Structure

Physi-Chem Properties

Molecular Weight:  586.42
Volume:  639.182
LogP:  8.604
LogD:  4.968
LogS:  -5.022
# Rotatable Bonds:  17
TPSA:  104.06
# H-Bond Aceptor:  6
# H-Bond Donor:  3
# Rings:  4
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.104
Synthetic Accessibility Score:  6.065
Fsp3:  0.833
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.932
MDCK Permeability:  2.2260706828092225e-05
Pgp-inhibitor:  0.992
Pgp-substrate:  0.746
Human Intestinal Absorption (HIA):  0.026
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.459
Plasma Protein Binding (PPB):  95.71295166015625%
Volume Distribution (VD):  1.241
Pgp-substrate:  1.8849869966506958%

ADMET: Metabolism

CYP1A2-inhibitor:  0.051
CYP1A2-substrate:  0.146
CYP2C19-inhibitor:  0.43
CYP2C19-substrate:  0.141
CYP2C9-inhibitor:  0.36
CYP2C9-substrate:  0.885
CYP2D6-inhibitor:  0.032
CYP2D6-substrate:  0.02
CYP3A4-inhibitor:  0.804
CYP3A4-substrate:  0.265

ADMET: Excretion

Clearance (CL):  6.004
Half-life (T1/2):  0.015

ADMET: Toxicity

hERG Blockers:  0.456
Human Hepatotoxicity (H-HT):  0.441
Drug-inuced Liver Injury (DILI):  0.18
AMES Toxicity:  0.014
Rat Oral Acute Toxicity:  0.673
Maximum Recommended Daily Dose:  0.927
Skin Sensitization:  0.898
Carcinogencity:  0.093
Eye Corrosion:  0.004
Eye Irritation:  0.015
Respiratory Toxicity:  0.981

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

  Natural Product: NPC308191

Natural Product ID:  NPC308191
Common Name*:   DOSPRDHNGNPKKJ-BYPUAWAASA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  DOSPRDHNGNPKKJ-BYPUAWAASA-N
Standard InCHI:  InChI=1S/C36H58O6/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-29(38)42-33-24(2)22-35-25(3)20-28-30(34(28,4)5)27(32(35)40)21-26(23-37)31(39)36(33,35)41/h21-22,25,27-28,30-31,33,37,39,41H,6-20,23H2,1-5H3/t25-,27+,28-,30+,31-,33+,35+,36+/m1/s1
SMILES:  CCCCCCCCCCCCCCCC(=O)O[C@H]1C(=C[C@]23[C@H](C)C[C@@H]4[C@H]([C@H](C=C(CO)[C@H]([C@]13O)O)C2=O)C4(C)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2430127
PubChem CID:   56841025
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
NPO520 Euphorbia lathyris Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[12542364]
NPO10036 Bruguiera cylindrica Species Rhizophoraceae Eukaryota Fruits n.a. n.a. PMID[15165157]
NPO2462 Machilus robusta Species Lauraceae Eukaryota bark n.a. n.a. PMID[21627109]
NPO2462 Machilus robusta Species Lauraceae Eukaryota n.a. bark n.a. PMID[21627109]
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]
NPO520 Euphorbia lathyris Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[30817151]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[31184480]
NPO9866 Symphytum tuberosum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO520 Euphorbia lathyris Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4235 Thymus magnus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4235 Thymus magnus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO520 Euphorbia lathyris Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9866 Symphytum tuberosum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO520 Euphorbia lathyris 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]
NPO520 Euphorbia lathyris 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[TM-MC]
NPO5571 Jacobaea arnautorum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4494 Ecbolium linneanum Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8283 Pseudophegopteris subaurita Species Thelypteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10733 Plantago uniflora Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2462 Machilus robusta Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10036 Bruguiera cylindrica Species Rhizophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9866 Symphytum tuberosum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10479 Ophiocoma echinata Species Ophiocomidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4235 Thymus magnus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3940 Erioderma chilense Species Pannariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1000 Thymus transcaucasicus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10833 Heteromma simplicifolium n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO520 Euphorbia lathyris Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10959 Kalanchoe marmorata Species Crassulaceae 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
NPT165 Cell Line HeLa Homo sapiens LC50 = 400000.0 nM PMID[468527]
NPT25 Cell Line MT4 Homo sapiens CC50 = 26300.0 nM PMID[468528]
NPT881 Individual Protein Protein kinase C delta Homo sapiens EC50 = 4.7 nM PMID[468527]
NPT2 Others Unspecified Emax = 109.0 % PMID[468527]
NPT2 Others Unspecified EC50 = 7.3 nM PMID[468527]
NPT2 Others Unspecified Emax = 115.0 % PMID[468527]
NPT2 Others Unspecified EC50 = 8.4 nM PMID[468527]
NPT2 Others Unspecified Emax = 106.0 % PMID[468527]
NPT2 Others Unspecified EC50 = 28.0 nM PMID[468527]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 IC50 = 4.1 nM PMID[468528]
NPT2 Others Unspecified Ratio CC50/IC50 = 6416.7 n.a. PMID[468528]

☑ 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 NPC308191 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
0.9798 High Similarity NPC179891
0.9706 High Similarity NPC287311
0.9608 High Similarity NPC257240
0.9429 High Similarity NPC133677
0.9429 High Similarity NPC138303
0.9429 High Similarity NPC67290
0.9333 High Similarity NPC106395
0.9333 High Similarity NPC46269
0.932 High Similarity NPC477102
0.9238 High Similarity NPC76550
0.9238 High Similarity NPC123855
0.9238 High Similarity NPC138757
0.9231 High Similarity NPC477103
0.9216 High Similarity NPC475661
0.9216 High Similarity NPC473488
0.9126 High Similarity NPC473911
0.8952 High Similarity NPC47951
0.8889 High Similarity NPC261341
0.8246 Intermediate Similarity NPC477092
0.8241 Intermediate Similarity NPC26617
0.8224 Intermediate Similarity NPC203659
0.8224 Intermediate Similarity NPC100487
0.8158 Intermediate Similarity NPC475401
0.8148 Intermediate Similarity NPC243998
0.8131 Intermediate Similarity NPC110989
0.8091 Intermediate Similarity NPC15218
0.807 Intermediate Similarity NPC475305
0.807 Intermediate Similarity NPC10721
0.8056 Intermediate Similarity NPC220964
0.8056 Intermediate Similarity NPC475676
0.8037 Intermediate Similarity NPC225353
0.8037 Intermediate Similarity NPC86077
0.8 Intermediate Similarity NPC474664
0.8 Intermediate Similarity NPC233379
0.8 Intermediate Similarity NPC477949
0.8 Intermediate Similarity NPC124676
0.8 Intermediate Similarity NPC169888
0.8 Intermediate Similarity NPC146280
0.8 Intermediate Similarity NPC14862
0.8 Intermediate Similarity NPC327286
0.8 Intermediate Similarity NPC55972
0.7982 Intermediate Similarity NPC223450
0.7982 Intermediate Similarity NPC234858
0.7982 Intermediate Similarity NPC154363
0.7982 Intermediate Similarity NPC471127
0.7966 Intermediate Similarity NPC472399
0.7963 Intermediate Similarity NPC4620
0.7963 Intermediate Similarity NPC474165
0.7963 Intermediate Similarity NPC475945
0.7963 Intermediate Similarity NPC69171
0.7963 Intermediate Similarity NPC475871
0.7949 Intermediate Similarity NPC52839
0.7944 Intermediate Similarity NPC150923
0.7909 Intermediate Similarity NPC324327
0.7909 Intermediate Similarity NPC194620
0.7909 Intermediate Similarity NPC72813
0.7909 Intermediate Similarity NPC326994
0.7909 Intermediate Similarity NPC474421
0.7895 Intermediate Similarity NPC472400
0.789 Intermediate Similarity NPC474741
0.7885 Intermediate Similarity NPC470010
0.7885 Intermediate Similarity NPC323008
0.7885 Intermediate Similarity NPC198853
0.7885 Intermediate Similarity NPC262133
0.7885 Intermediate Similarity NPC470013
0.7881 Intermediate Similarity NPC162009
0.7881 Intermediate Similarity NPC19464
0.7881 Intermediate Similarity NPC257017
0.787 Intermediate Similarity NPC474709
0.787 Intermediate Similarity NPC183571
0.787 Intermediate Similarity NPC474747
0.7863 Intermediate Similarity NPC475885
0.7863 Intermediate Similarity NPC471128
0.7863 Intermediate Similarity NPC157252
0.7863 Intermediate Similarity NPC145182
0.7863 Intermediate Similarity NPC472759
0.7863 Intermediate Similarity NPC329080
0.7863 Intermediate Similarity NPC471126
0.7857 Intermediate Similarity NPC115257
0.7857 Intermediate Similarity NPC161816
0.7851 Intermediate Similarity NPC236999
0.785 Intermediate Similarity NPC474718
0.7845 Intermediate Similarity NPC288679
0.7838 Intermediate Similarity NPC117604
0.783 Intermediate Similarity NPC161493
0.783 Intermediate Similarity NPC311904
0.7818 Intermediate Similarity NPC16313
0.7818 Intermediate Similarity NPC475802
0.7818 Intermediate Similarity NPC9303
0.781 Intermediate Similarity NPC52044
0.781 Intermediate Similarity NPC67584
0.781 Intermediate Similarity NPC14961
0.781 Intermediate Similarity NPC304886
0.781 Intermediate Similarity NPC469873
0.781 Intermediate Similarity NPC270013
0.781 Intermediate Similarity NPC220221
0.781 Intermediate Similarity NPC36954
0.7807 Intermediate Similarity NPC472757
0.7807 Intermediate Similarity NPC71889
0.7798 Intermediate Similarity NPC124881
0.7798 Intermediate Similarity NPC472755
0.7797 Intermediate Similarity NPC472401
0.7788 Intermediate Similarity NPC475912
0.7788 Intermediate Similarity NPC317107
0.7778 Intermediate Similarity NPC236918
0.7778 Intermediate Similarity NPC156745
0.7778 Intermediate Similarity NPC5989
0.7778 Intermediate Similarity NPC472753
0.7778 Intermediate Similarity NPC471108
0.7778 Intermediate Similarity NPC255081
0.7778 Intermediate Similarity NPC171759
0.7778 Intermediate Similarity NPC5991
0.7778 Intermediate Similarity NPC22628
0.7778 Intermediate Similarity NPC275696
0.7778 Intermediate Similarity NPC477950
0.7778 Intermediate Similarity NPC474742
0.7768 Intermediate Similarity NPC273433
0.7768 Intermediate Similarity NPC475922
0.7759 Intermediate Similarity NPC156252
0.7759 Intermediate Similarity NPC475323
0.7757 Intermediate Similarity NPC221615
0.7757 Intermediate Similarity NPC141191
0.775 Intermediate Similarity NPC473709
0.775 Intermediate Similarity NPC145238
0.775 Intermediate Similarity NPC473919
0.7739 Intermediate Similarity NPC474872
0.7736 Intermediate Similarity NPC476315
0.7736 Intermediate Similarity NPC213078
0.7727 Intermediate Similarity NPC475585
0.7727 Intermediate Similarity NPC473577
0.7727 Intermediate Similarity NPC472756
0.7727 Intermediate Similarity NPC474550
0.7719 Intermediate Similarity NPC170212
0.7719 Intermediate Similarity NPC317687
0.7719 Intermediate Similarity NPC17138
0.7719 Intermediate Similarity NPC221511
0.7719 Intermediate Similarity NPC473522
0.7719 Intermediate Similarity NPC151216
0.7719 Intermediate Similarity NPC475277
0.7719 Intermediate Similarity NPC477093
0.7719 Intermediate Similarity NPC215643
0.7719 Intermediate Similarity NPC89227
0.7719 Intermediate Similarity NPC101825
0.7719 Intermediate Similarity NPC265499
0.7714 Intermediate Similarity NPC474035
0.7714 Intermediate Similarity NPC167219
0.7714 Intermediate Similarity NPC477131
0.7714 Intermediate Similarity NPC81386
0.7712 Intermediate Similarity NPC185876
0.7712 Intermediate Similarity NPC19336
0.7706 Intermediate Similarity NPC472754
0.7706 Intermediate Similarity NPC105725
0.7692 Intermediate Similarity NPC475972
0.7692 Intermediate Similarity NPC161060
0.7692 Intermediate Similarity NPC471125
0.7692 Intermediate Similarity NPC472758
0.7692 Intermediate Similarity NPC476705
0.7692 Intermediate Similarity NPC131209
0.7692 Intermediate Similarity NPC30515
0.7692 Intermediate Similarity NPC133698
0.7692 Intermediate Similarity NPC184463
0.7692 Intermediate Similarity NPC472397
0.7692 Intermediate Similarity NPC171905
0.7692 Intermediate Similarity NPC472760
0.7685 Intermediate Similarity NPC288876
0.7685 Intermediate Similarity NPC70865
0.7679 Intermediate Similarity NPC94377
0.7667 Intermediate Similarity NPC473802
0.7664 Intermediate Similarity NPC213947
0.7664 Intermediate Similarity NPC108475
0.7664 Intermediate Similarity NPC170143
0.7664 Intermediate Similarity NPC474313
0.7664 Intermediate Similarity NPC169205
0.7658 Intermediate Similarity NPC60315
0.7658 Intermediate Similarity NPC475290
0.7658 Intermediate Similarity NPC54737
0.7652 Intermediate Similarity NPC474937
0.7652 Intermediate Similarity NPC209058
0.7647 Intermediate Similarity NPC473228
0.7647 Intermediate Similarity NPC470829
0.7642 Intermediate Similarity NPC170120
0.7642 Intermediate Similarity NPC475900
0.7642 Intermediate Similarity NPC213698
0.7636 Intermediate Similarity NPC475334
0.7636 Intermediate Similarity NPC475623
0.7636 Intermediate Similarity NPC474775
0.7636 Intermediate Similarity NPC473694
0.7632 Intermediate Similarity NPC475937
0.7632 Intermediate Similarity NPC474871
0.7632 Intermediate Similarity NPC475495
0.7632 Intermediate Similarity NPC260786
0.7632 Intermediate Similarity NPC96739
0.7632 Intermediate Similarity NPC174471
0.7632 Intermediate Similarity NPC158523
0.7627 Intermediate Similarity NPC180640
0.7623 Intermediate Similarity NPC471940
0.7619 Intermediate Similarity NPC476300
0.7619 Intermediate Similarity NPC212486
0.7619 Intermediate Similarity NPC475788
0.7615 Intermediate Similarity NPC164598

  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 NPC308191 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
0.9608 High Similarity NPD6371 Approved
0.8241 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7524 Intermediate Similarity NPD7983 Approved
0.7477 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7429 Intermediate Similarity NPD46 Approved
0.7429 Intermediate Similarity NPD5785 Approved
0.7429 Intermediate Similarity NPD6698 Approved
0.7333 Intermediate Similarity NPD1695 Approved
0.7167 Intermediate Similarity NPD7115 Discovery
0.7157 Intermediate Similarity NPD4270 Approved
0.7157 Intermediate Similarity NPD4269 Approved
0.7103 Intermediate Similarity NPD7838 Discovery
0.7087 Intermediate Similarity NPD5362 Discontinued
0.7059 Intermediate Similarity NPD5369 Approved
0.7048 Intermediate Similarity NPD5786 Approved
0.7034 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.6964 Remote Similarity NPD4225 Approved
0.6961 Remote Similarity NPD4252 Approved
0.6952 Remote Similarity NPD5363 Approved
0.6923 Remote Similarity NPD7154 Phase 3
0.6923 Remote Similarity NPD6686 Approved
0.6909 Remote Similarity NPD5282 Discontinued
0.6833 Remote Similarity NPD6053 Discontinued
0.6822 Remote Similarity NPD4251 Approved
0.6822 Remote Similarity NPD4250 Approved
0.6818 Remote Similarity NPD5778 Approved
0.6818 Remote Similarity NPD5779 Approved
0.68 Remote Similarity NPD8515 Approved
0.68 Remote Similarity NPD8517 Approved
0.68 Remote Similarity NPD8516 Approved
0.68 Remote Similarity NPD8513 Phase 3
0.6796 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6796 Remote Similarity NPD4820 Approved
0.6796 Remote Similarity NPD4819 Approved
0.6796 Remote Similarity NPD4822 Approved
0.6796 Remote Similarity NPD4821 Approved
0.6792 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6765 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6729 Remote Similarity NPD4249 Approved
0.6727 Remote Similarity NPD7637 Suspended
0.6719 Remote Similarity NPD8273 Phase 1
0.6696 Remote Similarity NPD5344 Discontinued
0.6692 Remote Similarity NPD7319 Approved
0.6667 Remote Similarity NPD5209 Approved
0.6667 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6435 Approved
0.6639 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6636 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6609 Remote Similarity NPD7640 Approved
0.6609 Remote Similarity NPD7639 Approved
0.6602 Remote Similarity NPD4268 Approved
0.6602 Remote Similarity NPD4271 Approved
0.6589 Remote Similarity NPD7507 Approved
0.6587 Remote Similarity NPD6319 Approved
0.6583 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6555 Remote Similarity NPD6412 Phase 2
0.6538 Remote Similarity NPD8074 Phase 3
0.6522 Remote Similarity NPD7638 Approved
0.6518 Remote Similarity NPD6399 Phase 3
0.6504 Remote Similarity NPD8133 Approved
0.6491 Remote Similarity NPD7839 Suspended
0.6476 Remote Similarity NPD5368 Approved
0.6449 Remote Similarity NPD5331 Approved
0.6449 Remote Similarity NPD5332 Approved
0.6435 Remote Similarity NPD6084 Phase 2
0.6435 Remote Similarity NPD6083 Phase 2
0.6429 Remote Similarity NPD6411 Approved
0.6423 Remote Similarity NPD8297 Approved
0.6415 Remote Similarity NPD4790 Discontinued
0.6412 Remote Similarity NPD8293 Discontinued
0.6406 Remote Similarity NPD8033 Approved
0.6393 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6385 Remote Similarity NPD7492 Approved
0.6371 Remote Similarity NPD4632 Approved
0.6364 Remote Similarity NPD7736 Approved
0.6364 Remote Similarity NPD7524 Approved
0.6336 Remote Similarity NPD6616 Approved
0.6333 Remote Similarity NPD6675 Approved
0.6333 Remote Similarity NPD7128 Approved
0.6333 Remote Similarity NPD6402 Approved
0.6333 Remote Similarity NPD5739 Approved
0.6333 Remote Similarity NPD6008 Approved
0.6328 Remote Similarity NPD8377 Approved
0.6328 Remote Similarity NPD6059 Approved
0.6328 Remote Similarity NPD8294 Approved
0.6328 Remote Similarity NPD6054 Approved
0.6325 Remote Similarity NPD6648 Approved
0.6311 Remote Similarity NPD6373 Approved
0.6311 Remote Similarity NPD6372 Approved
0.6308 Remote Similarity NPD7604 Phase 2
0.6299 Remote Similarity NPD7328 Approved
0.6299 Remote Similarity NPD7327 Approved
0.6288 Remote Similarity NPD7078 Approved
0.6279 Remote Similarity NPD8296 Approved
0.6279 Remote Similarity NPD8380 Approved
0.6279 Remote Similarity NPD8335 Approved
0.6279 Remote Similarity NPD8379 Approved
0.6279 Remote Similarity NPD8378 Approved
0.6261 Remote Similarity NPD5695 Phase 3
0.625 Remote Similarity NPD5370 Suspended
0.625 Remote Similarity NPD7516 Approved
0.625 Remote Similarity NPD6101 Approved
0.625 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6239 Remote Similarity NPD5696 Approved
0.6239 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6231 Remote Similarity NPD6370 Approved
0.623 Remote Similarity NPD6881 Approved
0.623 Remote Similarity NPD7320 Approved
0.623 Remote Similarity NPD6899 Approved
0.6212 Remote Similarity NPD8451 Approved
0.621 Remote Similarity NPD6649 Approved
0.621 Remote Similarity NPD6650 Approved
0.621 Remote Similarity NPD8130 Phase 1
0.6183 Remote Similarity NPD7642 Approved
0.6183 Remote Similarity NPD8328 Phase 3
0.6179 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6165 Remote Similarity NPD8448 Approved
0.6154 Remote Similarity NPD6016 Approved
0.6154 Remote Similarity NPD7503 Approved
0.6154 Remote Similarity NPD8444 Approved
0.6154 Remote Similarity NPD6015 Approved
0.6148 Remote Similarity NPD5701 Approved
0.6148 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6148 Remote Similarity NPD5697 Approved
0.6147 Remote Similarity NPD6695 Phase 3
0.614 Remote Similarity NPD4810 Clinical (unspecified phase)
0.6136 Remote Similarity NPD8299 Approved
0.6136 Remote Similarity NPD8342 Approved
0.6136 Remote Similarity NPD8341 Approved
0.6136 Remote Similarity NPD8340 Approved
0.6129 Remote Similarity NPD6883 Approved
0.6129 Remote Similarity NPD4634 Approved
0.6129 Remote Similarity NPD7102 Approved
0.6129 Remote Similarity NPD7290 Approved
0.6121 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6107 Remote Similarity NPD5988 Approved
0.6094 Remote Similarity NPD6009 Approved
0.6094 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6083 Remote Similarity NPD7632 Discontinued
0.608 Remote Similarity NPD6847 Approved
0.608 Remote Similarity NPD6869 Approved
0.608 Remote Similarity NPD6617 Approved
0.6071 Remote Similarity NPD7750 Discontinued
0.6061 Remote Similarity NPD7830 Approved
0.6061 Remote Similarity NPD7829 Approved
0.6055 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6055 Remote Similarity NPD4800 Clinical (unspecified phase)
0.6048 Remote Similarity NPD6013 Approved
0.6048 Remote Similarity NPD6014 Approved
0.6048 Remote Similarity NPD6012 Approved
0.6036 Remote Similarity NPD1694 Approved
0.6032 Remote Similarity NPD6882 Approved
0.6031 Remote Similarity NPD5983 Phase 2
0.6031 Remote Similarity NPD6921 Approved
0.6029 Remote Similarity NPD8392 Approved
0.6029 Remote Similarity NPD8391 Approved
0.6029 Remote Similarity NPD8390 Approved
0.6017 Remote Similarity NPD7902 Approved
0.6 Remote Similarity NPD5284 Approved
0.6 Remote Similarity NPD6421 Discontinued
0.6 Remote Similarity NPD6110 Phase 1
0.6 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6 Remote Similarity NPD5693 Phase 1
0.6 Remote Similarity NPD5281 Approved
0.6 Remote Similarity NPD8039 Approved
0.5982 Remote Similarity NPD5330 Approved
0.5982 Remote Similarity NPD6684 Approved
0.5982 Remote Similarity NPD6409 Approved
0.5982 Remote Similarity NPD7146 Approved
0.5982 Remote Similarity NPD7521 Approved
0.5982 Remote Similarity NPD7334 Approved
0.597 Remote Similarity NPD6336 Discontinued
0.5968 Remote Similarity NPD6011 Approved
0.5965 Remote Similarity NPD6051 Approved
0.5965 Remote Similarity NPD4753 Phase 2
0.5952 Remote Similarity NPD6401 Clinical (unspecified phase)
0.595 Remote Similarity NPD5211 Phase 2
0.5946 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5946 Remote Similarity NPD4786 Approved
0.5932 Remote Similarity NPD4792 Clinical (unspecified phase)
0.5897 Remote Similarity NPD7748 Approved
0.5882 Remote Similarity NPD6033 Approved
0.5882 Remote Similarity NPD4755 Approved
0.5877 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5877 Remote Similarity NPD6903 Approved
0.5872 Remote Similarity NPD6931 Approved
0.5872 Remote Similarity NPD7332 Phase 2
0.5872 Remote Similarity NPD6930 Phase 2
0.587 Remote Similarity NPD7260 Phase 2
0.5862 Remote Similarity NPD8035 Phase 2
0.5862 Remote Similarity NPD8034 Phase 2
0.5854 Remote Similarity NPD5141 Approved
0.5847 Remote Similarity NPD4629 Approved
0.5847 Remote Similarity NPD5210 Approved
0.5846 Remote Similarity NPD8137 Clinical (unspecified phase)
0.5841 Remote Similarity NPD6098 Approved
0.5827 Remote Similarity NPD2204 Approved
0.5826 Remote Similarity NPD6080 Approved
0.5826 Remote Similarity NPD6673 Approved
0.5826 Remote Similarity NPD6904 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