Structure

Physi-Chem Properties

Molecular Weight:  393.19
Volume:  408.58
LogP:  4.367
LogD:  3.521
LogS:  -5.365
# Rotatable Bonds:  4
TPSA:  40.16
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  5
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.608
Synthetic Accessibility Score:  2.931
Fsp3:  0.417
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:  -5.359
MDCK Permeability:  3.313868000986986e-05
Pgp-inhibitor:  0.964
Pgp-substrate:  0.978
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.03
30% Bioavailability (F30%):  0.318

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.87
Plasma Protein Binding (PPB):  73.61666107177734%
Volume Distribution (VD):  1.448
Pgp-substrate:  11.653019905090332%

ADMET: Metabolism

CYP1A2-inhibitor:  0.255
CYP1A2-substrate:  0.987
CYP2C19-inhibitor:  0.06
CYP2C19-substrate:  0.944
CYP2C9-inhibitor:  0.005
CYP2C9-substrate:  0.774
CYP2D6-inhibitor:  0.756
CYP2D6-substrate:  0.931
CYP3A4-inhibitor:  0.037
CYP3A4-substrate:  0.909

ADMET: Excretion

Clearance (CL):  9.726
Half-life (T1/2):  0.347

ADMET: Toxicity

hERG Blockers:  0.225
Human Hepatotoxicity (H-HT):  0.297
Drug-inuced Liver Injury (DILI):  0.956
AMES Toxicity:  0.654
Rat Oral Acute Toxicity:  0.638
Maximum Recommended Daily Dose:  0.93
Skin Sensitization:  0.933
Carcinogencity:  0.086
Eye Corrosion:  0.003
Eye Irritation:  0.014
Respiratory Toxicity:  0.935

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

  Natural Product: NPC130941

Natural Product ID:  NPC130941
Common Name*:   Tylophorine
IUPAC Name:   (13aR)-2,3,6,7-tetramethoxy-9,11,12,13,13a,14-hexahydrophenanthro[9,10-f]indolizine
Synonyms:   GNF-Pf-838
Standard InCHIKey:  SSEUDFYBEOIWGF-CQSZACIVSA-N
Standard InCHI:  InChI=1S/C24H27NO4/c1-26-21-9-16-15-8-14-6-5-7-25(14)13-20(15)19-12-24(29-4)23(28-3)11-18(19)17(16)10-22(21)27-2/h9-12,14H,5-8,13H2,1-4H3/t14-/m1/s1
SMILES:  COc1cc2c3C[C@H]4CCCN4Cc3c3c(c2cc1OC)cc(c(c3)OC)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL258137
PubChem CID:   10883727
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000025] Phenanthrenes and derivatives
        • [CHEMONTID:0001906] Phenanthroindolizidines

*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
NPO33385 cynanchum vincetoxicum Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[11087617]
NPO33385 cynanchum vincetoxicum Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[12350151]
NPO8035 Tylophora tanakae Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[12350151]
NPO6257 Ficus septica Species Moraceae Eukaryota Stems Tainan Hsien, Taiwan, Republic of China 2000-JAN PMID[16038551]
NPO6257 Ficus septica Species Moraceae Eukaryota leaves n.a. n.a. PMID[19938815]
NPO24043 Tylophora asthmatica Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5977 Tylophora crebriflora Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6257 Ficus septica Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24049 Tylophora floribunda Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30018 Vincetoxicum officinale Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9734 Vincetoxicum hirundinaria Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24049 Tylophora floribunda Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5977 Tylophora crebriflora Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24043 Tylophora asthmatica Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6257 Ficus septica Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24043 Tylophora asthmatica Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6257 Ficus septica Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5977 Tylophora crebriflora Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9734 Vincetoxicum hirundinaria Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24049 Tylophora floribunda Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8035 Tylophora tanakae Species Apocynaceae 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
NPT461 Cell Line PANC-1 Homo sapiens GI50 = 29.0 nM PMID[571104]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 = 67.0 nM PMID[571104]
NPT4162 Cell Line NUGC Homo sapiens Inhibition = 85.0 % PMID[571106]
NPT1229 Cell Line Huh-7 Homo sapiens CC50 > 7910.0 nM PMID[571107]
NPT165 Cell Line HeLa Homo sapiens IC50 = 3100.0 nM PMID[571108]
NPT116 Cell Line HL-60 Homo sapiens GI50 = 100.0 nM PMID[571109]
NPT81 Cell Line A549 Homo sapiens GI50 = 500.0 nM PMID[571109]
NPT83 Cell Line MCF7 Homo sapiens GI50 = 32.0 nM PMID[571110]
NPT113 Cell Line RAW264.7 Mus musculus CC50 = 1240.0 nM PMID[571111]
NPT113 Cell Line RAW264.7 Mus musculus EC50 = 270.0 nM PMID[571111]
NPT395 Cell Line SF-268 Homo sapiens GI50 = 270.0 nM PMID[571111]
NPT83 Cell Line MCF7 Homo sapiens GI50 = 240.0 nM PMID[571111]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 = 230.0 nM PMID[571111]
NPT2477 Cell Line NUGC-3 Homo sapiens GI50 = 190.0 nM PMID[571111]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 430.0 nM PMID[571115]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 823.0 nM PMID[571115]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 = 33.0 nM PMID[571104]
NPT2 Others Unspecified IC50 = 317.0 nM PMID[571104]
NPT2 Others Unspecified IC50 = 7910.0 nM PMID[571104]
NPT2 Others Unspecified IC50 = 2257.0 nM PMID[571104]
NPT2 Others Unspecified IC50 = 534.0 nM PMID[571104]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 214.0 nM PMID[571105]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 173.0 nM PMID[571105]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 80.0 % PMID[571106]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum EC50 > 509.0 nM PMID[571107]
NPT2 Others Unspecified IFI = 5.263 % PMID[571107]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum EC50 = 963.0 nM PMID[571107]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 12000.0 nM PMID[571108]
NPT35 Others n.a. Solubility = 10000000.0 nM PMID[571111]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 = 270.0 nM PMID[571111]
NPT4513 Organism Transmissible gastroenteritis virus Transmissible gastroenteritis virus EC50 = 80.0 nM PMID[571111]
NPT29 Organism Rattus norvegicus Rattus norvegicus F = 66.0 % PMID[571111]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Activity = 57.7 % PMID[571112]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Activity = 65.9 % PMID[571112]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Activity = 56.4 % PMID[571112]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Activity = 62.6 % PMID[571112]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Activity = 37.9 % PMID[571112]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Activity = 53.3 % PMID[571112]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Activity = 55.2 % PMID[571113]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Activity = 62.2 % PMID[571113]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Activity = 47.7 % PMID[571113]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus EC50 = 66.36 ug.mL-1 PMID[571113]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 0.0 % PMID[571113]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 5.3 % PMID[571113]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 55.2 % PMID[571113]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 62.1 % PMID[571113]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Activity = 22.5 % PMID[571114]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Activity = 47.6 % PMID[571114]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Activity = 26.4 % PMID[571114]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Activity = 44.2 % PMID[571114]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Activity = 15.1 % PMID[571114]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Activity = 39.0 % PMID[571114]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 21.1 % PMID[571114]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 49.7 % PMID[571114]
NPT2 Others Unspecified Activity = 4.0 % PMID[571115]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 208.0 nM PMID[571115]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 1215.0 nM PMID[571115]

☑ 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 NPC130941 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
0.9787 High Similarity NPC219162
0.9645 High Similarity NPC253883
0.9645 High Similarity NPC95075
0.9645 High Similarity NPC90844
0.9586 High Similarity NPC244112
0.9521 High Similarity NPC186063
0.9375 High Similarity NPC92541
0.9315 High Similarity NPC26601
0.9236 High Similarity NPC144863
0.9205 High Similarity NPC233650
0.9189 High Similarity NPC76079
0.9145 High Similarity NPC134858
0.9026 High Similarity NPC150879
0.9026 High Similarity NPC210140
0.8986 High Similarity NPC81733
0.8986 High Similarity NPC326316
0.8958 High Similarity NPC136860
0.8958 High Similarity NPC128019
0.8958 High Similarity NPC476567
0.8951 High Similarity NPC213206
0.8951 High Similarity NPC188163
0.8951 High Similarity NPC328750
0.8951 High Similarity NPC474915
0.8933 High Similarity NPC325871
0.8933 High Similarity NPC99659
0.8881 High Similarity NPC314682
0.8824 High Similarity NPC306902
0.8824 High Similarity NPC160298
0.8824 High Similarity NPC232924
0.8824 High Similarity NPC266753
0.8824 High Similarity NPC477559
0.8816 High Similarity NPC476572
0.8784 High Similarity NPC475959
0.8774 High Similarity NPC16805
0.8774 High Similarity NPC167546
0.8774 High Similarity NPC302527
0.8758 High Similarity NPC477080
0.8718 High Similarity NPC24264
0.8718 High Similarity NPC476432
0.8716 High Similarity NPC106295
0.8716 High Similarity NPC16107
0.8716 High Similarity NPC51957
0.8716 High Similarity NPC210437
0.8716 High Similarity NPC476144
0.869 High Similarity NPC470925
0.8675 High Similarity NPC210148
0.8675 High Similarity NPC233029
0.8662 High Similarity NPC247389
0.8662 High Similarity NPC210918
0.8658 High Similarity NPC7467
0.8654 High Similarity NPC225774
0.8645 High Similarity NPC60186
0.8627 High Similarity NPC170503
0.8627 High Similarity NPC126519
0.8627 High Similarity NPC203784
0.8601 High Similarity NPC11147
0.86 High Similarity NPC44869
0.8599 High Similarity NPC219341
0.859 High Similarity NPC324144
0.8581 High Similarity NPC145304
0.8581 High Similarity NPC27410
0.8581 High Similarity NPC185838
0.8581 High Similarity NPC166014
0.8562 High Similarity NPC138487
0.8562 High Similarity NPC216459
0.8562 High Similarity NPC41178
0.8544 High Similarity NPC298979
0.8543 High Similarity NPC192768
0.8543 High Similarity NPC151895
0.8543 High Similarity NPC88249
0.8543 High Similarity NPC97221
0.8543 High Similarity NPC220858
0.8535 High Similarity NPC253043
0.8535 High Similarity NPC136508
0.8535 High Similarity NPC477563
0.8535 High Similarity NPC196447
0.8535 High Similarity NPC169743
0.8535 High Similarity NPC78222
0.8535 High Similarity NPC212794
0.8535 High Similarity NPC306843
0.8535 High Similarity NPC13504
0.8535 High Similarity NPC96603
0.8533 High Similarity NPC135538
0.8533 High Similarity NPC246587
0.8533 High Similarity NPC476571
0.8533 High Similarity NPC428
0.8533 High Similarity NPC24233
0.8533 High Similarity NPC147390
0.8511 High Similarity NPC160193
0.8506 High Similarity NPC477132
0.8506 High Similarity NPC247639
0.8506 High Similarity NPC25084
0.8506 High Similarity NPC477133
0.8506 High Similarity NPC146288
0.85 High Similarity NPC19520
0.85 High Similarity NPC149090
0.8491 Intermediate Similarity NPC241055
0.8487 Intermediate Similarity NPC476568
0.8481 Intermediate Similarity NPC304659
0.8481 Intermediate Similarity NPC86144
0.8477 Intermediate Similarity NPC211296
0.8467 Intermediate Similarity NPC321505
0.8467 Intermediate Similarity NPC179825
0.8467 Intermediate Similarity NPC191376
0.8467 Intermediate Similarity NPC476151
0.8457 Intermediate Similarity NPC287588
0.8442 Intermediate Similarity NPC123323
0.8438 Intermediate Similarity NPC6152
0.8428 Intermediate Similarity NPC158376
0.8428 Intermediate Similarity NPC117188
0.8428 Intermediate Similarity NPC205421
0.8428 Intermediate Similarity NPC12053
0.8428 Intermediate Similarity NPC81218
0.8428 Intermediate Similarity NPC474931
0.8428 Intermediate Similarity NPC145832
0.8428 Intermediate Similarity NPC306555
0.8418 Intermediate Similarity NPC168409
0.8397 Intermediate Similarity NPC111485
0.8395 Intermediate Similarity NPC128560
0.8395 Intermediate Similarity NPC229166
0.8395 Intermediate Similarity NPC199465
0.8392 Intermediate Similarity NPC118419
0.8387 Intermediate Similarity NPC234392
0.8387 Intermediate Similarity NPC31311
0.8355 Intermediate Similarity NPC477565
0.8355 Intermediate Similarity NPC103379
0.8354 Intermediate Similarity NPC189470
0.8333 Intermediate Similarity NPC130926
0.8323 Intermediate Similarity NPC276588
0.8323 Intermediate Similarity NPC193949
0.8323 Intermediate Similarity NPC469817
0.8323 Intermediate Similarity NPC172765
0.8323 Intermediate Similarity NPC110416
0.8323 Intermediate Similarity NPC93593
0.8323 Intermediate Similarity NPC189266
0.8323 Intermediate Similarity NPC2413
0.8323 Intermediate Similarity NPC204828
0.8323 Intermediate Similarity NPC187022
0.8323 Intermediate Similarity NPC207757
0.8323 Intermediate Similarity NPC5238
0.8323 Intermediate Similarity NPC278799
0.8323 Intermediate Similarity NPC127674
0.8323 Intermediate Similarity NPC184026
0.8323 Intermediate Similarity NPC39701
0.8323 Intermediate Similarity NPC249797
0.8323 Intermediate Similarity NPC295691
0.8323 Intermediate Similarity NPC54379
0.8323 Intermediate Similarity NPC80129
0.8313 Intermediate Similarity NPC204947
0.8303 Intermediate Similarity NPC179704
0.8293 Intermediate Similarity NPC114364
0.8293 Intermediate Similarity NPC320223
0.8288 Intermediate Similarity NPC7018
0.828 Intermediate Similarity NPC221864
0.8272 Intermediate Similarity NPC239775
0.825 Intermediate Similarity NPC476573
0.825 Intermediate Similarity NPC35627
0.825 Intermediate Similarity NPC81247
0.8239 Intermediate Similarity NPC1229
0.8239 Intermediate Similarity NPC172403
0.8239 Intermediate Similarity NPC475393
0.8235 Intermediate Similarity NPC207824
0.8235 Intermediate Similarity NPC60538
0.8231 Intermediate Similarity NPC253429
0.8228 Intermediate Similarity NPC205167
0.8228 Intermediate Similarity NPC271388
0.8228 Intermediate Similarity NPC235143
0.8228 Intermediate Similarity NPC205255
0.8228 Intermediate Similarity NPC119649
0.8228 Intermediate Similarity NPC230956
0.8221 Intermediate Similarity NPC285941
0.821 Intermediate Similarity NPC477562
0.821 Intermediate Similarity NPC69712
0.821 Intermediate Similarity NPC26240
0.8205 Intermediate Similarity NPC78733
0.8194 Intermediate Similarity NPC470924
0.8187 Intermediate Similarity NPC232514
0.8187 Intermediate Similarity NPC276944
0.8187 Intermediate Similarity NPC76116
0.8187 Intermediate Similarity NPC238530
0.8182 Intermediate Similarity NPC190461
0.8182 Intermediate Similarity NPC23219
0.8176 Intermediate Similarity NPC79402
0.8176 Intermediate Similarity NPC80759
0.8165 Intermediate Similarity NPC7393
0.8165 Intermediate Similarity NPC216816
0.8153 Intermediate Similarity NPC147091
0.8144 Intermediate Similarity NPC116284
0.8144 Intermediate Similarity NPC248642
0.8137 Intermediate Similarity NPC317272
0.8137 Intermediate Similarity NPC250846
0.8137 Intermediate Similarity NPC42549
0.8137 Intermediate Similarity NPC256012
0.8137 Intermediate Similarity NPC240841
0.8137 Intermediate Similarity NPC268503
0.8133 Intermediate Similarity NPC126284
0.8133 Intermediate Similarity NPC470879
0.8133 Intermediate Similarity NPC258695
0.8129 Intermediate Similarity NPC277669
0.8129 Intermediate Similarity NPC476579

  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 NPC130941 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
0.8951 High Similarity NPD4664 Clinical (unspecified phase)
0.8716 High Similarity NPD4584 Approved
0.8354 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.8323 Intermediate Similarity NPD7298 Approved
0.8247 Intermediate Similarity NPD4017 Approved
0.8146 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.8125 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.8117 Intermediate Similarity NPD3639 Approved
0.8117 Intermediate Similarity NPD6031 Approved
0.8117 Intermediate Similarity NPD3640 Phase 3
0.8117 Intermediate Similarity NPD3641 Approved
0.8117 Intermediate Similarity NPD6030 Approved
0.8069 Intermediate Similarity NPD5718 Phase 2
0.8038 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD7831 Phase 2
0.8 Intermediate Similarity NPD7833 Phase 2
0.7987 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7987 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7974 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7963 Intermediate Similarity NPD7802 Discontinued
0.7959 Intermediate Similarity NPD3109 Approved
0.7959 Intermediate Similarity NPD3110 Approved
0.7939 Intermediate Similarity NPD8252 Approved
0.7939 Intermediate Similarity NPD8251 Approved
0.7939 Intermediate Similarity NPD8099 Discontinued
0.7937 Intermediate Similarity NPD6788 Approved
0.7922 Intermediate Similarity NPD2421 Approved
0.7922 Intermediate Similarity NPD2420 Approved
0.7911 Intermediate Similarity NPD4773 Phase 2
0.7911 Intermediate Similarity NPD4772 Phase 2
0.7908 Intermediate Similarity NPD5241 Discontinued
0.7892 Intermediate Similarity NPD8156 Discontinued
0.784 Intermediate Similarity NPD7400 Phase 3
0.7826 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7823 Intermediate Similarity NPD6812 Clinical (unspecified phase)
0.7808 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7805 Intermediate Similarity NPD3051 Approved
0.7805 Intermediate Similarity NPD4010 Discontinued
0.7805 Intermediate Similarity NPD4166 Phase 2
0.78 Intermediate Similarity NPD6895 Approved
0.78 Intermediate Similarity NPD6896 Approved
0.777 Intermediate Similarity NPD4475 Approved
0.777 Intermediate Similarity NPD4474 Approved
0.7742 Intermediate Similarity NPD3845 Phase 1
0.7711 Intermediate Similarity NPD4481 Phase 3
0.7711 Intermediate Similarity NPD2898 Approved
0.7692 Intermediate Similarity NPD3124 Discontinued
0.7673 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7654 Intermediate Similarity NPD5977 Approved
0.7654 Intermediate Similarity NPD5978 Approved
0.7651 Intermediate Similarity NPD2969 Approved
0.7651 Intermediate Similarity NPD2970 Approved
0.7636 Intermediate Similarity NPD6107 Approved
0.7616 Intermediate Similarity NPD8054 Approved
0.7616 Intermediate Similarity NPD8053 Approved
0.7605 Intermediate Similarity NPD2489 Approved
0.7605 Intermediate Similarity NPD27 Approved
0.758 Intermediate Similarity NPD7598 Phase 2
0.7564 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.756 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.7545 Intermediate Similarity NPD6687 Approved
0.7545 Intermediate Similarity NPD6688 Approved
0.75 Intermediate Similarity NPD8453 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD6071 Discontinued
0.7485 Intermediate Similarity NPD6996 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD7037 Approved
0.7469 Intermediate Similarity NPD7110 Phase 1
0.7469 Intermediate Similarity NPD7109 Clinical (unspecified phase)
0.7457 Intermediate Similarity NPD5917 Clinical (unspecified phase)
0.7439 Intermediate Similarity NPD2560 Approved
0.7439 Intermediate Similarity NPD2563 Approved
0.7436 Intermediate Similarity NPD4237 Approved
0.7436 Intermediate Similarity NPD4236 Phase 3
0.7415 Intermediate Similarity NPD7258 Clinical (unspecified phase)
0.7405 Intermediate Similarity NPD7124 Phase 2
0.7405 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.7389 Intermediate Similarity NPD5754 Discontinued
0.7389 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7389 Intermediate Similarity NPD6748 Discontinued
0.7386 Intermediate Similarity NPD7291 Discontinued
0.7386 Intermediate Similarity NPD7906 Approved
0.7386 Intermediate Similarity NPD4579 Clinical (unspecified phase)
0.7384 Intermediate Similarity NPD6297 Approved
0.7371 Intermediate Similarity NPD5087 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD5313 Approved
0.7368 Intermediate Similarity NPD5312 Approved
0.7356 Intermediate Similarity NPD2971 Approved
0.7356 Intermediate Similarity NPD2968 Approved
0.7351 Intermediate Similarity NPD7294 Phase 1
0.7347 Intermediate Similarity NPD1669 Approved
0.7346 Intermediate Similarity NPD6523 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD6662 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD5976 Discontinued
0.7329 Intermediate Similarity NPD4727 Phase 1
0.7303 Intermediate Similarity NPD554 Clinical (unspecified phase)
0.7301 Intermediate Similarity NPD6875 Approved
0.7301 Intermediate Similarity NPD6876 Approved
0.7278 Intermediate Similarity NPD6747 Phase 1
0.7278 Intermediate Similarity NPD6331 Phase 2
0.7267 Intermediate Similarity NPD6090 Discontinued
0.7261 Intermediate Similarity NPD7045 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD7312 Approved
0.7257 Intermediate Similarity NPD7311 Approved
0.7257 Intermediate Similarity NPD4578 Approved
0.7257 Intermediate Similarity NPD7310 Approved
0.7257 Intermediate Similarity NPD7313 Approved
0.7257 Intermediate Similarity NPD4577 Approved
0.7238 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7232 Intermediate Similarity NPD4663 Approved
0.7216 Intermediate Similarity NPD6851 Approved
0.7216 Intermediate Similarity NPD6853 Approved
0.7216 Intermediate Similarity NPD7309 Approved
0.7215 Intermediate Similarity NPD5177 Phase 3
0.7215 Intermediate Similarity NPD3060 Approved
0.7215 Intermediate Similarity NPD4162 Approved
0.7212 Intermediate Similarity NPD5720 Discontinued
0.7212 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD1424 Approved
0.72 Intermediate Similarity NPD7905 Discontinued
0.7183 Intermediate Similarity NPD5283 Phase 1
0.7178 Intermediate Similarity NPD4210 Discontinued
0.7171 Intermediate Similarity NPD5156 Approved
0.7171 Intermediate Similarity NPD5155 Approved
0.7161 Intermediate Similarity NPD2492 Phase 1
0.716 Intermediate Similarity NPD3647 Clinical (unspecified phase)
0.7159 Intermediate Similarity NPD7280 Phase 3
0.7159 Intermediate Similarity NPD7281 Phase 3
0.7159 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD7438 Suspended
0.7143 Intermediate Similarity NPD4055 Discovery
0.7134 Intermediate Similarity NPD4005 Discontinued
0.7133 Intermediate Similarity NPD4098 Discontinued
0.7126 Intermediate Similarity NPD7479 Phase 2
0.7126 Intermediate Similarity NPD3920 Phase 2
0.7126 Intermediate Similarity NPD5616 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD3301 Approved
0.712 Intermediate Similarity NPD8095 Phase 1
0.7119 Intermediate Similarity NPD6618 Phase 2
0.7117 Intermediate Similarity NPD1914 Approved
0.7111 Intermediate Similarity NPD2490 Approved
0.7111 Intermediate Similarity NPD2488 Approved
0.7105 Intermediate Similarity NPD2605 Approved
0.7105 Intermediate Similarity NPD3594 Approved
0.7105 Intermediate Similarity NPD3595 Approved
0.7105 Intermediate Similarity NPD2606 Approved
0.7104 Intermediate Similarity NPD7034 Discontinued
0.7104 Intermediate Similarity NPD5564 Approved
0.7099 Intermediate Similarity NPD7020 Approved
0.7099 Intermediate Similarity NPD7019 Approved
0.7093 Intermediate Similarity NPD6607 Clinical (unspecified phase)
0.709 Intermediate Similarity NPD4859 Phase 1
0.7086 Intermediate Similarity NPD7018 Phase 2
0.7078 Intermediate Similarity NPD2674 Phase 3
0.7075 Intermediate Similarity NPD2667 Approved
0.7075 Intermediate Similarity NPD2668 Approved
0.7072 Intermediate Similarity NPD3923 Approved
0.7072 Intermediate Similarity NPD3922 Approved
0.7072 Intermediate Similarity NPD3924 Approved
0.7072 Intermediate Similarity NPD3921 Approved
0.7066 Intermediate Similarity NPD2977 Approved
0.7066 Intermediate Similarity NPD5772 Approved
0.7066 Intermediate Similarity NPD5773 Approved
0.7066 Intermediate Similarity NPD2978 Approved
0.7065 Intermediate Similarity NPD4420 Approved
0.7063 Intermediate Similarity NPD3977 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD6037 Discontinued
0.7059 Intermediate Similarity NPD5677 Discontinued
0.7055 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD6873 Phase 2
0.7041 Intermediate Similarity NPD5604 Discontinued
0.7039 Intermediate Similarity NPD3636 Approved
0.7039 Intermediate Similarity NPD3637 Approved
0.7039 Intermediate Similarity NPD3635 Approved
0.7025 Intermediate Similarity NPD1632 Clinical (unspecified phase)
0.7017 Intermediate Similarity NPD5525 Clinical (unspecified phase)
0.7013 Intermediate Similarity NPD5109 Approved
0.7013 Intermediate Similarity NPD5110 Phase 2
0.7013 Intermediate Similarity NPD5111 Phase 2
0.7012 Intermediate Similarity NPD7427 Discontinued
0.7011 Intermediate Similarity NPD2975 Approved
0.7011 Intermediate Similarity NPD2974 Approved
0.7011 Intermediate Similarity NPD2973 Approved
0.7007 Intermediate Similarity NPD4093 Discontinued
0.7006 Intermediate Similarity NPD6111 Discontinued
0.7006 Intermediate Similarity NPD7718 Clinical (unspecified phase)
0.6994 Remote Similarity NPD4123 Phase 3
0.6989 Remote Similarity NPD6612 Phase 2
0.6987 Remote Similarity NPD3657 Discovery
0.6974 Remote Similarity NPD7247 Discontinued
0.6971 Remote Similarity NPD4873 Discontinued
0.6968 Remote Similarity NPD3530 Approved
0.6968 Remote Similarity NPD3531 Approved
0.6968 Remote Similarity NPD3532 Approved
0.6962 Remote Similarity NPD1753 Discontinued
0.6962 Remote Similarity NPD4108 Discontinued
0.6957 Remote Similarity NPD7466 Approved
0.6954 Remote Similarity NPD5966 Clinical (unspecified phase)
0.6954 Remote Similarity NPD5938 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