Structure

Physi-Chem Properties

Molecular Weight:  318.22
Volume:  347.268
LogP:  3.527
LogD:  3.429
LogS:  -4.697
# Rotatable Bonds:  2
TPSA:  46.53
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.621
Synthetic Accessibility Score:  4.81
Fsp3:  0.75
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.694
MDCK Permeability:  2.6092249754583463e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.033
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.022
30% Bioavailability (F30%):  0.036

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.977
Plasma Protein Binding (PPB):  54.296085357666016%
Volume Distribution (VD):  1.183
Pgp-substrate:  60.08005905151367%

ADMET: Metabolism

CYP1A2-inhibitor:  0.096
CYP1A2-substrate:  0.328
CYP2C19-inhibitor:  0.275
CYP2C19-substrate:  0.752
CYP2C9-inhibitor:  0.293
CYP2C9-substrate:  0.128
CYP2D6-inhibitor:  0.01
CYP2D6-substrate:  0.565
CYP3A4-inhibitor:  0.748
CYP3A4-substrate:  0.258

ADMET: Excretion

Clearance (CL):  12.658
Half-life (T1/2):  0.052

ADMET: Toxicity

hERG Blockers:  0.016
Human Hepatotoxicity (H-HT):  0.027
Drug-inuced Liver Injury (DILI):  0.05
AMES Toxicity:  0.01
Rat Oral Acute Toxicity:  0.673
Maximum Recommended Daily Dose:  0.949
Skin Sensitization:  0.077
Carcinogencity:  0.06
Eye Corrosion:  0.152
Eye Irritation:  0.182
Respiratory Toxicity:  0.952

Download Data

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

  Natural Product: NPC474396

Natural Product ID:  NPC474396
Common Name*:   Hedychia Lactone B
IUPAC Name:   (3E)-3-[2-[(1R,3S,8aS)-3-hydroxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]oxolan-2-one
Synonyms:  
Standard InCHIKey:  NTDYMFJJFRUEDG-JDALIJFYSA-N
Standard InCHI:  InChI=1S/C20H30O3/c1-13-15(7-6-14-8-11-23-18(14)22)20(4)10-5-9-19(2,3)17(20)12-16(13)21/h6,15-17,21H,1,5,7-12H2,2-4H3/b14-6+/t15-,16-,17?,20+/m0/s1
SMILES:  CC1(CCCC2(C1CC(C(=C)C2CC=C3CCOC3=O)O)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL466125
PubChem CID:   11099202
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000050] Lactones
        • [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO14969 Hedychium spicatum Species Zingiberaceae Eukaryota n.a. rhizome n.a. PMID[19027298]
NPO14969 Hedychium spicatum Species Zingiberaceae Eukaryota rhizomes n.a. n.a. PMID[19332371]
NPO14969 Hedychium spicatum Species Zingiberaceae Eukaryota rhizomes n.a. n.a. PMID[19782567]
NPO14969 Hedychium spicatum Species Zingiberaceae Eukaryota n.a. rhizome n.a. PMID[23422227]
NPO14969 Hedychium spicatum Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14969 Hedychium spicatum Species Zingiberaceae 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
NPT2 Others Unspecified Inhibition = 11.3 % PMID[545222]

☑ 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 NPC474396 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 NPC50488
0.9639 High Similarity NPC329692
0.954 High Similarity NPC57117
0.9535 High Similarity NPC72845
0.9222 High Similarity NPC474343
0.9195 High Similarity NPC182136
0.9121 High Similarity NPC124512
0.9121 High Similarity NPC159763
0.9121 High Similarity NPC278386
0.9011 High Similarity NPC73911
0.8977 High Similarity NPC310479
0.8913 High Similarity NPC473154
0.8824 High Similarity NPC311070
0.8791 High Similarity NPC183012
0.8778 High Similarity NPC205034
0.8778 High Similarity NPC139692
0.8778 High Similarity NPC162615
0.8778 High Similarity NPC152778
0.8764 High Similarity NPC78973
0.8764 High Similarity NPC221111
0.8764 High Similarity NPC280149
0.8736 High Similarity NPC131813
0.8696 High Similarity NPC242848
0.8696 High Similarity NPC234993
0.8696 High Similarity NPC473153
0.8696 High Similarity NPC134072
0.8667 High Similarity NPC177037
0.8667 High Similarity NPC186363
0.8667 High Similarity NPC472811
0.8667 High Similarity NPC472814
0.8667 High Similarity NPC233345
0.8652 High Similarity NPC79027
0.8636 High Similarity NPC181103
0.8621 High Similarity NPC86316
0.8621 High Similarity NPC476602
0.8621 High Similarity NPC106416
0.8588 High Similarity NPC159148
0.8571 High Similarity NPC472812
0.8571 High Similarity NPC53555
0.8556 High Similarity NPC158488
0.8542 High Similarity NPC476237
0.8526 High Similarity NPC303559
0.8506 High Similarity NPC96055
0.8495 Intermediate Similarity NPC16967
0.8478 Intermediate Similarity NPC470255
0.8478 Intermediate Similarity NPC191521
0.8471 Intermediate Similarity NPC281880
0.8444 Intermediate Similarity NPC168131
0.8427 Intermediate Similarity NPC473891
0.8427 Intermediate Similarity NPC312561
0.8427 Intermediate Similarity NPC305029
0.8427 Intermediate Similarity NPC166857
0.8421 Intermediate Similarity NPC47024
0.8409 Intermediate Similarity NPC30984
0.8409 Intermediate Similarity NPC217394
0.8409 Intermediate Similarity NPC65661
0.8409 Intermediate Similarity NPC52628
0.8404 Intermediate Similarity NPC253826
0.8391 Intermediate Similarity NPC42476
0.8391 Intermediate Similarity NPC79945
0.8372 Intermediate Similarity NPC170303
0.837 Intermediate Similarity NPC115021
0.8352 Intermediate Similarity NPC38952
0.8352 Intermediate Similarity NPC51486
0.8352 Intermediate Similarity NPC253186
0.8333 Intermediate Similarity NPC277771
0.8333 Intermediate Similarity NPC472809
0.8333 Intermediate Similarity NPC104560
0.8333 Intermediate Similarity NPC472810
0.8333 Intermediate Similarity NPC189206
0.8316 Intermediate Similarity NPC474440
0.8316 Intermediate Similarity NPC23364
0.8316 Intermediate Similarity NPC316598
0.8316 Intermediate Similarity NPC218107
0.8316 Intermediate Similarity NPC478056
0.8315 Intermediate Similarity NPC85698
0.8283 Intermediate Similarity NPC110496
0.828 Intermediate Similarity NPC250075
0.8276 Intermediate Similarity NPC178676
0.8261 Intermediate Similarity NPC329842
0.8261 Intermediate Similarity NPC477783
0.8256 Intermediate Similarity NPC10636
0.8247 Intermediate Similarity NPC469606
0.8247 Intermediate Similarity NPC476081
0.8247 Intermediate Similarity NPC273005
0.8247 Intermediate Similarity NPC31058
0.8242 Intermediate Similarity NPC146554
0.8242 Intermediate Similarity NPC472240
0.8242 Intermediate Similarity NPC116620
0.8242 Intermediate Similarity NPC262858
0.8242 Intermediate Similarity NPC5509
0.8242 Intermediate Similarity NPC251528
0.8242 Intermediate Similarity NPC174342
0.8242 Intermediate Similarity NPC73995
0.8229 Intermediate Similarity NPC476299
0.8229 Intermediate Similarity NPC474012
0.8229 Intermediate Similarity NPC476303
0.8229 Intermediate Similarity NPC251680
0.8229 Intermediate Similarity NPC201406
0.8222 Intermediate Similarity NPC470012
0.8211 Intermediate Similarity NPC475709
0.8202 Intermediate Similarity NPC471795
0.82 Intermediate Similarity NPC189075
0.82 Intermediate Similarity NPC275539
0.8191 Intermediate Similarity NPC209355
0.8191 Intermediate Similarity NPC472441
0.8191 Intermediate Similarity NPC276110
0.8182 Intermediate Similarity NPC476927
0.8182 Intermediate Similarity NPC470948
0.8182 Intermediate Similarity NPC22611
0.8182 Intermediate Similarity NPC472377
0.8172 Intermediate Similarity NPC38232
0.8172 Intermediate Similarity NPC166346
0.8172 Intermediate Similarity NPC472303
0.8163 Intermediate Similarity NPC120321
0.8163 Intermediate Similarity NPC176883
0.8152 Intermediate Similarity NPC477782
0.8152 Intermediate Similarity NPC232426
0.8152 Intermediate Similarity NPC281942
0.8152 Intermediate Similarity NPC232202
0.8152 Intermediate Similarity NPC152467
0.8144 Intermediate Similarity NPC471412
0.8144 Intermediate Similarity NPC81530
0.814 Intermediate Similarity NPC242767
0.8132 Intermediate Similarity NPC226863
0.8132 Intermediate Similarity NPC291665
0.8132 Intermediate Similarity NPC215831
0.8125 Intermediate Similarity NPC216478
0.8125 Intermediate Similarity NPC57079
0.8125 Intermediate Similarity NPC108368
0.8111 Intermediate Similarity NPC185638
0.8111 Intermediate Similarity NPC250981
0.8111 Intermediate Similarity NPC9231
0.8111 Intermediate Similarity NPC477920
0.8111 Intermediate Similarity NPC471219
0.8111 Intermediate Similarity NPC6979
0.8105 Intermediate Similarity NPC472363
0.8105 Intermediate Similarity NPC190713
0.8105 Intermediate Similarity NPC154526
0.8105 Intermediate Similarity NPC202833
0.8105 Intermediate Similarity NPC165632
0.8105 Intermediate Similarity NPC472362
0.81 Intermediate Similarity NPC187435
0.81 Intermediate Similarity NPC67321
0.809 Intermediate Similarity NPC102048
0.809 Intermediate Similarity NPC32223
0.809 Intermediate Similarity NPC306951
0.8085 Intermediate Similarity NPC477129
0.8085 Intermediate Similarity NPC119562
0.8085 Intermediate Similarity NPC477130
0.8085 Intermediate Similarity NPC24861
0.8085 Intermediate Similarity NPC476186
0.8085 Intermediate Similarity NPC105490
0.8085 Intermediate Similarity NPC279410
0.8085 Intermediate Similarity NPC469697
0.8081 Intermediate Similarity NPC118911
0.8068 Intermediate Similarity NPC256112
0.8068 Intermediate Similarity NPC2524
0.8068 Intermediate Similarity NPC200513
0.8068 Intermediate Similarity NPC226988
0.8068 Intermediate Similarity NPC155521
0.8068 Intermediate Similarity NPC471218
0.8065 Intermediate Similarity NPC141831
0.8065 Intermediate Similarity NPC289479
0.8065 Intermediate Similarity NPC473675
0.8065 Intermediate Similarity NPC49420
0.8065 Intermediate Similarity NPC303697
0.8065 Intermediate Similarity NPC74296
0.8065 Intermediate Similarity NPC110923
0.8061 Intermediate Similarity NPC58329
0.8061 Intermediate Similarity NPC155332
0.8061 Intermediate Similarity NPC136289
0.8061 Intermediate Similarity NPC475038
0.8061 Intermediate Similarity NPC32577
0.8061 Intermediate Similarity NPC109195
0.8061 Intermediate Similarity NPC114540
0.8043 Intermediate Similarity NPC288699
0.8043 Intermediate Similarity NPC470734
0.8043 Intermediate Similarity NPC82876
0.8043 Intermediate Similarity NPC314727
0.8043 Intermediate Similarity NPC206001
0.8043 Intermediate Similarity NPC218927
0.8041 Intermediate Similarity NPC471413
0.8041 Intermediate Similarity NPC472644
0.8041 Intermediate Similarity NPC476767
0.8041 Intermediate Similarity NPC38855
0.8041 Intermediate Similarity NPC476274
0.8041 Intermediate Similarity NPC266955
0.8041 Intermediate Similarity NPC117685
0.8023 Intermediate Similarity NPC184737
0.8021 Intermediate Similarity NPC287668
0.8021 Intermediate Similarity NPC224356
0.8021 Intermediate Similarity NPC132753
0.8021 Intermediate Similarity NPC175351
0.8021 Intermediate Similarity NPC141401
0.8021 Intermediate Similarity NPC170131
0.8021 Intermediate Similarity NPC121402
0.8021 Intermediate Similarity NPC151681
0.802 Intermediate Similarity NPC306265
0.8 Intermediate Similarity NPC478208

  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 NPC474396 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
0.9121 High Similarity NPD4225 Approved
0.8229 Intermediate Similarity NPD7640 Approved
0.8229 Intermediate Similarity NPD7639 Approved
0.8125 Intermediate Similarity NPD7638 Approved
0.8068 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7802 Intermediate Similarity NPD1694 Approved
0.7593 Intermediate Similarity NPD7115 Discovery
0.7527 Intermediate Similarity NPD3618 Phase 1
0.7525 Intermediate Similarity NPD7632 Discontinued
0.7423 Intermediate Similarity NPD6399 Phase 3
0.7396 Intermediate Similarity NPD5785 Approved
0.7347 Intermediate Similarity NPD7748 Approved
0.7333 Intermediate Similarity NPD6686 Approved
0.732 Intermediate Similarity NPD7637 Suspended
0.732 Intermediate Similarity NPD7515 Phase 2
0.7312 Intermediate Similarity NPD6400 Clinical (unspecified phase)
0.73 Intermediate Similarity NPD7902 Approved
0.7283 Intermediate Similarity NPD3667 Approved
0.7273 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD7521 Approved
0.7158 Intermediate Similarity NPD7334 Approved
0.7158 Intermediate Similarity NPD6409 Approved
0.7158 Intermediate Similarity NPD7146 Approved
0.7158 Intermediate Similarity NPD6684 Approved
0.7158 Intermediate Similarity NPD5330 Approved
0.7143 Intermediate Similarity NPD6079 Approved
0.7128 Intermediate Similarity NPD3666 Approved
0.7128 Intermediate Similarity NPD3133 Approved
0.7128 Intermediate Similarity NPD4786 Approved
0.7128 Intermediate Similarity NPD3665 Phase 1
0.7113 Intermediate Similarity NPD5328 Approved
0.7087 Intermediate Similarity NPD5344 Discontinued
0.7075 Intermediate Similarity NPD5697 Approved
0.701 Intermediate Similarity NPD6903 Approved
0.701 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD6011 Approved
0.7009 Intermediate Similarity NPD6881 Approved
0.7009 Intermediate Similarity NPD6899 Approved
0.7 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD7900 Approved
0.7 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.6981 Remote Similarity NPD5739 Approved
0.6981 Remote Similarity NPD6402 Approved
0.6981 Remote Similarity NPD7128 Approved
0.6981 Remote Similarity NPD6675 Approved
0.6972 Remote Similarity NPD6649 Approved
0.6972 Remote Similarity NPD6650 Approved
0.6961 Remote Similarity NPD6084 Phase 2
0.6961 Remote Similarity NPD6083 Phase 2
0.6944 Remote Similarity NPD6373 Approved
0.6944 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6944 Remote Similarity NPD6372 Approved
0.6944 Remote Similarity NPD6012 Approved
0.6944 Remote Similarity NPD6013 Approved
0.6944 Remote Similarity NPD6014 Approved
0.6939 Remote Similarity NPD6051 Approved
0.6916 Remote Similarity NPD5701 Approved
0.6907 Remote Similarity NPD3573 Approved
0.69 Remote Similarity NPD5779 Approved
0.69 Remote Similarity NPD4202 Approved
0.69 Remote Similarity NPD5778 Approved
0.6893 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6893 Remote Similarity NPD5696 Approved
0.6889 Remote Similarity NPD8264 Approved
0.6889 Remote Similarity NPD7339 Approved
0.6889 Remote Similarity NPD6942 Approved
0.6882 Remote Similarity NPD4695 Discontinued
0.6881 Remote Similarity NPD7102 Approved
0.6881 Remote Similarity NPD7290 Approved
0.6881 Remote Similarity NPD6883 Approved
0.6881 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6875 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6875 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6875 Remote Similarity NPD1696 Phase 3
0.6875 Remote Similarity NPD5363 Approved
0.6863 Remote Similarity NPD5221 Approved
0.6863 Remote Similarity NPD4697 Phase 3
0.6863 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6863 Remote Similarity NPD5222 Approved
0.6857 Remote Similarity NPD5211 Phase 2
0.6852 Remote Similarity NPD7320 Approved
0.6842 Remote Similarity NPD6695 Phase 3
0.6837 Remote Similarity NPD6672 Approved
0.6837 Remote Similarity NPD5737 Approved
0.6827 Remote Similarity NPD6648 Approved
0.6822 Remote Similarity NPD6008 Approved
0.6818 Remote Similarity NPD6617 Approved
0.6818 Remote Similarity NPD6869 Approved
0.6818 Remote Similarity NPD8130 Phase 1
0.6818 Remote Similarity NPD6847 Approved
0.6804 Remote Similarity NPD5279 Phase 3
0.6804 Remote Similarity NPD4623 Approved
0.6804 Remote Similarity NPD4519 Discontinued
0.68 Remote Similarity NPD8034 Phase 2
0.68 Remote Similarity NPD5693 Phase 1
0.68 Remote Similarity NPD8035 Phase 2
0.68 Remote Similarity NPD6411 Approved
0.6796 Remote Similarity NPD5173 Approved
0.6778 Remote Similarity NPD6926 Approved
0.6778 Remote Similarity NPD6924 Approved
0.6774 Remote Similarity NPD7645 Phase 2
0.6774 Remote Similarity NPD6929 Approved
0.6771 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6765 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6765 Remote Similarity NPD5695 Phase 3
0.6757 Remote Similarity NPD6882 Approved
0.6757 Remote Similarity NPD8297 Approved
0.6737 Remote Similarity NPD5209 Approved
0.6735 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6729 Remote Similarity NPD5141 Approved
0.6727 Remote Similarity NPD6371 Approved
0.6702 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6702 Remote Similarity NPD7525 Registered
0.6702 Remote Similarity NPD6930 Phase 2
0.6702 Remote Similarity NPD6931 Approved
0.67 Remote Similarity NPD6698 Approved
0.67 Remote Similarity NPD46 Approved
0.67 Remote Similarity NPD7838 Discovery
0.6667 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5362 Discontinued
0.6667 Remote Similarity NPD4696 Approved
0.6667 Remote Similarity NPD5286 Approved
0.6667 Remote Similarity NPD5285 Approved
0.6667 Remote Similarity NPD7154 Phase 3
0.6667 Remote Similarity NPD6001 Approved
0.6667 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6635 Remote Similarity NPD4755 Approved
0.6633 Remote Similarity NPD3574 Clinical (unspecified phase)
0.663 Remote Similarity NPD6933 Approved
0.6628 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6609 Remote Similarity NPD7328 Approved
0.6609 Remote Similarity NPD7327 Approved
0.6606 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6604 Remote Similarity NPD5223 Approved
0.6602 Remote Similarity NPD5210 Approved
0.6602 Remote Similarity NPD4629 Approved
0.66 Remote Similarity NPD5764 Clinical (unspecified phase)
0.66 Remote Similarity NPD6101 Approved
0.66 Remote Similarity NPD4753 Phase 2
0.6598 Remote Similarity NPD3668 Phase 3
0.6596 Remote Similarity NPD4195 Approved
0.6581 Remote Similarity NPD8033 Approved
0.6581 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6579 Remote Similarity NPD6868 Approved
0.6579 Remote Similarity NPD6274 Approved
0.6566 Remote Similarity NPD7524 Approved
0.6566 Remote Similarity NPD7750 Discontinued
0.6562 Remote Similarity NPD4269 Approved
0.6562 Remote Similarity NPD4223 Phase 3
0.6562 Remote Similarity NPD4221 Approved
0.6562 Remote Similarity NPD4270 Approved
0.6559 Remote Similarity NPD6925 Approved
0.6559 Remote Similarity NPD5776 Phase 2
0.6556 Remote Similarity NPD7152 Approved
0.6556 Remote Similarity NPD7151 Approved
0.6556 Remote Similarity NPD7150 Approved
0.6552 Remote Similarity NPD7516 Approved
0.6549 Remote Similarity NPD4632 Approved
0.6542 Remote Similarity NPD5226 Approved
0.6542 Remote Similarity NPD5225 Approved
0.6542 Remote Similarity NPD5224 Approved
0.6542 Remote Similarity NPD4633 Approved
0.6535 Remote Similarity NPD5207 Approved
0.6526 Remote Similarity NPD4821 Approved
0.6526 Remote Similarity NPD7514 Phase 3
0.6526 Remote Similarity NPD4819 Approved
0.6526 Remote Similarity NPD7509 Discontinued
0.6526 Remote Similarity NPD4822 Approved
0.6526 Remote Similarity NPD7332 Phase 2
0.6526 Remote Similarity NPD4820 Approved
0.6522 Remote Similarity NPD8039 Approved
0.6522 Remote Similarity NPD6317 Approved
0.6517 Remote Similarity NPD6922 Approved
0.6517 Remote Similarity NPD6923 Approved
0.6509 Remote Similarity NPD4700 Approved
0.65 Remote Similarity NPD7507 Approved
0.65 Remote Similarity NPD5208 Approved
0.6496 Remote Similarity NPD8377 Approved
0.6496 Remote Similarity NPD8294 Approved
0.6495 Remote Similarity NPD5331 Approved
0.6495 Remote Similarity NPD5332 Approved
0.6489 Remote Similarity NPD4271 Approved
0.6489 Remote Similarity NPD7145 Approved
0.6489 Remote Similarity NPD4268 Approved
0.6481 Remote Similarity NPD5175 Approved
0.6481 Remote Similarity NPD5174 Approved
0.6471 Remote Similarity NPD5281 Approved
0.6471 Remote Similarity NPD5284 Approved
0.6466 Remote Similarity NPD6335 Approved
0.6466 Remote Similarity NPD6313 Approved
0.6466 Remote Similarity NPD6314 Approved
0.6465 Remote Similarity NPD4249 Approved
0.6465 Remote Similarity NPD5786 Approved
0.646 Remote Similarity NPD6053 Discontinued
0.6458 Remote Similarity NPD4790 Discontinued
0.6458 Remote Similarity NPD6902 Approved
0.6455 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6444 Remote Similarity NPD7144 Approved
0.6444 Remote Similarity NPD7143 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