Structure

Physi-Chem Properties

Molecular Weight:  540.11
Volume:  524.453
LogP:  4.79
LogD:  2.844
LogS:  -4.698
# Rotatable Bonds:  3
TPSA:  177.89
# H-Bond Aceptor:  10
# H-Bond Donor:  6
# Rings:  6
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.186
Synthetic Accessibility Score:  3.767
Fsp3:  0.067
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  2
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.489
MDCK Permeability:  6.034629677742487e-06
Pgp-inhibitor:  0.04
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.746
20% Bioavailability (F20%):  0.95
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.001
Plasma Protein Binding (PPB):  97.79779815673828%
Volume Distribution (VD):  0.347
Pgp-substrate:  2.9463415145874023%

ADMET: Metabolism

CYP1A2-inhibitor:  0.678
CYP1A2-substrate:  0.119
CYP2C19-inhibitor:  0.775
CYP2C19-substrate:  0.041
CYP2C9-inhibitor:  0.828
CYP2C9-substrate:  0.965
CYP2D6-inhibitor:  0.171
CYP2D6-substrate:  0.323
CYP3A4-inhibitor:  0.454
CYP3A4-substrate:  0.108

ADMET: Excretion

Clearance (CL):  4.421
Half-life (T1/2):  0.371

ADMET: Toxicity

hERG Blockers:  0.038
Human Hepatotoxicity (H-HT):  0.143
Drug-inuced Liver Injury (DILI):  0.983
AMES Toxicity:  0.699
Rat Oral Acute Toxicity:  0.888
Maximum Recommended Daily Dose:  0.083
Skin Sensitization:  0.932
Carcinogencity:  0.088
Eye Corrosion:  0.003
Eye Irritation:  0.884
Respiratory Toxicity:  0.026

Download Data

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

  Natural Product: NPC32867

Natural Product ID:  NPC32867
Common Name*:   Volkensiflavone
IUPAC Name:   8-[(2R,3S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-3-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
Synonyms:   (+)-Volkensiflavone; (+/-)-Volkensiflavone; Volkensiflavone
Standard InCHIKey:  YOGANETYFUQWIM-PXJZQJOASA-N
Standard InCHI:  InChI=1S/C30H20O10/c31-15-5-1-13(2-6-15)22-12-21(37)24-19(35)11-20(36)26(30(24)39-22)27-28(38)25-18(34)9-17(33)10-23(25)40-29(27)14-3-7-16(32)8-4-14/h1-12,27,29,31-36H/t27-,29+/m1/s1
SMILES:  c1cc(ccc1c1cc(=O)c2c(cc(c([C@@H]3C(=O)c4c(cc(cc4O[C@H]3c3ccc(cc3)O)O)O)c2o1)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL463023
PubChem CID:   23844069
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001586] Biflavonoids and polyflavonoids

*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
NPO5638 Garcinia livingstonei Species Clusiaceae Eukaryota n.a. fruit n.a. DOI[10.1016/S0040-4020(01)89039-6]
NPO32446 calophyllum panciflorum Species Calophyllaceae Eukaryota n.a. n.a. n.a. PMID[10654415]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota stems n.a. n.a. PMID[12932126]
NPO21424 Garcinia xanthochymus Species Clusiaceae Eukaryota n.a. xylem n.a. PMID[14600386]
NPO21424 Garcinia xanthochymus Species Clusiaceae Eukaryota fruits n.a. n.a. PMID[15787435]
NPO5638 Garcinia livingstonei Species Clusiaceae Eukaryota root bark n.a. n.a. PMID[16562837]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota twigs n.a. n.a. PMID[20681570]
NPO30436 Rheedia edulis Species Clusiaceae Eukaryota n.a. seed n.a. PMID[21028890]
NPO5638 Garcinia livingstonei Species Clusiaceae Eukaryota n.a. fruit n.a. PMID[21028890]
NPO30436 Rheedia edulis Species Clusiaceae Eukaryota n.a. exocarp n.a. PMID[21028890]
NPO30436 Rheedia edulis Species Clusiaceae Eukaryota seeds and rinds n.a. n.a. PMID[21028890]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota Twigs and leaves Taichung, Taiwan 1993-Aug PMID[9322359]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21424 Garcinia xanthochymus Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22337 Garcinia dulcis Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22337 Garcinia dulcis Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21424 Garcinia xanthochymus Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21424 Garcinia xanthochymus Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5638 Garcinia livingstonei Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22337 Garcinia dulcis Species Clusiaceae 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 Inhibition = 30.0 % PMID[522545]
NPT459 Individual Protein Human immunodeficiency virus type 1 reverse transcriptase Human immunodeficiency virus 1 Inhibition = 45.3 % PMID[522545]
NPT80 Cell Line Raji Homo sapiens Activity = 70.0 % PMID[522546]
NPT80 Cell Line Raji Homo sapiens Activity > 80.0 % PMID[522546]
NPT660 Cell Line SW480 Homo sapiens IC50 = 185000.0 nM PMID[522547]
NPT171 Cell Line MRC5 Homo sapiens IC50 = 40000.0 nM PMID[522548]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 40.1 % PMID[522546]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 72.6 % PMID[522546]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 91.2 % PMID[522546]
NPT1 Others Radical scavenging activity IC50 = 298000.0 nM PMID[522547]
NPT471 Organism Trypanosoma brucei brucei Trypanosoma brucei brucei IC50 = 37000.0 nM PMID[522548]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi IC50 = 56000.0 nM PMID[522548]
NPT1021 Organism Leishmania infantum Leishmania infantum IC50 > 64000.0 nM PMID[522548]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 48000.0 nM PMID[522548]

☑ 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 NPC32867 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
0.9867 High Similarity NPC295090
0.9866 High Similarity NPC69531
0.9799 High Similarity NPC66441
0.9799 High Similarity NPC182555
0.9797 High Similarity NPC174086
0.9669 High Similarity NPC475184
0.9667 High Similarity NPC201227
0.9667 High Similarity NPC258474
0.9667 High Similarity NPC300668
0.9667 High Similarity NPC134171
0.9603 High Similarity NPC61112
0.9603 High Similarity NPC198489
0.9603 High Similarity NPC309648
0.96 High Similarity NPC121568
0.9539 High Similarity NPC287789
0.9539 High Similarity NPC271741
0.9539 High Similarity NPC257166
0.9539 High Similarity NPC1796
0.9527 High Similarity NPC122894
0.9487 High Similarity NPC171985
0.9487 High Similarity NPC320741
0.9484 High Similarity NPC63438
0.9481 High Similarity NPC301256
0.9481 High Similarity NPC312273
0.9477 High Similarity NPC51760
0.9477 High Similarity NPC105584
0.9477 High Similarity NPC15815
0.9477 High Similarity NPC51247
0.947 High Similarity NPC71061
0.947 High Similarity NPC290830
0.947 High Similarity NPC72425
0.947 High Similarity NPC303485
0.947 High Similarity NPC194593
0.9467 High Similarity NPC138299
0.9467 High Similarity NPC67322
0.9467 High Similarity NPC222713
0.9467 High Similarity NPC111112
0.9463 High Similarity NPC3642
0.9463 High Similarity NPC291746
0.9463 High Similarity NPC288840
0.9419 High Similarity NPC473012
0.9419 High Similarity NPC473011
0.9416 High Similarity NPC98023
0.9416 High Similarity NPC195136
0.9416 High Similarity NPC121647
0.9416 High Similarity NPC42965
0.9416 High Similarity NPC226462
0.9412 High Similarity NPC324358
0.9412 High Similarity NPC318527
0.9412 High Similarity NPC322459
0.9412 High Similarity NPC323627
0.9408 High Similarity NPC265624
0.9408 High Similarity NPC37253
0.9408 High Similarity NPC159707
0.9408 High Similarity NPC215203
0.9408 High Similarity NPC150908
0.9408 High Similarity NPC100049
0.9408 High Similarity NPC79375
0.9408 High Similarity NPC14606
0.9408 High Similarity NPC121649
0.9408 High Similarity NPC158027
0.9408 High Similarity NPC186227
0.9408 High Similarity NPC248739
0.9408 High Similarity NPC52611
0.9408 High Similarity NPC205026
0.9404 High Similarity NPC115601
0.9404 High Similarity NPC78324
0.9404 High Similarity NPC39154
0.9404 High Similarity NPC208011
0.94 High Similarity NPC29777
0.94 High Similarity NPC471115
0.9367 High Similarity NPC107627
0.9363 High Similarity NPC224851
0.9359 High Similarity NPC473009
0.9359 High Similarity NPC38591
0.9351 High Similarity NPC123544
0.9338 High Similarity NPC309512
0.9338 High Similarity NPC178484
0.9338 High Similarity NPC316960
0.9338 High Similarity NPC148945
0.9338 High Similarity NPC204561
0.9338 High Similarity NPC78835
0.9338 High Similarity NPC317715
0.9329 High Similarity NPC308200
0.9324 High Similarity NPC39045
0.9324 High Similarity NPC470135
0.9324 High Similarity NPC470136
0.9299 High Similarity NPC473010
0.929 High Similarity NPC292863
0.929 High Similarity NPC184326
0.9286 High Similarity NPC208258
0.9267 High Similarity NPC145467
0.9267 High Similarity NPC39195
0.9262 High Similarity NPC470131
0.9262 High Similarity NPC109183
0.9262 High Similarity NPC470132
0.9262 High Similarity NPC228779
0.9262 High Similarity NPC470134
0.9262 High Similarity NPC470133
0.9262 High Similarity NPC473078
0.9241 High Similarity NPC251336
0.9241 High Similarity NPC82330
0.9231 High Similarity NPC18380
0.9231 High Similarity NPC137232
0.9231 High Similarity NPC97812
0.9226 High Similarity NPC195167
0.9221 High Similarity NPC56049
0.9221 High Similarity NPC54830
0.9216 High Similarity NPC112701
0.9216 High Similarity NPC324447
0.9216 High Similarity NPC109594
0.9216 High Similarity NPC326592
0.9211 High Similarity NPC209846
0.9211 High Similarity NPC477897
0.9211 High Similarity NPC328740
0.9211 High Similarity NPC289774
0.9205 High Similarity NPC473016
0.9205 High Similarity NPC132345
0.9205 High Similarity NPC471114
0.92 High Similarity NPC296998
0.92 High Similarity NPC473077
0.9195 High Similarity NPC271288
0.9195 High Similarity NPC311144
0.9172 High Similarity NPC15374
0.9156 High Similarity NPC254351
0.915 High Similarity NPC150123
0.915 High Similarity NPC56232
0.915 High Similarity NPC244583
0.915 High Similarity NPC161881
0.915 High Similarity NPC10807
0.915 High Similarity NPC43345
0.9145 High Similarity NPC472633
0.9139 High Similarity NPC161191
0.9133 High Similarity NPC142405
0.9133 High Similarity NPC470647
0.9133 High Similarity NPC195621
0.9133 High Similarity NPC67805
0.9133 High Similarity NPC472629
0.9133 High Similarity NPC176229
0.9133 High Similarity NPC20488
0.9133 High Similarity NPC88964
0.9133 High Similarity NPC111786
0.9133 High Similarity NPC214774
0.9133 High Similarity NPC312973
0.9133 High Similarity NPC83357
0.9133 High Similarity NPC475052
0.9133 High Similarity NPC474161
0.9133 High Similarity NPC476088
0.9133 High Similarity NPC299011
0.9133 High Similarity NPC267375
0.9133 High Similarity NPC301276
0.9133 High Similarity NPC54577
0.9133 High Similarity NPC246948
0.913 High Similarity NPC472454
0.913 High Similarity NPC186847
0.913 High Similarity NPC257667
0.9128 High Similarity NPC223812
0.9128 High Similarity NPC107177
0.9128 High Similarity NPC85162
0.9128 High Similarity NPC278249
0.9128 High Similarity NPC77794
0.9128 High Similarity NPC81697
0.9128 High Similarity NPC125894
0.9128 High Similarity NPC113770
0.9125 High Similarity NPC53252
0.9122 High Similarity NPC14871
0.9114 High Similarity NPC290160
0.9108 High Similarity NPC175513
0.9103 High Similarity NPC55443
0.9103 High Similarity NPC18699
0.9091 High Similarity NPC268193
0.9091 High Similarity NPC244250
0.9091 High Similarity NPC20907
0.9085 High Similarity NPC476551
0.9085 High Similarity NPC476552
0.9085 High Similarity NPC476553
0.9079 High Similarity NPC5173
0.9079 High Similarity NPC317492
0.9074 High Similarity NPC168789
0.9073 High Similarity NPC283234
0.9073 High Similarity NPC23728
0.9073 High Similarity NPC261271
0.9073 High Similarity NPC475348
0.9073 High Similarity NPC110303
0.9073 High Similarity NPC10990
0.9073 High Similarity NPC300988
0.9068 High Similarity NPC8704
0.9068 High Similarity NPC287884
0.9067 High Similarity NPC470890
0.9067 High Similarity NPC131568
0.9067 High Similarity NPC319752
0.9067 High Similarity NPC303185
0.9067 High Similarity NPC224714
0.9067 High Similarity NPC473015
0.9067 High Similarity NPC184649
0.9067 High Similarity NPC473013
0.9067 High Similarity NPC131579
0.9067 High Similarity NPC473014
0.9067 High Similarity NPC124780
0.9067 High Similarity NPC235217

  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 NPC32867 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
0.9281 High Similarity NPD8443 Clinical (unspecified phase)
0.9108 High Similarity NPD6959 Discontinued
0.902 High Similarity NPD4380 Phase 2
0.894 High Similarity NPD4378 Clinical (unspecified phase)
0.894 High Similarity NPD7410 Clinical (unspecified phase)
0.8938 High Similarity NPD7852 Clinical (unspecified phase)
0.8851 High Similarity NPD1552 Clinical (unspecified phase)
0.8851 High Similarity NPD1550 Clinical (unspecified phase)
0.8839 High Similarity NPD7411 Suspended
0.8792 High Similarity NPD1549 Phase 2
0.8726 High Similarity NPD2393 Clinical (unspecified phase)
0.8679 High Similarity NPD4381 Clinical (unspecified phase)
0.8616 High Similarity NPD7768 Phase 2
0.8591 High Similarity NPD1510 Phase 2
0.8589 High Similarity NPD6167 Clinical (unspecified phase)
0.8589 High Similarity NPD6166 Phase 2
0.8589 High Similarity NPD6168 Clinical (unspecified phase)
0.8562 High Similarity NPD7075 Discontinued
0.8545 High Similarity NPD7804 Clinical (unspecified phase)
0.8533 High Similarity NPD2796 Approved
0.8491 Intermediate Similarity NPD7819 Suspended
0.8447 Intermediate Similarity NPD3749 Approved
0.8428 Intermediate Similarity NPD1934 Approved
0.8385 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8375 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8344 Intermediate Similarity NPD5494 Approved
0.8313 Intermediate Similarity NPD6801 Discontinued
0.8269 Intermediate Similarity NPD1511 Approved
0.8261 Intermediate Similarity NPD2801 Approved
0.8225 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8214 Intermediate Similarity NPD7054 Approved
0.8204 Intermediate Similarity NPD7473 Discontinued
0.82 Intermediate Similarity NPD1240 Approved
0.8194 Intermediate Similarity NPD3750 Approved
0.8188 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.8166 Intermediate Similarity NPD7074 Phase 3
0.8166 Intermediate Similarity NPD7472 Approved
0.8165 Intermediate Similarity NPD1512 Approved
0.8155 Intermediate Similarity NPD3818 Discontinued
0.8153 Intermediate Similarity NPD7390 Discontinued
0.8133 Intermediate Similarity NPD6232 Discontinued
0.8129 Intermediate Similarity NPD2800 Approved
0.8129 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.8118 Intermediate Similarity NPD6797 Phase 2
0.8092 Intermediate Similarity NPD1607 Approved
0.8081 Intermediate Similarity NPD8313 Approved
0.8081 Intermediate Similarity NPD8312 Approved
0.807 Intermediate Similarity NPD7251 Discontinued
0.8054 Intermediate Similarity NPD4908 Phase 1
0.8023 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8023 Intermediate Similarity NPD7808 Phase 3
0.8 Intermediate Similarity NPD5403 Approved
0.8 Intermediate Similarity NPD5844 Phase 1
0.7988 Intermediate Similarity NPD3817 Phase 2
0.7988 Intermediate Similarity NPD5402 Approved
0.7965 Intermediate Similarity NPD6559 Discontinued
0.7949 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7939 Intermediate Similarity NPD3882 Suspended
0.7925 Intermediate Similarity NPD6799 Approved
0.7919 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7888 Intermediate Similarity NPD920 Approved
0.7877 Intermediate Similarity NPD4363 Phase 3
0.7877 Intermediate Similarity NPD4360 Phase 2
0.7875 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7875 Intermediate Similarity NPD2534 Approved
0.7875 Intermediate Similarity NPD2533 Approved
0.7875 Intermediate Similarity NPD5401 Approved
0.7875 Intermediate Similarity NPD2532 Approved
0.7871 Intermediate Similarity NPD2799 Discontinued
0.7871 Intermediate Similarity NPD3748 Approved
0.7857 Intermediate Similarity NPD6651 Approved
0.7853 Intermediate Similarity NPD6599 Discontinued
0.7829 Intermediate Similarity NPD2313 Discontinued
0.7821 Intermediate Similarity NPD1551 Phase 2
0.7818 Intermediate Similarity NPD8455 Phase 2
0.7803 Intermediate Similarity NPD5953 Discontinued
0.7791 Intermediate Similarity NPD3226 Approved
0.7771 Intermediate Similarity NPD2344 Approved
0.7765 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7764 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.775 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7712 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7707 Intermediate Similarity NPD2935 Discontinued
0.7703 Intermediate Similarity NPD1610 Phase 2
0.7688 Intermediate Similarity NPD7286 Phase 2
0.7683 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7673 Intermediate Similarity NPD1243 Approved
0.7654 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7643 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7625 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7605 Intermediate Similarity NPD1465 Phase 2
0.7602 Intermediate Similarity NPD3787 Discontinued
0.7596 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7595 Intermediate Similarity NPD6099 Approved
0.7595 Intermediate Similarity NPD6100 Approved
0.759 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7584 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7578 Intermediate Similarity NPD2309 Approved
0.7576 Intermediate Similarity NPD7458 Discontinued
0.7564 Intermediate Similarity NPD5124 Phase 1
0.7564 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7547 Intermediate Similarity NPD2346 Discontinued
0.7529 Intermediate Similarity NPD3751 Discontinued
0.7516 Intermediate Similarity NPD4628 Phase 3
0.7516 Intermediate Similarity NPD7003 Approved
0.75 Intermediate Similarity NPD7229 Phase 3
0.7484 Intermediate Similarity NPD5404 Approved
0.7484 Intermediate Similarity NPD3268 Approved
0.7484 Intermediate Similarity NPD5408 Approved
0.7484 Intermediate Similarity NPD5406 Approved
0.7484 Intermediate Similarity NPD5405 Approved
0.7473 Intermediate Similarity NPD6776 Approved
0.7473 Intermediate Similarity NPD6778 Approved
0.7473 Intermediate Similarity NPD6781 Approved
0.7473 Intermediate Similarity NPD6779 Approved
0.7473 Intermediate Similarity NPD6780 Approved
0.7473 Intermediate Similarity NPD6782 Approved
0.7473 Intermediate Similarity NPD6777 Approved
0.7459 Intermediate Similarity NPD4287 Approved
0.7457 Intermediate Similarity NPD3926 Phase 2
0.7451 Intermediate Similarity NPD2798 Approved
0.7446 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7446 Intermediate Similarity NPD4361 Phase 2
0.7442 Intermediate Similarity NPD1247 Approved
0.7439 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7435 Intermediate Similarity NPD8151 Discontinued
0.7432 Intermediate Similarity NPD1548 Phase 1
0.7421 Intermediate Similarity NPD7033 Discontinued
0.7407 Intermediate Similarity NPD7871 Phase 2
0.7407 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD7870 Phase 2
0.7399 Intermediate Similarity NPD5711 Approved
0.7399 Intermediate Similarity NPD5710 Approved
0.7389 Intermediate Similarity NPD943 Approved
0.7386 Intermediate Similarity NPD1203 Approved
0.7386 Intermediate Similarity NPD2797 Approved
0.7355 Intermediate Similarity NPD6832 Phase 2
0.7354 Intermediate Similarity NPD7435 Discontinued
0.7354 Intermediate Similarity NPD7698 Approved
0.7354 Intermediate Similarity NPD7696 Phase 3
0.7354 Intermediate Similarity NPD7697 Approved
0.7348 Intermediate Similarity NPD8150 Discontinued
0.733 Intermediate Similarity NPD7584 Approved
0.7329 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7326 Intermediate Similarity NPD919 Approved
0.729 Intermediate Similarity NPD2861 Phase 2
0.7287 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD1613 Approved
0.7273 Intermediate Similarity NPD7212 Phase 2
0.7273 Intermediate Similarity NPD7213 Phase 3
0.7268 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7268 Intermediate Similarity NPD7783 Phase 2
0.7261 Intermediate Similarity NPD3764 Approved
0.7251 Intermediate Similarity NPD4288 Approved
0.725 Intermediate Similarity NPD7097 Phase 1
0.7246 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD7199 Phase 2
0.7235 Intermediate Similarity NPD6844 Discontinued
0.7235 Intermediate Similarity NPD37 Approved
0.7232 Intermediate Similarity NPD7177 Discontinued
0.7232 Intermediate Similarity NPD7228 Approved
0.7229 Intermediate Similarity NPD7447 Phase 1
0.7225 Intermediate Similarity NPD6234 Discontinued
0.7211 Intermediate Similarity NPD6823 Phase 2
0.7209 Intermediate Similarity NPD4967 Phase 2
0.7209 Intermediate Similarity NPD4965 Approved
0.7209 Intermediate Similarity NPD4966 Approved
0.7208 Intermediate Similarity NPD3225 Approved
0.7204 Intermediate Similarity NPD6534 Approved
0.7204 Intermediate Similarity NPD6535 Approved
0.7202 Intermediate Similarity NPD7701 Phase 2
0.7198 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD4625 Phase 3
0.7193 Intermediate Similarity NPD5760 Phase 2
0.7193 Intermediate Similarity NPD5761 Phase 2
0.7186 Intermediate Similarity NPD6273 Approved
0.7179 Intermediate Similarity NPD7801 Approved
0.7161 Intermediate Similarity NPD3266 Approved
0.7161 Intermediate Similarity NPD3267 Approved
0.7161 Intermediate Similarity NPD1470 Approved
0.7159 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD8434 Phase 2
0.7152 Intermediate Similarity NPD6798 Discontinued
0.7135 Intermediate Similarity NPD7577 Discontinued
0.7135 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7128 Intermediate Similarity NPD7874 Approved
0.7128 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7124 Intermediate Similarity NPD422 Phase 1
0.7124 Intermediate Similarity NPD1201 Approved
0.7099 Intermediate Similarity NPD4308 Phase 3
0.709 Intermediate Similarity NPD7700 Phase 2
0.709 Intermediate Similarity NPD7699 Phase 2
0.7078 Intermediate Similarity NPD9717 Approved
0.7078 Intermediate Similarity NPD1608 Approved
0.7076 Intermediate Similarity NPD5890 Approved
0.7076 Intermediate Similarity NPD5889 Approved
0.7073 Intermediate Similarity NPD2424 Discontinued
0.707 Intermediate Similarity NPD1530 Clinical (unspecified phase)

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data