Structure

Physi-Chem Properties

Molecular Weight:  478.28
Volume:  506.057
LogP:  4.983
LogD:  4.097
LogS:  -4.603
# Rotatable Bonds:  7
TPSA:  52.52
# H-Bond Aceptor:  6
# H-Bond Donor:  0
# Rings:  5
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.554
Synthetic Accessibility Score:  3.809
Fsp3:  0.552
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:  -5.458
MDCK Permeability:  2.1061032384750433e-05
Pgp-inhibitor:  0.998
Pgp-substrate:  0.998
Human Intestinal Absorption (HIA):  0.002
20% Bioavailability (F20%):  0.925
30% Bioavailability (F30%):  0.733

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.6
Plasma Protein Binding (PPB):  78.48273468017578%
Volume Distribution (VD):  1.598
Pgp-substrate:  3.935645818710327%

ADMET: Metabolism

CYP1A2-inhibitor:  0.062
CYP1A2-substrate:  0.949
CYP2C19-inhibitor:  0.063
CYP2C19-substrate:  0.952
CYP2C9-inhibitor:  0.032
CYP2C9-substrate:  0.461
CYP2D6-inhibitor:  0.424
CYP2D6-substrate:  0.938
CYP3A4-inhibitor:  0.196
CYP3A4-substrate:  0.937

ADMET: Excretion

Clearance (CL):  9.692
Half-life (T1/2):  0.421

ADMET: Toxicity

hERG Blockers:  0.954
Human Hepatotoxicity (H-HT):  0.168
Drug-inuced Liver Injury (DILI):  0.928
AMES Toxicity:  0.022
Rat Oral Acute Toxicity:  0.349
Maximum Recommended Daily Dose:  0.969
Skin Sensitization:  0.554
Carcinogencity:  0.027
Eye Corrosion:  0.003
Eye Irritation:  0.01
Respiratory Toxicity:  0.779

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

  Natural Product: NPC216816

Natural Product ID:  NPC216816
Common Name*:   O-Methylpsychotrine
IUPAC Name:   (2R,3R,11bS)-2-[(6,7-dimethoxy-3,4-dihydroisoquinolin-1-yl)methyl]-3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizine
Synonyms:   O-Methylpsychotrine
Standard InCHIKey:  FBRKYRSUSJWLHH-HMHJJOSWSA-N
Standard InCHI:  InChI=1S/C29H38N2O4/c1-6-18-17-31-10-8-20-14-27(33-3)29(35-5)16-23(20)25(31)12-21(18)11-24-22-15-28(34-4)26(32-2)13-19(22)7-9-30-24/h13-16,18,21,25H,6-12,17H2,1-5H3/p+1/t18-,21-,25-/m0/s1
SMILES:  CC[C@H]1CN2CCc3cc(c(cc3[C@@H]2C[C@@H]1CC1=[NH+]CCc2cc(c(cc12)OC)OC)OC)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL471812
PubChem CID:   65033
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0002659] Emetine alkaloids

*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
NPO27192 Maprounea africana Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[10075783]
NPO2719 Amauroascus aureus Species Onygenaceae Eukaryota n.a. n.a. n.a. PMID[5735362]
NPO27192 Maprounea africana Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[6631436]
NPO27192 Maprounea africana Species Euphorbiaceae Eukaryota n.a. root n.a. PMID[7515410]
NPO27192 Maprounea africana Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[7515410]
NPO27192 Maprounea africana Species Euphorbiaceae Eukaryota Roots n.a. n.a. PMID[7561895]
NPO24848 Acodontaster conspicuus Species Odontasteridae Eukaryota n.a. Antarctic n.a. PMID[9358635]
NPO24728 Tragopogon porrifolius Species Asteraceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO24728 Tragopogon porrifolius Species Asteraceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO24728 Tragopogon porrifolius Species Asteraceae Eukaryota n.a. n.a. Database[FooDB]
NPO24728 Tragopogon porrifolius Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2690 Carapichea ipecacuanha Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23138 Swainsona salsula Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2690 Carapichea ipecacuanha Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO24728 Tragopogon porrifolius Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24646 Coryphantha elephantidens Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23623 Hirsutella nivea Species Ophiocordycipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5056 Helichrysum heterolasium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27192 Maprounea africana Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18432 Poria corticola Species Coccinellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2719 Amauroascus aureus Species Onygenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24848 Acodontaster conspicuus Species Odontasteridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26128 Clonostachys rosea Species Bionectriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22548 Osteospermum jucundum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21010 Streptomyces avidinii Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO26637.1 Mentha aquatica var. citrata Varieties Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25360 Helminthosporium ravenelii Species Massarinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25098 Spinacia glabra Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25409 Ascochyta caulina Species Didymellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2690 Carapichea ipecacuanha Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24521 Helichrysum revolutum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24211 Parmelia cetrarioides Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24880 Bacterial str n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO23138 Swainsona salsula Species Fabaceae 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
NPT459 Individual Protein Human immunodeficiency virus type 1 reverse transcriptase Human immunodeficiency virus 1 IC50 = 14000.0 nM PMID[523665]

☑ 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 NPC216816 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
0.9548 High Similarity NPC66573
0.9333 High Similarity NPC476568
0.9054 High Similarity NPC128019
0.9054 High Similarity NPC476567
0.9054 High Similarity NPC136860
0.8903 High Similarity NPC187022
0.8903 High Similarity NPC80129
0.8882 High Similarity NPC7467
0.8816 High Similarity NPC106295
0.8816 High Similarity NPC16107
0.8816 High Similarity NPC51957
0.8816 High Similarity NPC210437
0.8816 High Similarity NPC476144
0.8792 High Similarity NPC213206
0.8792 High Similarity NPC188163
0.8792 High Similarity NPC474915
0.8792 High Similarity NPC328750
0.8726 High Similarity NPC247639
0.8726 High Similarity NPC25084
0.8725 High Similarity NPC314682
0.869 High Similarity NPC249996
0.8683 High Similarity NPC476202
0.8645 High Similarity NPC220858
0.8645 High Similarity NPC88249
0.8645 High Similarity NPC97221
0.8645 High Similarity NPC192768
0.8645 High Similarity NPC151895
0.8623 High Similarity NPC195538
0.8535 High Similarity NPC210148
0.8535 High Similarity NPC233029
0.8519 High Similarity NPC284183
0.8519 High Similarity NPC4138
0.8519 High Similarity NPC121275
0.8491 Intermediate Similarity NPC146288
0.8462 Intermediate Similarity NPC92541
0.8457 Intermediate Similarity NPC475393
0.8442 Intermediate Similarity NPC185838
0.8428 Intermediate Similarity NPC189266
0.8428 Intermediate Similarity NPC295691
0.8428 Intermediate Similarity NPC278799
0.8428 Intermediate Similarity NPC5238
0.8428 Intermediate Similarity NPC110416
0.8428 Intermediate Similarity NPC2413
0.8428 Intermediate Similarity NPC469817
0.8428 Intermediate Similarity NPC276588
0.8428 Intermediate Similarity NPC127674
0.8428 Intermediate Similarity NPC193949
0.8428 Intermediate Similarity NPC249797
0.8428 Intermediate Similarity NPC39701
0.8428 Intermediate Similarity NPC172765
0.8428 Intermediate Similarity NPC184026
0.8428 Intermediate Similarity NPC138487
0.8428 Intermediate Similarity NPC207757
0.8428 Intermediate Similarity NPC54379
0.8428 Intermediate Similarity NPC41178
0.8428 Intermediate Similarity NPC204828
0.8428 Intermediate Similarity NPC216459
0.8397 Intermediate Similarity NPC135538
0.8397 Intermediate Similarity NPC24233
0.8397 Intermediate Similarity NPC428
0.8397 Intermediate Similarity NPC147390
0.8397 Intermediate Similarity NPC476571
0.8397 Intermediate Similarity NPC475959
0.8397 Intermediate Similarity NPC246587
0.8354 Intermediate Similarity NPC42549
0.8354 Intermediate Similarity NPC250846
0.8354 Intermediate Similarity NPC256012
0.8354 Intermediate Similarity NPC240841
0.8354 Intermediate Similarity NPC268503
0.8354 Intermediate Similarity NPC317272
0.8333 Intermediate Similarity NPC179825
0.8333 Intermediate Similarity NPC144863
0.8333 Intermediate Similarity NPC321505
0.8333 Intermediate Similarity NPC191376
0.8313 Intermediate Similarity NPC109925
0.8286 Intermediate Similarity NPC85381
0.8276 Intermediate Similarity NPC318805
0.8276 Intermediate Similarity NPC41122
0.8272 Intermediate Similarity NPC111485
0.8261 Intermediate Similarity NPC234392
0.8261 Intermediate Similarity NPC31311
0.8243 Intermediate Similarity NPC160193
0.8239 Intermediate Similarity NPC326316
0.8239 Intermediate Similarity NPC476579
0.8239 Intermediate Similarity NPC81733
0.8217 Intermediate Similarity NPC476151
0.8199 Intermediate Similarity NPC99659
0.8199 Intermediate Similarity NPC325871
0.8165 Intermediate Similarity NPC130941
0.816 Intermediate Similarity NPC477080
0.8155 Intermediate Similarity NPC10908
0.8155 Intermediate Similarity NPC63646
0.8155 Intermediate Similarity NPC227060
0.8155 Intermediate Similarity NPC276890
0.8155 Intermediate Similarity NPC115284
0.8155 Intermediate Similarity NPC198498
0.8155 Intermediate Similarity NPC76682
0.8155 Intermediate Similarity NPC317145
0.8155 Intermediate Similarity NPC317439
0.8113 Intermediate Similarity NPC477565
0.8113 Intermediate Similarity NPC207824
0.8113 Intermediate Similarity NPC60538
0.8113 Intermediate Similarity NPC103379
0.8113 Intermediate Similarity NPC219162
0.8107 Intermediate Similarity NPC12424
0.8107 Intermediate Similarity NPC129518
0.8107 Intermediate Similarity NPC251580
0.8107 Intermediate Similarity NPC41376
0.8105 Intermediate Similarity NPC253429
0.8098 Intermediate Similarity NPC476572
0.8092 Intermediate Similarity NPC11147
0.809 Intermediate Similarity NPC234318
0.8089 Intermediate Similarity NPC130926
0.8086 Intermediate Similarity NPC93593
0.8075 Intermediate Similarity NPC37272
0.8072 Intermediate Similarity NPC276944
0.8072 Intermediate Similarity NPC24465
0.8072 Intermediate Similarity NPC232514
0.8072 Intermediate Similarity NPC238530
0.8067 Intermediate Similarity NPC476570
0.8047 Intermediate Similarity NPC108434
0.8047 Intermediate Similarity NPC475215
0.8024 Intermediate Similarity NPC13916
0.8024 Intermediate Similarity NPC264850
0.8012 Intermediate Similarity NPC76213
0.8012 Intermediate Similarity NPC277669
0.8012 Intermediate Similarity NPC293093
0.7987 Intermediate Similarity NPC172403
0.7987 Intermediate Similarity NPC253883
0.7987 Intermediate Similarity NPC90844
0.7987 Intermediate Similarity NPC95075
0.7963 Intermediate Similarity NPC476580
0.7927 Intermediate Similarity NPC170503
0.7927 Intermediate Similarity NPC203784
0.7927 Intermediate Similarity NPC126519
0.7919 Intermediate Similarity NPC243454
0.7919 Intermediate Similarity NPC475479
0.7904 Intermediate Similarity NPC476569
0.7904 Intermediate Similarity NPC324144
0.7895 Intermediate Similarity NPC118419
0.7892 Intermediate Similarity NPC27410
0.7892 Intermediate Similarity NPC477559
0.7892 Intermediate Similarity NPC266753
0.7892 Intermediate Similarity NPC166014
0.7892 Intermediate Similarity NPC160298
0.7892 Intermediate Similarity NPC306902
0.7892 Intermediate Similarity NPC232924
0.7877 Intermediate Similarity NPC471113
0.7874 Intermediate Similarity NPC286119
0.7874 Intermediate Similarity NPC239584
0.7866 Intermediate Similarity NPC244112
0.7857 Intermediate Similarity NPC169743
0.7857 Intermediate Similarity NPC167546
0.7857 Intermediate Similarity NPC136508
0.7857 Intermediate Similarity NPC253043
0.7857 Intermediate Similarity NPC13504
0.7857 Intermediate Similarity NPC477563
0.7857 Intermediate Similarity NPC212794
0.7857 Intermediate Similarity NPC196447
0.7857 Intermediate Similarity NPC16805
0.7857 Intermediate Similarity NPC306843
0.7857 Intermediate Similarity NPC96603
0.7857 Intermediate Similarity NPC302527
0.7857 Intermediate Similarity NPC78222
0.7843 Intermediate Similarity NPC160692
0.784 Intermediate Similarity NPC274026
0.7834 Intermediate Similarity NPC470925
0.7831 Intermediate Similarity NPC106786
0.7829 Intermediate Similarity NPC90998
0.7829 Intermediate Similarity NPC73492
0.7829 Intermediate Similarity NPC8836
0.7829 Intermediate Similarity NPC217748
0.7829 Intermediate Similarity NPC328155
0.7829 Intermediate Similarity NPC185639
0.7829 Intermediate Similarity NPC15414
0.7829 Intermediate Similarity NPC182052
0.7829 Intermediate Similarity NPC104196
0.7829 Intermediate Similarity NPC290005
0.7829 Intermediate Similarity NPC311973
0.7829 Intermediate Similarity NPC222661
0.7829 Intermediate Similarity NPC299990
0.7829 Intermediate Similarity NPC229373
0.7829 Intermediate Similarity NPC181796
0.7829 Intermediate Similarity NPC49075
0.7829 Intermediate Similarity NPC239824
0.7829 Intermediate Similarity NPC42663
0.7829 Intermediate Similarity NPC290582
0.7829 Intermediate Similarity NPC54654
0.7829 Intermediate Similarity NPC251735
0.7829 Intermediate Similarity NPC279228
0.7829 Intermediate Similarity NPC223690
0.7829 Intermediate Similarity NPC271013
0.7829 Intermediate Similarity NPC285931
0.7829 Intermediate Similarity NPC258657
0.7829 Intermediate Similarity NPC7715
0.7829 Intermediate Similarity NPC30779
0.7818 Intermediate Similarity NPC186063
0.7818 Intermediate Similarity NPC57512
0.7811 Intermediate Similarity NPC476432
0.7811 Intermediate Similarity NPC24264

  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 NPC216816 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
0.8903 High Similarity NPD7298 Approved
0.8816 High Similarity NPD4584 Approved
0.8792 High Similarity NPD4664 Clinical (unspecified phase)
0.865 High Similarity NPD5602 Clinical (unspecified phase)
0.8457 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.8344 Intermediate Similarity NPD3640 Phase 3
0.8344 Intermediate Similarity NPD3641 Approved
0.8344 Intermediate Similarity NPD3639 Approved
0.8312 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.825 Intermediate Similarity NPD4773 Phase 2
0.825 Intermediate Similarity NPD4772 Phase 2
0.8208 Intermediate Similarity NPD7291 Discontinued
0.8155 Intermediate Similarity NPD8251 Approved
0.8155 Intermediate Similarity NPD8252 Approved
0.8155 Intermediate Similarity NPD8099 Discontinued
0.8125 Intermediate Similarity NPD4017 Approved
0.8107 Intermediate Similarity NPD8156 Discontinued
0.8072 Intermediate Similarity NPD6107 Approved
0.7947 Intermediate Similarity NPD5718 Phase 2
0.7925 Intermediate Similarity NPD3124 Discontinued
0.7901 Intermediate Similarity NPD4005 Discontinued
0.7889 Intermediate Similarity NPD7034 Discontinued
0.7888 Intermediate Similarity NPD6031 Approved
0.7888 Intermediate Similarity NPD6030 Approved
0.7874 Intermediate Similarity NPD5917 Clinical (unspecified phase)
0.7871 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7871 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7829 Intermediate Similarity NPD8053 Approved
0.7829 Intermediate Similarity NPD8054 Approved
0.7816 Intermediate Similarity NPD7132 Clinical (unspecified phase)
0.7811 Intermediate Similarity NPD4166 Phase 2
0.7806 Intermediate Similarity NPD6896 Approved
0.7806 Intermediate Similarity NPD6895 Approved
0.7791 Intermediate Similarity NPD5313 Approved
0.7791 Intermediate Similarity NPD5312 Approved
0.7763 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7751 Intermediate Similarity NPD7802 Discontinued
0.7712 Intermediate Similarity NPD5110 Phase 2
0.7712 Intermediate Similarity NPD5109 Approved
0.7712 Intermediate Similarity NPD5111 Phase 2
0.7711 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7706 Intermediate Similarity NPD4010 Discontinued
0.7644 Intermediate Similarity NPD3920 Phase 2
0.7619 Intermediate Similarity NPD6788 Approved
0.76 Intermediate Similarity NPD6996 Clinical (unspecified phase)
0.7582 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7578 Intermediate Similarity NPD5241 Discontinued
0.7576 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7574 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7574 Intermediate Similarity NPD7833 Phase 2
0.7574 Intermediate Similarity NPD7831 Phase 2
0.7569 Intermediate Similarity NPD3924 Approved
0.7569 Intermediate Similarity NPD3923 Approved
0.7569 Intermediate Similarity NPD3921 Approved
0.7569 Intermediate Similarity NPD3922 Approved
0.7561 Intermediate Similarity NPD2122 Discontinued
0.7516 Intermediate Similarity NPD6331 Phase 2
0.7485 Intermediate Similarity NPD7110 Phase 1
0.7485 Intermediate Similarity NPD7109 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD7598 Phase 2
0.744 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7439 Intermediate Similarity NPD4123 Phase 3
0.7436 Intermediate Similarity NPD2674 Phase 3
0.743 Intermediate Similarity NPD6618 Phase 2
0.7423 Intermediate Similarity NPD7124 Phase 2
0.7401 Intermediate Similarity NPD6297 Approved
0.7391 Intermediate Similarity NPD7045 Clinical (unspecified phase)
0.7389 Intermediate Similarity NPD3110 Approved
0.7389 Intermediate Similarity NPD3109 Approved
0.738 Intermediate Similarity NPD6612 Phase 2
0.7372 Intermediate Similarity NPD3145 Approved
0.7372 Intermediate Similarity NPD3144 Approved
0.7371 Intermediate Similarity NPD5966 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD4055 Discovery
0.7368 Intermediate Similarity NPD5604 Discontinued
0.7362 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7362 Intermediate Similarity NPD3692 Discontinued
0.7356 Intermediate Similarity NPD4083 Discontinued
0.7356 Intermediate Similarity NPD6688 Approved
0.7356 Intermediate Similarity NPD6687 Approved
0.7353 Intermediate Similarity NPD5977 Approved
0.7353 Intermediate Similarity NPD5978 Approved
0.7333 Intermediate Similarity NPD6853 Approved
0.7333 Intermediate Similarity NPD6851 Approved
0.7333 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7326 Intermediate Similarity NPD8095 Phase 1
0.7321 Intermediate Similarity NPD6875 Approved
0.7321 Intermediate Similarity NPD6876 Approved
0.7317 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7314 Intermediate Similarity NPD4481 Phase 3
0.7314 Intermediate Similarity NPD2898 Approved
0.7305 Intermediate Similarity NPD2883 Discontinued
0.7299 Intermediate Similarity NPD3051 Approved
0.7299 Intermediate Similarity NPD6071 Discontinued
0.7294 Intermediate Similarity NPD5773 Approved
0.7294 Intermediate Similarity NPD5772 Approved
0.7284 Intermediate Similarity NPD7153 Discontinued
0.7257 Intermediate Similarity NPD2969 Approved
0.7257 Intermediate Similarity NPD2970 Approved
0.7256 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD6662 Clinical (unspecified phase)
0.7243 Intermediate Similarity NPD6046 Clinical (unspecified phase)
0.7235 Intermediate Similarity NPD5720 Discontinued
0.7231 Intermediate Similarity NPD3816 Phase 1
0.7231 Intermediate Similarity NPD3815 Phase 1
0.7219 Intermediate Similarity NPD4678 Approved
0.7219 Intermediate Similarity NPD4675 Approved
0.7216 Intermediate Similarity NPD27 Approved
0.7216 Intermediate Similarity NPD2489 Approved
0.7208 Intermediate Similarity NPD2922 Phase 1
0.7208 Intermediate Similarity NPD7258 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD6380 Phase 1
0.7186 Intermediate Similarity NPD52 Approved
0.7186 Intermediate Similarity NPD7526 Approved
0.7186 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.7169 Intermediate Similarity NPD2421 Approved
0.7169 Intermediate Similarity NPD2420 Approved
0.7166 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD2161 Phase 2
0.7143 Intermediate Similarity NPD1669 Approved
0.7135 Intermediate Similarity NPD5525 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD5177 Phase 3
0.7134 Intermediate Similarity NPD44 Approved
0.7134 Intermediate Similarity NPD6364 Approved
0.7127 Intermediate Similarity NPD8453 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD1424 Approved
0.712 Intermediate Similarity NPD3349 Phase 2
0.7117 Intermediate Similarity NPD3656 Approved
0.7115 Intermediate Similarity NPD7905 Discontinued
0.7108 Intermediate Similarity NPD3845 Phase 1
0.7108 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD4475 Approved
0.7107 Intermediate Similarity NPD4474 Approved
0.7091 Intermediate Similarity NPD6748 Discontinued
0.7088 Intermediate Similarity NPD7313 Approved
0.7088 Intermediate Similarity NPD7281 Phase 3
0.7088 Intermediate Similarity NPD7310 Approved
0.7088 Intermediate Similarity NPD7312 Approved
0.7088 Intermediate Similarity NPD7280 Phase 3
0.7088 Intermediate Similarity NPD7311 Approved
0.7083 Intermediate Similarity NPD3647 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD3408 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD7438 Suspended
0.7073 Intermediate Similarity NPD2808 Discontinued
0.7069 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7056 Intermediate Similarity NPD7225 Discontinued
0.7052 Intermediate Similarity NPD2560 Approved
0.7052 Intermediate Similarity NPD2563 Approved
0.7049 Intermediate Similarity NPD7309 Approved
0.7039 Intermediate Similarity NPD7493 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD6111 Discontinued
0.7011 Intermediate Similarity NPD5087 Clinical (unspecified phase)
0.6994 Remote Similarity NPD4108 Discontinued
0.6989 Remote Similarity NPD5677 Discontinued
0.6988 Remote Similarity NPD5754 Discontinued
0.6988 Remote Similarity NPD3977 Clinical (unspecified phase)
0.6982 Remote Similarity NPD5261 Clinical (unspecified phase)
0.698 Remote Similarity NPD5070 Clinical (unspecified phase)
0.698 Remote Similarity NPD5283 Phase 1
0.6973 Remote Similarity NPD6257 Clinical (unspecified phase)
0.697 Remote Similarity NPD1044 Clinical (unspecified phase)
0.6959 Remote Similarity NPD6523 Clinical (unspecified phase)
0.6954 Remote Similarity NPD6063 Approved
0.6954 Remote Similarity NPD2358 Clinical (unspecified phase)
0.6951 Remote Similarity NPD1632 Clinical (unspecified phase)
0.695 Remote Similarity NPD8149 Discontinued
0.6943 Remote Similarity NPD4098 Discontinued
0.6939 Remote Similarity NPD5658 Approved
0.6937 Remote Similarity NPD6812 Clinical (unspecified phase)
0.6935 Remote Similarity NPD7906 Approved
0.6932 Remote Similarity NPD6862 Phase 2
0.6928 Remote Similarity NPD3060 Approved
0.6928 Remote Similarity NPD2460 Phase 3
0.6928 Remote Similarity NPD4162 Approved
0.6928 Remote Similarity NPD2458 Approved
0.6928 Remote Similarity NPD2459 Approved
0.6923 Remote Similarity NPD2874 Phase 2
0.6923 Remote Similarity NPD3676 Clinical (unspecified phase)
0.6902 Remote Similarity NPD2971 Approved
0.6902 Remote Similarity NPD3534 Clinical (unspecified phase)
0.6902 Remote Similarity NPD2968 Approved
0.6901 Remote Similarity NPD5267 Discontinued
0.6897 Remote Similarity NPD6737 Phase 2
0.6897 Remote Similarity NPD6060 Clinical (unspecified phase)
0.6897 Remote Similarity NPD6738 Phase 2
0.6894 Remote Similarity NPD554 Clinical (unspecified phase)
0.6894 Remote Similarity NPD7477 Discontinued
0.6883 Remote Similarity NPD2668 Approved
0.6883 Remote Similarity NPD2667 Approved
0.6882 Remote Similarity NPD6090 Discontinued
0.6879 Remote Similarity NPD5090 Approved
0.6879 Remote Similarity NPD5089 Approved
0.6879 Remote Similarity NPD6873 Phase 2
0.6875 Remote Similarity NPD3837 Clinical (unspecified phase)
0.6872 Remote Similarity NPD5680 Clinical (unspecified phase)
0.6871 Remote Similarity NPD4579 Clinical (unspecified phase)
0.6869 Remote Similarity NPD4997 Clinical (unspecified phase)
0.6862 Remote Similarity NPD6656 Clinical (unspecified phase)
0.686 Remote Similarity NPD6357 Discontinued
0.6857 Remote Similarity NPD5967 Approved

  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