Structure

Physi-Chem Properties

Molecular Weight:  502.2
Volume:  517.184
LogP:  7.087
LogD:  4.034
LogS:  -2.1
# Rotatable Bonds:  3
TPSA:  109.36
# H-Bond Aceptor:  7
# H-Bond Donor:  3
# Rings:  5
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.271
Synthetic Accessibility Score:  4.24
Fsp3:  0.3
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.856
MDCK Permeability:  1.3854567441740073e-05
Pgp-inhibitor:  0.98
Pgp-substrate:  0.414
Human Intestinal Absorption (HIA):  0.383
20% Bioavailability (F20%):  0.011
30% Bioavailability (F30%):  0.031

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.002
Plasma Protein Binding (PPB):  86.71444702148438%
Volume Distribution (VD):  0.698
Pgp-substrate:  13.592846870422363%

ADMET: Metabolism

CYP1A2-inhibitor:  0.147
CYP1A2-substrate:  0.216
CYP2C19-inhibitor:  0.847
CYP2C19-substrate:  0.066
CYP2C9-inhibitor:  0.897
CYP2C9-substrate:  0.923
CYP2D6-inhibitor:  0.282
CYP2D6-substrate:  0.182
CYP3A4-inhibitor:  0.196
CYP3A4-substrate:  0.148

ADMET: Excretion

Clearance (CL):  1.467
Half-life (T1/2):  0.109

ADMET: Toxicity

hERG Blockers:  0.009
Human Hepatotoxicity (H-HT):  0.989
Drug-inuced Liver Injury (DILI):  0.983
AMES Toxicity:  0.411
Rat Oral Acute Toxicity:  0.936
Maximum Recommended Daily Dose:  0.79
Skin Sensitization:  0.658
Carcinogencity:  0.09
Eye Corrosion:  0.003
Eye Irritation:  0.432
Respiratory Toxicity:  0.767

Download Data

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

  Natural Product: NPC194427

Natural Product ID:  NPC194427
Common Name*:   Cycloheterphyllin
IUPAC Name:   n.a.
Synonyms:   Cycloheterphyllin
Standard InCHIKey:  ZZPIXEJZTXAVCX-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C30H30O7/c1-14(2)7-8-17-27-16(9-10-30(5,6)37-27)25(33)24-26(34)23-22(11-15(3)4)35-21-13-20(32)19(31)12-18(21)29(23)36-28(17)24/h7,9-13,22,31-33H,8H2,1-6H3
SMILES:  CC(=CCc1c2OC(C)(C)C=Cc2c(c2c1oc1c3cc(O)c(cc3OC(c1c2=O)C=C(C)C)O)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL461820
PubChem CID:   5316250
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0003520] Pyranoflavonoids

*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
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota n.a. root n.a. DOI[10.1016/0031-9422(95)00135-T]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. root n.a. PMID[11395279]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota whole plants Shawnee National Forest, Harrisburg, IL, US n.a. PMID[11678652]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota whole plants n.a. n.a. PMID[11678652]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. PMID[12419367]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota leaves Kaohsiung, Taiwan 2006-SEP PMID[18986201]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota Fruits n.a. n.a. PMID[19296617]
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota Wood n.a. n.a. PMID[23113717]
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota n.a. formosan n.a. PMID[8864236]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. formosan n.a. PMID[8864236]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. PMID[9358644]
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota n.a. n.a. Database[FooDB]
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota n.a. n.a. Database[FooDB]
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota Latex Exudate n.a. n.a. Database[FooDB]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7780 Thalictrum foetidum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7780 Thalictrum foetidum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7780 Thalictrum foetidum Species Ranunculaceae 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
NPT1254 Individual Protein Streptokinase A Streptococcus pyogenes serotype M1 EC50 = 1883.0 nM PMID[521676]
NPT1254 Individual Protein Streptokinase A Streptococcus pyogenes serotype M1 EC50 > 150000.0 nM PMID[521676]
NPT532 Individual Protein Lysine-specific demethylase 4A Homo sapiens Potency n.a. 35481.3 nM PMID[521676]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 29092.9 nM PMID[521676]
NPT1273 Individual Protein ATP-dependent molecular chaperone HSP82 Candida albicans (strain WO-1) (Yeast) EC50 = 12991.0 nM PMID[521676]
NPT135 Individual Protein Chromobox protein homolog 1 Homo sapiens Potency n.a. 14125.4 nM PMID[521676]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 2310.9 nM PMID[521676]
NPT156 Individual Protein Sphingomyelin phosphodiesterase Homo sapiens Potency n.a. 398107.2 nM PMID[521676]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 730.8 nM PMID[521676]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 29092.9 nM PMID[521676]
NPT535 Individual Protein Parathyroid hormone receptor Homo sapiens Potency n.a. 22387.2 nM PMID[521676]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 4.5 % PMID[521675]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 82.4 % PMID[521675]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 33.8 % PMID[521675]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 0.0 % PMID[521675]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 10900.0 nM PMID[521675]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 35.5 % PMID[521675]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 55.1 % PMID[521675]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 61.6 % PMID[521675]
NPT2 Others Unspecified IC50 = 26.1 ug.mL-1 PMID[521675]
NPT174 Organism Streptococcus Streptococcus EC50 = 4009.0 nM PMID[521676]
NPT1252 Organism Streptococcus sp. 'group A' Streptococcus sp. 'group A' EC50 = 2952.0 nM PMID[521676]
NPT2 Others Unspecified EC50 > 38000.0 nM PMID[521676]
NPT2 Others Unspecified Potency n.a. 16360.1 nM PMID[521676]
NPT2 Others Unspecified EC50 = 16487.0 nM PMID[521676]
NPT2 Others Unspecified Potency n.a. 50118.7 nM PMID[521676]
NPT2 Others Unspecified Potency n.a. 11220.2 nM PMID[521676]
NPT2 Others Unspecified Potency n.a. 10000.0 nM PMID[521676]
NPT2 Others Unspecified Potency n.a. 35481.3 nM PMID[521676]

☑ 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 NPC194427 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
0.9677 High Similarity NPC198829
0.9675 High Similarity NPC469658
0.9673 High Similarity NPC276444
0.961 High Similarity NPC476630
0.961 High Similarity NPC218871
0.9551 High Similarity NPC40037
0.9545 High Similarity NPC170026
0.9545 High Similarity NPC282307
0.9542 High Similarity NPC170492
0.949 High Similarity NPC261470
0.9487 High Similarity NPC118256
0.9487 High Similarity NPC192686
0.9487 High Similarity NPC119209
0.9484 High Similarity NPC471209
0.9427 High Similarity NPC474038
0.9427 High Similarity NPC259456
0.9423 High Similarity NPC184755
0.9423 High Similarity NPC74178
0.9419 High Similarity NPC471985
0.9416 High Similarity NPC192083
0.9416 High Similarity NPC74924
0.9416 High Similarity NPC213896
0.9371 High Similarity NPC50960
0.9371 High Similarity NPC156432
0.9367 High Similarity NPC472448
0.9367 High Similarity NPC83922
0.9363 High Similarity NPC28241
0.9363 High Similarity NPC204290
0.9363 High Similarity NPC476980
0.9363 High Similarity NPC328102
0.9363 High Similarity NPC475784
0.9359 High Similarity NPC284820
0.9359 High Similarity NPC237418
0.9359 High Similarity NPC473272
0.9359 High Similarity NPC223787
0.9359 High Similarity NPC27337
0.9355 High Similarity NPC321779
0.9351 High Similarity NPC106976
0.9351 High Similarity NPC249570
0.9346 High Similarity NPC3825
0.9346 High Similarity NPC88804
0.9321 High Similarity NPC475669
0.9313 High Similarity NPC120593
0.9308 High Similarity NPC472625
0.9308 High Similarity NPC186686
0.9304 High Similarity NPC472632
0.9304 High Similarity NPC26326
0.9304 High Similarity NPC29876
0.9304 High Similarity NPC167678
0.9304 High Similarity NPC471210
0.9299 High Similarity NPC53545
0.9299 High Similarity NPC117418
0.9299 High Similarity NPC250214
0.9299 High Similarity NPC95936
0.9295 High Similarity NPC195796
0.9295 High Similarity NPC291878
0.9295 High Similarity NPC278778
0.9295 High Similarity NPC35038
0.929 High Similarity NPC476631
0.929 High Similarity NPC298692
0.9286 High Similarity NPC154345
0.925 High Similarity NPC239752
0.925 High Similarity NPC472450
0.925 High Similarity NPC275780
0.9245 High Similarity NPC474033
0.9245 High Similarity NPC329760
0.9245 High Similarity NPC474150
0.9245 High Similarity NPC474034
0.9245 High Similarity NPC474162
0.9245 High Similarity NPC81679
0.9241 High Similarity NPC174953
0.9241 High Similarity NPC472624
0.9241 High Similarity NPC476283
0.9236 High Similarity NPC472598
0.9236 High Similarity NPC475267
0.9236 High Similarity NPC476981
0.9236 High Similarity NPC474836
0.9236 High Similarity NPC78071
0.9236 High Similarity NPC470402
0.9236 High Similarity NPC474208
0.9236 High Similarity NPC291508
0.9236 High Similarity NPC52889
0.9236 High Similarity NPC156057
0.9236 High Similarity NPC48208
0.9236 High Similarity NPC162869
0.9236 High Similarity NPC474055
0.9236 High Similarity NPC78225
0.9231 High Similarity NPC45849
0.9231 High Similarity NPC200761
0.9231 High Similarity NPC470327
0.9231 High Similarity NPC234255
0.9231 High Similarity NPC133392
0.9231 High Similarity NPC213622
0.9231 High Similarity NPC113906
0.9231 High Similarity NPC477503
0.9226 High Similarity NPC157784
0.9226 High Similarity NPC323626
0.9226 High Similarity NPC63187
0.9226 High Similarity NPC37684
0.9226 High Similarity NPC471982
0.9226 High Similarity NPC324233
0.9221 High Similarity NPC472633
0.9221 High Similarity NPC184136
0.9221 High Similarity NPC37348
0.9216 High Similarity NPC321623
0.9216 High Similarity NPC189087
0.9198 High Similarity NPC476637
0.9198 High Similarity NPC165456
0.9198 High Similarity NPC471287
0.9198 High Similarity NPC177480
0.9193 High Similarity NPC472449
0.9193 High Similarity NPC39091
0.9193 High Similarity NPC272502
0.9193 High Similarity NPC43319
0.9187 High Similarity NPC476295
0.9187 High Similarity NPC12461
0.9187 High Similarity NPC23298
0.9187 High Similarity NPC207690
0.9187 High Similarity NPC189473
0.9182 High Similarity NPC289771
0.9182 High Similarity NPC471212
0.9182 High Similarity NPC258331
0.9182 High Similarity NPC134783
0.9182 High Similarity NPC266314
0.9182 High Similarity NPC472634
0.9182 High Similarity NPC471211
0.9182 High Similarity NPC142252
0.9177 High Similarity NPC22192
0.9177 High Similarity NPC204879
0.9177 High Similarity NPC210459
0.9177 High Similarity NPC187792
0.9177 High Similarity NPC473990
0.9172 High Similarity NPC470328
0.9172 High Similarity NPC24640
0.9172 High Similarity NPC472455
0.9172 High Similarity NPC191146
0.9172 High Similarity NPC180340
0.9172 High Similarity NPC209614
0.9172 High Similarity NPC255106
0.9172 High Similarity NPC68093
0.9172 High Similarity NPC235165
0.9172 High Similarity NPC472626
0.9167 High Similarity NPC145379
0.9167 High Similarity NPC274327
0.9167 High Similarity NPC69394
0.9167 High Similarity NPC47781
0.9167 High Similarity NPC255350
0.9167 High Similarity NPC160951
0.9167 High Similarity NPC231018
0.9167 High Similarity NPC176775
0.9167 High Similarity NPC183878
0.9167 High Similarity NPC22519
0.9167 High Similarity NPC18727
0.9161 High Similarity NPC304295
0.9161 High Similarity NPC204515
0.9161 High Similarity NPC205046
0.9161 High Similarity NPC59162
0.9156 High Similarity NPC5173
0.9156 High Similarity NPC38545
0.9156 High Similarity NPC171916
0.915 High Similarity NPC108406
0.9141 High Similarity NPC472276
0.9141 High Similarity NPC101107
0.9136 High Similarity NPC471288
0.9136 High Similarity NPC158761
0.9136 High Similarity NPC218226
0.9136 High Similarity NPC8965
0.9136 High Similarity NPC117854
0.9136 High Similarity NPC243877
0.9136 High Similarity NPC477154
0.9136 High Similarity NPC6588
0.913 High Similarity NPC293319
0.913 High Similarity NPC62261
0.913 High Similarity NPC259757
0.913 High Similarity NPC303174
0.913 High Similarity NPC130920
0.913 High Similarity NPC470457
0.913 High Similarity NPC85057
0.913 High Similarity NPC224280
0.9125 High Similarity NPC206605
0.9125 High Similarity NPC476247
0.9125 High Similarity NPC229632
0.9125 High Similarity NPC472635
0.9125 High Similarity NPC78332
0.9125 High Similarity NPC220912
0.9119 High Similarity NPC472630
0.9119 High Similarity NPC287328
0.9119 High Similarity NPC297212
0.9119 High Similarity NPC282009
0.9119 High Similarity NPC472631
0.9119 High Similarity NPC471976
0.9119 High Similarity NPC246478
0.9119 High Similarity NPC476280
0.9119 High Similarity NPC321399
0.9119 High Similarity NPC36217
0.9114 High Similarity NPC472914
0.9114 High Similarity NPC245758
0.9114 High Similarity NPC472911
0.9114 High Similarity NPC218313
0.9114 High Similarity NPC210084

  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 NPC194427 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
0.9416 High Similarity NPD2393 Clinical (unspecified phase)
0.9167 High Similarity NPD2801 Approved
0.9103 High Similarity NPD1934 Approved
0.8954 High Similarity NPD1511 Approved
0.8896 High Similarity NPD6167 Clinical (unspecified phase)
0.8896 High Similarity NPD6166 Phase 2
0.8896 High Similarity NPD6168 Clinical (unspecified phase)
0.8839 High Similarity NPD1512 Approved
0.8774 High Similarity NPD4378 Clinical (unspecified phase)
0.8735 High Similarity NPD7054 Approved
0.8734 High Similarity NPD4380 Phase 2
0.8683 High Similarity NPD7074 Phase 3
0.8683 High Similarity NPD7472 Approved
0.865 High Similarity NPD5494 Approved
0.8631 High Similarity NPD6797 Phase 2
0.858 High Similarity NPD7251 Discontinued
0.858 High Similarity NPD3882 Suspended
0.8563 High Similarity NPD3818 Discontinued
0.8535 High Similarity NPD7410 Clinical (unspecified phase)
0.8529 High Similarity NPD4338 Clinical (unspecified phase)
0.8519 High Similarity NPD3817 Phase 2
0.8466 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8442 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8442 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8421 Intermediate Similarity NPD7808 Phase 3
0.8415 Intermediate Similarity NPD7075 Discontinued
0.8415 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8405 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8402 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8387 Intermediate Similarity NPD1549 Phase 2
0.8377 Intermediate Similarity NPD2796 Approved
0.8373 Intermediate Similarity NPD6959 Discontinued
0.8344 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8312 Intermediate Similarity NPD1510 Phase 2
0.8294 Intermediate Similarity NPD5844 Phase 1
0.8293 Intermediate Similarity NPD5402 Approved
0.8282 Intermediate Similarity NPD6801 Discontinued
0.8232 Intermediate Similarity NPD7819 Suspended
0.8221 Intermediate Similarity NPD7411 Suspended
0.8107 Intermediate Similarity NPD6232 Discontinued
0.8092 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.807 Intermediate Similarity NPD7473 Discontinued
0.8052 Intermediate Similarity NPD1240 Approved
0.8047 Intermediate Similarity NPD1247 Approved
0.8025 Intermediate Similarity NPD2935 Discontinued
0.8012 Intermediate Similarity NPD6799 Approved
0.8012 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7975 Intermediate Similarity NPD5403 Approved
0.7949 Intermediate Similarity NPD1607 Approved
0.7943 Intermediate Similarity NPD6559 Discontinued
0.7935 Intermediate Similarity NPD943 Approved
0.7917 Intermediate Similarity NPD7768 Phase 2
0.7853 Intermediate Similarity NPD5401 Approved
0.7833 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7831 Intermediate Similarity NPD6599 Discontinued
0.7826 Intermediate Similarity NPD3750 Approved
0.7824 Intermediate Similarity NPD919 Approved
0.7821 Intermediate Similarity NPD1613 Approved
0.7821 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7812 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7798 Intermediate Similarity NPD1465 Phase 2
0.7764 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7764 Intermediate Similarity NPD2800 Approved
0.7747 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7744 Intermediate Similarity NPD2533 Approved
0.7744 Intermediate Similarity NPD2532 Approved
0.7744 Intermediate Similarity NPD2534 Approved
0.7677 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7661 Intermediate Similarity NPD3749 Approved
0.7658 Intermediate Similarity NPD230 Phase 1
0.7651 Intermediate Similarity NPD920 Approved
0.7628 Intermediate Similarity NPD3027 Phase 3
0.7614 Intermediate Similarity NPD3751 Discontinued
0.7613 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7598 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7586 Intermediate Similarity NPD3787 Discontinued
0.758 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7578 Intermediate Similarity NPD1551 Phase 2
0.7576 Intermediate Similarity NPD7390 Discontinued
0.7546 Intermediate Similarity NPD1243 Approved
0.7543 Intermediate Similarity NPD3926 Phase 2
0.753 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD3748 Approved
0.7515 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1653 Approved
0.75 Intermediate Similarity NPD6651 Approved
0.75 Intermediate Similarity NPD4628 Phase 3
0.7486 Intermediate Similarity NPD5953 Discontinued
0.7473 Intermediate Similarity NPD4363 Phase 3
0.7473 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7473 Intermediate Similarity NPD4360 Phase 2
0.7472 Intermediate Similarity NPD7286 Phase 2
0.7469 Intermediate Similarity NPD6100 Approved
0.7469 Intermediate Similarity NPD6099 Approved
0.7468 Intermediate Similarity NPD2313 Discontinued
0.7468 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.746 Intermediate Similarity NPD6780 Approved
0.746 Intermediate Similarity NPD6779 Approved
0.746 Intermediate Similarity NPD6782 Approved
0.746 Intermediate Similarity NPD6777 Approved
0.746 Intermediate Similarity NPD6776 Approved
0.746 Intermediate Similarity NPD6781 Approved
0.746 Intermediate Similarity NPD6778 Approved
0.7456 Intermediate Similarity NPD3226 Approved
0.7455 Intermediate Similarity NPD6190 Approved
0.744 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7438 Intermediate Similarity NPD5124 Phase 1
0.7438 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7414 Intermediate Similarity NPD6234 Discontinued
0.7407 Intermediate Similarity NPD7033 Discontinued
0.7407 Intermediate Similarity NPD2799 Discontinued
0.7407 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7363 Intermediate Similarity NPD8312 Approved
0.7363 Intermediate Similarity NPD8313 Approved
0.7344 Intermediate Similarity NPD7435 Discontinued
0.7342 Intermediate Similarity NPD4908 Phase 1
0.7337 Intermediate Similarity NPD8150 Discontinued
0.733 Intermediate Similarity NPD7199 Phase 2
0.7329 Intermediate Similarity NPD447 Suspended
0.7326 Intermediate Similarity NPD6844 Discontinued
0.7321 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD7584 Approved
0.7318 Intermediate Similarity NPD7228 Approved
0.7317 Intermediate Similarity NPD2346 Discontinued
0.7317 Intermediate Similarity NPD2344 Approved
0.7289 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7262 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7259 Intermediate Similarity NPD7783 Phase 2
0.7259 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7254 Intermediate Similarity NPD7696 Phase 3
0.7254 Intermediate Similarity NPD7698 Approved
0.7254 Intermediate Similarity NPD7697 Approved
0.7253 Intermediate Similarity NPD7685 Pre-registration
0.7247 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7243 Intermediate Similarity NPD8434 Phase 2
0.7226 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7225 Intermediate Similarity NPD37 Approved
0.7219 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7216 Intermediate Similarity NPD7870 Phase 2
0.7216 Intermediate Similarity NPD7871 Phase 2
0.7202 Intermediate Similarity NPD6823 Phase 2
0.72 Intermediate Similarity NPD4966 Approved
0.72 Intermediate Similarity NPD4967 Phase 2
0.72 Intermediate Similarity NPD4965 Approved
0.7196 Intermediate Similarity NPD6535 Approved
0.7196 Intermediate Similarity NPD6534 Approved
0.7194 Intermediate Similarity NPD7701 Phase 2
0.7191 Intermediate Similarity NPD5710 Approved
0.7191 Intermediate Similarity NPD5711 Approved
0.719 Intermediate Similarity NPD1548 Phase 1
0.7188 Intermediate Similarity NPD4625 Phase 3
0.717 Intermediate Similarity NPD9494 Approved
0.717 Intermediate Similarity NPD2861 Phase 2
0.7168 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD4361 Phase 2
0.7157 Intermediate Similarity NPD8151 Discontinued
0.7152 Intermediate Similarity NPD1203 Approved
0.7151 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7151 Intermediate Similarity NPD7458 Discontinued
0.7143 Intermediate Similarity NPD2309 Approved
0.7143 Intermediate Similarity NPD3268 Approved
0.7134 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD6832 Phase 2
0.7121 Intermediate Similarity NPD7874 Approved
0.7121 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.712 Intermediate Similarity NPD7549 Discontinued
0.7117 Intermediate Similarity NPD1933 Approved
0.7117 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD1610 Phase 2
0.7107 Intermediate Similarity NPD2798 Approved
0.7099 Intermediate Similarity NPD6233 Phase 2
0.7095 Intermediate Similarity NPD7229 Phase 3
0.7091 Intermediate Similarity NPD4308 Phase 3
0.7089 Intermediate Similarity NPD3225 Approved
0.7086 Intermediate Similarity NPD8455 Phase 2
0.7085 Intermediate Similarity NPD7801 Approved
0.7083 Intermediate Similarity NPD7700 Phase 2
0.7083 Intermediate Similarity NPD7699 Phase 2
0.7066 Intermediate Similarity NPD2424 Discontinued
0.7044 Intermediate Similarity NPD2797 Approved
0.7037 Intermediate Similarity NPD6798 Discontinued
0.7017 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD422 Phase 1
0.6982 Remote Similarity NPD8166 Discontinued
0.6962 Remote Similarity NPD9269 Phase 2
0.6962 Remote Similarity NPD1608 Approved
0.6962 Remote Similarity NPD9717 Approved
0.6961 Remote Similarity NPD5242 Approved
0.6957 Remote Similarity NPD1729 Discontinued
0.6951 Remote Similarity NPD4060 Phase 1
0.6949 Remote Similarity NPD4288 Approved
0.6946 Remote Similarity NPD5404 Approved
0.6946 Remote Similarity NPD5405 Approved
0.6946 Remote Similarity NPD5406 Approved
0.6946 Remote Similarity NPD5408 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