Structure

Physi-Chem Properties

Molecular Weight:  328.09
Volume:  325.865
LogP:  1.727
LogD:  1.934
LogS:  -4.135
# Rotatable Bonds:  4
TPSA:  96.22
# H-Bond Aceptor:  6
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.452
Synthetic Accessibility Score:  3.431
Fsp3:  0.167
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.799
MDCK Permeability:  1.0000032489188015e-05
Pgp-inhibitor:  0.01
Pgp-substrate:  0.007
Human Intestinal Absorption (HIA):  0.013
20% Bioavailability (F20%):  0.008
30% Bioavailability (F30%):  0.935

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.043
Plasma Protein Binding (PPB):  92.25337982177734%
Volume Distribution (VD):  0.584
Pgp-substrate:  6.397604942321777%

ADMET: Metabolism

CYP1A2-inhibitor:  0.384
CYP1A2-substrate:  0.066
CYP2C19-inhibitor:  0.1
CYP2C19-substrate:  0.061
CYP2C9-inhibitor:  0.232
CYP2C9-substrate:  0.895
CYP2D6-inhibitor:  0.35
CYP2D6-substrate:  0.777
CYP3A4-inhibitor:  0.718
CYP3A4-substrate:  0.195

ADMET: Excretion

Clearance (CL):  11.636
Half-life (T1/2):  0.782

ADMET: Toxicity

hERG Blockers:  0.049
Human Hepatotoxicity (H-HT):  0.1
Drug-inuced Liver Injury (DILI):  0.383
AMES Toxicity:  0.499
Rat Oral Acute Toxicity:  0.105
Maximum Recommended Daily Dose:  0.035
Skin Sensitization:  0.919
Carcinogencity:  0.872
Eye Corrosion:  0.004
Eye Irritation:  0.922
Respiratory Toxicity:  0.108

Download Data

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

  Natural Product: NPC214729

Natural Product ID:  NPC214729
Common Name*:   Americanin A
IUPAC Name:   (E)-3-[(2S,3S)-2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]prop-2-enal
Synonyms:  
Standard InCHIKey:  NTXXGPYGMQQSML-QLJMBOKNSA-N
Standard InCHI:  InChI=1S/C18H16O6/c19-7-1-2-11-3-6-15-16(8-11)23-17(10-20)18(24-15)12-4-5-13(21)14(22)9-12/h1-9,17-18,20-22H,10H2/b2-1+/t17-,18-/m0/s1
SMILES:  C(=Cc1ccc2c(c1)O[C@@H](CO)[C@H](c1ccc(c(c1)O)O)O2)/C=O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL482240
PubChem CID:   44575382
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0002699] Benzodioxanes
        • [CHEMONTID:0002704] Phenylbenzodioxanes
          • [CHEMONTID:0002707] Phenylbenzo-1,4-dioxanes

*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
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. leaf n.a. PMID[11348221]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota fruit n.a. n.a. PMID[15844957]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota fruits n.a. n.a. PMID[16378361]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota fruits Tahiti n.a. PMID[17378609]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota Fruits n.a. n.a. PMID[17480098]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota roots n.a. n.a. PMID[18076142]
NPO17551 Phytolacca americana Species Phytolaccaceae Eukaryota roots n.a. n.a. PMID[18177012]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[24224843]
NPO17551 Phytolacca americana Species Phytolaccaceae Eukaryota Seeds n.a. n.a. PMID[26595875]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[27196335]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota Fruits n.a. n.a. PMID[32083868]
NPO17551 Phytolacca americana Species Phytolaccaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO17551 Phytolacca americana Species Phytolaccaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO17551 Phytolacca americana Species Phytolaccaceae Eukaryota n.a. n.a. Database[FooDB]
NPO17551 Phytolacca americana Species Phytolaccaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17957 Solanum sodomeum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17551 Phytolacca americana Species Phytolaccaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17957 Solanum sodomeum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5114 Canis lupus familiaris Species Canidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17551 Phytolacca americana Species Phytolaccaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17551 Phytolacca americana Species Phytolaccaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22716 Petalostemon gattingeri Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17551 Phytolacca americana Species Phytolaccaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5114 Canis lupus familiaris Species Canidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17957 Solanum sodomeum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19056 Allium nutans Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18517 Phthorimaea operculella Species Gelechiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15872 Stachys mucronata Species Lamiaceae 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
NPT71 Cell Line HEK293 Homo sapiens Inhibition = 55.0 % PMID[476204]
NPT81 Cell Line A549 Homo sapiens IC50 = 39100.0 nM PMID[476206]
NPT308 Cell Line CAKI-1 Homo sapiens IC50 = 66400.0 nM PMID[476206]
NPT111 Cell Line K562 Homo sapiens IC50 = 12900.0 nM PMID[476206]
NPT171 Cell Line MRC5 Homo sapiens IC50 > 100000.0 nM PMID[476206]
NPT660 Cell Line SW480 Homo sapiens IC50 = 27400.0 nM PMID[476206]
NPT2170 Cell Line RKO Homo sapiens IC50 = 24400.0 nM PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 55.4 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 15.6 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 27.5 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 1.9 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 47.5 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 17.9 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 31.8 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 3.0 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 39.0 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 18.4 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 38.9 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 4.0 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 55.2 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 13.5 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 19.0 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 7.6 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 23.4 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 8.2 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 20.3 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 37.9 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 16.4 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 8.4 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 52.0 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 2.0 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 10.4 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 84.6 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 0.4 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 11.1 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 76.3 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 12.2 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 5.2 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 18.9 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 30.6 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 32.8 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 7.9 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 47.4 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 9.9 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 5.1 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 36.5 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 51.4 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 7.0 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 73.2 % PMID[476206]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 2.7 % PMID[476206]
NPT1 Others Radical scavenging activity IC50 = 16900.0 nM PMID[476203]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 3300.0 nM PMID[476203]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 25800.0 nM PMID[476203]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 7600.0 nM PMID[476206]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 12500.0 nM PMID[476206]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 24100.0 nM PMID[476206]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 9600.0 nM PMID[476206]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 8700.0 nM PMID[476206]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 7800.0 nM PMID[476206]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. TGI = 45.0 % PMID[476206]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. TGI = 55.7 % PMID[476206]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 8300.0 nM PMID[476206]

☑ 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 NPC214729 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
0.9767 High Similarity NPC237594
0.9767 High Similarity NPC119060
0.9767 High Similarity NPC249791
0.9767 High Similarity NPC476387
0.9624 High Similarity NPC224876
0.9624 High Similarity NPC83375
0.9618 High Similarity NPC471665
0.9618 High Similarity NPC471664
0.9552 High Similarity NPC278469
0.9552 High Similarity NPC193722
0.9545 High Similarity NPC126206
0.9453 High Similarity NPC72529
0.9403 High Similarity NPC267291
0.938 High Similarity NPC86030
0.938 High Similarity NPC5851
0.9242 High Similarity NPC36490
0.9225 High Similarity NPC118787
0.9225 High Similarity NPC111247
0.9225 High Similarity NPC183181
0.9225 High Similarity NPC319625
0.9225 High Similarity NPC163332
0.9225 High Similarity NPC147821
0.9225 High Similarity NPC292056
0.9225 High Similarity NPC41706
0.9219 High Similarity NPC87113
0.9173 High Similarity NPC135127
0.9154 High Similarity NPC252307
0.9154 High Similarity NPC245826
0.9154 High Similarity NPC474178
0.9147 High Similarity NPC58607
0.9147 High Similarity NPC178284
0.9147 High Similarity NPC191037
0.913 High Similarity NPC93433
0.913 High Similarity NPC284881
0.913 High Similarity NPC264706
0.913 High Similarity NPC474444
0.907 High Similarity NPC194519
0.9058 High Similarity NPC478239
0.9051 High Similarity NPC186406
0.903 High Similarity NPC170694
0.9 High Similarity NPC9370
0.9 High Similarity NPC287495
0.8993 High Similarity NPC232228
0.8992 High Similarity NPC94276
0.8992 High Similarity NPC109822
0.8992 High Similarity NPC48990
0.8992 High Similarity NPC293701
0.8992 High Similarity NPC114901
0.8986 High Similarity NPC140502
0.8986 High Similarity NPC157816
0.8947 High Similarity NPC472597
0.8936 High Similarity NPC476347
0.8929 High Similarity NPC274960
0.8929 High Similarity NPC473909
0.8929 High Similarity NPC143120
0.8897 High Similarity NPC16435
0.8897 High Similarity NPC302701
0.8897 High Similarity NPC306441
0.8897 High Similarity NPC269091
0.8889 High Similarity NPC478085
0.8881 High Similarity NPC184447
0.8881 High Similarity NPC35932
0.8881 High Similarity NPC201587
0.8881 High Similarity NPC160991
0.8881 High Similarity NPC16208
0.8881 High Similarity NPC253105
0.8881 High Similarity NPC7903
0.8881 High Similarity NPC470752
0.8873 High Similarity NPC187398
0.8873 High Similarity NPC473408
0.8873 High Similarity NPC476348
0.8872 High Similarity NPC472338
0.8865 High Similarity NPC199928
0.8857 High Similarity NPC292443
0.8841 High Similarity NPC202700
0.8837 High Similarity NPC71090
0.8832 High Similarity NPC470413
0.8832 High Similarity NPC138738
0.8824 High Similarity NPC47398
0.8824 High Similarity NPC94750
0.8824 High Similarity NPC164787
0.8824 High Similarity NPC112246
0.8824 High Similarity NPC474206
0.8824 High Similarity NPC121812
0.8824 High Similarity NPC112939
0.8824 High Similarity NPC470356
0.8824 High Similarity NPC260898
0.8824 High Similarity NPC234333
0.8824 High Similarity NPC61946
0.8824 High Similarity NPC55040
0.8811 High Similarity NPC106138
0.8811 High Similarity NPC476394
0.8811 High Similarity NPC98809
0.8806 High Similarity NPC309787
0.8797 High Similarity NPC190629
0.8797 High Similarity NPC202582
0.8797 High Similarity NPC210623
0.8797 High Similarity NPC218856
0.8797 High Similarity NPC470258
0.8797 High Similarity NPC285339
0.8797 High Similarity NPC273295
0.8797 High Similarity NPC226788
0.8797 High Similarity NPC3439
0.8797 High Similarity NPC222004
0.8794 High Similarity NPC34587
0.8794 High Similarity NPC252292
0.8794 High Similarity NPC476864
0.8794 High Similarity NPC476868
0.8794 High Similarity NPC163898
0.8794 High Similarity NPC34927
0.8794 High Similarity NPC476869
0.8794 High Similarity NPC476382
0.8794 High Similarity NPC476866
0.8794 High Similarity NPC100998
0.8788 High Similarity NPC165045
0.8788 High Similarity NPC118533
0.8769 High Similarity NPC471693
0.8768 High Similarity NPC100389
0.876 High Similarity NPC470804
0.876 High Similarity NPC127389
0.876 High Similarity NPC290451
0.8759 High Similarity NPC186418
0.8759 High Similarity NPC230734
0.8759 High Similarity NPC474639
0.8759 High Similarity NPC227503
0.875 High Similarity NPC120426
0.875 High Similarity NPC294522
0.875 High Similarity NPC310854
0.875 High Similarity NPC21184
0.875 High Similarity NPC205727
0.8741 High Similarity NPC61477
0.8741 High Similarity NPC261619
0.8741 High Similarity NPC78770
0.8741 High Similarity NPC185604
0.8741 High Similarity NPC236166
0.8741 High Similarity NPC219876
0.8741 High Similarity NPC15658
0.8741 High Similarity NPC126029
0.8732 High Similarity NPC40222
0.8732 High Similarity NPC268515
0.8732 High Similarity NPC476865
0.8731 High Similarity NPC64201
0.8731 High Similarity NPC153739
0.8731 High Similarity NPC42300
0.8731 High Similarity NPC145305
0.8731 High Similarity NPC242807
0.8731 High Similarity NPC241522
0.8731 High Similarity NPC77040
0.8731 High Similarity NPC187998
0.8731 High Similarity NPC174495
0.8731 High Similarity NPC92164
0.8731 High Similarity NPC257582
0.8723 High Similarity NPC476867
0.8714 High Similarity NPC67467
0.8712 High Similarity NPC120225
0.8712 High Similarity NPC213552
0.8705 High Similarity NPC106944
0.8705 High Similarity NPC55793
0.8699 High Similarity NPC470769
0.8696 High Similarity NPC102904
0.8696 High Similarity NPC326797
0.8696 High Similarity NPC474282
0.8696 High Similarity NPC107551
0.8696 High Similarity NPC103976
0.8696 High Similarity NPC474390
0.8696 High Similarity NPC211549
0.8696 High Similarity NPC176051
0.8686 High Similarity NPC151224
0.8686 High Similarity NPC472337
0.8681 High Similarity NPC176903
0.8681 High Similarity NPC30688
0.8681 High Similarity NPC475250
0.8676 High Similarity NPC475840
0.8676 High Similarity NPC263064
0.8676 High Similarity NPC168059
0.8676 High Similarity NPC229442
0.8676 High Similarity NPC11060
0.8671 High Similarity NPC232992
0.8667 High Similarity NPC469613
0.8667 High Similarity NPC30043
0.8667 High Similarity NPC469625
0.8667 High Similarity NPC220825
0.8667 High Similarity NPC277804
0.8667 High Similarity NPC268342
0.8667 High Similarity NPC470096
0.8667 High Similarity NPC42760
0.8667 High Similarity NPC268266
0.8667 High Similarity NPC470095
0.8657 High Similarity NPC476968
0.8657 High Similarity NPC170844
0.8657 High Similarity NPC475875
0.8647 High Similarity NPC474119
0.8647 High Similarity NPC5428
0.8647 High Similarity NPC210355
0.8643 High Similarity NPC471389
0.8643 High Similarity NPC469661
0.8636 High Similarity NPC289459
0.8636 High Similarity NPC148627
0.8633 High Similarity NPC22517
0.8623 High Similarity NPC177160

  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 NPC214729 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
0.8741 High Similarity NPD1613 Approved
0.8741 High Similarity NPD1612 Clinical (unspecified phase)
0.8657 High Similarity NPD3027 Phase 3
0.8444 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.837 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.8369 Intermediate Similarity NPD7266 Discontinued
0.8346 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.8299 Intermediate Similarity NPD1653 Approved
0.82 Intermediate Similarity NPD1934 Approved
0.8039 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8026 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7971 Intermediate Similarity NPD2861 Phase 2
0.7911 Intermediate Similarity NPD6166 Phase 2
0.7911 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7911 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7908 Intermediate Similarity NPD2801 Approved
0.7907 Intermediate Similarity NPD228 Approved
0.7891 Intermediate Similarity NPD6190 Approved
0.782 Intermediate Similarity NPD5536 Phase 2
0.7812 Intermediate Similarity NPD3818 Discontinued
0.7806 Intermediate Similarity NPD3882 Suspended
0.7785 Intermediate Similarity NPD1511 Approved
0.7764 Intermediate Similarity NPD7054 Approved
0.7716 Intermediate Similarity NPD7074 Phase 3
0.7716 Intermediate Similarity NPD7472 Approved
0.7714 Intermediate Similarity NPD9494 Approved
0.7703 Intermediate Similarity NPD4628 Phase 3
0.7692 Intermediate Similarity NPD1558 Phase 1
0.7682 Intermediate Similarity NPD1512 Approved
0.7664 Intermediate Similarity NPD1091 Approved
0.7664 Intermediate Similarity NPD1610 Phase 2
0.766 Intermediate Similarity NPD4908 Phase 1
0.7655 Intermediate Similarity NPD4536 Approved
0.7655 Intermediate Similarity NPD4538 Approved
0.7655 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7652 Intermediate Similarity NPD5283 Phase 1
0.7639 Intermediate Similarity NPD4340 Discontinued
0.7635 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.763 Intermediate Similarity NPD1548 Phase 1
0.7603 Intermediate Similarity NPD5588 Approved
0.7603 Intermediate Similarity NPD5960 Phase 3
0.7597 Intermediate Similarity NPD4380 Phase 2
0.7576 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7569 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7569 Intermediate Similarity NPD3620 Phase 2
0.7569 Intermediate Similarity NPD4060 Phase 1
0.7561 Intermediate Similarity NPD6797 Phase 2
0.7561 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7552 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.755 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7546 Intermediate Similarity NPD5844 Phase 1
0.7538 Intermediate Similarity NPD2684 Approved
0.7532 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7517 Intermediate Similarity NPD6674 Discontinued
0.7517 Intermediate Similarity NPD1652 Phase 2
0.7516 Intermediate Similarity NPD3817 Phase 2
0.7515 Intermediate Similarity NPD7251 Discontinued
0.75 Intermediate Similarity NPD6233 Phase 2
0.747 Intermediate Similarity NPD7808 Phase 3
0.7452 Intermediate Similarity NPD1465 Phase 2
0.745 Intermediate Similarity NPD1549 Phase 2
0.7444 Intermediate Similarity NPD7843 Approved
0.7429 Intermediate Similarity NPD2983 Phase 2
0.7429 Intermediate Similarity NPD2982 Phase 2
0.741 Intermediate Similarity NPD7685 Pre-registration
0.741 Intermediate Similarity NPD3705 Approved
0.741 Intermediate Similarity NPD6559 Discontinued
0.7407 Intermediate Similarity NPD7157 Approved
0.74 Intermediate Similarity NPD3060 Approved
0.7391 Intermediate Similarity NPD5846 Approved
0.7391 Intermediate Similarity NPD6516 Phase 2
0.7385 Intermediate Similarity NPD968 Approved
0.7383 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7383 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7383 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7375 Intermediate Similarity NPD6234 Discontinued
0.7368 Intermediate Similarity NPD5058 Phase 3
0.7361 Intermediate Similarity NPD7095 Approved
0.7357 Intermediate Similarity NPD2981 Phase 2
0.7355 Intermediate Similarity NPD3687 Approved
0.7355 Intermediate Similarity NPD3686 Approved
0.7348 Intermediate Similarity NPD3021 Approved
0.7348 Intermediate Similarity NPD3022 Approved
0.7343 Intermediate Similarity NPD3018 Phase 2
0.7338 Intermediate Similarity NPD3496 Discontinued
0.7333 Intermediate Similarity NPD2424 Discontinued
0.7329 Intermediate Similarity NPD5494 Approved
0.7328 Intermediate Similarity NPD290 Approved
0.732 Intermediate Similarity NPD4357 Discontinued
0.7319 Intermediate Similarity NPD1357 Approved
0.7312 Intermediate Similarity NPD7075 Discontinued
0.731 Intermediate Similarity NPD6798 Discontinued
0.7296 Intermediate Similarity NPD5402 Approved
0.7286 Intermediate Similarity NPD422 Phase 1
0.7285 Intermediate Similarity NPD4162 Approved
0.7285 Intermediate Similarity NPD4237 Approved
0.7285 Intermediate Similarity NPD4236 Phase 3
0.7284 Intermediate Similarity NPD8127 Discontinued
0.7279 Intermediate Similarity NPD230 Phase 1
0.7279 Intermediate Similarity NPD5124 Phase 1
0.7279 Intermediate Similarity NPD6671 Approved
0.7279 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD37 Approved
0.7273 Intermediate Similarity NPD7228 Approved
0.7273 Intermediate Similarity NPD6584 Phase 3
0.7273 Intermediate Similarity NPD4123 Phase 3
0.7254 Intermediate Similarity NPD8651 Approved
0.725 Intermediate Similarity NPD4966 Approved
0.725 Intermediate Similarity NPD4967 Phase 2
0.725 Intermediate Similarity NPD4965 Approved
0.7241 Intermediate Similarity NPD4625 Phase 3
0.7237 Intermediate Similarity NPD4110 Phase 3
0.7237 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7235 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7234 Intermediate Similarity NPD2231 Phase 2
0.7234 Intermediate Similarity NPD2235 Phase 2
0.7233 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.723 Intermediate Similarity NPD6653 Approved
0.7209 Intermediate Similarity NPD291 Approved
0.7202 Intermediate Similarity NPD7038 Approved
0.7202 Intermediate Similarity NPD7039 Approved
0.72 Intermediate Similarity NPD1551 Phase 2
0.7197 Intermediate Similarity NPD1358 Approved
0.7197 Intermediate Similarity NPD3866 Clinical (unspecified phase)
0.7192 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7192 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.719 Intermediate Similarity NPD2677 Approved
0.7185 Intermediate Similarity NPD5535 Approved
0.7183 Intermediate Similarity NPD4749 Approved
0.7179 Intermediate Similarity NPD5403 Approved
0.7178 Intermediate Similarity NPD7199 Phase 2
0.7172 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7171 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7171 Intermediate Similarity NPD5177 Phase 3
0.7169 Intermediate Similarity NPD3751 Discontinued
0.7162 Intermediate Similarity NPD5735 Approved
0.7162 Intermediate Similarity NPD447 Suspended
0.7162 Intermediate Similarity NPD6355 Discontinued
0.7161 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7161 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD7549 Discontinued
0.7152 Intermediate Similarity NPD5762 Approved
0.7152 Intermediate Similarity NPD4678 Approved
0.7152 Intermediate Similarity NPD5763 Approved
0.7152 Intermediate Similarity NPD4675 Approved
0.7143 Intermediate Similarity NPD4062 Phase 3
0.7133 Intermediate Similarity NPD3225 Approved
0.7133 Intermediate Similarity NPD1510 Phase 2
0.7133 Intermediate Similarity NPD7033 Discontinued
0.7125 Intermediate Similarity NPD2977 Approved
0.7125 Intermediate Similarity NPD2978 Approved
0.7125 Intermediate Similarity NPD5772 Approved
0.7125 Intermediate Similarity NPD8455 Phase 2
0.7125 Intermediate Similarity NPD5773 Approved
0.7124 Intermediate Similarity NPD4535 Phase 3
0.7124 Intermediate Similarity NPD6331 Phase 2
0.7124 Intermediate Similarity NPD3750 Approved
0.7115 Intermediate Similarity NPD7314 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD6799 Approved
0.7097 Intermediate Similarity NPD1774 Approved
0.7095 Intermediate Similarity NPD4140 Approved
0.7086 Intermediate Similarity NPD2796 Approved
0.7086 Intermediate Similarity NPD2935 Discontinued
0.707 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD2122 Discontinued
0.7067 Intermediate Similarity NPD7097 Phase 1
0.7063 Intermediate Similarity NPD6583 Phase 3
0.7063 Intermediate Similarity NPD6582 Phase 2
0.7063 Intermediate Similarity NPD6801 Discontinued
0.7051 Intermediate Similarity NPD5401 Approved
0.7051 Intermediate Similarity NPD3536 Discontinued
0.7047 Intermediate Similarity NPD1933 Approved
0.7042 Intermediate Similarity NPD1535 Discovery
0.7039 Intermediate Similarity NPD1375 Discontinued
0.703 Intermediate Similarity NPD3787 Discontinued
0.703 Intermediate Similarity NPD6232 Discontinued
0.7027 Intermediate Similarity NPD1726 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD2674 Phase 3
0.7024 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.702 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.702 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD7819 Suspended
0.7019 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7013 Intermediate Similarity NPD8166 Discontinued
0.7013 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD1241 Discontinued
0.7006 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6385 Approved
0.7 Intermediate Similarity NPD6386 Approved
0.7 Intermediate Similarity NPD1894 Discontinued
0.6993 Remote Similarity NPD1481 Phase 2
0.6993 Remote Similarity NPD1608 Approved
0.6992 Remote Similarity NPD3134 Approved
0.6988 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6981 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6981 Remote Similarity NPD3455 Phase 2
0.698 Remote Similarity NPD3062 Approved
0.698 Remote Similarity NPD3061 Approved
0.698 Remote Similarity NPD3059 Approved
0.698 Remote Similarity NPD5837 Clinical (unspecified phase)

  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