Structure

Physi-Chem Properties

Molecular Weight:  540.31
Volume:  570.879
LogP:  5.459
LogD:  4.328
LogS:  -4.796
# Rotatable Bonds:  11
TPSA:  110.13
# H-Bond Aceptor:  7
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.19
Synthetic Accessibility Score:  6.485
Fsp3:  0.656
Lipinski Rule-of-5:  Rejected
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:  -4.791
MDCK Permeability:  2.334872988285497e-05
Pgp-inhibitor:  0.999
Pgp-substrate:  0.583
Human Intestinal Absorption (HIA):  0.032
20% Bioavailability (F20%):  0.98
30% Bioavailability (F30%):  0.961

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.37
Plasma Protein Binding (PPB):  94.34957885742188%
Volume Distribution (VD):  1.291
Pgp-substrate:  2.255175828933716%

ADMET: Metabolism

CYP1A2-inhibitor:  0.039
CYP1A2-substrate:  0.075
CYP2C19-inhibitor:  0.218
CYP2C19-substrate:  0.459
CYP2C9-inhibitor:  0.732
CYP2C9-substrate:  0.081
CYP2D6-inhibitor:  0.014
CYP2D6-substrate:  0.075
CYP3A4-inhibitor:  0.837
CYP3A4-substrate:  0.475

ADMET: Excretion

Clearance (CL):  4.086
Half-life (T1/2):  0.08

ADMET: Toxicity

hERG Blockers:  0.656
Human Hepatotoxicity (H-HT):  0.268
Drug-inuced Liver Injury (DILI):  0.148
AMES Toxicity:  0.025
Rat Oral Acute Toxicity:  0.689
Maximum Recommended Daily Dose:  0.95
Skin Sensitization:  0.956
Carcinogencity:  0.328
Eye Corrosion:  0.004
Eye Irritation:  0.011
Respiratory Toxicity:  0.972

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

  Natural Product: NPC133677

Natural Product ID:  NPC133677
Common Name*:   SYXKKJDQNXPUSI-HDJUQUQRSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  SYXKKJDQNXPUSI-HDJUQUQRSA-N
Standard InCHI:  InChI=1S/C32H44O7/c1-7-8-9-10-11-12-13-14-25(34)39-29-19(2)17-31-20(3)15-24-26(30(24,5)6)23(28(31)36)16-22(18-38-21(4)33)27(35)32(29,31)37/h11-14,16-17,20,23-24,26-27,29,35,37H,7-10,15,18H2,1-6H3/b12-11+,14-13+/t20-,23+,24-,26+,27-,29+,31+,32+/m1/s1
SMILES:  CCCCC/C=C/C=C/C(=O)O[C@H]1C(=C[C@]23[C@]1(O)[C@H](O)C(=C[C@H](C3=O)[C@H]1[C@@H](C[C@H]2C)C1(C)C)COC(=O)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL444960
PubChem CID:   11620845
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
NPO14260 Euphorbia kansui Species Euphorbiaceae Eukaryota roots n.a. n.a. PMID[12350140]
NPO14260 Euphorbia kansui Species Euphorbiaceae Eukaryota Roots n.a. n.a. PMID[12762796]
NPO14260 Euphorbia kansui Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[15387657]
NPO14260 Euphorbia kansui Species Euphorbiaceae Eukaryota n.a. root n.a. PMID[1955882]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota roots n.a. n.a. PMID[24660966]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota Roots n.a. n.a. PMID[29148766]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[31184480]
NPO14260 Euphorbia kansui Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14260 Euphorbia kansui Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14260 Euphorbia kansui Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14260 Euphorbia kansui Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14260 Euphorbia kansui 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
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 700.0 nM PMID[538950]
NPT25 Cell Line MT4 Homo sapiens CC50 > 900.0 nM PMID[538951]
NPT2 Others Unspecified Activity > 75.0 % PMID[538949]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 IC50 = 5.0 nM PMID[538951]
NPT2 Others Unspecified Ratio CC50/IC50 > 185.2 n.a. PMID[538951]

☑ 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 NPC133677 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 NPC138303
1.0 High Similarity NPC67290
0.9905 High Similarity NPC46269
0.9905 High Similarity NPC106395
0.981 High Similarity NPC123855
0.981 High Similarity NPC76550
0.981 High Similarity NPC138757
0.9619 High Similarity NPC257240
0.9524 High Similarity NPC47951
0.9429 High Similarity NPC308191
0.934 High Similarity NPC477102
0.9252 High Similarity NPC477103
0.9238 High Similarity NPC179891
0.9167 High Similarity NPC287311
0.8704 High Similarity NPC475661
0.8704 High Similarity NPC473488
0.8624 High Similarity NPC473911
0.844 Intermediate Similarity NPC203659
0.8381 Intermediate Similarity NPC261341
0.8376 Intermediate Similarity NPC472759
0.8376 Intermediate Similarity NPC329080
0.8376 Intermediate Similarity NPC475885
0.8349 Intermediate Similarity NPC110989
0.8347 Intermediate Similarity NPC236999
0.8291 Intermediate Similarity NPC236918
0.8291 Intermediate Similarity NPC477092
0.8291 Intermediate Similarity NPC156745
0.8288 Intermediate Similarity NPC26617
0.8273 Intermediate Similarity NPC100487
0.8257 Intermediate Similarity NPC225353
0.825 Intermediate Similarity NPC145238
0.822 Intermediate Similarity NPC19336
0.822 Intermediate Similarity NPC185876
0.8205 Intermediate Similarity NPC472760
0.8205 Intermediate Similarity NPC146280
0.8205 Intermediate Similarity NPC475401
0.8205 Intermediate Similarity NPC124676
0.8198 Intermediate Similarity NPC243998
0.8182 Intermediate Similarity NPC475945
0.8182 Intermediate Similarity NPC475871
0.8151 Intermediate Similarity NPC473228
0.8151 Intermediate Similarity NPC470829
0.8136 Intermediate Similarity NPC180640
0.812 Intermediate Similarity NPC475305
0.812 Intermediate Similarity NPC10721
0.812 Intermediate Similarity NPC471145
0.8115 Intermediate Similarity NPC471940
0.8108 Intermediate Similarity NPC474741
0.8108 Intermediate Similarity NPC309190
0.8091 Intermediate Similarity NPC86077
0.8091 Intermediate Similarity NPC474747
0.8083 Intermediate Similarity NPC257017
0.8083 Intermediate Similarity NPC162009
0.8037 Intermediate Similarity NPC304886
0.8036 Intermediate Similarity NPC223450
0.8034 Intermediate Similarity NPC154363
0.8034 Intermediate Similarity NPC471127
0.8034 Intermediate Similarity NPC234858
0.8033 Intermediate Similarity NPC471939
0.8017 Intermediate Similarity NPC472399
0.8 Intermediate Similarity NPC52839
0.8 Intermediate Similarity NPC71680
0.8 Intermediate Similarity NPC150923
0.8 Intermediate Similarity NPC474742
0.7982 Intermediate Similarity NPC161855
0.7982 Intermediate Similarity NPC141191
0.7966 Intermediate Similarity NPC153651
0.7963 Intermediate Similarity NPC473291
0.7951 Intermediate Similarity NPC473709
0.7951 Intermediate Similarity NPC473919
0.7949 Intermediate Similarity NPC472400
0.7944 Intermediate Similarity NPC167219
0.7934 Intermediate Similarity NPC19464
0.7931 Intermediate Similarity NPC241477
0.7917 Intermediate Similarity NPC157252
0.7917 Intermediate Similarity NPC471126
0.7917 Intermediate Similarity NPC471128
0.7917 Intermediate Similarity NPC145182
0.7913 Intermediate Similarity NPC15551
0.7913 Intermediate Similarity NPC181298
0.7899 Intermediate Similarity NPC13710
0.7899 Intermediate Similarity NPC288679
0.789 Intermediate Similarity NPC477949
0.789 Intermediate Similarity NPC169205
0.7869 Intermediate Similarity NPC473802
0.7863 Intermediate Similarity NPC71889
0.7863 Intermediate Similarity NPC472757
0.7863 Intermediate Similarity NPC209058
0.7857 Intermediate Similarity NPC472755
0.7851 Intermediate Similarity NPC472401
0.7838 Intermediate Similarity NPC171759
0.7838 Intermediate Similarity NPC116139
0.7838 Intermediate Similarity NPC472753
0.7833 Intermediate Similarity NPC255081
0.7833 Intermediate Similarity NPC471108
0.7833 Intermediate Similarity NPC5991
0.7833 Intermediate Similarity NPC5989
0.7833 Intermediate Similarity NPC22628
0.7833 Intermediate Similarity NPC275696
0.783 Intermediate Similarity NPC473448
0.7826 Intermediate Similarity NPC475274
0.7826 Intermediate Similarity NPC15218
0.7815 Intermediate Similarity NPC475323
0.7815 Intermediate Similarity NPC156252
0.7815 Intermediate Similarity NPC471146
0.7798 Intermediate Similarity NPC185553
0.7797 Intermediate Similarity NPC305044
0.7797 Intermediate Similarity NPC474872
0.7797 Intermediate Similarity NPC265290
0.7788 Intermediate Similarity NPC472756
0.7788 Intermediate Similarity NPC475676
0.7788 Intermediate Similarity NPC220964
0.7778 Intermediate Similarity NPC323008
0.7778 Intermediate Similarity NPC262133
0.7778 Intermediate Similarity NPC17138
0.7778 Intermediate Similarity NPC470010
0.7778 Intermediate Similarity NPC473522
0.7778 Intermediate Similarity NPC151216
0.7778 Intermediate Similarity NPC221511
0.7778 Intermediate Similarity NPC477093
0.7778 Intermediate Similarity NPC477131
0.7778 Intermediate Similarity NPC215643
0.7778 Intermediate Similarity NPC470013
0.7778 Intermediate Similarity NPC198853
0.7778 Intermediate Similarity NPC65829
0.7778 Intermediate Similarity NPC475277
0.7778 Intermediate Similarity NPC101825
0.7778 Intermediate Similarity NPC89227
0.7778 Intermediate Similarity NPC265499
0.7778 Intermediate Similarity NPC170212
0.7768 Intermediate Similarity NPC472754
0.7768 Intermediate Similarity NPC473596
0.7768 Intermediate Similarity NPC66110
0.7757 Intermediate Similarity NPC476705
0.775 Intermediate Similarity NPC171905
0.775 Intermediate Similarity NPC472758
0.775 Intermediate Similarity NPC471125
0.775 Intermediate Similarity NPC472397
0.7748 Intermediate Similarity NPC475053
0.7748 Intermediate Similarity NPC288876
0.7739 Intermediate Similarity NPC327286
0.7739 Intermediate Similarity NPC55972
0.7739 Intermediate Similarity NPC233379
0.7739 Intermediate Similarity NPC169888
0.7739 Intermediate Similarity NPC14862
0.7739 Intermediate Similarity NPC474664
0.7727 Intermediate Similarity NPC161493
0.7727 Intermediate Similarity NPC108475
0.7727 Intermediate Similarity NPC170143
0.7727 Intermediate Similarity NPC40812
0.7727 Intermediate Similarity NPC213947
0.7727 Intermediate Similarity NPC311904
0.7721 Intermediate Similarity NPC134131
0.7721 Intermediate Similarity NPC25043
0.7719 Intermediate Similarity NPC54737
0.7712 Intermediate Similarity NPC469463
0.7712 Intermediate Similarity NPC474937
0.7712 Intermediate Similarity NPC469454
0.7712 Intermediate Similarity NPC469496
0.7706 Intermediate Similarity NPC36954
0.7706 Intermediate Similarity NPC48803
0.7706 Intermediate Similarity NPC193645
0.7706 Intermediate Similarity NPC275960
0.7706 Intermediate Similarity NPC469873
0.7706 Intermediate Similarity NPC90121
0.7706 Intermediate Similarity NPC270013
0.7706 Intermediate Similarity NPC14961
0.7706 Intermediate Similarity NPC52044
0.7706 Intermediate Similarity NPC67584
0.7706 Intermediate Similarity NPC220221
0.7705 Intermediate Similarity NPC67569
0.7705 Intermediate Similarity NPC46570
0.7699 Intermediate Similarity NPC475873
0.7699 Intermediate Similarity NPC4620
0.7699 Intermediate Similarity NPC124881
0.7692 Intermediate Similarity NPC158523
0.7692 Intermediate Similarity NPC317107
0.7692 Intermediate Similarity NPC475937
0.7692 Intermediate Similarity NPC260786
0.7692 Intermediate Similarity NPC474871
0.7692 Intermediate Similarity NPC96739
0.7692 Intermediate Similarity NPC470961
0.7692 Intermediate Similarity NPC174471
0.7692 Intermediate Similarity NPC475495
0.7685 Intermediate Similarity NPC475912
0.7679 Intermediate Similarity NPC164598
0.7679 Intermediate Similarity NPC206079
0.7679 Intermediate Similarity NPC477950
0.7679 Intermediate Similarity NPC62670
0.7679 Intermediate Similarity NPC474339
0.7672 Intermediate Similarity NPC273433
0.7661 Intermediate Similarity NPC144625
0.7661 Intermediate Similarity NPC8374
0.7658 Intermediate Similarity NPC221615
0.7658 Intermediate Similarity NPC64742
0.7658 Intermediate Similarity NPC244411
0.7658 Intermediate Similarity NPC83895
0.7658 Intermediate Similarity NPC187761
0.7656 Intermediate Similarity NPC469673
0.7652 Intermediate Similarity NPC72813

  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 NPC133677 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
0.9619 High Similarity NPD6371 Approved
0.8288 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7706 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7664 Intermediate Similarity NPD7838 Discovery
0.7664 Intermediate Similarity NPD5785 Approved
0.7593 Intermediate Similarity NPD7983 Approved
0.7377 Intermediate Similarity NPD7115 Discovery
0.7339 Intermediate Similarity NPD46 Approved
0.7339 Intermediate Similarity NPD6698 Approved
0.7248 Intermediate Similarity NPD1695 Approved
0.7238 Intermediate Similarity NPD5209 Approved
0.7196 Intermediate Similarity NPD5363 Approved
0.7193 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.7043 Intermediate Similarity NPD4225 Approved
0.7 Intermediate Similarity NPD6686 Approved
0.6991 Remote Similarity NPD5282 Discontinued
0.6923 Remote Similarity NPD5344 Discontinued
0.6916 Remote Similarity NPD4269 Approved
0.6916 Remote Similarity NPD4270 Approved
0.6903 Remote Similarity NPD5779 Approved
0.6903 Remote Similarity NPD5778 Approved
0.6875 Remote Similarity NPD8517 Approved
0.6875 Remote Similarity NPD8513 Phase 3
0.6875 Remote Similarity NPD8516 Approved
0.6875 Remote Similarity NPD8515 Approved
0.6852 Remote Similarity NPD5362 Discontinued
0.6838 Remote Similarity NPD6648 Approved
0.6829 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6822 Remote Similarity NPD5369 Approved
0.6818 Remote Similarity NPD5786 Approved
0.6814 Remote Similarity NPD7637 Suspended
0.6797 Remote Similarity NPD6319 Approved
0.6794 Remote Similarity NPD8273 Phase 1
0.6774 Remote Similarity NPD6053 Discontinued
0.6729 Remote Similarity NPD4252 Approved
0.6697 Remote Similarity NPD7154 Phase 3
0.6642 Remote Similarity NPD7319 Approved
0.664 Remote Similarity NPD8297 Approved
0.6617 Remote Similarity NPD8074 Phase 3
0.6615 Remote Similarity NPD7503 Approved
0.6607 Remote Similarity NPD4251 Approved
0.6607 Remote Similarity NPD4250 Approved
0.6591 Remote Similarity NPD7492 Approved
0.6587 Remote Similarity NPD4632 Approved
0.6581 Remote Similarity NPD7839 Suspended
0.6577 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6574 Remote Similarity NPD4821 Approved
0.6574 Remote Similarity NPD4819 Approved
0.6574 Remote Similarity NPD4820 Approved
0.6574 Remote Similarity NPD4822 Approved
0.6574 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6567 Remote Similarity NPD7736 Approved
0.6555 Remote Similarity NPD7640 Approved
0.6555 Remote Similarity NPD7639 Approved
0.6542 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6541 Remote Similarity NPD6616 Approved
0.6541 Remote Similarity NPD7507 Approved
0.6538 Remote Similarity NPD6054 Approved
0.6532 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6522 Remote Similarity NPD6411 Approved
0.6518 Remote Similarity NPD4249 Approved
0.6515 Remote Similarity NPD7829 Approved
0.6515 Remote Similarity NPD7604 Phase 2
0.6515 Remote Similarity NPD7830 Approved
0.6504 Remote Similarity NPD6412 Phase 2
0.6493 Remote Similarity NPD7078 Approved
0.6471 Remote Similarity NPD7638 Approved
0.6455 Remote Similarity NPD6435 Approved
0.6452 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6452 Remote Similarity NPD6881 Approved
0.6452 Remote Similarity NPD6899 Approved
0.6439 Remote Similarity NPD6370 Approved
0.6429 Remote Similarity NPD6650 Approved
0.6429 Remote Similarity NPD6649 Approved
0.6429 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6429 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6429 Remote Similarity NPD8130 Phase 1
0.6391 Remote Similarity NPD7642 Approved
0.6389 Remote Similarity NPD4271 Approved
0.6389 Remote Similarity NPD4268 Approved
0.6387 Remote Similarity NPD6083 Phase 2
0.6387 Remote Similarity NPD6084 Phase 2
0.6379 Remote Similarity NPD5284 Approved
0.6379 Remote Similarity NPD5281 Approved
0.6371 Remote Similarity NPD5697 Approved
0.637 Remote Similarity NPD8293 Discontinued
0.6364 Remote Similarity NPD6015 Approved
0.6364 Remote Similarity NPD6016 Approved
0.6364 Remote Similarity NPD8033 Approved
0.6349 Remote Similarity NPD7290 Approved
0.6349 Remote Similarity NPD7102 Approved
0.6349 Remote Similarity NPD6883 Approved
0.6349 Remote Similarity NPD4634 Approved
0.6349 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6348 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6348 Remote Similarity NPD6101 Approved
0.6316 Remote Similarity NPD5988 Approved
0.6316 Remote Similarity NPD7524 Approved
0.6308 Remote Similarity NPD6009 Approved
0.6304 Remote Similarity NPD7260 Phase 2
0.6299 Remote Similarity NPD6847 Approved
0.6299 Remote Similarity NPD6869 Approved
0.6299 Remote Similarity NPD6617 Approved
0.6296 Remote Similarity NPD8451 Approved
0.629 Remote Similarity NPD6008 Approved
0.629 Remote Similarity NPD6402 Approved
0.629 Remote Similarity NPD6675 Approved
0.629 Remote Similarity NPD5739 Approved
0.629 Remote Similarity NPD7128 Approved
0.6288 Remote Similarity NPD8377 Approved
0.6288 Remote Similarity NPD6059 Approved
0.6288 Remote Similarity NPD8294 Approved
0.6283 Remote Similarity NPD1694 Approved
0.6273 Remote Similarity NPD5368 Approved
0.627 Remote Similarity NPD6012 Approved
0.627 Remote Similarity NPD6373 Approved
0.627 Remote Similarity NPD6014 Approved
0.627 Remote Similarity NPD6372 Approved
0.627 Remote Similarity NPD6013 Approved
0.626 Remote Similarity NPD7328 Approved
0.626 Remote Similarity NPD7327 Approved
0.625 Remote Similarity NPD8448 Approved
0.625 Remote Similarity NPD5332 Approved
0.625 Remote Similarity NPD5331 Approved
0.625 Remote Similarity NPD6882 Approved
0.6241 Remote Similarity NPD8335 Approved
0.6241 Remote Similarity NPD8379 Approved
0.6241 Remote Similarity NPD8378 Approved
0.6241 Remote Similarity NPD8444 Approved
0.6241 Remote Similarity NPD8296 Approved
0.6241 Remote Similarity NPD8380 Approved
0.6241 Remote Similarity NPD5983 Phase 2
0.6222 Remote Similarity NPD8342 Approved
0.6222 Remote Similarity NPD8299 Approved
0.6222 Remote Similarity NPD8341 Approved
0.6222 Remote Similarity NPD8340 Approved
0.6218 Remote Similarity NPD5695 Phase 3
0.6216 Remote Similarity NPD4790 Discontinued
0.6212 Remote Similarity NPD7516 Approved
0.6202 Remote Similarity NPD8133 Approved
0.6198 Remote Similarity NPD5696 Approved
0.6195 Remote Similarity NPD7338 Clinical (unspecified phase)
0.619 Remote Similarity NPD6011 Approved
0.619 Remote Similarity NPD7320 Approved
0.6186 Remote Similarity NPD6399 Phase 3
0.6183 Remote Similarity NPD7500 Approved
0.6179 Remote Similarity NPD5211 Phase 2
0.6176 Remote Similarity NPD6336 Discontinued
0.6161 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6148 Remote Similarity NPD8328 Phase 3
0.6136 Remote Similarity NPD7641 Discontinued
0.6115 Remote Similarity NPD8392 Approved
0.6115 Remote Similarity NPD8390 Approved
0.6115 Remote Similarity NPD8391 Approved
0.6111 Remote Similarity NPD8039 Approved
0.6111 Remote Similarity NPD5701 Approved
0.6111 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6106 Remote Similarity NPD6695 Phase 3
0.6083 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6083 Remote Similarity NPD5210 Approved
0.6083 Remote Similarity NPD4629 Approved
0.608 Remote Similarity NPD5141 Approved
0.6068 Remote Similarity NPD5370 Suspended
0.6048 Remote Similarity NPD7632 Discontinued
0.6034 Remote Similarity NPD7750 Discontinued
0.6018 Remote Similarity NPD4800 Clinical (unspecified phase)
0.6017 Remote Similarity NPD5207 Approved
0.6016 Remote Similarity NPD5285 Approved
0.6016 Remote Similarity NPD4696 Approved
0.6016 Remote Similarity NPD5286 Approved
0.6 Remote Similarity NPD1696 Phase 3
0.6 Remote Similarity NPD5956 Approved
0.5984 Remote Similarity NPD7902 Approved
0.5982 Remote Similarity NPD7332 Phase 2
0.597 Remote Similarity NPD7100 Approved
0.597 Remote Similarity NPD4522 Approved
0.597 Remote Similarity NPD7101 Approved
0.5966 Remote Similarity NPD6050 Approved
0.5966 Remote Similarity NPD4810 Clinical (unspecified phase)
0.5966 Remote Similarity NPD5694 Approved
0.5966 Remote Similarity NPD5693 Phase 1
0.5965 Remote Similarity NPD6110 Phase 1
0.5948 Remote Similarity NPD6684 Approved
0.5948 Remote Similarity NPD7334 Approved
0.5948 Remote Similarity NPD5330 Approved
0.5948 Remote Similarity NPD7521 Approved
0.5948 Remote Similarity NPD7146 Approved
0.5948 Remote Similarity NPD6409 Approved
0.5932 Remote Similarity NPD4753 Phase 2
0.5929 Remote Similarity NPD6902 Approved
0.5923 Remote Similarity NPD7116 Clinical (unspecified phase)
0.5923 Remote Similarity NPD6401 Clinical (unspecified phase)
0.592 Remote Similarity NPD5225 Approved
0.592 Remote Similarity NPD5226 Approved
0.592 Remote Similarity NPD4633 Approved
0.592 Remote Similarity NPD5224 Approved
0.5915 Remote Similarity NPD6845 Suspended
0.5913 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5896 Remote Similarity NPD6335 Approved
0.5891 Remote Similarity NPD8132 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