Structure

Physi-Chem Properties

Molecular Weight:  662.24
Volume:  653.718
LogP:  5.355
LogD:  3.458
LogS:  -3.726
# Rotatable Bonds:  9
TPSA:  154.76
# H-Bond Aceptor:  12
# H-Bond Donor:  4
# Rings:  6
# Heavy Atoms:  12

MedChem Properties

QED Drug-Likeness Score:  0.158
Synthetic Accessibility Score:  4.075
Fsp3:  0.333
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.267
MDCK Permeability:  2.9494325644918717e-05
Pgp-inhibitor:  0.979
Pgp-substrate:  0.94
Human Intestinal Absorption (HIA):  0.011
20% Bioavailability (F20%):  0.0
30% Bioavailability (F30%):  0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.001
Plasma Protein Binding (PPB):  74.88770294189453%
Volume Distribution (VD):  0.492
Pgp-substrate:  66.14784240722656%

ADMET: Metabolism

CYP1A2-inhibitor:  0.036
CYP1A2-substrate:  0.99
CYP2C19-inhibitor:  0.158
CYP2C19-substrate:  0.668
CYP2C9-inhibitor:  0.505
CYP2C9-substrate:  0.904
CYP2D6-inhibitor:  0.001
CYP2D6-substrate:  0.912
CYP3A4-inhibitor:  0.189
CYP3A4-substrate:  0.924

ADMET: Excretion

Clearance (CL):  7.373
Half-life (T1/2):  0.554

ADMET: Toxicity

hERG Blockers:  0.402
Human Hepatotoxicity (H-HT):  0.072
Drug-inuced Liver Injury (DILI):  0.674
AMES Toxicity:  0.04
Rat Oral Acute Toxicity:  0.514
Maximum Recommended Daily Dose:  0.957
Skin Sensitization:  0.97
Carcinogencity:  0.015
Eye Corrosion:  0.003
Eye Irritation:  0.246
Respiratory Toxicity:  0.383

Download Data

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

  Natural Product: NPC321657

Natural Product ID:  NPC321657
Common Name*:   (M)(2S),(2''s)-,(P)-(2S),(2''s)-8,8''-5'5'''-Tetrahydroxy-7,7''-3',3'''-4',4'''-Hexamethoxy-5,5''-Biflavan
IUPAC Name:   (2S)-2-(3-hydroxy-4,5-dimethoxyphenyl)-5-[(2S)-8-hydroxy-2-(3-hydroxy-4,5-dimethoxyphenyl)-7-methoxy-3,4-dihydro-2H-chromen-5-yl]-7-methoxy-3,4-dihydro-2H-chromen-8-ol
Synonyms:  
Standard InCHIKey:  GBQSWSKEZIAPTN-UIOOFZCWSA-N
Standard InCHI:  InChI=1S/C36H38O12/c1-41-27-15-21(19-7-9-25(47-33(19)31(27)39)17-11-23(37)35(45-5)29(13-17)43-3)22-16-28(42-2)32(40)34-20(22)8-10-26(48-34)18-12-24(38)36(46-6)30(14-18)44-4/h11-16,25-26,37-40H,7-10H2,1-6H3/t25-,26-/m0/s1
SMILES:  COC1=CC(=CC(=C1OC)O)C2CCC3=C(O2)C(=C(C=C3C4=CC(=C(C5=C4CCC(O5)C6=CC(=C(C(=C6)OC)OC)O)O)OC)OC)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL503775
PubChem CID:   44567058
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0002585] O-methylated flavonoids
          • [CHEMONTID:0002592] 7-O-methylated flavonoids

*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
NPO8046 Muntingia calabura Species Muntingiaceae Eukaryota Roots n.a. n.a. PMID[2045815]
NPO8046 Muntingia calabura Species Muntingiaceae Eukaryota n.a. root n.a. PMID[2045815]
NPO8046 Muntingia calabura Species Muntingiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8046 Muntingia calabura Species Muntingiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8046 Muntingia calabura Species Muntingiaceae 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
NPT168 Cell Line P388 Mus musculus ED50 = 4.8 ug ml-1 PMID[548052]
NPT453 Cell Line HT-1080 Homo sapiens ED50 = 5.0 ug ml-1 PMID[548052]
NPT91 Cell Line KB Homo sapiens ED50 = 5.2 ug ml-1 PMID[548052]
NPT147 Cell Line SK-MEL-2 Homo sapiens ED50 = 8.7 ug ml-1 PMID[548052]
NPT1851 Cell Line Col2 Homo sapiens ED50 = 9.0 ug ml-1 PMID[548052]
NPT91 Cell Line KB Homo sapiens ED50 = 12.6 ug ml-1 PMID[548052]
NPT1034 Cell Line Lu1 Homo sapiens ED50 = 15.6 ug ml-1 PMID[548052]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 16.0 ug ml-1 PMID[548052]

☑ 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 NPC321657 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
1.0 High Similarity NPC318373
0.9514 High Similarity NPC281549
0.9448 High Similarity NPC476969
0.9384 High Similarity NPC477612
0.9371 High Similarity NPC28440
0.9371 High Similarity NPC171932
0.9315 High Similarity NPC211561
0.9241 High Similarity NPC150714
0.9241 High Similarity NPC95652
0.9241 High Similarity NPC96576
0.9225 High Similarity NPC472092
0.9225 High Similarity NPC22317
0.9225 High Similarity NPC472091
0.9225 High Similarity NPC472090
0.9225 High Similarity NPC262189
0.9178 High Similarity NPC236202
0.9178 High Similarity NPC294558
0.9178 High Similarity NPC82917
0.9178 High Similarity NPC153182
0.9178 High Similarity NPC70409
0.9178 High Similarity NPC262911
0.9178 High Similarity NPC108811
0.9178 High Similarity NPC263940
0.9178 High Similarity NPC202742
0.9178 High Similarity NPC262297
0.9178 High Similarity NPC170103
0.9178 High Similarity NPC58190
0.9178 High Similarity NPC174251
0.9178 High Similarity NPC204770
0.9178 High Similarity NPC18185
0.9155 High Similarity NPC55947
0.9133 High Similarity NPC157333
0.9128 High Similarity NPC226809
0.9128 High Similarity NPC279406
0.911 High Similarity NPC215678
0.911 High Similarity NPC274454
0.9103 High Similarity NPC304894
0.9103 High Similarity NPC473108
0.9103 High Similarity NPC15659
0.9097 High Similarity NPC472087
0.9097 High Similarity NPC472088
0.9085 High Similarity NPC211549
0.9085 High Similarity NPC100936
0.9085 High Similarity NPC1253
0.9067 High Similarity NPC224161
0.906 High Similarity NPC324517
0.906 High Similarity NPC329343
0.906 High Similarity NPC321972
0.9034 High Similarity NPC173203
0.9034 High Similarity NPC163508
0.9034 High Similarity NPC469630
0.9028 High Similarity NPC178054
0.9028 High Similarity NPC472089
0.9021 High Similarity NPC22517
0.9014 High Similarity NPC234952
0.9007 High Similarity NPC46335
0.8986 High Similarity NPC473876
0.8986 High Similarity NPC227516
0.8986 High Similarity NPC329836
0.8986 High Similarity NPC20757
0.898 High Similarity NPC126291
0.8973 High Similarity NPC50250
0.8958 High Similarity NPC291101
0.8958 High Similarity NPC266197
0.8951 High Similarity NPC474390
0.8951 High Similarity NPC48956
0.8947 High Similarity NPC202104
0.8944 High Similarity NPC112246
0.8944 High Similarity NPC121812
0.8944 High Similarity NPC47398
0.8944 High Similarity NPC470356
0.8944 High Similarity NPC234333
0.8944 High Similarity NPC112939
0.8944 High Similarity NPC474206
0.8944 High Similarity NPC94750
0.8944 High Similarity NPC260898
0.8926 High Similarity NPC473266
0.8926 High Similarity NPC470826
0.8926 High Similarity NPC470098
0.8919 High Similarity NPC320970
0.8919 High Similarity NPC328567
0.8919 High Similarity NPC474397
0.8919 High Similarity NPC320671
0.8919 High Similarity NPC327412
0.8889 High Similarity NPC471183
0.8889 High Similarity NPC32630
0.8881 High Similarity NPC306441
0.8881 High Similarity NPC227503
0.8881 High Similarity NPC248727
0.8881 High Similarity NPC270456
0.8881 High Similarity NPC16435
0.8881 High Similarity NPC162659
0.8881 High Similarity NPC265433
0.8881 High Similarity NPC230734
0.8881 High Similarity NPC474639
0.8874 High Similarity NPC226108
0.8874 High Similarity NPC476391
0.8874 High Similarity NPC44192
0.8874 High Similarity NPC322899
0.8874 High Similarity NPC272552
0.8874 High Similarity NPC21902
0.8874 High Similarity NPC134911
0.8874 High Similarity NPC46283
0.8874 High Similarity NPC469944
0.8873 High Similarity NPC256307
0.8873 High Similarity NPC66840
0.8867 High Similarity NPC205501
0.8867 High Similarity NPC118000
0.8867 High Similarity NPC162976
0.8865 High Similarity NPC127624
0.8851 High Similarity NPC233980
0.8851 High Similarity NPC324492
0.8851 High Similarity NPC260397
0.8851 High Similarity NPC317053
0.8844 High Similarity NPC475492
0.8836 High Similarity NPC183709
0.8831 High Similarity NPC147743
0.8831 High Similarity NPC4809
0.8831 High Similarity NPC73517
0.8828 High Similarity NPC309124
0.8828 High Similarity NPC184797
0.8819 High Similarity NPC326797
0.8819 High Similarity NPC102904
0.8819 High Similarity NPC107551
0.8819 High Similarity NPC176051
0.8819 High Similarity NPC474282
0.8819 High Similarity NPC103976
0.8816 High Similarity NPC306267
0.8816 High Similarity NPC20050
0.8811 High Similarity NPC61946
0.8811 High Similarity NPC151224
0.8803 High Similarity NPC11060
0.8784 High Similarity NPC161700
0.8784 High Similarity NPC181615
0.8784 High Similarity NPC277867
0.8774 High Similarity NPC151474
0.8774 High Similarity NPC205613
0.8774 High Similarity NPC212614
0.8774 High Similarity NPC185231
0.8774 High Similarity NPC86630
0.8774 High Similarity NPC471404
0.8774 High Similarity NPC106601
0.8774 High Similarity NPC159526
0.8767 High Similarity NPC471389
0.8767 High Similarity NPC247291
0.8767 High Similarity NPC277331
0.8767 High Similarity NPC100482
0.8767 High Similarity NPC470372
0.8767 High Similarity NPC265075
0.8759 High Similarity NPC70682
0.8759 High Similarity NPC260741
0.8759 High Similarity NPC232164
0.8759 High Similarity NPC245207
0.8759 High Similarity NPC6300
0.8759 High Similarity NPC236306
0.8759 High Similarity NPC127218
0.8759 High Similarity NPC230124
0.8759 High Similarity NPC319647
0.8759 High Similarity NPC25966
0.8759 High Similarity NPC114171
0.8759 High Similarity NPC473739
0.875 High Similarity NPC269091
0.875 High Similarity NPC202846
0.875 High Similarity NPC325860
0.875 High Similarity NPC233467
0.875 High Similarity NPC302701
0.875 High Similarity NPC143139
0.875 High Similarity NPC133025
0.875 High Similarity NPC470802
0.875 High Similarity NPC157783
0.8742 High Similarity NPC185955
0.8742 High Similarity NPC145979
0.8742 High Similarity NPC9933
0.8742 High Similarity NPC214326
0.8742 High Similarity NPC260781
0.8742 High Similarity NPC225815
0.8742 High Similarity NPC469706
0.8742 High Similarity NPC218041
0.8742 High Similarity NPC182368
0.8742 High Similarity NPC469707
0.8741 High Similarity NPC170694
0.8741 High Similarity NPC476617
0.8741 High Similarity NPC476616
0.8741 High Similarity NPC125649
0.8741 High Similarity NPC476615
0.8741 High Similarity NPC317380
0.8732 High Similarity NPC131128
0.8732 High Similarity NPC202762
0.8732 High Similarity NPC86655
0.8732 High Similarity NPC474134
0.8725 High Similarity NPC112251
0.8725 High Similarity NPC125755
0.8725 High Similarity NPC99515
0.8725 High Similarity NPC190714
0.8716 High Similarity NPC473845
0.8716 High Similarity NPC470097
0.8716 High Similarity NPC471415
0.8716 High Similarity NPC63879
0.8716 High Similarity NPC114119
0.871 High Similarity NPC470827

  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 NPC321657 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
0.8601 High Similarity NPD1612 Clinical (unspecified phase)
0.8601 High Similarity NPD1613 Approved
0.8511 High Similarity NPD1530 Clinical (unspecified phase)
0.8451 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.8392 Intermediate Similarity NPD3027 Phase 3
0.8322 Intermediate Similarity NPD4908 Phase 1
0.8207 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.816 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.816 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.816 Intermediate Similarity NPD6166 Phase 2
0.8063 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8061 Intermediate Similarity NPD7228 Approved
0.8047 Intermediate Similarity NPD8053 Approved
0.8047 Intermediate Similarity NPD8054 Approved
0.8024 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7975 Intermediate Similarity NPD6959 Discontinued
0.7908 Intermediate Similarity NPD6674 Discontinued
0.7891 Intermediate Similarity NPD4625 Phase 3
0.7875 Intermediate Similarity NPD1934 Approved
0.7857 Intermediate Similarity NPD7074 Phase 3
0.7853 Intermediate Similarity NPD6234 Discontinued
0.7832 Intermediate Similarity NPD1610 Phase 2
0.7826 Intermediate Similarity NPD1465 Phase 2
0.7798 Intermediate Similarity NPD7054 Approved
0.7798 Intermediate Similarity NPD5844 Phase 1
0.7751 Intermediate Similarity NPD7472 Approved
0.7716 Intermediate Similarity NPD8455 Phase 2
0.7716 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD8156 Discontinued
0.7654 Intermediate Similarity NPD37 Approved
0.7651 Intermediate Similarity NPD7199 Phase 2
0.7635 Intermediate Similarity NPD2861 Phase 2
0.7633 Intermediate Similarity NPD8099 Discontinued
0.7633 Intermediate Similarity NPD8252 Approved
0.7633 Intermediate Similarity NPD8251 Approved
0.7625 Intermediate Similarity NPD1653 Approved
0.7622 Intermediate Similarity NPD4966 Approved
0.7622 Intermediate Similarity NPD4967 Phase 2
0.7622 Intermediate Similarity NPD4965 Approved
0.7616 Intermediate Similarity NPD7808 Phase 3
0.7603 Intermediate Similarity NPD4749 Approved
0.76 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7564 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.756 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7558 Intermediate Similarity NPD7251 Discontinued
0.7558 Intermediate Similarity NPD7240 Approved
0.7552 Intermediate Similarity NPD1548 Phase 1
0.7547 Intermediate Similarity NPD7447 Phase 1
0.7517 Intermediate Similarity NPD3018 Phase 2
0.75 Intermediate Similarity NPD2801 Approved
0.75 Intermediate Similarity NPD6232 Discontinued
0.75 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD3620 Phase 2
0.75 Intermediate Similarity NPD6797 Phase 2
0.7484 Intermediate Similarity NPD7212 Phase 2
0.7484 Intermediate Similarity NPD7213 Phase 3
0.7471 Intermediate Similarity NPD7473 Discontinued
0.7458 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7455 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD7266 Discontinued
0.741 Intermediate Similarity NPD7768 Phase 2
0.7401 Intermediate Similarity NPD7906 Approved
0.7396 Intermediate Similarity NPD3787 Discontinued
0.7386 Intermediate Similarity NPD4060 Phase 1
0.7365 Intermediate Similarity NPD2982 Phase 2
0.7365 Intermediate Similarity NPD2983 Phase 2
0.7329 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7326 Intermediate Similarity NPD3818 Discontinued
0.7325 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7314 Intermediate Similarity NPD7549 Discontinued
0.731 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD3882 Suspended
0.7297 Intermediate Similarity NPD2981 Phase 2
0.7289 Intermediate Similarity NPD7819 Suspended
0.7283 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD5494 Approved
0.7273 Intermediate Similarity NPD8313 Approved
0.7273 Intermediate Similarity NPD8312 Approved
0.7267 Intermediate Similarity NPD1511 Approved
0.7261 Intermediate Similarity NPD6100 Approved
0.7261 Intermediate Similarity NPD6099 Approved
0.7258 Intermediate Similarity NPD7680 Approved
0.7246 Intermediate Similarity NPD3817 Phase 2
0.723 Intermediate Similarity NPD3705 Approved
0.7228 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7216 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7216 Intermediate Similarity NPD8453 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD4380 Phase 2
0.7203 Intermediate Similarity NPD5283 Phase 1
0.72 Intermediate Similarity NPD8651 Approved
0.7191 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7183 Intermediate Similarity NPD228 Approved
0.7178 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.7178 Intermediate Similarity NPD1512 Approved
0.7175 Intermediate Similarity NPD7312 Approved
0.7175 Intermediate Similarity NPD7311 Approved
0.7175 Intermediate Similarity NPD7310 Approved
0.7175 Intermediate Similarity NPD7313 Approved
0.716 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD7075 Discontinued
0.716 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD6055 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD4005 Discontinued
0.7143 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6374 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD7309 Approved
0.7135 Intermediate Similarity NPD8127 Discontinued
0.7134 Intermediate Similarity NPD7097 Phase 1
0.7133 Intermediate Similarity NPD7843 Approved
0.7126 Intermediate Similarity NPD3751 Discontinued
0.7117 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD5735 Approved
0.7114 Intermediate Similarity NPD1091 Approved
0.7103 Intermediate Similarity NPD7157 Approved
0.7103 Intermediate Similarity NPD6671 Approved
0.7093 Intermediate Similarity NPD7229 Phase 3
0.7089 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD3750 Approved
0.7081 Intermediate Similarity NPD7466 Approved
0.7079 Intermediate Similarity NPD4578 Approved
0.7079 Intermediate Similarity NPD4577 Approved
0.7062 Intermediate Similarity NPD6559 Discontinued
0.7056 Intermediate Similarity NPD4663 Approved
0.7055 Intermediate Similarity NPD7040 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD7041 Phase 2
0.7051 Intermediate Similarity NPD1558 Phase 1
0.7037 Intermediate Similarity NPD2677 Approved
0.7037 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7032 Intermediate Similarity NPD6798 Discontinued
0.7025 Intermediate Similarity NPD4536 Approved
0.7025 Intermediate Similarity NPD4538 Approved
0.7025 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.702 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.702 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD1652 Phase 2
0.7012 Intermediate Similarity NPD7446 Clinical (unspecified phase)
0.7012 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD27 Approved
0.7011 Intermediate Similarity NPD2489 Approved
0.7006 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD4678 Approved
0.7006 Intermediate Similarity NPD5124 Phase 1
0.7006 Intermediate Similarity NPD4675 Approved
0.7 Intermediate Similarity NPD5762 Approved
0.7 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD3540 Phase 1
0.7 Intermediate Similarity NPD5763 Approved
0.6994 Remote Similarity NPD3051 Approved
0.6993 Remote Similarity NPD6584 Phase 3
0.6982 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6979 Remote Similarity NPD8151 Discontinued
0.6975 Remote Similarity NPD3892 Phase 2
0.6975 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6974 Remote Similarity NPD6696 Suspended
0.6968 Remote Similarity NPD7095 Approved
0.6964 Remote Similarity NPD7411 Suspended
0.6959 Remote Similarity NPD7831 Phase 2
0.6959 Remote Similarity NPD4055 Discovery
0.6959 Remote Similarity NPD3749 Approved
0.6959 Remote Similarity NPD7832 Clinical (unspecified phase)
0.6959 Remote Similarity NPD7833 Phase 2
0.6957 Remote Similarity NPD1549 Phase 2
0.6954 Remote Similarity NPD2970 Approved
0.6954 Remote Similarity NPD2969 Approved
0.6951 Remote Similarity NPD7390 Discontinued
0.6946 Remote Similarity NPD8158 Clinical (unspecified phase)
0.6944 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6943 Remote Similarity NPD5837 Clinical (unspecified phase)
0.6937 Remote Similarity NPD3539 Phase 1
0.6923 Remote Similarity NPD3021 Approved
0.6923 Remote Similarity NPD6841 Approved
0.6923 Remote Similarity NPD6843 Phase 3
0.6923 Remote Similarity NPD6842 Approved
0.6923 Remote Similarity NPD3022 Approved
0.6914 Remote Similarity NPD5177 Phase 3
0.6909 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6909 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6908 Remote Similarity NPD5327 Phase 3
0.6902 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6899 Remote Similarity NPD6355 Discontinued
0.6897 Remote Similarity NPD6071 Discontinued
0.6887 Remote Similarity NPD422 Phase 1
0.6882 Remote Similarity NPD6818 Clinical (unspecified phase)
0.6879 Remote Similarity NPD6233 Phase 2
0.6875 Remote Similarity NPD5960 Phase 3
0.6875 Remote Similarity NPD5588 Approved
0.6871 Remote Similarity NPD6658 Clinical (unspecified phase)
0.6871 Remote Similarity NPD8166 Discontinued
0.6867 Remote Similarity NPD6516 Phase 2
0.6867 Remote Similarity NPD5846 Approved
0.6867 Remote Similarity NPD5261 Clinical (unspecified phase)
0.6864 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6862 Remote Similarity NPD8095 Phase 1
0.6853 Remote Similarity NPD2684 Approved
0.6852 Remote Similarity NPD7037 Approved
0.6848 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6845 Remote Similarity NPD5808 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