Structure

Physi-Chem Properties

Molecular Weight:  369.12
Volume:  362.897
LogP:  2.079
LogD:  2.381
LogS:  -5.066
# Rotatable Bonds:  5
TPSA:  82.12
# H-Bond Aceptor:  7
# H-Bond Donor:  0
# Rings:  4
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.395
Synthetic Accessibility Score:  2.79
Fsp3:  0.3
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.962
MDCK Permeability:  3.7379602872533724e-05
Pgp-inhibitor:  0.071
Pgp-substrate:  0.013
Human Intestinal Absorption (HIA):  0.046
20% Bioavailability (F20%):  0.024
30% Bioavailability (F30%):  0.05

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.177
Plasma Protein Binding (PPB):  74.5654067993164%
Volume Distribution (VD):  1.942
Pgp-substrate:  27.35527229309082%

ADMET: Metabolism

CYP1A2-inhibitor:  0.851
CYP1A2-substrate:  0.984
CYP2C19-inhibitor:  0.02
CYP2C19-substrate:  0.911
CYP2C9-inhibitor:  0.072
CYP2C9-substrate:  0.863
CYP2D6-inhibitor:  0.032
CYP2D6-substrate:  0.911
CYP3A4-inhibitor:  0.152
CYP3A4-substrate:  0.491

ADMET: Excretion

Clearance (CL):  5.412
Half-life (T1/2):  0.261

ADMET: Toxicity

hERG Blockers:  0.374
Human Hepatotoxicity (H-HT):  0.981
Drug-inuced Liver Injury (DILI):  0.988
AMES Toxicity:  0.37
Rat Oral Acute Toxicity:  0.931
Maximum Recommended Daily Dose:  0.174
Skin Sensitization:  0.901
Carcinogencity:  0.85
Eye Corrosion:  0.013
Eye Irritation:  0.012
Respiratory Toxicity:  0.884

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

  Natural Product: NPC227683

Natural Product ID:  NPC227683
Common Name*:   Taspine
IUPAC Name:   n.a.
Synonyms:   NSC-76022
Standard InCHIKey:  MTAWKURMWOXCEO-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C20H19NO6/c1-21(2)8-7-10-9-13(25-4)18-16-14(10)20(23)27-17-12(24-3)6-5-11(15(16)17)19(22)26-18/h5-6,9H,7-8H2,1-4H3
SMILES:  CN(C)CCc1cc(c2c3c1c(=O)oc1c(ccc(c31)c(=O)o2)OC)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL470867
PubChem CID:   215159
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000145] Coumarins and derivatives

*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
NPO32603 blue cohosh Species n.a. n.a. rhizomes n.a. n.a. PMID[10543898]
NPO686 Magnolia x soulangiana Hybrid Species Magnoliaceae Eukaryota n.a. n.a. n.a. PMID[16989531]
NPO33087 croton spp. Species Euphorbiaceae Eukaryota n.a. South American n.a. PMID[8350090]
NPO5494 Croton draconoide Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25912 Leontice smirnowii Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6657 Croton lechleri Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12214 Leontice robustum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25912 Leontice smirnowii Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6657 Croton lechleri Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12214 Leontice robustum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5494 Croton draconoide Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12214 Leontice robustum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO121 Fraxinus malacophylla Species Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12214 Leontice robustum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25912 Leontice smirnowii Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1059 Sphaeranthus bullatus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6657 Croton lechleri Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19930 [clostridium] symbiosum Species Lachnospiraceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO686 Magnolia x soulangiana Hybrid Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3886 Leontice alberti Species Berberidaceae 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
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus IC50 = 330.0 nM PMID[557269]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens IC50 = 540.0 nM PMID[557269]
NPT81 Cell Line A549 Homo sapiens IC50 = 4.18 nM PMID[557271]
NPT492 Cell Line Caco-2 Homo sapiens IC50 = 153.0 nM PMID[557271]
NPT3911 Cell Line ECV-304 Homo sapiens IC50 = 22.3 nM PMID[557271]
NPT492 Cell Line Caco-2 Homo sapiens IC50 = 153000.0 nM PMID[557272]
NPT81 Cell Line A549 Homo sapiens IC50 = 4180.0 nM PMID[557272]
NPT71 Cell Line HEK293 Homo sapiens IC50 = 15950.0 nM PMID[557272]
NPT762 Cell Line A-431 Homo sapiens IC50 = 11200.0 nM PMID[557272]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 7816.28 nM PMID[557273]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 7780.37 nM PMID[557273]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 5701.64 nM PMID[557273]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 9268.3 nM PMID[557273]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 8472.27 nM PMID[557273]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 8241.38 nM PMID[557273]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 1836.54 nM PMID[557273]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 8511.38 nM PMID[557273]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 7294.58 nM PMID[557273]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 6886.52 nM PMID[557273]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 10327.61 nM PMID[557273]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 9862.79 nM PMID[557273]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 6792.04 nM PMID[557273]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 7464.49 nM PMID[557273]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 6934.26 nM PMID[557273]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 9682.78 nM PMID[557273]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 11668.1 nM PMID[557273]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 8933.05 nM PMID[557273]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 8550.67 nM PMID[557273]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 256.45 nM PMID[557273]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 8689.6 nM PMID[557273]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 5861.38 nM PMID[557273]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 6412.1 nM PMID[557273]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 6760.83 nM PMID[557273]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 9311.08 nM PMID[557273]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 8511.38 nM PMID[557273]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 8531.0 nM PMID[557273]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 8433.35 nM PMID[557273]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 7816.28 nM PMID[557273]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 7744.62 nM PMID[557273]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 12105.98 nM PMID[557273]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 8452.79 nM PMID[557273]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 8165.82 nM PMID[557273]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 5105.05 nM PMID[557273]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 5260.17 nM PMID[557273]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 7328.25 nM PMID[557273]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 7550.92 nM PMID[557273]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 5861.38 nM PMID[557273]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 10519.62 nM PMID[557273]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 8472.27 nM PMID[557273]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 9354.06 nM PMID[557273]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 2404.36 nM PMID[557273]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 8974.29 nM PMID[557273]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 8452.79 nM PMID[557273]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 6998.42 nM PMID[557273]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 8317.64 nM PMID[557273]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 3026.91 nM PMID[557273]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 10280.16 nM PMID[557273]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 762.08 nM PMID[557273]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 3311.31 nM PMID[557273]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 948.42 nM PMID[557273]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 5508.08 nM PMID[557273]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 24154.61 nM PMID[557273]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 1011.58 nM PMID[557273]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 7961.59 nM PMID[557273]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 9162.2 nM PMID[557273]
NPT32 Organism Mus musculus Mus musculus ED50 = 15.0 mg.kg-1 PMID[557267]
NPT67 Individual Protein Cholinesterase Equus caballus IC50 > 100000.0 nM PMID[557269]
NPT2 Others Unspecified Activity = 27.6 % PMID[557270]
NPT2 Others Unspecified Activity = 27.7 % PMID[557270]
NPT35 Others n.a. LogD = 8.21 n.a. PMID[557271]
NPT35 Others n.a. pKa = 0.021 n.a. PMID[557271]
NPT35 Others n.a. Solubility = 74300.0 ug.mL-1 PMID[557271]
NPT27 Others Unspecified IC50 = 22300.0 nM PMID[557272]
NPT317 Uncleic Acid Nucleic Acid Delta Tm = 1.7 degrees C PMID[557274]
NPT317 Uncleic Acid Nucleic Acid Delta Tm = 13.2 degrees C PMID[557274]
NPT317 Uncleic Acid Nucleic Acid Delta Tm = 24.0 degrees C PMID[557274]

☑ 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 NPC227683 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
0.8457 Intermediate Similarity NPC300983
0.843 Intermediate Similarity NPC35680
0.8282 Intermediate Similarity NPC475848
0.8282 Intermediate Similarity NPC474306
0.8274 Intermediate Similarity NPC153631
0.8242 Intermediate Similarity NPC83019
0.8232 Intermediate Similarity NPC474305
0.8187 Intermediate Similarity NPC204580
0.8146 Intermediate Similarity NPC18306
0.8107 Intermediate Similarity NPC296044
0.8107 Intermediate Similarity NPC167098
0.8101 Intermediate Similarity NPC162694
0.8059 Intermediate Similarity NPC267627
0.8059 Intermediate Similarity NPC40702
0.8059 Intermediate Similarity NPC37502
0.8056 Intermediate Similarity NPC141440
0.8046 Intermediate Similarity NPC303581
0.8046 Intermediate Similarity NPC67978
0.8033 Intermediate Similarity NPC477258
0.8024 Intermediate Similarity NPC118332
0.8011 Intermediate Similarity NPC241704
0.8011 Intermediate Similarity NPC311781
0.8 Intermediate Similarity NPC247713
0.7975 Intermediate Similarity NPC472840
0.7955 Intermediate Similarity NPC308267
0.7955 Intermediate Similarity NPC52598
0.7944 Intermediate Similarity NPC214629
0.7927 Intermediate Similarity NPC308006
0.7921 Intermediate Similarity NPC32154
0.7919 Intermediate Similarity NPC108767
0.791 Intermediate Similarity NPC222524
0.7907 Intermediate Similarity NPC47623
0.7904 Intermediate Similarity NPC474648
0.7901 Intermediate Similarity NPC474009
0.7882 Intermediate Similarity NPC222185
0.7874 Intermediate Similarity NPC474350
0.7862 Intermediate Similarity NPC311339
0.7857 Intermediate Similarity NPC208890
0.7857 Intermediate Similarity NPC58661
0.7849 Intermediate Similarity NPC215098
0.7849 Intermediate Similarity NPC46744
0.7849 Intermediate Similarity NPC70290
0.7849 Intermediate Similarity NPC14622
0.7849 Intermediate Similarity NPC73020
0.7849 Intermediate Similarity NPC124302
0.7849 Intermediate Similarity NPC125713
0.7846 Intermediate Similarity NPC38964
0.7844 Intermediate Similarity NPC183236
0.7844 Intermediate Similarity NPC472839
0.7838 Intermediate Similarity NPC470646
0.7838 Intermediate Similarity NPC33256
0.7836 Intermediate Similarity NPC474983
0.7836 Intermediate Similarity NPC109765
0.7836 Intermediate Similarity NPC261484
0.7829 Intermediate Similarity NPC86469
0.7824 Intermediate Similarity NPC186507
0.7824 Intermediate Similarity NPC178134
0.7816 Intermediate Similarity NPC144843
0.7811 Intermediate Similarity NPC473732
0.7811 Intermediate Similarity NPC474663
0.7811 Intermediate Similarity NPC198615
0.7803 Intermediate Similarity NPC24627
0.7803 Intermediate Similarity NPC477164
0.7803 Intermediate Similarity NPC298093
0.7798 Intermediate Similarity NPC119669
0.7797 Intermediate Similarity NPC329992
0.7791 Intermediate Similarity NPC26353
0.7791 Intermediate Similarity NPC82733
0.7791 Intermediate Similarity NPC76458
0.7791 Intermediate Similarity NPC202495
0.7784 Intermediate Similarity NPC211296
0.7784 Intermediate Similarity NPC471923
0.7778 Intermediate Similarity NPC115906
0.7771 Intermediate Similarity NPC477689
0.7771 Intermediate Similarity NPC67959
0.7766 Intermediate Similarity NPC72788
0.7766 Intermediate Similarity NPC82056
0.7766 Intermediate Similarity NPC120671
0.7766 Intermediate Similarity NPC226652
0.7766 Intermediate Similarity NPC314100
0.7765 Intermediate Similarity NPC475116
0.7765 Intermediate Similarity NPC121400
0.7765 Intermediate Similarity NPC40033
0.7765 Intermediate Similarity NPC166201
0.776 Intermediate Similarity NPC469437
0.7759 Intermediate Similarity NPC35345
0.7759 Intermediate Similarity NPC165549
0.7758 Intermediate Similarity NPC473090
0.7758 Intermediate Similarity NPC50954
0.7753 Intermediate Similarity NPC313304
0.7753 Intermediate Similarity NPC207721
0.7751 Intermediate Similarity NPC29056
0.7746 Intermediate Similarity NPC328122
0.7746 Intermediate Similarity NPC15764
0.7742 Intermediate Similarity NPC174783
0.774 Intermediate Similarity NPC234331
0.774 Intermediate Similarity NPC475453
0.774 Intermediate Similarity NPC473531
0.7738 Intermediate Similarity NPC63256
0.7738 Intermediate Similarity NPC10304
0.7738 Intermediate Similarity NPC476394
0.7738 Intermediate Similarity NPC476342
0.7738 Intermediate Similarity NPC98809
0.7733 Intermediate Similarity NPC239113
0.7733 Intermediate Similarity NPC115123
0.773 Intermediate Similarity NPC94499
0.7722 Intermediate Similarity NPC27887
0.7719 Intermediate Similarity NPC472408
0.7714 Intermediate Similarity NPC19948
0.7714 Intermediate Similarity NPC229632
0.7711 Intermediate Similarity NPC473934
0.7711 Intermediate Similarity NPC472836
0.7711 Intermediate Similarity NPC213900
0.7711 Intermediate Similarity NPC113397
0.7709 Intermediate Similarity NPC38438
0.7709 Intermediate Similarity NPC473697
0.7706 Intermediate Similarity NPC474414
0.7706 Intermediate Similarity NPC228662
0.7706 Intermediate Similarity NPC124842
0.7705 Intermediate Similarity NPC169387
0.7705 Intermediate Similarity NPC477259
0.7702 Intermediate Similarity NPC95485
0.7702 Intermediate Similarity NPC88065
0.7702 Intermediate Similarity NPC89504
0.7701 Intermediate Similarity NPC53889
0.7701 Intermediate Similarity NPC139876
0.7697 Intermediate Similarity NPC49487
0.7697 Intermediate Similarity NPC99613
0.7688 Intermediate Similarity NPC165977
0.7688 Intermediate Similarity NPC217677
0.7688 Intermediate Similarity NPC143328
0.7684 Intermediate Similarity NPC119818
0.7684 Intermediate Similarity NPC328700
0.7684 Intermediate Similarity NPC202771
0.7684 Intermediate Similarity NPC2173
0.7684 Intermediate Similarity NPC29160
0.7684 Intermediate Similarity NPC263212
0.7683 Intermediate Similarity NPC326065
0.7679 Intermediate Similarity NPC470088
0.7679 Intermediate Similarity NPC470511
0.7676 Intermediate Similarity NPC226708
0.7674 Intermediate Similarity NPC476572
0.7674 Intermediate Similarity NPC80489
0.7674 Intermediate Similarity NPC3273
0.7674 Intermediate Similarity NPC471746
0.7674 Intermediate Similarity NPC20541
0.767 Intermediate Similarity NPC236521
0.767 Intermediate Similarity NPC152659
0.767 Intermediate Similarity NPC248638
0.767 Intermediate Similarity NPC284842
0.767 Intermediate Similarity NPC45943
0.7669 Intermediate Similarity NPC470962
0.7667 Intermediate Similarity NPC46640
0.7667 Intermediate Similarity NPC219600
0.7667 Intermediate Similarity NPC263119
0.7667 Intermediate Similarity NPC166674
0.7667 Intermediate Similarity NPC473550
0.7667 Intermediate Similarity NPC34436
0.7665 Intermediate Similarity NPC136278
0.7665 Intermediate Similarity NPC131766
0.7661 Intermediate Similarity NPC295646
0.7661 Intermediate Similarity NPC144162
0.7661 Intermediate Similarity NPC131121
0.7661 Intermediate Similarity NPC60211
0.7657 Intermediate Similarity NPC309335
0.7657 Intermediate Similarity NPC474187
0.7657 Intermediate Similarity NPC469889
0.7657 Intermediate Similarity NPC296540
0.7656 Intermediate Similarity NPC314946
0.7654 Intermediate Similarity NPC109827
0.7654 Intermediate Similarity NPC77955
0.7654 Intermediate Similarity NPC124470
0.765 Intermediate Similarity NPC53680
0.765 Intermediate Similarity NPC208797
0.7647 Intermediate Similarity NPC189270
0.7647 Intermediate Similarity NPC5840
0.7647 Intermediate Similarity NPC474660
0.7644 Intermediate Similarity NPC87317
0.764 Intermediate Similarity NPC298847
0.763 Intermediate Similarity NPC301897
0.763 Intermediate Similarity NPC54928
0.7627 Intermediate Similarity NPC239752
0.7627 Intermediate Similarity NPC472450
0.7627 Intermediate Similarity NPC275780
0.7627 Intermediate Similarity NPC293319
0.7622 Intermediate Similarity NPC223336
0.7619 Intermediate Similarity NPC231013
0.7619 Intermediate Similarity NPC473927
0.7616 Intermediate Similarity NPC128961
0.7616 Intermediate Similarity NPC475895
0.7616 Intermediate Similarity NPC473664
0.7616 Intermediate Similarity NPC54179
0.7616 Intermediate Similarity NPC62051
0.7614 Intermediate Similarity NPC52204
0.7614 Intermediate Similarity NPC249070
0.7614 Intermediate Similarity NPC475144
0.7614 Intermediate Similarity NPC25152
0.7614 Intermediate Similarity NPC474858
0.7611 Intermediate Similarity NPC471921
0.7611 Intermediate Similarity NPC129930

  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 NPC227683 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
0.8466 Intermediate Similarity NPD6385 Approved
0.8466 Intermediate Similarity NPD6386 Approved
0.815 Intermediate Similarity NPD7177 Discontinued
0.8081 Intermediate Similarity NPD5242 Approved
0.8054 Intermediate Similarity NPD4107 Approved
0.8024 Intermediate Similarity NPD6873 Phase 2
0.8011 Intermediate Similarity NPD4482 Phase 3
0.8 Intermediate Similarity NPD5844 Phase 1
0.7988 Intermediate Similarity NPD5977 Approved
0.7988 Intermediate Similarity NPD5978 Approved
0.7957 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7865 Intermediate Similarity NPD7039 Approved
0.7865 Intermediate Similarity NPD7038 Approved
0.7849 Intermediate Similarity NPD4420 Approved
0.7829 Intermediate Similarity NPD4481 Phase 3
0.7824 Intermediate Similarity NPD1465 Phase 2
0.7803 Intermediate Similarity NPD5494 Approved
0.7778 Intermediate Similarity NPD5616 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD2971 Approved
0.7778 Intermediate Similarity NPD2968 Approved
0.7764 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7764 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7751 Intermediate Similarity NPD1337 Clinical (unspecified phase)
0.7742 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.774 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7713 Intermediate Similarity NPD8285 Discontinued
0.7706 Intermediate Similarity NPD7110 Phase 1
0.7706 Intermediate Similarity NPD7109 Clinical (unspecified phase)
0.7684 Intermediate Similarity NPD5005 Approved
0.7684 Intermediate Similarity NPD5006 Approved
0.7679 Intermediate Similarity NPD6662 Clinical (unspecified phase)
0.7674 Intermediate Similarity NPD5353 Approved
0.7619 Intermediate Similarity NPD3647 Clinical (unspecified phase)
0.7614 Intermediate Similarity NPD6232 Discontinued
0.7607 Intermediate Similarity NPD4476 Approved
0.7607 Intermediate Similarity NPD4477 Approved
0.7606 Intermediate Similarity NPD2974 Approved
0.7606 Intermediate Similarity NPD2975 Approved
0.7606 Intermediate Similarity NPD2973 Approved
0.7592 Intermediate Similarity NPD3057 Approved
0.7582 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7574 Intermediate Similarity NPD7427 Discontinued
0.7544 Intermediate Similarity NPD6875 Approved
0.7544 Intermediate Similarity NPD6876 Approved
0.7538 Intermediate Similarity NPD5980 Discovery
0.7529 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD2897 Discontinued
0.7514 Intermediate Similarity NPD7819 Suspended
0.75 Intermediate Similarity NPD5889 Approved
0.75 Intermediate Similarity NPD3533 Approved
0.75 Intermediate Similarity NPD2972 Approved
0.75 Intermediate Similarity NPD5890 Approved
0.7487 Intermediate Similarity NPD4580 Approved
0.7486 Intermediate Similarity NPD7473 Discontinued
0.7456 Intermediate Similarity NPD4584 Approved
0.7456 Intermediate Similarity NPD3146 Approved
0.7456 Intermediate Similarity NPD3688 Clinical (unspecified phase)
0.7448 Intermediate Similarity NPD2493 Approved
0.7448 Intermediate Similarity NPD2494 Approved
0.7446 Intermediate Similarity NPD6618 Phase 2
0.7442 Intermediate Similarity NPD6585 Discontinued
0.744 Intermediate Similarity NPD6666 Approved
0.744 Intermediate Similarity NPD6667 Approved
0.7433 Intermediate Similarity NPD2488 Approved
0.7433 Intermediate Similarity NPD2490 Approved
0.7432 Intermediate Similarity NPD7549 Discontinued
0.7423 Intermediate Similarity NPD2653 Approved
0.7419 Intermediate Similarity NPD7291 Discontinued
0.7409 Intermediate Similarity NPD2491 Approved
0.7407 Intermediate Similarity NPD3142 Approved
0.7407 Intermediate Similarity NPD3140 Approved
0.7402 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD8005 Clinical (unspecified phase)
0.7384 Intermediate Similarity NPD3226 Approved
0.7375 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7374 Intermediate Similarity NPD5676 Approved
0.7371 Intermediate Similarity NPD3817 Phase 2
0.7368 Intermediate Similarity NPD3640 Phase 3
0.7368 Intermediate Similarity NPD3639 Approved
0.7368 Intermediate Similarity NPD3641 Approved
0.7365 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7362 Intermediate Similarity NPD4618 Approved
0.7362 Intermediate Similarity NPD4622 Approved
0.7358 Intermediate Similarity NPD3450 Approved
0.7358 Intermediate Similarity NPD3452 Approved
0.7356 Intermediate Similarity NPD6844 Discontinued
0.7349 Intermediate Similarity NPD2346 Discontinued
0.7345 Intermediate Similarity NPD919 Approved
0.7337 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD4582 Approved
0.7333 Intermediate Similarity NPD4583 Approved
0.7333 Intermediate Similarity NPD3748 Approved
0.733 Intermediate Similarity NPD5019 Clinical (unspecified phase)
0.7326 Intermediate Similarity NPD3686 Approved
0.7326 Intermediate Similarity NPD3687 Approved
0.732 Intermediate Similarity NPD3448 Approved
0.7314 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.7287 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7282 Intermediate Similarity NPD4004 Approved
0.7282 Intermediate Similarity NPD4002 Approved
0.7278 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD5689 Approved
0.7273 Intermediate Similarity NPD5688 Approved
0.7267 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7258 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD1934 Approved
0.7253 Intermediate Similarity NPD8252 Approved
0.7253 Intermediate Similarity NPD8251 Approved
0.7253 Intermediate Similarity NPD8099 Discontinued
0.724 Intermediate Similarity NPD5564 Approved
0.7225 Intermediate Similarity NPD4413 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD3051 Approved
0.7222 Intermediate Similarity NPD5711 Approved
0.7222 Intermediate Similarity NPD5710 Approved
0.722 Intermediate Similarity NPD7907 Approved
0.7219 Intermediate Similarity NPD4628 Phase 3
0.7216 Intermediate Similarity NPD2801 Approved
0.7216 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7213 Intermediate Similarity NPD8156 Discontinued
0.7213 Intermediate Similarity NPD5312 Approved
0.7213 Intermediate Similarity NPD5313 Approved
0.7209 Intermediate Similarity NPD7314 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD2186 Approved
0.7207 Intermediate Similarity NPD5677 Discontinued
0.7206 Intermediate Similarity NPD4665 Approved
0.7206 Intermediate Similarity NPD4111 Phase 1
0.72 Intermediate Similarity NPD7783 Phase 2
0.72 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7194 Intermediate Similarity NPD7497 Discontinued
0.7193 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD7837 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD6032 Approved
0.7184 Intermediate Similarity NPD824 Approved
0.7182 Intermediate Similarity NPD2970 Approved
0.7182 Intermediate Similarity NPD2969 Approved
0.7178 Intermediate Similarity NPD5718 Phase 2
0.7174 Intermediate Similarity NPD5441 Clinical (unspecified phase)
0.7167 Intermediate Similarity NPD8127 Discontinued
0.7159 Intermediate Similarity NPD7577 Discontinued
0.7158 Intermediate Similarity NPD3808 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD1933 Approved
0.7143 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6166 Phase 2
0.7143 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD3451 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD4363 Phase 3
0.7135 Intermediate Similarity NPD4360 Phase 2
0.7135 Intermediate Similarity NPD3823 Discontinued
0.7135 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7127 Intermediate Similarity NPD6808 Phase 2
0.7127 Intermediate Similarity NPD6747 Phase 1
0.7126 Intermediate Similarity NPD2799 Discontinued
0.7126 Intermediate Similarity NPD4210 Discontinued
0.712 Intermediate Similarity NPD3050 Clinical (unspecified phase)
0.7118 Intermediate Similarity NPD3750 Approved
0.7105 Intermediate Similarity NPD6377 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD7235 Clinical (unspecified phase)
0.7102 Intermediate Similarity NPD7411 Suspended
0.7095 Intermediate Similarity NPD3749 Approved
0.7095 Intermediate Similarity NPD7075 Discontinued
0.7091 Intermediate Similarity NPD2979 Phase 3
0.709 Intermediate Similarity NPD3863 Clinical (unspecified phase)
0.7088 Intermediate Similarity NPD3926 Phase 2
0.7086 Intermediate Similarity NPD2649 Approved
0.7086 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD2651 Approved
0.7083 Intermediate Similarity NPD6181 Discontinued
0.7081 Intermediate Similarity NPD7074 Phase 3
0.7073 Intermediate Similarity NPD6812 Clinical (unspecified phase)
0.7072 Intermediate Similarity NPD1247 Approved
0.7072 Intermediate Similarity NPD6107 Approved
0.7072 Intermediate Similarity NPD6959 Discontinued
0.7069 Intermediate Similarity NPD920 Approved
0.7069 Intermediate Similarity NPD6031 Approved
0.7069 Intermediate Similarity NPD6030 Approved
0.7068 Intermediate Similarity NPD5525 Clinical (unspecified phase)
0.7066 Intermediate Similarity NPD6895 Approved
0.7066 Intermediate Similarity NPD6896 Approved
0.7065 Intermediate Similarity NPD2163 Approved
0.7062 Intermediate Similarity NPD6279 Approved
0.7062 Intermediate Similarity NPD6280 Approved
0.7056 Intermediate Similarity NPD5709 Phase 3
0.7053 Intermediate Similarity NPD7693 Approved
0.705 Intermediate Similarity NPD7701 Phase 2
0.7049 Intermediate Similarity NPD27 Approved
0.7049 Intermediate Similarity NPD4575 Clinical (unspecified phase)
0.7049 Intermediate Similarity NPD2489 Approved
0.7048 Intermediate Similarity NPD447 Suspended
0.7043 Intermediate Similarity NPD6297 Approved
0.7039 Intermediate Similarity NPD4947 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD3882 Suspended
0.7035 Intermediate Similarity NPD7124 Phase 2
0.7033 Intermediate Similarity NPD7315 Approved
0.7027 Intermediate Similarity NPD7054 Approved
0.7025 Intermediate Similarity NPD17 Approved
0.7021 Intermediate Similarity NPD6146 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD7003 Approved
0.7018 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7017 Intermediate Similarity NPD4666 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