Structure

Physi-Chem Properties

Molecular Weight:  512.28
Volume:  536.287
LogP:  3.915
LogD:  2.933
LogS:  -4.644
# Rotatable Bonds:  9
TPSA:  110.13
# H-Bond Aceptor:  7
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.303
Synthetic Accessibility Score:  5.407
Fsp3:  0.633
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.777
MDCK Permeability:  1.4274849490902852e-05
Pgp-inhibitor:  0.998
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.387
20% Bioavailability (F20%):  0.018
30% Bioavailability (F30%):  0.249

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.672
Plasma Protein Binding (PPB):  73.8860092163086%
Volume Distribution (VD):  0.828
Pgp-substrate:  20.36231231689453%

ADMET: Metabolism

CYP1A2-inhibitor:  0.046
CYP1A2-substrate:  0.06
CYP2C19-inhibitor:  0.107
CYP2C19-substrate:  0.327
CYP2C9-inhibitor:  0.325
CYP2C9-substrate:  0.061
CYP2D6-inhibitor:  0.015
CYP2D6-substrate:  0.105
CYP3A4-inhibitor:  0.771
CYP3A4-substrate:  0.26

ADMET: Excretion

Clearance (CL):  2.638
Half-life (T1/2):  0.831

ADMET: Toxicity

hERG Blockers:  0.789
Human Hepatotoxicity (H-HT):  0.978
Drug-inuced Liver Injury (DILI):  0.444
AMES Toxicity:  0.024
Rat Oral Acute Toxicity:  0.814
Maximum Recommended Daily Dose:  0.984
Skin Sensitization:  0.925
Carcinogencity:  0.041
Eye Corrosion:  0.003
Eye Irritation:  0.01
Respiratory Toxicity:  0.956

Download Data

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

  Natural Product: NPC156745

Natural Product ID:  NPC156745
Common Name*:   ALKHEZOKTHCOBM-MGZHOKCZSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  ALKHEZOKTHCOBM-MGZHOKCZSA-N
Standard InCHI:  InChI=1S/C30H40O7/c1-7-8-9-10-11-12-24(33)36-27-18(3)29(35)22-13-17(2)25(34)21(22)14-20(16-31)15-23(29)26-28(5,6)30(26,27)37-19(4)32/h9-13,15,18,21-23,26-27,31,35H,7-8,14,16H2,1-6H3/b10-9+,12-11-/t18-,21+,22-,23+,26-,27-,29+,30-/m1/s1
SMILES:  CCC/C=C/C=CC(=O)O[C@@H]1[C@@H](C)[C@@]2([C@@H]3C=C(C)C(=O)[C@H]3CC(=C[C@H]2[C@@H]2C(C)(C)[C@]12OC(=O)C)CO)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL518848
PubChem CID:   5281385
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] Diterpenoids
          • [CHEMONTID:0002875] Tigliane and ingenane diterpenoids

*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
NPO7612 Euphorbia tirucalli Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[469552]
NPO7612 Euphorbia tirucalli Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7612 Euphorbia tirucalli Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7612 Euphorbia tirucalli Species Euphorbiaceae 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
NPT32 Organism Mus musculus Mus musculus ID50 = 0.04 ug PMID[489473]
NPT32 Organism Mus musculus Mus musculus ID50 = 0.07 ug PMID[489473]

☑ 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 NPC156745 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 NPC236918
0.9909 High Similarity NPC472759
0.9909 High Similarity NPC329080
0.9909 High Similarity NPC475885
0.9725 High Similarity NPC234858
0.9725 High Similarity NPC154363
0.9725 High Similarity NPC471127
0.9636 High Similarity NPC10721
0.9561 High Similarity NPC145238
0.955 High Similarity NPC124676
0.955 High Similarity NPC146280
0.9541 High Similarity NPC472757
0.9455 High Similarity NPC472400
0.9381 High Similarity NPC471126
0.9381 High Similarity NPC471128
0.9381 High Similarity NPC145182
0.9381 High Similarity NPC157252
0.9298 High Similarity NPC52839
0.9217 High Similarity NPC257017
0.9217 High Similarity NPC162009
0.9211 High Similarity NPC19336
0.9211 High Similarity NPC185876
0.9204 High Similarity NPC171905
0.9204 High Similarity NPC472758
0.9204 High Similarity NPC471125
0.9204 High Similarity NPC472760
0.9204 High Similarity NPC472397
0.9138 High Similarity NPC472399
0.9123 High Similarity NPC5989
0.9123 High Similarity NPC471108
0.9123 High Similarity NPC255081
0.9123 High Similarity NPC5991
0.9123 High Similarity NPC180640
0.9123 High Similarity NPC275696
0.9123 High Similarity NPC22628
0.9115 High Similarity NPC156252
0.9018 High Similarity NPC71889
0.8966 High Similarity NPC472401
0.8947 High Similarity NPC153651
0.8938 High Similarity NPC474872
0.8889 High Similarity NPC19464
0.8839 High Similarity NPC475937
0.8839 High Similarity NPC174471
0.8839 High Similarity NPC158523
0.8839 High Similarity NPC260786
0.8839 High Similarity NPC474871
0.8839 High Similarity NPC96739
0.8761 High Similarity NPC170212
0.8761 High Similarity NPC221511
0.8761 High Similarity NPC265499
0.8761 High Similarity NPC17138
0.8761 High Similarity NPC89227
0.8761 High Similarity NPC101825
0.8761 High Similarity NPC151216
0.8761 High Similarity NPC215643
0.8761 High Similarity NPC475391
0.875 High Similarity NPC153036
0.875 High Similarity NPC471940
0.8684 High Similarity NPC474937
0.8678 High Similarity NPC236999
0.8678 High Similarity NPC270109
0.8667 High Similarity NPC471939
0.8632 High Similarity NPC472667
0.8583 High Similarity NPC473709
0.8583 High Similarity NPC473919
0.8548 High Similarity NPC476111
0.8512 High Similarity NPC222307
0.85 High Similarity NPC473802
0.8496 Intermediate Similarity NPC163004
0.8496 Intermediate Similarity NPC273433
0.8403 Intermediate Similarity NPC143755
0.8362 Intermediate Similarity NPC469463
0.8362 Intermediate Similarity NPC469496
0.8362 Intermediate Similarity NPC469454
0.8362 Intermediate Similarity NPC46269
0.8362 Intermediate Similarity NPC477091
0.8362 Intermediate Similarity NPC106395
0.8361 Intermediate Similarity NPC293112
0.8333 Intermediate Similarity NPC310511
0.832 Intermediate Similarity NPC90814
0.832 Intermediate Similarity NPC189393
0.8319 Intermediate Similarity NPC470186
0.8319 Intermediate Similarity NPC67321
0.8319 Intermediate Similarity NPC187435
0.8305 Intermediate Similarity NPC469684
0.8291 Intermediate Similarity NPC67290
0.8291 Intermediate Similarity NPC138303
0.8291 Intermediate Similarity NPC133677
0.8276 Intermediate Similarity NPC76550
0.8276 Intermediate Similarity NPC123855
0.8276 Intermediate Similarity NPC138757
0.825 Intermediate Similarity NPC475003
0.8235 Intermediate Similarity NPC284707
0.8226 Intermediate Similarity NPC470850
0.822 Intermediate Similarity NPC470793
0.822 Intermediate Similarity NPC179626
0.8205 Intermediate Similarity NPC471204
0.8197 Intermediate Similarity NPC469789
0.8197 Intermediate Similarity NPC11895
0.8195 Intermediate Similarity NPC140021
0.819 Intermediate Similarity NPC474846
0.819 Intermediate Similarity NPC304180
0.819 Intermediate Similarity NPC469655
0.819 Intermediate Similarity NPC469656
0.819 Intermediate Similarity NPC179798
0.8189 Intermediate Similarity NPC100017
0.8189 Intermediate Similarity NPC182266
0.8189 Intermediate Similarity NPC471137
0.8189 Intermediate Similarity NPC475500
0.8189 Intermediate Similarity NPC223356
0.8189 Intermediate Similarity NPC473548
0.8189 Intermediate Similarity NPC471136
0.8189 Intermediate Similarity NPC475154
0.8182 Intermediate Similarity NPC67569
0.816 Intermediate Similarity NPC104382
0.816 Intermediate Similarity NPC470851
0.8158 Intermediate Similarity NPC143609
0.8151 Intermediate Similarity NPC98249
0.8151 Intermediate Similarity NPC53396
0.8151 Intermediate Similarity NPC474518
0.8136 Intermediate Similarity NPC73314
0.813 Intermediate Similarity NPC81736
0.813 Intermediate Similarity NPC172154
0.8125 Intermediate Similarity NPC476081
0.8125 Intermediate Similarity NPC478156
0.812 Intermediate Similarity NPC472002
0.8115 Intermediate Similarity NPC470265
0.8115 Intermediate Similarity NPC23786
0.8115 Intermediate Similarity NPC170538
0.8103 Intermediate Similarity NPC253906
0.8103 Intermediate Similarity NPC257240
0.8103 Intermediate Similarity NPC5103
0.8099 Intermediate Similarity NPC4548
0.8095 Intermediate Similarity NPC477189
0.8095 Intermediate Similarity NPC251564
0.8095 Intermediate Similarity NPC475606
0.8095 Intermediate Similarity NPC475314
0.8087 Intermediate Similarity NPC306265
0.8087 Intermediate Similarity NPC102843
0.807 Intermediate Similarity NPC34768
0.807 Intermediate Similarity NPC111952
0.8067 Intermediate Similarity NPC471816
0.8067 Intermediate Similarity NPC176840
0.8065 Intermediate Similarity NPC473635
0.8062 Intermediate Similarity NPC68282
0.8062 Intermediate Similarity NPC243902
0.8053 Intermediate Similarity NPC23584
0.8051 Intermediate Similarity NPC474271
0.8051 Intermediate Similarity NPC56448
0.8051 Intermediate Similarity NPC25909
0.8049 Intermediate Similarity NPC473979
0.8034 Intermediate Similarity NPC188738
0.8034 Intermediate Similarity NPC470076
0.8031 Intermediate Similarity NPC474508
0.8031 Intermediate Similarity NPC473485
0.8031 Intermediate Similarity NPC475139
0.8031 Intermediate Similarity NPC180902
0.8017 Intermediate Similarity NPC475041
0.8017 Intermediate Similarity NPC228477
0.8017 Intermediate Similarity NPC137911
0.8017 Intermediate Similarity NPC47951
0.8017 Intermediate Similarity NPC469380
0.8017 Intermediate Similarity NPC469370
0.8016 Intermediate Similarity NPC231529
0.8016 Intermediate Similarity NPC175186
0.8 Intermediate Similarity NPC475323
0.8 Intermediate Similarity NPC284068
0.8 Intermediate Similarity NPC470493
0.8 Intermediate Similarity NPC473656
0.8 Intermediate Similarity NPC284518
0.8 Intermediate Similarity NPC23046
0.8 Intermediate Similarity NPC183580
0.8 Intermediate Similarity NPC312824
0.7984 Intermediate Similarity NPC8369
0.7983 Intermediate Similarity NPC238667
0.7982 Intermediate Similarity NPC118911
0.7982 Intermediate Similarity NPC239162
0.7966 Intermediate Similarity NPC470063
0.7966 Intermediate Similarity NPC269530
0.7966 Intermediate Similarity NPC236217
0.7966 Intermediate Similarity NPC234042
0.7966 Intermediate Similarity NPC152117
0.7966 Intermediate Similarity NPC476801
0.7965 Intermediate Similarity NPC11956
0.7965 Intermediate Similarity NPC137430
0.7965 Intermediate Similarity NPC162973
0.7953 Intermediate Similarity NPC471170
0.7951 Intermediate Similarity NPC268530
0.7951 Intermediate Similarity NPC48692
0.7951 Intermediate Similarity NPC476962
0.7951 Intermediate Similarity NPC154491
0.7949 Intermediate Similarity NPC477103
0.7949 Intermediate Similarity NPC472214
0.7949 Intermediate Similarity NPC472215
0.7946 Intermediate Similarity NPC474718
0.7946 Intermediate Similarity NPC470074
0.7946 Intermediate Similarity NPC47024
0.7934 Intermediate Similarity NPC186525
0.7934 Intermediate Similarity NPC50774
0.7934 Intermediate Similarity NPC108581

  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 NPC156745 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
0.8103 Intermediate Similarity NPD6371 Approved
0.7946 Intermediate Similarity NPD6648 Approved
0.7876 Intermediate Similarity NPD5344 Discontinued
0.7851 Intermediate Similarity NPD7115 Discovery
0.7712 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7479 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7395 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD4225 Approved
0.7328 Intermediate Similarity NPD7639 Approved
0.7328 Intermediate Similarity NPD7640 Approved
0.7241 Intermediate Similarity NPD7638 Approved
0.7236 Intermediate Similarity NPD8297 Approved
0.7209 Intermediate Similarity NPD7604 Phase 2
0.719 Intermediate Similarity NPD6881 Approved
0.719 Intermediate Similarity NPD6686 Approved
0.719 Intermediate Similarity NPD6899 Approved
0.7177 Intermediate Similarity NPD4632 Approved
0.7154 Intermediate Similarity NPD6650 Approved
0.7154 Intermediate Similarity NPD6649 Approved
0.713 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7109 Intermediate Similarity NPD6319 Approved
0.7107 Intermediate Similarity NPD5697 Approved
0.7099 Intermediate Similarity NPD7507 Approved
0.708 Intermediate Similarity NPD46 Approved
0.708 Intermediate Similarity NPD7838 Discovery
0.708 Intermediate Similarity NPD6698 Approved
0.7073 Intermediate Similarity NPD7102 Approved
0.7073 Intermediate Similarity NPD6883 Approved
0.7073 Intermediate Similarity NPD7290 Approved
0.7068 Intermediate Similarity NPD7319 Approved
0.7031 Intermediate Similarity NPD7516 Approved
0.7025 Intermediate Similarity NPD7128 Approved
0.7025 Intermediate Similarity NPD6008 Approved
0.7025 Intermediate Similarity NPD5739 Approved
0.7025 Intermediate Similarity NPD6675 Approved
0.7025 Intermediate Similarity NPD6402 Approved
0.7023 Intermediate Similarity NPD7492 Approved
0.7016 Intermediate Similarity NPD8130 Phase 1
0.7016 Intermediate Similarity NPD6847 Approved
0.7016 Intermediate Similarity NPD6617 Approved
0.7016 Intermediate Similarity NPD6869 Approved
0.7008 Intermediate Similarity NPD6009 Approved
0.6992 Remote Similarity NPD6014 Approved
0.6992 Remote Similarity NPD6013 Approved
0.6992 Remote Similarity NPD6372 Approved
0.6992 Remote Similarity NPD6373 Approved
0.6992 Remote Similarity NPD6012 Approved
0.6977 Remote Similarity NPD6054 Approved
0.697 Remote Similarity NPD6616 Approved
0.6967 Remote Similarity NPD7899 Clinical (unspecified phase)
0.696 Remote Similarity NPD6882 Approved
0.696 Remote Similarity NPD6053 Discontinued
0.6957 Remote Similarity NPD5779 Approved
0.6957 Remote Similarity NPD5778 Approved
0.6953 Remote Similarity NPD7327 Approved
0.6953 Remote Similarity NPD7328 Approved
0.6949 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6923 Remote Similarity NPD7503 Approved
0.6923 Remote Similarity NPD5983 Phase 2
0.6923 Remote Similarity NPD8513 Phase 3
0.6923 Remote Similarity NPD8516 Approved
0.6923 Remote Similarity NPD8517 Approved
0.6923 Remote Similarity NPD8515 Approved
0.6917 Remote Similarity NPD5211 Phase 2
0.6917 Remote Similarity NPD7078 Approved
0.6911 Remote Similarity NPD6011 Approved
0.6911 Remote Similarity NPD7320 Approved
0.687 Remote Similarity NPD7637 Suspended
0.687 Remote Similarity NPD7983 Approved
0.687 Remote Similarity NPD6370 Approved
0.6866 Remote Similarity NPD7736 Approved
0.6842 Remote Similarity NPD6336 Discontinued
0.6838 Remote Similarity NPD7260 Phase 2
0.6829 Remote Similarity NPD5701 Approved
0.681 Remote Similarity NPD6399 Phase 3
0.6803 Remote Similarity NPD5141 Approved
0.6794 Remote Similarity NPD6015 Approved
0.6794 Remote Similarity NPD6016 Approved
0.6794 Remote Similarity NPD6921 Approved
0.6786 Remote Similarity NPD1694 Approved
0.6786 Remote Similarity NPD1696 Phase 3
0.6783 Remote Similarity NPD5785 Approved
0.6777 Remote Similarity NPD7632 Discontinued
0.675 Remote Similarity NPD5285 Approved
0.675 Remote Similarity NPD5286 Approved
0.675 Remote Similarity NPD4696 Approved
0.6742 Remote Similarity NPD5988 Approved
0.6724 Remote Similarity NPD6079 Approved
0.6723 Remote Similarity NPD7902 Approved
0.6718 Remote Similarity NPD6059 Approved
0.6696 Remote Similarity NPD1695 Approved
0.6667 Remote Similarity NPD8380 Approved
0.6667 Remote Similarity NPD8335 Approved
0.6667 Remote Similarity NPD4634 Approved
0.6667 Remote Similarity NPD8379 Approved
0.6667 Remote Similarity NPD7524 Approved
0.6667 Remote Similarity NPD8296 Approved
0.6667 Remote Similarity NPD8293 Discontinued
0.6667 Remote Similarity NPD8074 Phase 3
0.6667 Remote Similarity NPD8033 Approved
0.6667 Remote Similarity NPD8378 Approved
0.6641 Remote Similarity NPD7101 Approved
0.6641 Remote Similarity NPD7100 Approved
0.6639 Remote Similarity NPD4633 Approved
0.6639 Remote Similarity NPD5226 Approved
0.6639 Remote Similarity NPD5224 Approved
0.6639 Remote Similarity NPD5225 Approved
0.6614 Remote Similarity NPD6401 Clinical (unspecified phase)
0.661 Remote Similarity NPD7748 Approved
0.661 Remote Similarity NPD5282 Discontinued
0.6591 Remote Similarity NPD8377 Approved
0.6591 Remote Similarity NPD8294 Approved
0.6587 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6585 Remote Similarity NPD5174 Approved
0.6585 Remote Similarity NPD5175 Approved
0.6583 Remote Similarity NPD6083 Phase 2
0.6583 Remote Similarity NPD6084 Phase 2
0.6583 Remote Similarity NPD4755 Approved
0.6581 Remote Similarity NPD6411 Approved
0.6581 Remote Similarity NPD5281 Approved
0.6581 Remote Similarity NPD5284 Approved
0.6581 Remote Similarity NPD7515 Phase 2
0.6567 Remote Similarity NPD8328 Phase 3
0.6565 Remote Similarity NPD6335 Approved
0.656 Remote Similarity NPD6412 Phase 2
0.6557 Remote Similarity NPD5223 Approved
0.6555 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6552 Remote Similarity NPD5328 Approved
0.6549 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6538 Remote Similarity NPD6274 Approved
0.6518 Remote Similarity NPD5209 Approved
0.6518 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6512 Remote Similarity NPD8133 Approved
0.65 Remote Similarity NPD5221 Approved
0.65 Remote Similarity NPD5222 Approved
0.65 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6491 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6489 Remote Similarity NPD6317 Approved
0.6484 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6475 Remote Similarity NPD4700 Approved
0.6471 Remote Similarity NPD7900 Approved
0.6471 Remote Similarity NPD7901 Clinical (unspecified phase)
0.646 Remote Similarity NPD6695 Phase 3
0.6446 Remote Similarity NPD5173 Approved
0.6439 Remote Similarity NPD6314 Approved
0.6439 Remote Similarity NPD6313 Approved
0.6435 Remote Similarity NPD3618 Phase 1
0.6429 Remote Similarity NPD6845 Suspended
0.6418 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6417 Remote Similarity NPD5695 Phase 3
0.6412 Remote Similarity NPD6868 Approved
0.641 Remote Similarity NPD6101 Approved
0.641 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6393 Remote Similarity NPD5696 Approved
0.6387 Remote Similarity NPD4202 Approved
0.6379 Remote Similarity NPD3573 Approved
0.6378 Remote Similarity NPD4729 Approved
0.6378 Remote Similarity NPD4730 Approved
0.6364 Remote Similarity NPD4697 Phase 3
0.6348 Remote Similarity NPD5363 Approved
0.6339 Remote Similarity NPD7332 Phase 2
0.6316 Remote Similarity NPD7154 Phase 3
0.6316 Remote Similarity NPD5362 Discontinued
0.6306 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6303 Remote Similarity NPD8034 Phase 2
0.6303 Remote Similarity NPD8035 Phase 2
0.6296 Remote Similarity NPD6908 Approved
0.6296 Remote Similarity NPD6909 Approved
0.6283 Remote Similarity NPD6902 Approved
0.6281 Remote Similarity NPD5210 Approved
0.6281 Remote Similarity NPD4629 Approved
0.6279 Remote Similarity NPD5250 Approved
0.6279 Remote Similarity NPD5249 Phase 3
0.6279 Remote Similarity NPD5247 Approved
0.6279 Remote Similarity NPD5251 Approved
0.6279 Remote Similarity NPD5248 Approved
0.6261 Remote Similarity NPD4786 Approved
0.6259 Remote Similarity NPD6033 Approved
0.625 Remote Similarity NPD5128 Approved
0.6241 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6239 Remote Similarity NPD7750 Discontinued
0.6231 Remote Similarity NPD5215 Approved
0.6231 Remote Similarity NPD5216 Approved
0.6231 Remote Similarity NPD5217 Approved
0.623 Remote Similarity NPD7839 Suspended
0.6225 Remote Similarity NPD7236 Approved
0.622 Remote Similarity NPD4767 Approved
0.622 Remote Similarity NPD4768 Approved
0.6218 Remote Similarity NPD5207 Approved
0.6198 Remote Similarity NPD6001 Approved
0.6195 Remote Similarity NPD7514 Phase 3
0.6195 Remote Similarity NPD6930 Phase 2
0.6195 Remote Similarity NPD6931 Approved
0.619 Remote Similarity NPD4754 Approved
0.6186 Remote Similarity NPD5737 Approved
0.6186 Remote Similarity NPD6672 Approved
0.6167 Remote Similarity NPD6050 Approved
0.6167 Remote Similarity NPD5693 Phase 1
0.6167 Remote Similarity NPD5694 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