Structure

Physi-Chem Properties

Molecular Weight:  304.2
Volume:  329.972
LogP:  4.106
LogD:  3.586
LogS:  -4.46
# Rotatable Bonds:  2
TPSA:  53.6
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.802
Synthetic Accessibility Score:  4.746
Fsp3:  0.684
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.849
MDCK Permeability:  1.7517691958346404e-05
Pgp-inhibitor:  0.103
Pgp-substrate:  0.016
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.026
30% Bioavailability (F30%):  0.041

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.134
Plasma Protein Binding (PPB):  96.33281707763672%
Volume Distribution (VD):  1.159
Pgp-substrate:  5.412916660308838%

ADMET: Metabolism

CYP1A2-inhibitor:  0.093
CYP1A2-substrate:  0.648
CYP2C19-inhibitor:  0.156
CYP2C19-substrate:  0.819
CYP2C9-inhibitor:  0.257
CYP2C9-substrate:  0.808
CYP2D6-inhibitor:  0.189
CYP2D6-substrate:  0.542
CYP3A4-inhibitor:  0.661
CYP3A4-substrate:  0.317

ADMET: Excretion

Clearance (CL):  7.218
Half-life (T1/2):  0.211

ADMET: Toxicity

hERG Blockers:  0.007
Human Hepatotoxicity (H-HT):  0.292
Drug-inuced Liver Injury (DILI):  0.097
AMES Toxicity:  0.034
Rat Oral Acute Toxicity:  0.221
Maximum Recommended Daily Dose:  0.359
Skin Sensitization:  0.118
Carcinogencity:  0.72
Eye Corrosion:  0.014
Eye Irritation:  0.436
Respiratory Toxicity:  0.957

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

  Natural Product: NPC471795

Natural Product ID:  NPC471795
Common Name*:   Ebractenoid A
IUPAC Name:   (3aR,6aR,8R,10aS)-8-ethenyl-10a-(hydroxymethyl)-4,4,8-trimethyl-5,6,6a,7,9,10-hexahydro-3aH-benzo[6,7]cyclohepta[4,6-c]furan-2-one
Synonyms:  
Standard InCHIKey:  NIKHROFAFUSZHD-HQJJXPTPSA-N
Standard InCHI:  InChI=1S/C19H28O3/c1-5-18(4)8-9-19(12-20)13(11-18)6-7-17(2,3)16-14(19)10-15(21)22-16/h5,10,13,16,20H,1,6-9,11-12H2,2-4H3/t13-,16+,18-,19+/m1/s1
SMILES:  C=C[C@]1(C)CC[C@@]2([C@@H](C1)CCC([C@@H]1C2=CC(=O)O1)(C)C)CO
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3234212
PubChem CID:   90670335
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001983] Dihydrofurans
        • [CHEMONTID:0001982] Furanones
          • [CHEMONTID:0002223] Butenolides

*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
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]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
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]
NPO299 Euphorbia ebracteolata 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 = 7500.0 nM PMID[521238]

☑ 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 NPC471795 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
0.9512 High Similarity NPC471796
0.8795 High Similarity NPC311070
0.8605 High Similarity NPC312561
0.8571 High Similarity NPC472377
0.8571 High Similarity NPC23748
0.8571 High Similarity NPC42476
0.8523 High Similarity NPC182136
0.8523 High Similarity NPC310479
0.8523 High Similarity NPC78973
0.8488 Intermediate Similarity NPC471219
0.8488 Intermediate Similarity NPC131813
0.8415 Intermediate Similarity NPC184737
0.8409 Intermediate Similarity NPC470734
0.8372 Intermediate Similarity NPC42586
0.8372 Intermediate Similarity NPC473251
0.8353 Intermediate Similarity NPC49208
0.8353 Intermediate Similarity NPC474809
0.8352 Intermediate Similarity NPC276110
0.8333 Intermediate Similarity NPC152778
0.8333 Intermediate Similarity NPC162615
0.8333 Intermediate Similarity NPC53555
0.8333 Intermediate Similarity NPC205034
0.8315 Intermediate Similarity NPC281942
0.8315 Intermediate Similarity NPC232426
0.8315 Intermediate Similarity NPC280149
0.8315 Intermediate Similarity NPC221111
0.8313 Intermediate Similarity NPC242767
0.8295 Intermediate Similarity NPC472378
0.8295 Intermediate Similarity NPC472810
0.8295 Intermediate Similarity NPC472809
0.8242 Intermediate Similarity NPC470255
0.8242 Intermediate Similarity NPC104925
0.8242 Intermediate Similarity NPC105490
0.8242 Intermediate Similarity NPC469697
0.8242 Intermediate Similarity NPC298973
0.8235 Intermediate Similarity NPC471218
0.8222 Intermediate Similarity NPC141831
0.8222 Intermediate Similarity NPC472811
0.8202 Intermediate Similarity NPC474396
0.8202 Intermediate Similarity NPC5509
0.8202 Intermediate Similarity NPC50488
0.8161 Intermediate Similarity NPC30984
0.8161 Intermediate Similarity NPC86316
0.8161 Intermediate Similarity NPC106416
0.814 Intermediate Similarity NPC193198
0.8132 Intermediate Similarity NPC7349
0.8132 Intermediate Similarity NPC472812
0.8132 Intermediate Similarity NPC115021
0.8118 Intermediate Similarity NPC475944
0.809 Intermediate Similarity NPC474629
0.8072 Intermediate Similarity NPC262747
0.8068 Intermediate Similarity NPC329692
0.8065 Intermediate Similarity NPC473153
0.8065 Intermediate Similarity NPC16967
0.8065 Intermediate Similarity NPC162346
0.8046 Intermediate Similarity NPC96055
0.8043 Intermediate Similarity NPC191521
0.8022 Intermediate Similarity NPC329842
0.8022 Intermediate Similarity NPC177037
0.8022 Intermediate Similarity NPC472814
0.8022 Intermediate Similarity NPC72845
0.8022 Intermediate Similarity NPC303697
0.8 Intermediate Similarity NPC38855
0.8 Intermediate Similarity NPC473647
0.8 Intermediate Similarity NPC474592
0.8 Intermediate Similarity NPC174342
0.8 Intermediate Similarity NPC233332
0.7979 Intermediate Similarity NPC208094
0.7978 Intermediate Similarity NPC473891
0.7976 Intermediate Similarity NPC209135
0.7976 Intermediate Similarity NPC474816
0.7957 Intermediate Similarity NPC295347
0.7957 Intermediate Similarity NPC472441
0.7957 Intermediate Similarity NPC209355
0.7955 Intermediate Similarity NPC474013
0.7955 Intermediate Similarity NPC65661
0.7935 Intermediate Similarity NPC139692
0.7931 Intermediate Similarity NPC12283
0.7931 Intermediate Similarity NPC477124
0.7931 Intermediate Similarity NPC474193
0.7912 Intermediate Similarity NPC51486
0.7907 Intermediate Similarity NPC159148
0.7895 Intermediate Similarity NPC278673
0.7895 Intermediate Similarity NPC474440
0.7895 Intermediate Similarity NPC316598
0.7889 Intermediate Similarity NPC93411
0.7882 Intermediate Similarity NPC100906
0.7872 Intermediate Similarity NPC165632
0.7857 Intermediate Similarity NPC189206
0.7857 Intermediate Similarity NPC283619
0.7849 Intermediate Similarity NPC53685
0.7849 Intermediate Similarity NPC201725
0.7849 Intermediate Similarity NPC57117
0.7849 Intermediate Similarity NPC469491
0.7841 Intermediate Similarity NPC470800
0.7841 Intermediate Similarity NPC82297
0.7841 Intermediate Similarity NPC471301
0.7841 Intermediate Similarity NPC46320
0.7841 Intermediate Similarity NPC474693
0.7841 Intermediate Similarity NPC471302
0.7835 Intermediate Similarity NPC476081
0.7826 Intermediate Similarity NPC477122
0.7826 Intermediate Similarity NPC233345
0.7826 Intermediate Similarity NPC234335
0.7826 Intermediate Similarity NPC186363
0.7816 Intermediate Similarity NPC256112
0.7816 Intermediate Similarity NPC471298
0.7812 Intermediate Similarity NPC474012
0.7812 Intermediate Similarity NPC324841
0.7812 Intermediate Similarity NPC227865
0.7812 Intermediate Similarity NPC476299
0.7802 Intermediate Similarity NPC82876
0.7802 Intermediate Similarity NPC177141
0.7802 Intermediate Similarity NPC261320
0.7802 Intermediate Similarity NPC168131
0.7791 Intermediate Similarity NPC281880
0.7791 Intermediate Similarity NPC268827
0.7789 Intermediate Similarity NPC231751
0.7789 Intermediate Similarity NPC98112
0.7789 Intermediate Similarity NPC51499
0.7789 Intermediate Similarity NPC53844
0.7789 Intermediate Similarity NPC477718
0.7789 Intermediate Similarity NPC202705
0.7789 Intermediate Similarity NPC477719
0.7778 Intermediate Similarity NPC476600
0.7778 Intermediate Similarity NPC166857
0.7778 Intermediate Similarity NPC45957
0.7778 Intermediate Similarity NPC471657
0.7766 Intermediate Similarity NPC183012
0.7765 Intermediate Similarity NPC172066
0.7755 Intermediate Similarity NPC297617
0.7753 Intermediate Similarity NPC475860
0.7753 Intermediate Similarity NPC474694
0.7753 Intermediate Similarity NPC472442
0.7753 Intermediate Similarity NPC35933
0.7753 Intermediate Similarity NPC473659
0.7753 Intermediate Similarity NPC329630
0.7753 Intermediate Similarity NPC189311
0.7753 Intermediate Similarity NPC109528
0.7742 Intermediate Similarity NPC166346
0.7742 Intermediate Similarity NPC156553
0.7738 Intermediate Similarity NPC476317
0.7732 Intermediate Similarity NPC472554
0.7732 Intermediate Similarity NPC11974
0.7727 Intermediate Similarity NPC471297
0.7727 Intermediate Similarity NPC321385
0.7727 Intermediate Similarity NPC476927
0.7727 Intermediate Similarity NPC79945
0.7727 Intermediate Similarity NPC472440
0.7727 Intermediate Similarity NPC57370
0.7723 Intermediate Similarity NPC228477
0.7723 Intermediate Similarity NPC137911
0.7717 Intermediate Similarity NPC209816
0.7717 Intermediate Similarity NPC273199
0.7717 Intermediate Similarity NPC477782
0.7717 Intermediate Similarity NPC220216
0.7708 Intermediate Similarity NPC473154
0.7708 Intermediate Similarity NPC325229
0.7708 Intermediate Similarity NPC222303
0.7708 Intermediate Similarity NPC275086
0.7708 Intermediate Similarity NPC98868
0.7701 Intermediate Similarity NPC325031
0.7701 Intermediate Similarity NPC112868
0.7701 Intermediate Similarity NPC170303
0.7701 Intermediate Similarity NPC142163
0.7692 Intermediate Similarity NPC477128
0.7692 Intermediate Similarity NPC226863
0.7684 Intermediate Similarity NPC242848
0.7684 Intermediate Similarity NPC154526
0.7684 Intermediate Similarity NPC134072
0.7684 Intermediate Similarity NPC234993
0.7684 Intermediate Similarity NPC472363
0.7684 Intermediate Similarity NPC472362
0.7677 Intermediate Similarity NPC272632
0.7674 Intermediate Similarity NPC80471
0.7674 Intermediate Similarity NPC5908
0.7674 Intermediate Similarity NPC110373
0.7674 Intermediate Similarity NPC17550
0.7674 Intermediate Similarity NPC233295
0.766 Intermediate Similarity NPC477130
0.766 Intermediate Similarity NPC477129
0.766 Intermediate Similarity NPC324078
0.7654 Intermediate Similarity NPC101622
0.7653 Intermediate Similarity NPC32577
0.7653 Intermediate Similarity NPC472552
0.7653 Intermediate Similarity NPC31058
0.7653 Intermediate Similarity NPC114540
0.7653 Intermediate Similarity NPC469606
0.7653 Intermediate Similarity NPC109195
0.7653 Intermediate Similarity NPC155332
0.7653 Intermediate Similarity NPC273005
0.7653 Intermediate Similarity NPC475038
0.7653 Intermediate Similarity NPC11956
0.7647 Intermediate Similarity NPC476439
0.764 Intermediate Similarity NPC302360
0.764 Intermediate Similarity NPC32223
0.764 Intermediate Similarity NPC306951
0.764 Intermediate Similarity NPC102048
0.764 Intermediate Similarity NPC318515
0.7634 Intermediate Similarity NPC249034

  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 NPC471795 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
0.7614 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7526 Intermediate Similarity NPD7638 Approved
0.7526 Intermediate Similarity NPD4225 Approved
0.7449 Intermediate Similarity NPD7640 Approved
0.7449 Intermediate Similarity NPD7639 Approved
0.7444 Intermediate Similarity NPD6400 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7174 Intermediate Similarity NPD1694 Approved
0.7115 Intermediate Similarity NPD6686 Approved
0.7053 Intermediate Similarity NPD6051 Approved
0.703 Intermediate Similarity NPD5344 Discontinued
0.701 Intermediate Similarity NPD6399 Phase 3
0.6979 Remote Similarity NPD7838 Discovery
0.6979 Remote Similarity NPD5785 Approved
0.6951 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6932 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6915 Remote Similarity NPD7334 Approved
0.6915 Remote Similarity NPD6409 Approved
0.6915 Remote Similarity NPD6684 Approved
0.6915 Remote Similarity NPD7146 Approved
0.6915 Remote Similarity NPD7521 Approved
0.6915 Remote Similarity NPD5330 Approved
0.6907 Remote Similarity NPD7637 Suspended
0.6882 Remote Similarity NPD3665 Phase 1
0.6882 Remote Similarity NPD3666 Approved
0.6882 Remote Similarity NPD3133 Approved
0.6848 Remote Similarity NPD3667 Approved
0.6818 Remote Similarity NPD6942 Approved
0.6818 Remote Similarity NPD7339 Approved
0.6813 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6809 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6804 Remote Similarity NPD46 Approved
0.6804 Remote Similarity NPD6698 Approved
0.6796 Remote Similarity NPD7632 Discontinued
0.6771 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6771 Remote Similarity NPD6903 Approved
0.6768 Remote Similarity NPD7748 Approved
0.6765 Remote Similarity NPD6648 Approved
0.6757 Remote Similarity NPD7115 Discovery
0.6737 Remote Similarity NPD3618 Phase 1
0.6735 Remote Similarity NPD7515 Phase 2
0.6733 Remote Similarity NPD7902 Approved
0.6733 Remote Similarity NPD6084 Phase 2
0.6733 Remote Similarity NPD6083 Phase 2
0.6729 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6705 Remote Similarity NPD6926 Approved
0.6705 Remote Similarity NPD6924 Approved
0.6703 Remote Similarity NPD4195 Approved
0.6702 Remote Similarity NPD4786 Approved
0.6702 Remote Similarity NPD7338 Clinical (unspecified phase)
0.67 Remote Similarity NPD5695 Phase 3
0.6698 Remote Similarity NPD5697 Approved
0.6697 Remote Similarity NPD6053 Discontinued
0.6696 Remote Similarity NPD7327 Approved
0.6696 Remote Similarity NPD7328 Approved
0.6667 Remote Similarity NPD5209 Approved
0.6667 Remote Similarity NPD6371 Approved
0.6667 Remote Similarity NPD8033 Approved
0.6637 Remote Similarity NPD7516 Approved
0.6636 Remote Similarity NPD6881 Approved
0.6636 Remote Similarity NPD6011 Approved
0.6636 Remote Similarity NPD6899 Approved
0.663 Remote Similarity NPD4819 Approved
0.663 Remote Similarity NPD4822 Approved
0.663 Remote Similarity NPD4821 Approved
0.663 Remote Similarity NPD7525 Registered
0.663 Remote Similarity NPD4820 Approved
0.6629 Remote Similarity NPD8039 Approved
0.6629 Remote Similarity NPD8264 Approved
0.6627 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6604 Remote Similarity NPD6675 Approved
0.6604 Remote Similarity NPD7128 Approved
0.6604 Remote Similarity NPD6402 Approved
0.6604 Remote Similarity NPD5739 Approved
0.6598 Remote Similarity NPD5737 Approved
0.6598 Remote Similarity NPD6672 Approved
0.6596 Remote Similarity NPD7154 Phase 3
0.6596 Remote Similarity NPD5362 Discontinued
0.6596 Remote Similarity NPD6695 Phase 3
0.6593 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6593 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6593 Remote Similarity NPD4271 Approved
0.6593 Remote Similarity NPD4268 Approved
0.6579 Remote Similarity NPD8294 Approved
0.6579 Remote Similarity NPD8377 Approved
0.6574 Remote Similarity NPD6012 Approved
0.6574 Remote Similarity NPD6014 Approved
0.6574 Remote Similarity NPD6013 Approved
0.6566 Remote Similarity NPD6411 Approved
0.6566 Remote Similarity NPD5693 Phase 1
0.6566 Remote Similarity NPD5284 Approved
0.6566 Remote Similarity NPD5281 Approved
0.6566 Remote Similarity NPD6079 Approved
0.6562 Remote Similarity NPD5279 Phase 3
0.6562 Remote Similarity NPD4519 Discontinued
0.6562 Remote Similarity NPD4623 Approved
0.6556 Remote Similarity NPD6933 Approved
0.6552 Remote Similarity NPD7143 Approved
0.6552 Remote Similarity NPD7144 Approved
0.6542 Remote Similarity NPD5701 Approved
0.6531 Remote Similarity NPD5328 Approved
0.6522 Remote Similarity NPD8378 Approved
0.6522 Remote Similarity NPD8380 Approved
0.6522 Remote Similarity NPD8335 Approved
0.6522 Remote Similarity NPD7503 Approved
0.6522 Remote Similarity NPD7645 Phase 2
0.6522 Remote Similarity NPD6929 Approved
0.6522 Remote Similarity NPD8296 Approved
0.6522 Remote Similarity NPD8379 Approved
0.6514 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6514 Remote Similarity NPD6883 Approved
0.6514 Remote Similarity NPD7102 Approved
0.6514 Remote Similarity NPD7290 Approved
0.6505 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6505 Remote Similarity NPD5696 Approved
0.65 Remote Similarity NPD5779 Approved
0.65 Remote Similarity NPD4202 Approved
0.65 Remote Similarity NPD5778 Approved
0.6495 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6481 Remote Similarity NPD7320 Approved
0.6477 Remote Similarity NPD7150 Approved
0.6477 Remote Similarity NPD7151 Approved
0.6477 Remote Similarity NPD7152 Approved
0.6471 Remote Similarity NPD4792 Clinical (unspecified phase)
0.6458 Remote Similarity NPD5363 Approved
0.6455 Remote Similarity NPD6650 Approved
0.6455 Remote Similarity NPD8130 Phase 1
0.6455 Remote Similarity NPD6869 Approved
0.6455 Remote Similarity NPD6617 Approved
0.6455 Remote Similarity NPD6847 Approved
0.6455 Remote Similarity NPD6649 Approved
0.6452 Remote Similarity NPD7514 Phase 3
0.6452 Remote Similarity NPD6931 Approved
0.6452 Remote Similarity NPD7509 Discontinued
0.6452 Remote Similarity NPD6930 Phase 2
0.6452 Remote Similarity NPD7332 Phase 2
0.6437 Remote Similarity NPD6923 Approved
0.6437 Remote Similarity NPD6922 Approved
0.6436 Remote Similarity NPD7900 Approved
0.6436 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6422 Remote Similarity NPD6372 Approved
0.6422 Remote Similarity NPD6373 Approved
0.6421 Remote Similarity NPD5332 Approved
0.6421 Remote Similarity NPD5331 Approved
0.6413 Remote Similarity NPD7145 Approved
0.6396 Remote Similarity NPD6882 Approved
0.6396 Remote Similarity NPD8297 Approved
0.6392 Remote Similarity NPD4249 Approved
0.6389 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6386 Remote Similarity NPD4194 Approved
0.6386 Remote Similarity NPD4193 Approved
0.6386 Remote Similarity NPD4191 Approved
0.6386 Remote Similarity NPD368 Approved
0.6386 Remote Similarity NPD4192 Approved
0.6383 Remote Similarity NPD4790 Discontinued
0.6383 Remote Similarity NPD6902 Approved
0.6364 Remote Similarity NPD4753 Phase 2
0.6364 Remote Similarity NPD6101 Approved
0.6364 Remote Similarity NPD1695 Approved
0.6364 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6333 Remote Similarity NPD4785 Approved
0.6333 Remote Similarity NPD4784 Approved
0.6327 Remote Similarity NPD7524 Approved
0.6327 Remote Similarity NPD3573 Approved
0.6327 Remote Similarity NPD4251 Approved
0.6327 Remote Similarity NPD4250 Approved
0.6327 Remote Similarity NPD7750 Discontinued
0.6321 Remote Similarity NPD5211 Phase 2
0.6316 Remote Similarity NPD6435 Approved
0.6316 Remote Similarity NPD4270 Approved
0.6316 Remote Similarity NPD4221 Approved
0.6316 Remote Similarity NPD4269 Approved
0.6316 Remote Similarity NPD4223 Phase 3
0.6311 Remote Similarity NPD5221 Approved
0.6311 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6311 Remote Similarity NPD5222 Approved
0.6306 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6304 Remote Similarity NPD6932 Approved
0.6304 Remote Similarity NPD6925 Approved
0.6304 Remote Similarity NPD5776 Phase 2
0.6303 Remote Similarity NPD7507 Approved
0.63 Remote Similarity NPD5207 Approved
0.6289 Remote Similarity NPD1696 Phase 3
0.6289 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6286 Remote Similarity NPD4696 Approved
0.6286 Remote Similarity NPD5285 Approved
0.6286 Remote Similarity NPD5286 Approved
0.6277 Remote Similarity NPD4695 Discontinued
0.6275 Remote Similarity NPD5282 Discontinued
0.6263 Remote Similarity NPD5208 Approved
0.625 Remote Similarity NPD4755 Approved
0.625 Remote Similarity NPD5173 Approved
0.6239 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6239 Remote Similarity NPD6412 Phase 2
0.6238 Remote Similarity NPD8035 Phase 2
0.6238 Remote Similarity NPD5694 Approved
0.6238 Remote Similarity NPD8034 Phase 2
0.6226 Remote Similarity NPD5223 Approved
0.6224 Remote Similarity NPD5690 Phase 2
0.6224 Remote Similarity NPD5786 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