244371
0.8393 Intermediate Similarity NPC311912
0.8393 Intermediate Similarity NPC475453
0.8393 Intermediate Similarity NPC473531
0.8387 Intermediate Similarity NPC246474
0.8387 Intermediate Similarity NPC162851
0.8387 Intermediate Similarity NPC218092
0.8385 Intermediate Similarity NPC473732
0.8385 Intermediate Similarity NPC151425
0.8383 Intermediate Similarity NPC222531
0.8382 Intermediate Similarity NPC170203
0.8375 Intermediate Similarity NPC474648
0.8373 Intermediate Similarity NPC18284
0.8373 Intermediate Similarity NPC273021
0.8373 Intermediate Similarity NPC469575
0.8366 Intermediate Similarity NPC11453
0.8365 Intermediate Similarity NPC474999

  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 NPC209411 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
0.8961 High Similarity NPD6980 Clinical (unspecified phase)
0.875 High Similarity NPD4967 Phase 2
0.875 High Similarity NPD4965 Approved
0.875 High Similarity NPD4966 Approved
0.8642 High Similarity NPD6234 Discontinued
0.8562 High Similarity NPD37 Approved
0.8443 Intermediate Similarity NPD7473 Discontinued
0.8373 Intermediate Similarity NPD6232 Discontinued
0.8313 Intermediate Similarity NPD7199 Phase 2
0.8284 Intermediate Similarity NPD7228 Approved
0.8253 Intermediate Similarity NPD5494 Approved
0.8214 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.8176 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.8176 Intermediate Similarity NPD3818 Discontinued
0.8092 Intermediate Similarity NPD7240 Approved
0.8061 Intermediate Similarity NPD7819 Suspended
0.8012 Intermediate Similarity NPD3817 Phase 2
0.8011 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7919 Intermediate Similarity NPD5844 Phase 1
0.7895 Intermediate Similarity NPD3926 Phase 2
0.787 Intermediate Similarity NPD919 Approved
0.7857 Intermediate Similarity NPD3882 Suspended
0.7857 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7853 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7791 Intermediate Similarity NPD2533 Approved
0.7791 Intermediate Similarity NPD2534 Approved
0.7791 Intermediate Similarity NPD2532 Approved
0.7771 Intermediate Similarity NPD7074 Phase 3
0.774 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7714 Intermediate Similarity NPD7054 Approved
0.7692 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7684 Intermediate Similarity NPD6559 Discontinued
0.768 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7679 Intermediate Similarity NPD1934 Approved
0.767 Intermediate Similarity NPD7472 Approved
0.7665 Intermediate Similarity NPD6599 Discontinued
0.764 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7633 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7633 Intermediate Similarity NPD1465 Phase 2
0.7633 Intermediate Similarity NPD2801 Approved
0.7633 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7625 Intermediate Similarity NPD2796 Approved
0.7622 Intermediate Similarity NPD6799 Approved
0.7619 Intermediate Similarity NPD7411 Suspended
0.7602 Intermediate Similarity NPD7075 Discontinued
0.7602 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7586 Intermediate Similarity NPD5242 Approved
0.7574 Intermediate Similarity NPD6801 Discontinued
0.7572 Intermediate Similarity NPD1247 Approved
0.7562 Intermediate Similarity NPD3748 Approved
0.7543 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7543 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7543 Intermediate Similarity NPD6166 Phase 2
0.7542 Intermediate Similarity NPD7808 Phase 3
0.7528 Intermediate Similarity NPD6797 Phase 2
0.7513 Intermediate Similarity NPD5005 Approved
0.7513 Intermediate Similarity NPD5006 Approved
0.75 Intermediate Similarity NPD3226 Approved
0.75 Intermediate Similarity NPD3749 Approved
0.75 Intermediate Similarity NPD7458 Discontinued
0.7486 Intermediate Similarity NPD7251 Discontinued
0.7486 Intermediate Similarity NPD7685 Pre-registration
0.7485 Intermediate Similarity NPD1243 Approved
0.7485 Intermediate Similarity NPD5353 Approved
0.7485 Intermediate Similarity NPD920 Approved
0.7484 Intermediate Similarity NPD1933 Approved
0.7471 Intermediate Similarity NPD6959 Discontinued
0.7461 Intermediate Similarity NPD8151 Discontinued
0.7456 Intermediate Similarity NPD4380 Phase 2
0.7447 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.743 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD8312 Approved
0.7403 Intermediate Similarity NPD8313 Approved
0.7394 Intermediate Similarity NPD4420 Approved
0.7386 Intermediate Similarity NPD3705 Approved
0.7384 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7377 Intermediate Similarity NPD8434 Phase 2
0.7375 Intermediate Similarity NPD230 Phase 1
0.7365 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7353 Intermediate Similarity NPD7028 Phase 2
0.7349 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7346 Intermediate Similarity NPD1510 Phase 2
0.7346 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7345 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD3750 Approved
0.7333 Intermediate Similarity NPD4628 Phase 3
0.7333 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7318 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD6385 Approved
0.731 Intermediate Similarity NPD6386 Approved
0.7305 Intermediate Similarity NPD1511 Approved
0.7301 Intermediate Similarity NPD2438 Suspended
0.7292 Intermediate Similarity NPD7435 Discontinued
0.7292 Intermediate Similarity NPD7680 Approved
0.7283 Intermediate Similarity NPD5402 Approved
0.7273 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7263 Intermediate Similarity NPD3751 Discontinued
0.7262 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7262 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD7768 Phase 2
0.7232 Intermediate Similarity NPD5710 Approved
0.7232 Intermediate Similarity NPD7229 Phase 3
0.7232 Intermediate Similarity NPD5711 Approved
0.7225 Intermediate Similarity NPD6779 Approved
0.7225 Intermediate Similarity NPD6776 Approved
0.7225 Intermediate Similarity NPD6781 Approved
0.7225 Intermediate Similarity NPD6778 Approved
0.7225 Intermediate Similarity NPD6782 Approved
0.7225 Intermediate Similarity NPD6780 Approved
0.7225 Intermediate Similarity NPD6777 Approved
0.7222 Intermediate Similarity NPD1607 Approved
0.7219 Intermediate Similarity NPD1512 Approved
0.7219 Intermediate Similarity NPD6273 Approved
0.7212 Intermediate Similarity NPD1549 Phase 2
0.7205 Intermediate Similarity NPD1240 Approved
0.7188 Intermediate Similarity NPD3764 Approved
0.7176 Intermediate Similarity NPD5403 Approved
0.7175 Intermediate Similarity NPD8127 Discontinued
0.716 Intermediate Similarity NPD5401 Approved
0.7152 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD2346 Discontinued
0.7152 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD1471 Phase 3
0.7135 Intermediate Similarity NPD3787 Discontinued
0.7134 Intermediate Similarity NPD1876 Approved
0.7134 Intermediate Similarity NPD2799 Discontinued
0.7113 Intermediate Similarity NPD7697 Approved
0.7113 Intermediate Similarity NPD7696 Phase 3
0.7113 Intermediate Similarity NPD7698 Approved
0.7099 Intermediate Similarity NPD2979 Phase 3
0.7091 Intermediate Similarity NPD2935 Discontinued
0.7086 Intermediate Similarity NPD5978 Approved
0.7086 Intermediate Similarity NPD5977 Approved
0.7083 Intermediate Similarity NPD6190 Approved
0.7081 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7077 Intermediate Similarity NPD7870 Phase 2
0.7077 Intermediate Similarity NPD7871 Phase 2
0.7071 Intermediate Similarity NPD7874 Approved
0.7071 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD6832 Phase 2
0.7051 Intermediate Similarity NPD1281 Approved
0.7049 Intermediate Similarity NPD5953 Discontinued
0.7047 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD2798 Approved
0.7037 Intermediate Similarity NPD8032 Phase 2
0.7032 Intermediate Similarity NPD17 Approved
0.7024 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD3972 Approved
0.7005 Intermediate Similarity NPD8150 Discontinued
0.7 Intermediate Similarity NPD7390 Discontinued
0.7 Intermediate Similarity NPD7827 Phase 1
0.6994 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6994 Remote Similarity NPD943 Approved
0.699 Remote Similarity NPD8320 Phase 1
0.699 Remote Similarity NPD8319 Approved
0.6988 Remote Similarity NPD1551 Phase 2
0.6978 Remote Similarity NPD7893 Clinical (unspecified phase)
0.697 Remote Similarity NPD7701 Phase 2
0.6964 Remote Similarity NPD2800 Approved
0.6963 Remote Similarity NPD6534 Approved
0.6963 Remote Similarity NPD6535 Approved
0.6959 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6951 Remote Similarity NPD447 Suspended
0.695 Remote Similarity NPD7801 Approved
0.6949 Remote Similarity NPD5019 Clinical (unspecified phase)
0.6948 Remote Similarity NPD5536 Phase 2
0.6947 Remote Similarity NPD7296 Approved
0.6936 Remote Similarity NPD1653 Approved
0.6923 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6923 Remote Similarity NPD7003 Approved
0.6923 Remote Similarity NPD8166 Discontinued
0.6923 Remote Similarity NPD4110 Phase 3
0.6918 Remote Similarity NPD1283 Approved
0.6914 Remote Similarity NPD6873 Phase 2
0.6899 Remote Similarity NPD1608 Approved
0.6888 Remote Similarity NPD6823 Phase 2
0.6886 Remote Similarity NPD6100 Approved
0.6886 Remote Similarity NPD6099 Approved
0.6886 Remote Similarity NPD2531 Phase 2
0.6885 Remote Similarity NPD7799 Discontinued
0.6868 Remote Similarity NPD2403 Approved
0.6866 Remote Similarity NPD7783 Phase 2
0.6866 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6864 Remote Similarity NPD6674 Discontinued
0.6864 Remote Similarity NPD2654 Approved
0.686 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6859 Remote Similarity NPD1651 Approved
0.6856 Remote Similarity NPD7699 Phase 2
0.6856 Remote Similarity NPD7700 Phase 2
0.6848 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6845 Remote Similarity NPD7266 Discontinued
0.6845 Remote Similarity NPD2344 Approved
0.6845 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6836 Remote Similarity NPD5760 Phase 2
0.6836 Remote Similarity NPD5761 Phase 2
0.6836 Remote Similarity NPD8455 Phase 2
0.6821 Remote Similarity NPD8285 Discontinued
0.681 Remote Similarity NPD3027 Phase 3

  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