Structure

Physi-Chem Properties

Molecular Weight:  362.25
Volume:  390.65
LogP:  4.689
LogD:  4.363
LogS:  -4.995
# Rotatable Bonds:  5
TPSA:  59.67
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.786
Synthetic Accessibility Score:  4.41
Fsp3:  0.773
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.633
MDCK Permeability:  2.2500289560412057e-05
Pgp-inhibitor:  0.875
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.584
30% Bioavailability (F30%):  0.959

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.111
Plasma Protein Binding (PPB):  97.19766998291016%
Volume Distribution (VD):  2.342
Pgp-substrate:  4.245429039001465%

ADMET: Metabolism

CYP1A2-inhibitor:  0.099
CYP1A2-substrate:  0.104
CYP2C19-inhibitor:  0.561
CYP2C19-substrate:  0.752
CYP2C9-inhibitor:  0.826
CYP2C9-substrate:  0.331
CYP2D6-inhibitor:  0.178
CYP2D6-substrate:  0.178
CYP3A4-inhibitor:  0.777
CYP3A4-substrate:  0.384

ADMET: Excretion

Clearance (CL):  8.06
Half-life (T1/2):  0.173

ADMET: Toxicity

hERG Blockers:  0.085
Human Hepatotoxicity (H-HT):  0.339
Drug-inuced Liver Injury (DILI):  0.32
AMES Toxicity:  0.015
Rat Oral Acute Toxicity:  0.905
Maximum Recommended Daily Dose:  0.128
Skin Sensitization:  0.157
Carcinogencity:  0.532
Eye Corrosion:  0.016
Eye Irritation:  0.095
Respiratory Toxicity:  0.959

Download Data

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

  Natural Product: NPC121158

Natural Product ID:  NPC121158
Common Name*:   Rotundifuran
IUPAC Name:   [(1R,3R,4R,4aS,8aS)-4-[2-(furan-3-yl)ethyl]-4-hydroxy-3,4a,8,8-tetramethyl-2,3,5,6,7,8a-hexahydro-1H-naphthalen-1-yl] acetate
Synonyms:  
Standard InCHIKey:  QKHCQFQIJKXMOE-UGFIEOPBSA-N
Standard InCHI:  InChI=1S/C22H34O4/c1-15-13-18(26-16(2)23)19-20(3,4)9-6-10-21(19,5)22(15,24)11-7-17-8-12-25-14-17/h8,12,14-15,18-19,24H,6-7,9-11,13H2,1-5H3/t15-,18-,19+,21+,22-/m1/s1
SMILES:  CC(=O)O[C@@H]1C[C@@H](C)[C@]([C@@]2([C@@H]1C(C)(C)CCC2)C)(O)CCc1cocc1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2391697
PubChem CID:   9841926
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] Diterpenoids
          • [CHEMONTID:0001757] Colensane and clerodane diterpenoids

*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
NPO15454 Vitex rotundifolia Species Lamiaceae Eukaryota Fruits n.a. n.a. PMID[10579867]
NPO15454 Vitex rotundifolia Species Lamiaceae Eukaryota subterranean part n.a. n.a. PMID[11374949]
NPO15454 Vitex rotundifolia Species Lamiaceae Eukaryota n.a. fruit n.a. PMID[11536386]
NPO15454 Vitex rotundifolia Species Lamiaceae Eukaryota fruits n.a. n.a. PMID[11975496]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota n.a. fruit n.a. PMID[15577254]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[15621610]
NPO17785 Avrainvillea nigricans Species Udoteaceae Eukaryota n.a. n.a. n.a. PMID[16180830]
NPO22123 Disepalum plagioneurum Species Annonaceae Eukaryota leaves Tam Kim, Cao Bang Province, in North Vietnam 2000-JUN PMID[16989521]
NPO20954 Haloxylon salicornicum Species Chenopodiaceae Eukaryota whole plant Cholistan desert near district Bahawalpur (Punjab), Pakistan 2003-Oct PMID[20542692]
NPO23218 Viscum coloratum Species Viscaceae Eukaryota n.a. aerial part n.a. PMID[2082684]
NPO18212 Rhododendron ferrugineum Species Ericaceae Eukaryota n.a. leaf n.a. PMID[21443171]
NPO23218 Viscum coloratum Species Viscaceae Eukaryota n.a. aerial part n.a. PMID[21922656]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota fruits n.a. n.a. PMID[23327905]
NPO15454 Vitex rotundifolia Species Lamiaceae Eukaryota fruits n.a. n.a. PMID[24035341]
NPO18530 Shigella flexneri Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[26918643]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota Leaves n.a. n.a. PMID[28453270]
NPO23218 Viscum coloratum Species Viscaceae Eukaryota n.a. aerial part n.a. PMID[3254039]
NPO23218 Viscum coloratum Species Viscaceae Eukaryota n.a. aerial part n.a. PMID[3256207]
NPO17785 Avrainvillea nigricans Species Udoteaceae Eukaryota n.a. n.a. n.a. PMID[3668556]
NPO22188 Piper aequale Species Piperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23218 Viscum coloratum Species Viscaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23135 Formica fusca Species Formicidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22819 Rodgersia podophylla Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19694 Senecio scandens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15454 Vitex rotundifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23178 Jasminum grandiflorum Species Oleaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30555 Mentha rotundifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23178 Jasminum grandiflorum Species Oleaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22188 Piper aequale Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20954 Haloxylon salicornicum Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21875 Persea indica Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10561 Mentha suaveolens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23218 Viscum coloratum Species Viscaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22819 Rodgersia podophylla Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19694 Senecio scandens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23135 Formica fusca Species Formicidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15454 Vitex rotundifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO30555 Mentha rotundifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23135 Formica fusca Species Formicidae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15454 Vitex rotundifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO19694 Senecio scandens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO23218 Viscum coloratum Species Viscaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22248 Alkanna hirsutissima Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21113 Coronophora gregaria Species Nitschkiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22710 Acrocomia sclerocarpa Species Arecaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18212 Rhododendron ferrugineum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10561 Mentha suaveolens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15454 Vitex rotundifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23218 Viscum coloratum Species Viscaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21998 Corydalis cornuta Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19921 Polyphaga sinensis Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14247 Melaleuca uncinata Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22940 Delphinium campylocentrum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19694 Senecio scandens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20043 Vallaris solanacea Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23178 Jasminum grandiflorum Species Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22188 Piper aequale Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18530 Shigella flexneri Species Enterobacteriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO18571 Drypetes roxburghii Species Putranjivaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20360 Mentha pulegiformis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7080 Monascus purpureus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23135 Formica fusca Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19074 Buddleja variabilis Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22454 Picris radicata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21298 Leucanthemum maximum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17785 Avrainvillea nigricans Species Udoteaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16146 Osmundaria colensoi Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21247 Nephroma australe Species Nephromataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20808 Halopitys incurvus n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO20954 Haloxylon salicornicum Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21798 Dacrydium biforme Species Mytilidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20678 Grindelia nana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20536 Salvia nubicola Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7865 Scapania nemorea Species Scapaniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20184 Streptomyces misawanensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO22819 Rodgersia podophylla Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21875 Persea indica Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21636 Didemnum inarmatum Species Didemnidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21736 Abies nobilis Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21505 Calea megacephala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14394 Hakea saligna Species Proteaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17108 Lecanora lividocinerea Species Lecanoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22123 Disepalum plagioneurum Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22062 Leptothorax acervorum Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22323 Pinus picea Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22762 Eremophila serrulata Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22582 Smenospongia echina Species Thorectidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12225 Amsinckia menziesii Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23057 Primula hirsuta Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22994 Cordyline indivisa Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5952 Phegopteris bukoensis Species Thelypteridaceae 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
NPT994 Cell Line ZR-75-30 Homo sapiens IC50 < 5.0 ug.mL-1 PMID[524002]
NPT116 Cell Line HL-60 Homo sapiens IC50 < 5.0 ug.mL-1 PMID[524002]
NPT393 Cell Line HCT-116 Homo sapiens IC50 < 5.0 ug.mL-1 PMID[524002]
NPT81 Cell Line A549 Homo sapiens IC50 < 5.0 ug.mL-1 PMID[524002]

☑ 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 NPC121158 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.9708 High Similarity NPC251865
0.9704 High Similarity NPC67003
0.964 High Similarity NPC255414
0.9504 High Similarity NPC69647
0.9504 High Similarity NPC125182
0.9357 High Similarity NPC5676
0.9231 High Similarity NPC472654
0.9225 High Similarity NPC471174
0.9225 High Similarity NPC216755
0.9172 High Similarity NPC268905
0.9167 High Similarity NPC212257
0.9124 High Similarity NPC46896
0.911 High Similarity NPC282445
0.9097 High Similarity NPC195325
0.9078 High Similarity NPC243577
0.9054 High Similarity NPC195954
0.9041 High Similarity NPC469503
0.9037 High Similarity NPC89133
0.9034 High Similarity NPC476122
0.8986 High Similarity NPC41880
0.898 High Similarity NPC30222
0.898 High Similarity NPC57998
0.898 High Similarity NPC178932
0.8966 High Similarity NPC470791
0.8966 High Similarity NPC470790
0.8958 High Similarity NPC221809
0.8929 High Similarity NPC90953
0.8926 High Similarity NPC88007
0.8926 High Similarity NPC472772
0.8926 High Similarity NPC194499
0.8926 High Similarity NPC249021
0.8921 High Similarity NPC310043
0.8919 High Similarity NPC469336
0.8919 High Similarity NPC92979
0.8919 High Similarity NPC35000
0.8913 High Similarity NPC476947
0.8913 High Similarity NPC158525
0.8912 High Similarity NPC121615
0.8912 High Similarity NPC75906
0.8912 High Similarity NPC294511
0.8912 High Similarity NPC246164
0.8904 High Similarity NPC477404
0.8904 High Similarity NPC156189
0.8904 High Similarity NPC228842
0.8904 High Similarity NPC196864
0.8897 High Similarity NPC61788
0.8881 High Similarity NPC476944
0.8874 High Similarity NPC200782
0.8873 High Similarity NPC263337
0.8865 High Similarity NPC56197
0.8859 High Similarity NPC104736
0.8849 High Similarity NPC214572
0.8844 High Similarity NPC272590
0.8844 High Similarity NPC18135
0.8836 High Similarity NPC211625
0.8828 High Similarity NPC470941
0.8828 High Similarity NPC71821
0.8819 High Similarity NPC41182
0.8816 High Similarity NPC51568
0.8816 High Similarity NPC234660
0.8808 High Similarity NPC335761
0.8808 High Similarity NPC472653
0.8808 High Similarity NPC470789
0.8806 High Similarity NPC46536
0.8806 High Similarity NPC138139
0.88 High Similarity NPC214495
0.88 High Similarity NPC304692
0.88 High Similarity NPC475066
0.88 High Similarity NPC299038
0.88 High Similarity NPC470118
0.88 High Similarity NPC470119
0.88 High Similarity NPC7059
0.8792 High Similarity NPC214541
0.8792 High Similarity NPC141538
0.8792 High Similarity NPC155939
0.8792 High Similarity NPC296807
0.8792 High Similarity NPC44675
0.8792 High Similarity NPC264943
0.8792 High Similarity NPC476262
0.8786 High Similarity NPC4764
0.8784 High Similarity NPC476201
0.8784 High Similarity NPC472672
0.8776 High Similarity NPC470997
0.8776 High Similarity NPC159927
0.8776 High Similarity NPC469335
0.8759 High Similarity NPC346
0.8758 High Similarity NPC476858
0.8758 High Similarity NPC476857
0.8758 High Similarity NPC476856
0.875 High Similarity NPC329938
0.875 High Similarity NPC68848
0.875 High Similarity NPC5079
0.875 High Similarity NPC472771
0.875 High Similarity NPC82851
0.8742 High Similarity NPC474611
0.8742 High Similarity NPC475967
0.8742 High Similarity NPC475226
0.8742 High Similarity NPC472671
0.8732 High Similarity NPC90296
0.8731 High Similarity NPC179354
0.8725 High Similarity NPC34421
0.8725 High Similarity NPC253201
0.8725 High Similarity NPC237259
0.8725 High Similarity NPC302054
0.8725 High Similarity NPC98206
0.8707 High Similarity NPC234494
0.8707 High Similarity NPC471001
0.8701 High Similarity NPC472141
0.8699 High Similarity NPC250228
0.8693 High Similarity NPC39986
0.8693 High Similarity NPC419
0.8693 High Similarity NPC134254
0.8693 High Similarity NPC302369
0.8693 High Similarity NPC292389
0.8693 High Similarity NPC472773
0.8693 High Similarity NPC224394
0.8693 High Similarity NPC477405
0.8693 High Similarity NPC469338
0.8693 High Similarity NPC663
0.8684 High Similarity NPC8389
0.8684 High Similarity NPC287559
0.8684 High Similarity NPC25255
0.8681 High Similarity NPC223415
0.8681 High Similarity NPC476946
0.8676 High Similarity NPC207294
0.8676 High Similarity NPC112706
0.8675 High Similarity NPC45101
0.8675 High Similarity NPC261597
0.8675 High Similarity NPC197137
0.8667 High Similarity NPC469850
0.8662 High Similarity NPC202260
0.8658 High Similarity NPC33938
0.8658 High Similarity NPC308205
0.8658 High Similarity NPC29695
0.8658 High Similarity NPC182427
0.8658 High Similarity NPC322546
0.8645 High Similarity NPC472774
0.8645 High Similarity NPC472775
0.8645 High Similarity NPC476850
0.8645 High Similarity NPC476853
0.8645 High Similarity NPC476861
0.8639 High Similarity NPC471007
0.8636 High Similarity NPC469849
0.8636 High Similarity NPC276551
0.8636 High Similarity NPC470940
0.8636 High Similarity NPC476860
0.8636 High Similarity NPC470182
0.8633 High Similarity NPC218838
0.863 High Similarity NPC471292
0.8627 High Similarity NPC188649
0.8627 High Similarity NPC193798
0.8627 High Similarity NPC79571
0.8627 High Similarity NPC470792
0.8627 High Similarity NPC18347
0.8627 High Similarity NPC69028
0.8627 High Similarity NPC149896
0.8621 High Similarity NPC238843
0.8621 High Similarity NPC199044
0.8618 High Similarity NPC477403
0.8618 High Similarity NPC473473
0.8618 High Similarity NPC307383
0.8618 High Similarity NPC475295
0.8613 High Similarity NPC223063
0.8613 High Similarity NPC198904
0.8613 High Similarity NPC120836
0.8609 High Similarity NPC209364
0.8609 High Similarity NPC126723
0.8609 High Similarity NPC107646
0.8603 High Similarity NPC83178
0.8601 High Similarity NPC148374
0.86 High Similarity NPC114880
0.8592 High Similarity NPC471996
0.8592 High Similarity NPC476943
0.8591 High Similarity NPC116717
0.8582 High Similarity NPC16922
0.8581 High Similarity NPC470998
0.8581 High Similarity NPC478178
0.8581 High Similarity NPC470875
0.8581 High Similarity NPC97574
0.8581 High Similarity NPC23387
0.8581 High Similarity NPC93172
0.8571 High Similarity NPC283209
0.8571 High Similarity NPC88841
0.8571 High Similarity NPC286038
0.8571 High Similarity NPC472139
0.8571 High Similarity NPC165218
0.8571 High Similarity NPC285567
0.8571 High Similarity NPC288602
0.8562 High Similarity NPC185456
0.8562 High Similarity NPC477402
0.8553 High Similarity NPC187149
0.8553 High Similarity NPC472776
0.8553 High Similarity NPC472777
0.8553 High Similarity NPC81405
0.8553 High Similarity NPC167142
0.8553 High Similarity NPC36655
0.8553 High Similarity NPC472778
0.8553 High Similarity NPC286722
0.8552 High Similarity NPC470741
0.8552 High Similarity NPC267632

  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 NPC121158 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
0.8667 High Similarity NPD5760 Phase 2
0.8667 High Similarity NPD5761 Phase 2
0.8072 Intermediate Similarity NPD8434 Phase 2
0.7987 Intermediate Similarity NPD4628 Phase 3
0.7879 Intermediate Similarity NPD6765 Approved
0.7879 Intermediate Similarity NPD6764 Approved
0.7785 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD6784 Approved
0.7692 Intermediate Similarity NPD6785 Approved
0.7613 Intermediate Similarity NPD6273 Approved
0.7566 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7819 Suspended
0.7436 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7423 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.7413 Intermediate Similarity NPD1608 Approved
0.7403 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7342 Intermediate Similarity NPD920 Approved
0.7333 Intermediate Similarity NPD8127 Discontinued
0.7312 Intermediate Similarity NPD6599 Discontinued
0.7303 Intermediate Similarity NPD2799 Discontinued
0.7284 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD5844 Phase 1
0.725 Intermediate Similarity NPD3226 Approved
0.725 Intermediate Similarity NPD7458 Discontinued
0.7248 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD6355 Discontinued
0.7215 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7215 Intermediate Similarity NPD2533 Approved
0.7215 Intermediate Similarity NPD2532 Approved
0.7215 Intermediate Similarity NPD2534 Approved
0.7208 Intermediate Similarity NPD1471 Phase 3
0.7208 Intermediate Similarity NPD2346 Discontinued
0.7203 Intermediate Similarity NPD17 Approved
0.7197 Intermediate Similarity NPD7236 Approved
0.7197 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD7003 Approved
0.7152 Intermediate Similarity NPD7075 Discontinued
0.7152 Intermediate Similarity NPD3749 Approved
0.7151 Intermediate Similarity NPD6559 Discontinued
0.7143 Intermediate Similarity NPD2935 Discontinued
0.7143 Intermediate Similarity NPD1551 Phase 2
0.7143 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6099 Approved
0.7143 Intermediate Similarity NPD6100 Approved
0.7133 Intermediate Similarity NPD3764 Approved
0.7118 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD6002 Phase 3
0.7097 Intermediate Similarity NPD2344 Approved
0.7097 Intermediate Similarity NPD6004 Phase 3
0.7097 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD6005 Phase 3
0.7086 Intermediate Similarity NPD8032 Phase 2
0.7086 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD1778 Approved
0.7078 Intermediate Similarity NPD7033 Discontinued
0.707 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD4110 Phase 3
0.707 Intermediate Similarity NPD3750 Approved
0.7066 Intermediate Similarity NPD5494 Approved
0.7055 Intermediate Similarity NPD7411 Suspended
0.7055 Intermediate Similarity NPD3972 Approved
0.7051 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD6799 Approved
0.7039 Intermediate Similarity NPD4140 Approved
0.7032 Intermediate Similarity NPD2796 Approved
0.703 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.702 Intermediate Similarity NPD1699 Clinical (unspecified phase)
0.702 Intermediate Similarity NPD2313 Discontinued
0.7006 Intermediate Similarity NPD1243 Approved
0.7006 Intermediate Similarity NPD919 Approved
0.7 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6832 Phase 2
0.6988 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6988 Remote Similarity NPD7768 Phase 2
0.6987 Remote Similarity NPD5762 Approved
0.6987 Remote Similarity NPD5763 Approved
0.6982 Remote Similarity NPD7229 Phase 3
0.6979 Remote Similarity NPD8404 Phase 2
0.6975 Remote Similarity NPD7239 Suspended
0.697 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6968 Remote Similarity NPD4308 Phase 3
0.6968 Remote Similarity NPD3748 Approved
0.6959 Remote Similarity NPD1283 Approved
0.6944 Remote Similarity NPD9545 Approved
0.6943 Remote Similarity NPD1549 Phase 2
0.6937 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6928 Remote Similarity NPD2979 Phase 3
0.6919 Remote Similarity NPD7177 Discontinued
0.6918 Remote Similarity NPD2309 Approved
0.6913 Remote Similarity NPD2797 Approved
0.6909 Remote Similarity NPD6801 Discontinued
0.6908 Remote Similarity NPD3268 Approved
0.6899 Remote Similarity NPD2800 Approved
0.6897 Remote Similarity NPD5585 Approved
0.6879 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6879 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6867 Remote Similarity NPD6007 Clinical (unspecified phase)
0.686 Remote Similarity NPD7473 Discontinued
0.6852 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6846 Remote Similarity NPD6696 Suspended
0.6842 Remote Similarity NPD7095 Approved
0.6842 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6826 Remote Similarity NPD5616 Clinical (unspecified phase)
0.6826 Remote Similarity NPD3817 Phase 2
0.6824 Remote Similarity NPD1247 Approved
0.6824 Remote Similarity NPD6959 Discontinued
0.6818 Remote Similarity NPD4307 Phase 2
0.6815 Remote Similarity NPD4476 Approved
0.6815 Remote Similarity NPD4477 Approved
0.6813 Remote Similarity NPD3887 Approved
0.6807 Remote Similarity NPD37 Approved
0.6807 Remote Similarity NPD1934 Approved
0.6803 Remote Similarity NPD3496 Discontinued
0.6802 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6797 Remote Similarity NPD6798 Discontinued
0.6796 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6795 Remote Similarity NPD7097 Phase 1
0.6791 Remote Similarity NPD7497 Discontinued
0.679 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6788 Remote Similarity NPD4380 Phase 2
0.6786 Remote Similarity NPD4967 Phase 2
0.6786 Remote Similarity NPD4965 Approved
0.6786 Remote Similarity NPD3882 Suspended
0.6786 Remote Similarity NPD4966 Approved
0.6784 Remote Similarity NPD6232 Discontinued
0.678 Remote Similarity NPD8313 Approved
0.678 Remote Similarity NPD8312 Approved
0.6774 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6757 Remote Similarity NPD1281 Approved
0.6755 Remote Similarity NPD2798 Approved
0.6753 Remote Similarity NPD6663 Approved
0.6753 Remote Similarity NPD6233 Phase 2
0.6752 Remote Similarity NPD1510 Phase 2
0.675 Remote Similarity NPD8166 Discontinued
0.6746 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6733 Remote Similarity NPD1876 Approved
0.6731 Remote Similarity NPD1607 Approved
0.6726 Remote Similarity NPD5402 Approved
0.6725 Remote Similarity NPD7199 Phase 2
0.6724 Remote Similarity NPD3818 Discontinued
0.6724 Remote Similarity NPD7799 Discontinued
0.6711 Remote Similarity NPD9717 Approved
0.6711 Remote Similarity NPD5736 Approved
0.6711 Remote Similarity NPD2861 Phase 2
0.671 Remote Similarity NPD1240 Approved
0.671 Remote Similarity NPD4060 Phase 1
0.6709 Remote Similarity NPD2438 Suspended
0.6708 Remote Similarity NPD2354 Approved
0.6707 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6706 Remote Similarity NPD6234 Discontinued
0.6705 Remote Similarity NPD3451 Clinical (unspecified phase)
0.6689 Remote Similarity NPD3266 Approved
0.6689 Remote Similarity NPD3267 Approved
0.6689 Remote Similarity NPD1203 Approved
0.6686 Remote Similarity NPD5711 Approved
0.6686 Remote Similarity NPD5710 Approved
0.6686 Remote Similarity NPD6808 Phase 2
0.6685 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5327 Phase 3
0.6667 Remote Similarity NPD5691 Approved
0.6667 Remote Similarity NPD8455 Phase 2
0.6667 Remote Similarity NPD2801 Approved
0.6667 Remote Similarity NPD4359 Approved
0.6667 Remote Similarity NPD5735 Approved
0.6667 Remote Similarity NPD7685 Pre-registration
0.6667 Remote Similarity NPD7440 Discontinued
0.6647 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6647 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6647 Remote Similarity NPD6386 Approved
0.6647 Remote Similarity NPD6385 Approved
0.6644 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6631 Remote Similarity NPD4107 Approved
0.6625 Remote Similarity NPD4534 Discontinued
0.6624 Remote Similarity NPD6653 Approved
0.6624 Remote Similarity NPD6353 Approved
0.6622 Remote Similarity NPD4626 Approved
0.6622 Remote Similarity NPD3412 Clinical (unspecified phase)
0.662 Remote Similarity NPD2181 Clinical (unspecified phase)
0.6609 Remote Similarity NPD4575 Clinical (unspecified phase)
0.6606 Remote Similarity NPD5403 Approved
0.6604 Remote Similarity NPD2531 Phase 2
0.66 Remote Similarity NPD1481 Phase 2
0.6599 Remote Similarity NPD1894 Discontinued
0.6597 Remote Similarity NPD1241 Discontinued
0.6591 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6591 Remote Similarity NPD7286 Phase 2
0.659 Remote Similarity NPD7315 Approved
0.6588 Remote Similarity NPD7058 Phase 2
0.6588 Remote Similarity NPD7057 Phase 3
0.6587 Remote Similarity NPD7028 Phase 2
0.6585 Remote Similarity NPD5401 Approved
0.6581 Remote Similarity NPD411 Approved
0.6581 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6579 Remote Similarity NPD6362 Approved
0.6575 Remote Similarity NPD8150 Discontinued
0.6568 Remote Similarity NPD1465 Phase 2
0.6562 Remote Similarity NPD2353 Approved
0.6562 Remote Similarity NPD2355 Clinical (unspecified phase)
0.6561 Remote Similarity NPD5124 Phase 1

  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