Structure

Physi-Chem Properties

Molecular Weight:  434.23
Volume:  446.34
LogP:  2.167
LogD:  1.129
LogS:  -2.612
# Rotatable Bonds:  7
TPSA:  106.97
# H-Bond Aceptor:  7
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.403
Synthetic Accessibility Score:  4.934
Fsp3:  0.75
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  3
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.86
MDCK Permeability:  7.522931991843507e-05
Pgp-inhibitor:  0.006
Pgp-substrate:  0.004
Human Intestinal Absorption (HIA):  0.887
20% Bioavailability (F20%):  0.017
30% Bioavailability (F30%):  0.595

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.554
Plasma Protein Binding (PPB):  61.06064987182617%
Volume Distribution (VD):  1.006
Pgp-substrate:  45.59678649902344%

ADMET: Metabolism

CYP1A2-inhibitor:  0.009
CYP1A2-substrate:  0.074
CYP2C19-inhibitor:  0.018
CYP2C19-substrate:  0.297
CYP2C9-inhibitor:  0.032
CYP2C9-substrate:  0.129
CYP2D6-inhibitor:  0.006
CYP2D6-substrate:  0.123
CYP3A4-inhibitor:  0.428
CYP3A4-substrate:  0.269

ADMET: Excretion

Clearance (CL):  3.097
Half-life (T1/2):  0.494

ADMET: Toxicity

hERG Blockers:  0.033
Human Hepatotoxicity (H-HT):  0.297
Drug-inuced Liver Injury (DILI):  0.55
AMES Toxicity:  0.053
Rat Oral Acute Toxicity:  0.285
Maximum Recommended Daily Dose:  0.821
Skin Sensitization:  0.435
Carcinogencity:  0.179
Eye Corrosion:  0.045
Eye Irritation:  0.038
Respiratory Toxicity:  0.971

Download Data

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

  Natural Product: NPC272635

Natural Product ID:  NPC272635
Common Name*:   6Beta,19-Diacetoxy-6Beta-Hydroxy-7,16-Dioxo-Ent-Abieta-15(17)-Ene
IUPAC Name:   [(1R,2S,4aS,4bR,7R,8aR,10S,10aS)-2-acetyloxy-10-hydroxy-1,4a-dimethyl-9-oxo-7-(3-oxoprop-1-en-2-yl)-3,4,4b,5,6,7,8,8a,10,10a-decahydro-2H-phenanthren-1-yl]methyl acetate
Synonyms:   3-acetyleriocasin C
Standard InCHIKey:  LKBMNVLYWWORRA-QLKQUVKYSA-N
Standard InCHI:  InChI=1S/C24H34O7/c1-13(11-25)16-6-7-18-17(10-16)20(28)21(29)22-23(18,4)9-8-19(31-15(3)27)24(22,5)12-30-14(2)26/h11,16-19,21-22,29H,1,6-10,12H2,2-5H3/t16-,17-,18-,19+,21-,22+,23+,24-/m1/s1
SMILES:  O=CC(=C)[C@@H]1CC[C@@H]2[C@@H](C1)C(=O)[C@H]([C@H]1[C@@]2(C)CC[C@@H]([C@@]1(C)COC(=O)C)OC(=O)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1641889
PubChem CID:   50901034
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0001295] Hydroxysteroids
          • [CHEMONTID:0003238] 7-hydroxysteroids
            • [CHEMONTID:0003239] 7-alpha-hydroxysteroids

*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
NPO1927 Isodon eriocalyx Species Lamiaceae Eukaryota n.a. leaf n.a. PMID[17020288]
NPO1927 Isodon eriocalyx Species Lamiaceae Eukaryota n.a. aerial part n.a. PMID[20949916]
NPO1927 Isodon eriocalyx Species Lamiaceae Eukaryota aerial parts n.a. n.a. PMID[20949916]
NPO1927 Isodon eriocalyx Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[22624550]
NPO1927 Isodon eriocalyx Species Lamiaceae 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
NPT139 Cell Line HT-29 Homo sapiens IC50 > 10000.0 nM PMID[558466]
NPT181 Cell Line Bel-7402 Homo sapiens IC50 > 10000.0 nM PMID[558466]
NPT146 Cell Line SK-OV-3 Homo sapiens IC50 > 10000.0 nM PMID[558466]

☑ 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 NPC272635 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 NPC169751
0.9556 High Similarity NPC219353
0.9457 High Similarity NPC293890
0.9195 High Similarity NPC34190
0.9011 High Similarity NPC294263
0.8817 High Similarity NPC98639
0.8737 High Similarity NPC38296
0.8737 High Similarity NPC162459
0.8737 High Similarity NPC38471
0.8737 High Similarity NPC20479
0.8737 High Similarity NPC98837
0.8737 High Similarity NPC28864
0.8723 High Similarity NPC200054
0.8723 High Similarity NPC165616
0.8723 High Similarity NPC29410
0.8646 High Similarity NPC293866
0.8632 High Similarity NPC10864
0.8614 High Similarity NPC100908
0.8586 High Similarity NPC265127
0.8557 High Similarity NPC148279
0.8557 High Similarity NPC46848
0.8542 High Similarity NPC89099
0.8542 High Similarity NPC474793
0.8542 High Similarity NPC471038
0.8526 High Similarity NPC13949
0.8526 High Similarity NPC329910
0.8526 High Similarity NPC471039
0.85 High Similarity NPC176949
0.85 High Similarity NPC201908
0.8495 Intermediate Similarity NPC250753
0.8495 Intermediate Similarity NPC198054
0.8469 Intermediate Similarity NPC275990
0.8421 Intermediate Similarity NPC470229
0.8421 Intermediate Similarity NPC210214
0.8421 Intermediate Similarity NPC470232
0.8404 Intermediate Similarity NPC477436
0.8404 Intermediate Similarity NPC477435
0.8384 Intermediate Similarity NPC95585
0.8384 Intermediate Similarity NPC282233
0.8384 Intermediate Similarity NPC96217
0.8384 Intermediate Similarity NPC87927
0.8367 Intermediate Similarity NPC163963
0.8367 Intermediate Similarity NPC52899
0.8367 Intermediate Similarity NPC252614
0.8367 Intermediate Similarity NPC289148
0.8367 Intermediate Similarity NPC236585
0.8352 Intermediate Similarity NPC471042
0.8351 Intermediate Similarity NPC26270
0.8333 Intermediate Similarity NPC104568
0.8316 Intermediate Similarity NPC475118
0.8316 Intermediate Similarity NPC471040
0.8316 Intermediate Similarity NPC470386
0.8316 Intermediate Similarity NPC47853
0.8316 Intermediate Similarity NPC470385
0.83 Intermediate Similarity NPC47281
0.83 Intermediate Similarity NPC301787
0.8298 Intermediate Similarity NPC211403
0.8298 Intermediate Similarity NPC198242
0.8298 Intermediate Similarity NPC99380
0.8283 Intermediate Similarity NPC76866
0.8283 Intermediate Similarity NPC286519
0.8283 Intermediate Similarity NPC88203
0.8283 Intermediate Similarity NPC246736
0.8283 Intermediate Similarity NPC304832
0.8283 Intermediate Similarity NPC214946
0.8283 Intermediate Similarity NPC148628
0.8265 Intermediate Similarity NPC287676
0.8261 Intermediate Similarity NPC174619
0.8235 Intermediate Similarity NPC211224
0.8229 Intermediate Similarity NPC274417
0.8229 Intermediate Similarity NPC477438
0.8229 Intermediate Similarity NPC29112
0.8229 Intermediate Similarity NPC477437
0.8229 Intermediate Similarity NPC142352
0.8229 Intermediate Similarity NPC139570
0.8222 Intermediate Similarity NPC471037
0.8218 Intermediate Similarity NPC200957
0.8218 Intermediate Similarity NPC222833
0.8218 Intermediate Similarity NPC138908
0.8218 Intermediate Similarity NPC28791
0.8218 Intermediate Similarity NPC50535
0.8211 Intermediate Similarity NPC59350
0.82 Intermediate Similarity NPC139347
0.82 Intermediate Similarity NPC470310
0.82 Intermediate Similarity NPC469985
0.82 Intermediate Similarity NPC277074
0.82 Intermediate Similarity NPC209298
0.82 Intermediate Similarity NPC122811
0.8191 Intermediate Similarity NPC328141
0.8182 Intermediate Similarity NPC60947
0.8182 Intermediate Similarity NPC121218
0.8182 Intermediate Similarity NPC253886
0.8163 Intermediate Similarity NPC109059
0.8163 Intermediate Similarity NPC288
0.8163 Intermediate Similarity NPC476806
0.8163 Intermediate Similarity NPC476807
0.8163 Intermediate Similarity NPC16911
0.8163 Intermediate Similarity NPC471966
0.8163 Intermediate Similarity NPC78427
0.8161 Intermediate Similarity NPC474433
0.8152 Intermediate Similarity NPC185638
0.8144 Intermediate Similarity NPC470387
0.8144 Intermediate Similarity NPC223169
0.8137 Intermediate Similarity NPC44063
0.8137 Intermediate Similarity NPC86852
0.8137 Intermediate Similarity NPC166993
0.8137 Intermediate Similarity NPC251824
0.8132 Intermediate Similarity NPC146683
0.8125 Intermediate Similarity NPC303863
0.8125 Intermediate Similarity NPC293086
0.8125 Intermediate Similarity NPC269729
0.8125 Intermediate Similarity NPC477439
0.8125 Intermediate Similarity NPC469982
0.8119 Intermediate Similarity NPC98603
0.8105 Intermediate Similarity NPC474525
0.8105 Intermediate Similarity NPC470230
0.81 Intermediate Similarity NPC15396
0.81 Intermediate Similarity NPC170615
0.81 Intermediate Similarity NPC136289
0.8081 Intermediate Similarity NPC475202
0.8081 Intermediate Similarity NPC470388
0.8081 Intermediate Similarity NPC475385
0.8081 Intermediate Similarity NPC475392
0.8068 Intermediate Similarity NPC476810
0.8065 Intermediate Similarity NPC476932
0.8065 Intermediate Similarity NPC33768
0.8065 Intermediate Similarity NPC153604
0.8065 Intermediate Similarity NPC269360
0.8065 Intermediate Similarity NPC264005
0.8061 Intermediate Similarity NPC473456
0.8058 Intermediate Similarity NPC218123
0.8058 Intermediate Similarity NPC112895
0.8058 Intermediate Similarity NPC273155
0.8058 Intermediate Similarity NPC231278
0.8041 Intermediate Similarity NPC205173
0.8041 Intermediate Similarity NPC266431
0.8022 Intermediate Similarity NPC243347
0.8022 Intermediate Similarity NPC118800
0.8021 Intermediate Similarity NPC86368
0.8021 Intermediate Similarity NPC214756
0.8021 Intermediate Similarity NPC224060
0.8021 Intermediate Similarity NPC473690
0.8021 Intermediate Similarity NPC59170
0.8021 Intermediate Similarity NPC287118
0.8021 Intermediate Similarity NPC244356
0.8021 Intermediate Similarity NPC471902
0.8021 Intermediate Similarity NPC295643
0.8021 Intermediate Similarity NPC272075
0.8021 Intermediate Similarity NPC199543
0.802 Intermediate Similarity NPC216114
0.802 Intermediate Similarity NPC179208
0.8 Intermediate Similarity NPC71706
0.8 Intermediate Similarity NPC81530
0.8 Intermediate Similarity NPC46441
0.8 Intermediate Similarity NPC130278
0.8 Intermediate Similarity NPC470281
0.8 Intermediate Similarity NPC169933
0.8 Intermediate Similarity NPC328264
0.8 Intermediate Similarity NPC180849
0.7981 Intermediate Similarity NPC2766
0.798 Intermediate Similarity NPC474724
0.798 Intermediate Similarity NPC260149
0.798 Intermediate Similarity NPC58942
0.7979 Intermediate Similarity NPC4309
0.7979 Intermediate Similarity NPC472739
0.7979 Intermediate Similarity NPC474925
0.7979 Intermediate Similarity NPC56413
0.7979 Intermediate Similarity NPC474719
0.7959 Intermediate Similarity NPC305483
0.7959 Intermediate Similarity NPC469545
0.7959 Intermediate Similarity NPC96859
0.7959 Intermediate Similarity NPC328162
0.7959 Intermediate Similarity NPC476318
0.7959 Intermediate Similarity NPC476327
0.7959 Intermediate Similarity NPC264979
0.7959 Intermediate Similarity NPC61369
0.7959 Intermediate Similarity NPC256227
0.7959 Intermediate Similarity NPC5532
0.7959 Intermediate Similarity NPC157113
0.7959 Intermediate Similarity NPC98874
0.7959 Intermediate Similarity NPC62516
0.7959 Intermediate Similarity NPC135548
0.7957 Intermediate Similarity NPC98236
0.7957 Intermediate Similarity NPC12774
0.7957 Intermediate Similarity NPC269396
0.7957 Intermediate Similarity NPC325594
0.7957 Intermediate Similarity NPC2783
0.7957 Intermediate Similarity NPC73038
0.7957 Intermediate Similarity NPC187545
0.7955 Intermediate Similarity NPC476811
0.7941 Intermediate Similarity NPC29705
0.7941 Intermediate Similarity NPC101842
0.7941 Intermediate Similarity NPC84928
0.7941 Intermediate Similarity NPC310586
0.7938 Intermediate Similarity NPC222047
0.7938 Intermediate Similarity NPC474529
0.7938 Intermediate Similarity NPC74751
0.7921 Intermediate Similarity NPC272472
0.7917 Intermediate Similarity NPC158030
0.7917 Intermediate Similarity NPC475416

  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 NPC272635 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
0.8235 Intermediate Similarity NPD6881 Approved
0.8235 Intermediate Similarity NPD6899 Approved
0.8218 Intermediate Similarity NPD6402 Approved
0.8218 Intermediate Similarity NPD6675 Approved
0.8218 Intermediate Similarity NPD5739 Approved
0.8218 Intermediate Similarity NPD7128 Approved
0.8137 Intermediate Similarity NPD5697 Approved
0.8077 Intermediate Similarity NPD7290 Approved
0.8077 Intermediate Similarity NPD6883 Approved
0.8077 Intermediate Similarity NPD7102 Approved
0.8058 Intermediate Similarity NPD7320 Approved
0.8 Intermediate Similarity NPD6869 Approved
0.8 Intermediate Similarity NPD6650 Approved
0.8 Intermediate Similarity NPD6617 Approved
0.8 Intermediate Similarity NPD6649 Approved
0.8 Intermediate Similarity NPD6847 Approved
0.8 Intermediate Similarity NPD8130 Phase 1
0.7981 Intermediate Similarity NPD6012 Approved
0.7981 Intermediate Similarity NPD6372 Approved
0.7981 Intermediate Similarity NPD6013 Approved
0.7981 Intermediate Similarity NPD6014 Approved
0.7981 Intermediate Similarity NPD6373 Approved
0.7961 Intermediate Similarity NPD5701 Approved
0.7938 Intermediate Similarity NPD7748 Approved
0.7925 Intermediate Similarity NPD6882 Approved
0.7925 Intermediate Similarity NPD8297 Approved
0.7917 Intermediate Similarity NPD8035 Phase 2
0.7917 Intermediate Similarity NPD7515 Phase 2
0.7917 Intermediate Similarity NPD8034 Phase 2
0.7885 Intermediate Similarity NPD6011 Approved
0.7879 Intermediate Similarity NPD7902 Approved
0.7849 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD4697 Phase 3
0.7723 Intermediate Similarity NPD4696 Approved
0.7723 Intermediate Similarity NPD5285 Approved
0.7723 Intermediate Similarity NPD5286 Approved
0.77 Intermediate Similarity NPD4755 Approved
0.7664 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD5222 Approved
0.76 Intermediate Similarity NPD5221 Approved
0.7576 Intermediate Similarity NPD7900 Approved
0.7576 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7573 Intermediate Similarity NPD5225 Approved
0.7573 Intermediate Similarity NPD5211 Phase 2
0.7573 Intermediate Similarity NPD5226 Approved
0.7573 Intermediate Similarity NPD4633 Approved
0.7573 Intermediate Similarity NPD5224 Approved
0.7551 Intermediate Similarity NPD6079 Approved
0.7549 Intermediate Similarity NPD4700 Approved
0.7547 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7545 Intermediate Similarity NPD6274 Approved
0.7526 Intermediate Similarity NPD5328 Approved
0.7525 Intermediate Similarity NPD5173 Approved
0.7525 Intermediate Similarity NPD6083 Phase 2
0.7525 Intermediate Similarity NPD6084 Phase 2
0.75 Intermediate Similarity NPD5175 Approved
0.75 Intermediate Similarity NPD7100 Approved
0.75 Intermediate Similarity NPD7101 Approved
0.75 Intermediate Similarity NPD5174 Approved
0.7476 Intermediate Similarity NPD5223 Approved
0.7475 Intermediate Similarity NPD6399 Phase 3
0.7429 Intermediate Similarity NPD5141 Approved
0.7411 Intermediate Similarity NPD6335 Approved
0.7387 Intermediate Similarity NPD6868 Approved
0.7364 Intermediate Similarity NPD4632 Approved
0.7363 Intermediate Similarity NPD6116 Phase 1
0.7321 Intermediate Similarity NPD6317 Approved
0.732 Intermediate Similarity NPD3573 Approved
0.7282 Intermediate Similarity NPD7638 Approved
0.7281 Intermediate Similarity NPD6319 Approved
0.7263 Intermediate Similarity NPD4788 Approved
0.7257 Intermediate Similarity NPD6313 Approved
0.7257 Intermediate Similarity NPD6314 Approved
0.7253 Intermediate Similarity NPD6117 Approved
0.7245 Intermediate Similarity NPD6672 Approved
0.7245 Intermediate Similarity NPD5737 Approved
0.7241 Intermediate Similarity NPD8328 Phase 3
0.7222 Intermediate Similarity NPD5128 Approved
0.7222 Intermediate Similarity NPD4730 Approved
0.7222 Intermediate Similarity NPD4729 Approved
0.7217 Intermediate Similarity NPD6909 Approved
0.7217 Intermediate Similarity NPD6908 Approved
0.7216 Intermediate Similarity NPD3618 Phase 1
0.7212 Intermediate Similarity NPD7639 Approved
0.7212 Intermediate Similarity NPD7640 Approved
0.72 Intermediate Similarity NPD6411 Approved
0.7196 Intermediate Similarity NPD4768 Approved
0.7196 Intermediate Similarity NPD4767 Approved
0.7179 Intermediate Similarity NPD7492 Approved
0.717 Intermediate Similarity NPD4754 Approved
0.7168 Intermediate Similarity NPD6009 Approved
0.7157 Intermediate Similarity NPD5695 Phase 3
0.7143 Intermediate Similarity NPD7736 Approved
0.713 Intermediate Similarity NPD6054 Approved
0.7119 Intermediate Similarity NPD6616 Approved
0.7115 Intermediate Similarity NPD5696 Approved
0.7097 Intermediate Similarity NPD6115 Approved
0.7097 Intermediate Similarity NPD6114 Approved
0.7097 Intermediate Similarity NPD6118 Approved
0.7097 Intermediate Similarity NPD6697 Approved
0.7094 Intermediate Similarity NPD7604 Phase 2
0.7091 Intermediate Similarity NPD4634 Approved
0.7091 Intermediate Similarity NPD5249 Phase 3
0.7091 Intermediate Similarity NPD5247 Approved
0.7091 Intermediate Similarity NPD5248 Approved
0.7091 Intermediate Similarity NPD5251 Approved
0.7091 Intermediate Similarity NPD5250 Approved
0.7071 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7069 Intermediate Similarity NPD5983 Phase 2
0.7069 Intermediate Similarity NPD6291 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD7078 Approved
0.7041 Intermediate Similarity NPD7146 Approved
0.7041 Intermediate Similarity NPD7521 Approved
0.7041 Intermediate Similarity NPD7334 Approved
0.7041 Intermediate Similarity NPD6684 Approved
0.7041 Intermediate Similarity NPD5330 Approved
0.7041 Intermediate Similarity NPD6409 Approved
0.7033 Intermediate Similarity NPD6113 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD5216 Approved
0.7027 Intermediate Similarity NPD5217 Approved
0.7027 Intermediate Similarity NPD5215 Approved
0.7018 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.701 Intermediate Similarity NPD4786 Approved
0.7009 Intermediate Similarity NPD6370 Approved
0.7 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD4753 Phase 2
0.7 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6101 Approved
0.6983 Remote Similarity NPD6059 Approved
0.6979 Remote Similarity NPD3667 Approved
0.6975 Remote Similarity NPD6336 Discontinued
0.6975 Remote Similarity NPD7507 Approved
0.6961 Remote Similarity NPD4202 Approved
0.6957 Remote Similarity NPD3703 Phase 2
0.6947 Remote Similarity NPD4695 Discontinued
0.6937 Remote Similarity NPD5135 Approved
0.6937 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6937 Remote Similarity NPD5169 Approved
0.6923 Remote Similarity NPD6016 Approved
0.6923 Remote Similarity NPD6015 Approved
0.6917 Remote Similarity NPD8293 Discontinued
0.6909 Remote Similarity NPD5168 Approved
0.69 Remote Similarity NPD6903 Approved
0.6881 Remote Similarity NPD6008 Approved
0.6875 Remote Similarity NPD5127 Approved
0.687 Remote Similarity NPD7115 Discovery
0.6864 Remote Similarity NPD5988 Approved
0.6847 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6842 Remote Similarity NPD7645 Phase 2
0.6837 Remote Similarity NPD3666 Approved
0.6837 Remote Similarity NPD3665 Phase 1
0.6837 Remote Similarity NPD3133 Approved
0.6832 Remote Similarity NPD6673 Approved
0.6832 Remote Similarity NPD6904 Approved
0.6832 Remote Similarity NPD6080 Approved
0.6827 Remote Similarity NPD4629 Approved
0.6827 Remote Similarity NPD5210 Approved
0.6813 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6813 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6803 Remote Similarity NPD7319 Approved
0.6792 Remote Similarity NPD4225 Approved
0.678 Remote Similarity NPD6921 Approved
0.6778 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6778 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6771 Remote Similarity NPD7525 Registered
0.6759 Remote Similarity NPD7632 Discontinued
0.6757 Remote Similarity NPD6686 Approved
0.6754 Remote Similarity NPD8133 Approved
0.6703 Remote Similarity NPD4789 Approved
0.67 Remote Similarity NPD6098 Approved
0.67 Remote Similarity NPD5279 Phase 3
0.6696 Remote Similarity NPD5167 Approved
0.6696 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6412 Phase 2
0.6635 Remote Similarity NPD5779 Approved
0.6635 Remote Similarity NPD5778 Approved
0.6633 Remote Similarity NPD6435 Approved
0.6633 Remote Similarity NPD4752 Clinical (unspecified phase)
0.663 Remote Similarity NPD5777 Approved
0.6604 Remote Similarity NPD7614 Phase 1
0.66 Remote Similarity NPD5329 Approved
0.6562 Remote Similarity NPD3617 Approved
0.6538 Remote Similarity NPD5693 Phase 1
0.6538 Remote Similarity NPD6050 Approved
0.6535 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6522 Remote Similarity NPD4244 Approved
0.6522 Remote Similarity NPD4245 Approved
0.6509 Remote Similarity NPD1698 Clinical (unspecified phase)
0.65 Remote Similarity NPD3668 Phase 3
0.65 Remote Similarity NPD4197 Approved
0.6491 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6452 Remote Similarity NPD6081 Approved
0.6452 Remote Similarity NPD6033 Approved
0.6449 Remote Similarity NPD7732 Phase 3
0.6444 Remote Similarity NPD4224 Phase 2
0.6442 Remote Similarity NPD5692 Phase 3
0.6436 Remote Similarity NPD1694 Approved
0.6429 Remote Similarity NPD5368 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