Structure

Physi-Chem Properties

Molecular Weight:  810.31
Volume:  792.655
LogP:  2.102
LogD:  2.505
LogS:  -4.174
# Rotatable Bonds:  18
TPSA:  213.68
# H-Bond Aceptor:  16
# H-Bond Donor:  6
# Rings:  6
# Heavy Atoms:  16

MedChem Properties

QED Drug-Likeness Score:  0.083
Synthetic Accessibility Score:  5.169
Fsp3:  0.429
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:  -6.004
MDCK Permeability:  3.0625924409832805e-05
Pgp-inhibitor:  0.926
Pgp-substrate:  0.89
Human Intestinal Absorption (HIA):  0.022
20% Bioavailability (F20%):  0.001
30% Bioavailability (F30%):  0.04

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.066
Plasma Protein Binding (PPB):  57.41053009033203%
Volume Distribution (VD):  0.392
Pgp-substrate:  40.648983001708984%

ADMET: Metabolism

CYP1A2-inhibitor:  0.003
CYP1A2-substrate:  0.145
CYP2C19-inhibitor:  0.021
CYP2C19-substrate:  0.821
CYP2C9-inhibitor:  0.098
CYP2C9-substrate:  0.726
CYP2D6-inhibitor:  0.025
CYP2D6-substrate:  0.329
CYP3A4-inhibitor:  0.791
CYP3A4-substrate:  0.916

ADMET: Excretion

Clearance (CL):  9.139
Half-life (T1/2):  0.668

ADMET: Toxicity

hERG Blockers:  0.508
Human Hepatotoxicity (H-HT):  0.087
Drug-inuced Liver Injury (DILI):  0.275
AMES Toxicity:  0.063
Rat Oral Acute Toxicity:  0.044
Maximum Recommended Daily Dose:  0.478
Skin Sensitization:  0.816
Carcinogencity:  0.037
Eye Corrosion:  0.003
Eye Irritation:  0.011
Respiratory Toxicity:  0.007

Download Data

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

  Natural Product: NPC324517

Natural Product ID:  NPC324517
Common Name*:   (+)-(7R,7'r,7''s,7'''s,8S,8's,8''s,8'''s)-4'',4'''-Dihydroxy-3,3',3'',3''',5,5'-Hexamethoxy-7,9':7',9-Diepoxy-4,8'':4',8'''-Bisoxy-8,8'-Dineolignan-7'',7''',9'',9'''-Tetraol
IUPAC Name:   (1S,2S)-2-[4-[(3R,3aS,6R,6aS)-6-[4-[(1S,2S)-1,3-dihydroxy-1-(3-hydroxy-2-methoxyphenyl)propan-2-yl]oxy-3,5-dimethoxyphenyl]-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2,6-dimethoxyphenoxy]-1-(4-hydroxy-3-methoxyphenyl)propane-1,3-diol
Synonyms:  
Standard InCHIKey:  NQKMDFWGODIBLN-POWQJAJFSA-N
Standard InCHI:  InChI=1S/C42H50O16/c1-49-29-12-21(10-11-27(29)45)36(47)34(17-43)57-41-30(50-2)13-22(14-31(41)51-3)38-25-19-56-39(26(25)20-55-38)23-15-32(52-4)42(33(16-23)53-5)58-35(18-44)37(48)24-8-7-9-28(46)40(24)54-6/h7-16,25-26,34-39,43-48H,17-20H2,1-6H3/t25-,26-,34+,35+,36+,37+,38+,39+/m1/s1
SMILES:  COC1=CC(=CC(=C1OC(CO)C(C2=CC(=C(C=C2)O)OC)O)OC)C3C4COC(C4CO3)C5=CC(=C(C(=C5)OC)OC(CO)C(C6=C(C(=CC=C6)O)OC)O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1797778
PubChem CID:   56663001
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds
      • [CHEMONTID:0003686] Furanoid lignans

*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
NPO19192 Sinocalamus affinis Species n.a. n.a. n.a. stem n.a. PMID[21469695]
NPO19192 Sinocalamus affinis Species n.a. n.a. skin-removed stems Pingle Town, Sichuang Province, China 2008-AUG PMID[21469695]
NPO19192 Sinocalamus affinis Species n.a. n.a. n.a. n.a. n.a. PMID[22690646]
NPO19192 Sinocalamus affinis Species n.a. n.a. 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
NPT2 Others Unspecified Inhibition < 30.0 % PMID[458203]

☑ 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 NPC324517 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 NPC321972
1.0 High Similarity NPC329343
0.986 High Similarity NPC470098
0.986 High Similarity NPC470826
0.986 High Similarity NPC473266
0.972 High Similarity NPC328567
0.972 High Similarity NPC320970
0.972 High Similarity NPC320671
0.972 High Similarity NPC327412
0.965 High Similarity NPC317053
0.965 High Similarity NPC324492
0.951 High Similarity NPC470097
0.951 High Similarity NPC471415
0.951 High Similarity NPC114119
0.9396 High Similarity NPC157333
0.9388 High Similarity NPC477612
0.9379 High Similarity NPC260397
0.931 High Similarity NPC181615
0.9301 High Similarity NPC470372
0.9276 High Similarity NPC470828
0.9252 High Similarity NPC20757
0.9252 High Similarity NPC227516
0.9252 High Similarity NPC329836
0.9241 High Similarity NPC15659
0.9241 High Similarity NPC304894
0.9231 High Similarity NPC266197
0.9231 High Similarity NPC291101
0.9231 High Similarity NPC22317
0.9211 High Similarity NPC470827
0.9205 High Similarity NPC202104
0.9189 High Similarity NPC211561
0.9172 High Similarity NPC163508
0.9172 High Similarity NPC173203
0.9167 High Similarity NPC178054
0.9161 High Similarity NPC260842
0.9133 High Similarity NPC279406
0.9133 High Similarity NPC226809
0.9122 High Similarity NPC281549
0.9122 High Similarity NPC226153
0.9122 High Similarity NPC304048
0.911 High Similarity NPC28440
0.911 High Similarity NPC171932
0.9097 High Similarity NPC184797
0.9097 High Similarity NPC55793
0.9097 High Similarity NPC309124
0.9091 High Similarity NPC474390
0.9085 High Similarity NPC125495
0.9073 High Similarity NPC224161
0.906 High Similarity NPC318373
0.906 High Similarity NPC321657
0.906 High Similarity NPC476969
0.9054 High Similarity NPC18185
0.9054 High Similarity NPC204770
0.9054 High Similarity NPC262911
0.9054 High Similarity NPC294558
0.9054 High Similarity NPC70409
0.9054 High Similarity NPC263940
0.9054 High Similarity NPC108811
0.9054 High Similarity NPC236202
0.9054 High Similarity NPC58190
0.9054 High Similarity NPC202742
0.9054 High Similarity NPC170103
0.9054 High Similarity NPC82917
0.9034 High Similarity NPC87725
0.9034 High Similarity NPC263261
0.9034 High Similarity NPC311530
0.9028 High Similarity NPC236306
0.9028 High Similarity NPC22517
0.9028 High Similarity NPC232164
0.9028 High Similarity NPC473739
0.9021 High Similarity NPC77861
0.9013 High Similarity NPC46335
0.8986 High Similarity NPC96576
0.8986 High Similarity NPC241846
0.8986 High Similarity NPC93610
0.8973 High Similarity NPC107161
0.8966 High Similarity NPC254759
0.8966 High Similarity NPC160283
0.8966 High Similarity NPC472090
0.8966 High Similarity NPC262189
0.8966 High Similarity NPC472091
0.8966 High Similarity NPC472092
0.8951 High Similarity NPC24490
0.8951 High Similarity NPC165155
0.8951 High Similarity NPC126409
0.8951 High Similarity NPC141765
0.8951 High Similarity NPC34103
0.8951 High Similarity NPC93783
0.8951 High Similarity NPC99572
0.8947 High Similarity NPC470769
0.8933 High Similarity NPC51328
0.8933 High Similarity NPC55158
0.8933 High Similarity NPC286235
0.8924 High Similarity NPC59516
0.8912 High Similarity NPC477616
0.8904 High Similarity NPC471389
0.8904 High Similarity NPC247291
0.8897 High Similarity NPC292882
0.8889 High Similarity NPC306441
0.8889 High Similarity NPC248727
0.8889 High Similarity NPC270456
0.8889 High Similarity NPC16435
0.8889 High Similarity NPC162659
0.8889 High Similarity NPC265433
0.8882 High Similarity NPC476391
0.8881 High Similarity NPC66840
0.8881 High Similarity NPC287745
0.8881 High Similarity NPC256307
0.8881 High Similarity NPC326095
0.8881 High Similarity NPC244983
0.8867 High Similarity NPC248132
0.8867 High Similarity NPC130449
0.8859 High Similarity NPC14468
0.8851 High Similarity NPC280092
0.8851 High Similarity NPC63879
0.8851 High Similarity NPC12641
0.8851 High Similarity NPC45257
0.8851 High Similarity NPC93323
0.8846 High Similarity NPC1253
0.8846 High Similarity NPC100936
0.8844 High Similarity NPC472088
0.8844 High Similarity NPC472087
0.8839 High Similarity NPC147743
0.8839 High Similarity NPC4809
0.8839 High Similarity NPC73517
0.8836 High Similarity NPC27495
0.8828 High Similarity NPC477938
0.8828 High Similarity NPC211549
0.8824 High Similarity NPC115203
0.8819 High Similarity NPC121812
0.8819 High Similarity NPC112939
0.8819 High Similarity NPC260898
0.8819 High Similarity NPC234333
0.8819 High Similarity NPC61946
0.8819 High Similarity NPC47398
0.8819 High Similarity NPC470356
0.8819 High Similarity NPC112246
0.8819 High Similarity NPC474206
0.8819 High Similarity NPC94750
0.8811 High Similarity NPC475840
0.8811 High Similarity NPC158331
0.8808 High Similarity NPC55715
0.8808 High Similarity NPC475250
0.8808 High Similarity NPC95392
0.8808 High Similarity NPC35877
0.88 High Similarity NPC39657
0.88 High Similarity NPC99183
0.88 High Similarity NPC101376
0.88 High Similarity NPC16269
0.88 High Similarity NPC21776
0.8792 High Similarity NPC149633
0.8784 High Similarity NPC85264
0.8784 High Similarity NPC469630
0.8784 High Similarity NPC47633
0.8784 High Similarity NPC102044
0.8782 High Similarity NPC185231
0.8782 High Similarity NPC159526
0.8782 High Similarity NPC86630
0.8782 High Similarity NPC205613
0.8782 High Similarity NPC212614
0.8782 High Similarity NPC151474
0.8782 High Similarity NPC106601
0.8782 High Similarity NPC471404
0.8776 High Similarity NPC472089
0.8767 High Similarity NPC471388
0.8767 High Similarity NPC55947
0.8767 High Similarity NPC70682
0.8767 High Similarity NPC260741
0.8767 High Similarity NPC245207
0.8767 High Similarity NPC127218
0.8767 High Similarity NPC319647
0.8767 High Similarity NPC25966
0.8759 High Similarity NPC263367
0.8759 High Similarity NPC472336
0.8759 High Similarity NPC141717
0.8759 High Similarity NPC54743
0.8759 High Similarity NPC230734
0.8759 High Similarity NPC477939
0.8759 High Similarity NPC209985
0.8759 High Similarity NPC269091
0.8759 High Similarity NPC177160
0.8759 High Similarity NPC29799
0.8759 High Similarity NPC156502
0.8759 High Similarity NPC472334
0.8759 High Similarity NPC474639
0.8759 High Similarity NPC227503
0.8759 High Similarity NPC10737
0.8759 High Similarity NPC302701
0.8758 High Similarity NPC44192
0.8758 High Similarity NPC272552
0.8758 High Similarity NPC134911
0.8758 High Similarity NPC233467
0.8758 High Similarity NPC226108
0.8758 High Similarity NPC46283
0.8758 High Similarity NPC157783
0.8758 High Similarity NPC59692
0.8758 High Similarity NPC322899
0.8758 High Similarity NPC469944
0.875 High Similarity NPC472709
0.875 High Similarity NPC475224

  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 NPC324517 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
0.8611 High Similarity NPD1612 Clinical (unspecified phase)
0.8611 High Similarity NPD1613 Approved
0.8531 High Similarity NPD3027 Phase 3
0.8333 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD4908 Phase 1
0.8264 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.8219 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.8086 Intermediate Similarity NPD6234 Discontinued
0.8072 Intermediate Similarity NPD7228 Approved
0.7988 Intermediate Similarity NPD7199 Phase 2
0.7963 Intermediate Similarity NPD4967 Phase 2
0.7963 Intermediate Similarity NPD4966 Approved
0.7963 Intermediate Similarity NPD4965 Approved
0.7952 Intermediate Similarity NPD6166 Phase 2
0.7952 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7952 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7853 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7847 Intermediate Similarity NPD1610 Phase 2
0.7824 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7784 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD1934 Approved
0.7778 Intermediate Similarity NPD37 Approved
0.777 Intermediate Similarity NPD2861 Phase 2
0.7692 Intermediate Similarity NPD6674 Discontinued
0.7674 Intermediate Similarity NPD7240 Approved
0.7661 Intermediate Similarity NPD7472 Approved
0.7661 Intermediate Similarity NPD7074 Phase 3
0.7647 Intermediate Similarity NPD3818 Discontinued
0.764 Intermediate Similarity NPD1653 Approved
0.7622 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7616 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7602 Intermediate Similarity NPD7054 Approved
0.7569 Intermediate Similarity NPD1548 Phase 1
0.7543 Intermediate Similarity NPD8053 Approved
0.7543 Intermediate Similarity NPD8054 Approved
0.7533 Intermediate Similarity NPD3018 Phase 2
0.753 Intermediate Similarity NPD3882 Suspended
0.7529 Intermediate Similarity NPD7808 Phase 3
0.7516 Intermediate Similarity NPD3620 Phase 2
0.7516 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD8455 Phase 2
0.7515 Intermediate Similarity NPD2801 Approved
0.75 Intermediate Similarity NPD5844 Phase 1
0.75 Intermediate Similarity NPD4749 Approved
0.7471 Intermediate Similarity NPD7251 Discontinued
0.747 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7434 Intermediate Similarity NPD4625 Phase 3
0.7414 Intermediate Similarity NPD6797 Phase 2
0.7401 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD5494 Approved
0.7383 Intermediate Similarity NPD2983 Phase 2
0.7383 Intermediate Similarity NPD2982 Phase 2
0.7381 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7366 Intermediate Similarity NPD7680 Approved
0.7365 Intermediate Similarity NPD6374 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7355 Intermediate Similarity NPD5735 Approved
0.7353 Intermediate Similarity NPD8127 Discontinued
0.7346 Intermediate Similarity NPD7447 Phase 1
0.7343 Intermediate Similarity NPD5283 Phase 1
0.7342 Intermediate Similarity NPD7266 Discontinued
0.7333 Intermediate Similarity NPD8651 Approved
0.7321 Intermediate Similarity NPD7768 Phase 2
0.7318 Intermediate Similarity NPD7906 Approved
0.7315 Intermediate Similarity NPD2981 Phase 2
0.7312 Intermediate Similarity NPD7466 Approved
0.729 Intermediate Similarity NPD4060 Phase 1
0.7284 Intermediate Similarity NPD1511 Approved
0.7284 Intermediate Similarity NPD7213 Phase 3
0.7284 Intermediate Similarity NPD7212 Phase 2
0.7283 Intermediate Similarity NPD7473 Discontinued
0.7273 Intermediate Similarity NPD7843 Approved
0.7273 Intermediate Similarity NPD6055 Clinical (unspecified phase)
0.7262 Intermediate Similarity NPD3817 Phase 2
0.7251 Intermediate Similarity NPD6959 Discontinued
0.7243 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD7157 Approved
0.7239 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7237 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7232 Intermediate Similarity NPD7549 Discontinued
0.7232 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7229 Intermediate Similarity NPD4380 Phase 2
0.7209 Intermediate Similarity NPD6232 Discontinued
0.7203 Intermediate Similarity NPD228 Approved
0.7202 Intermediate Similarity NPD1465 Phase 2
0.72 Intermediate Similarity NPD8156 Discontinued
0.7195 Intermediate Similarity NPD1512 Approved
0.7178 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7175 Intermediate Similarity NPD6559 Discontinued
0.7167 Intermediate Similarity NPD4663 Approved
0.7161 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7151 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD8099 Discontinued
0.7143 Intermediate Similarity NPD8251 Approved
0.7143 Intermediate Similarity NPD8252 Approved
0.7134 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD5124 Phase 1
0.7134 Intermediate Similarity NPD6355 Discontinued
0.7133 Intermediate Similarity NPD3705 Approved
0.7133 Intermediate Similarity NPD1091 Approved
0.7126 Intermediate Similarity NPD2489 Approved
0.7126 Intermediate Similarity NPD27 Approved
0.7125 Intermediate Similarity NPD5762 Approved
0.7125 Intermediate Similarity NPD5763 Approved
0.711 Intermediate Similarity NPD7229 Phase 3
0.711 Intermediate Similarity NPD3051 Approved
0.7107 Intermediate Similarity NPD5588 Approved
0.7102 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD3892 Phase 2
0.7095 Intermediate Similarity NPD7311 Approved
0.7095 Intermediate Similarity NPD8312 Approved
0.7095 Intermediate Similarity NPD7313 Approved
0.7095 Intermediate Similarity NPD8313 Approved
0.7095 Intermediate Similarity NPD7310 Approved
0.7095 Intermediate Similarity NPD4577 Approved
0.7095 Intermediate Similarity NPD7312 Approved
0.7095 Intermediate Similarity NPD4578 Approved
0.7088 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD7075 Discontinued
0.707 Intermediate Similarity NPD1558 Phase 1
0.7069 Intermediate Similarity NPD2970 Approved
0.7069 Intermediate Similarity NPD2969 Approved
0.7063 Intermediate Similarity NPD6100 Approved
0.7063 Intermediate Similarity NPD3022 Approved
0.7063 Intermediate Similarity NPD6099 Approved
0.7063 Intermediate Similarity NPD3021 Approved
0.7056 Intermediate Similarity NPD7309 Approved
0.7055 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7051 Intermediate Similarity NPD6798 Discontinued
0.7048 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD7097 Phase 1
0.7044 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD4536 Approved
0.7044 Intermediate Similarity NPD4538 Approved
0.7039 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD1652 Phase 2
0.7037 Intermediate Similarity NPD5177 Phase 3
0.703 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7024 Intermediate Similarity NPD4675 Approved
0.7024 Intermediate Similarity NPD4678 Approved
0.7019 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD3540 Phase 1
0.7013 Intermediate Similarity NPD6584 Phase 3
0.7012 Intermediate Similarity NPD5058 Phase 3
0.7011 Intermediate Similarity NPD3787 Discontinued
0.7007 Intermediate Similarity NPD6671 Approved
0.7 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD7819 Suspended
0.7 Intermediate Similarity NPD6516 Phase 2
0.7 Intermediate Similarity NPD5846 Approved
0.6994 Remote Similarity NPD6331 Phase 2
0.6993 Remote Similarity NPD2684 Approved
0.6987 Remote Similarity NPD7095 Approved
0.6983 Remote Similarity NPD7685 Pre-registration
0.6977 Remote Similarity NPD7832 Clinical (unspecified phase)
0.6977 Remote Similarity NPD7833 Phase 2
0.6977 Remote Similarity NPD7831 Phase 2
0.6975 Remote Similarity NPD7037 Approved
0.6964 Remote Similarity NPD4005 Discontinued
0.6959 Remote Similarity NPD2560 Approved
0.6959 Remote Similarity NPD2563 Approved
0.6959 Remote Similarity NPD5402 Approved
0.6957 Remote Similarity NPD3539 Phase 1
0.6951 Remote Similarity NPD2677 Approved
0.6951 Remote Similarity NPD6190 Approved
0.6933 Remote Similarity NPD4237 Approved
0.6933 Remote Similarity NPD4236 Phase 3
0.6933 Remote Similarity NPD1357 Approved
0.6928 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6928 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6928 Remote Similarity NPD7446 Clinical (unspecified phase)
0.6928 Remote Similarity NPD5327 Phase 3
0.6928 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6923 Remote Similarity NPD290 Approved
0.6914 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6914 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6914 Remote Similarity NPD6071 Discontinued
0.6909 Remote Similarity NPD7124 Phase 2
0.6908 Remote Similarity NPD422 Phase 1
0.6901 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6901 Remote Similarity NPD6818 Clinical (unspecified phase)
0.6899 Remote Similarity NPD6233 Phase 2
0.6894 Remote Similarity NPD5960 Phase 3
0.689 Remote Similarity NPD4110 Phase 3
0.689 Remote Similarity NPD6398 Clinical (unspecified phase)
0.689 Remote Similarity NPD4109 Clinical (unspecified phase)
0.689 Remote Similarity NPD3750 Approved
0.6886 Remote Similarity NPD1940 Clinical (unspecified phase)
0.6883 Remote Similarity NPD6696 Suspended
0.6882 Remote Similarity NPD7411 Suspended
0.6882 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6875 Remote Similarity NPD6653 Approved
0.6875 Remote Similarity NPD3926 Phase 2
0.6875 Remote Similarity NPD6353 Approved
0.6871 Remote Similarity NPD1549 Phase 2
0.6867 Remote Similarity NPD7041 Phase 2
0.6867 Remote Similarity NPD7040 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