Structure

Physi-Chem Properties

Molecular Weight:  336.16
Volume:  336.41
LogP:  1.247
LogD:  1.261
LogS:  -3.494
# Rotatable Bonds:  4
TPSA:  89.9
# H-Bond Aceptor:  6
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.621
Synthetic Accessibility Score:  4.557
Fsp3:  0.722
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  2
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.818
MDCK Permeability:  2.116437281074468e-05
Pgp-inhibitor:  0.037
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.027
20% Bioavailability (F20%):  0.939
30% Bioavailability (F30%):  0.755

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.779
Plasma Protein Binding (PPB):  39.52910232543945%
Volume Distribution (VD):  0.525
Pgp-substrate:  64.57937622070312%

ADMET: Metabolism

CYP1A2-inhibitor:  0.147
CYP1A2-substrate:  0.466
CYP2C19-inhibitor:  0.156
CYP2C19-substrate:  0.49
CYP2C9-inhibitor:  0.052
CYP2C9-substrate:  0.192
CYP2D6-inhibitor:  0.012
CYP2D6-substrate:  0.071
CYP3A4-inhibitor:  0.271
CYP3A4-substrate:  0.288

ADMET: Excretion

Clearance (CL):  7.229
Half-life (T1/2):  0.808

ADMET: Toxicity

hERG Blockers:  0.013
Human Hepatotoxicity (H-HT):  0.121
Drug-inuced Liver Injury (DILI):  0.127
AMES Toxicity:  0.067
Rat Oral Acute Toxicity:  0.168
Maximum Recommended Daily Dose:  0.892
Skin Sensitization:  0.667
Carcinogencity:  0.485
Eye Corrosion:  0.019
Eye Irritation:  0.07
Respiratory Toxicity:  0.637

Download Data

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

  Natural Product: NPC473273

Natural Product ID:  NPC473273
Common Name*:   Chiapin B
IUPAC Name:   [(3aS,6aR,9aS,9bR)-6a-hydroxy-9a-methyl-3-methylidene-2,9-dioxo-4,5,6,7,8,9b-hexahydro-3aH-azuleno[4,5-b]furan-6-yl]methyl propanoate
Synonyms:  
Standard InCHIKey:  VNEOIQPRCFAFBK-KKTJJFPLSA-N
Standard InCHI:  InChI=1S/C18H24O6/c1-4-14(20)23-9-11-5-6-12-10(2)16(21)24-15(12)17(3)13(19)7-8-18(11,17)22/h11-12,15,22H,2,4-9H2,1,3H3/t11?,12-,15+,17-,18+/m0/s1
SMILES:  CCC(=O)OCC1CC[C@@H]2[C@H]([C@]3([C@@]1(O)CCC3=O)C)OC(=O)C2=C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL389845
PubChem CID:   44421651
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones
          • [CHEMONTID:0001543] Sesquiterpene lactones
            • [CHEMONTID:0002046] Ambrosanolides and secoambrosanolides

*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
NPO33481 parthenium hispitum Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[17291045]

☑ 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
NPT191 Organism Hepatitis C virus Hepatitis C virus Inhibition = 26.0 % PMID[570244]

☑ 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 NPC473273 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 NPC473234
1.0 High Similarity NPC60386
1.0 High Similarity NPC308656
1.0 High Similarity NPC473263
0.9556 High Similarity NPC213947
0.9556 High Similarity NPC108475
0.9556 High Similarity NPC170143
0.9545 High Similarity NPC153590
0.9444 High Similarity NPC142529
0.9444 High Similarity NPC91771
0.9419 High Similarity NPC201658
0.9326 High Similarity NPC200237
0.9213 High Similarity NPC286341
0.9213 High Similarity NPC191339
0.913 High Similarity NPC311904
0.9101 High Similarity NPC54065
0.9101 High Similarity NPC297474
0.9043 High Similarity NPC171759
0.9011 High Similarity NPC473331
0.9 High Similarity NPC171360
0.9 High Similarity NPC35959
0.9 High Similarity NPC133888
0.9 High Similarity NPC29821
0.9 High Similarity NPC184063
0.9 High Similarity NPC293001
0.9 High Similarity NPC57304
0.9 High Similarity NPC63193
0.8989 High Similarity NPC12872
0.8989 High Similarity NPC155935
0.8989 High Similarity NPC168679
0.8977 High Similarity NPC118601
0.8913 High Similarity NPC163228
0.8889 High Similarity NPC35809
0.8889 High Similarity NPC19087
0.8876 High Similarity NPC178875
0.8876 High Similarity NPC79549
0.8864 High Similarity NPC238593
0.8864 High Similarity NPC56593
0.8778 High Similarity NPC38392
0.8778 High Similarity NPC215556
0.8764 High Similarity NPC24728
0.875 High Similarity NPC204105
0.875 High Similarity NPC284534
0.875 High Similarity NPC300082
0.871 High Similarity NPC476053
0.8681 High Similarity NPC216284
0.8667 High Similarity NPC207114
0.8667 High Similarity NPC471149
0.8667 High Similarity NPC217983
0.8652 High Similarity NPC304558
0.8617 High Similarity NPC18019
0.8617 High Similarity NPC24956
0.8617 High Similarity NPC126156
0.8605 High Similarity NPC6823
0.8587 High Similarity NPC155215
0.8571 High Similarity NPC283409
0.8526 High Similarity NPC474313
0.8526 High Similarity NPC471150
0.8523 High Similarity NPC245665
0.8523 High Similarity NPC54468
0.8511 High Similarity NPC475900
0.8511 High Similarity NPC472873
0.8495 Intermediate Similarity NPC258216
0.8444 Intermediate Similarity NPC187661
0.8444 Intermediate Similarity NPC67493
0.8444 Intermediate Similarity NPC236692
0.8444 Intermediate Similarity NPC309757
0.8421 Intermediate Similarity NPC476009
0.8409 Intermediate Similarity NPC246076
0.8404 Intermediate Similarity NPC127019
0.8391 Intermediate Similarity NPC290508
0.8391 Intermediate Similarity NPC73052
0.8391 Intermediate Similarity NPC293418
0.8387 Intermediate Similarity NPC133698
0.837 Intermediate Similarity NPC472872
0.8352 Intermediate Similarity NPC190753
0.8351 Intermediate Similarity NPC186861
0.8333 Intermediate Similarity NPC235792
0.8316 Intermediate Similarity NPC67584
0.8316 Intermediate Similarity NPC213698
0.8298 Intermediate Similarity NPC135776
0.8295 Intermediate Similarity NPC47635
0.8242 Intermediate Similarity NPC470242
0.8229 Intermediate Similarity NPC213078
0.8222 Intermediate Similarity NPC224386
0.8222 Intermediate Similarity NPC156485
0.8222 Intermediate Similarity NPC194859
0.8211 Intermediate Similarity NPC167219
0.8211 Intermediate Similarity NPC198853
0.8211 Intermediate Similarity NPC477131
0.82 Intermediate Similarity NPC203659
0.8191 Intermediate Similarity NPC131209
0.8191 Intermediate Similarity NPC475925
0.8182 Intermediate Similarity NPC156658
0.8182 Intermediate Similarity NPC258965
0.8182 Intermediate Similarity NPC225353
0.8163 Intermediate Similarity NPC471381
0.8152 Intermediate Similarity NPC270270
0.8144 Intermediate Similarity NPC477949
0.8144 Intermediate Similarity NPC169205
0.8144 Intermediate Similarity NPC161493
0.8125 Intermediate Similarity NPC275960
0.8125 Intermediate Similarity NPC170120
0.8125 Intermediate Similarity NPC48803
0.8125 Intermediate Similarity NPC90121
0.8125 Intermediate Similarity NPC52044
0.8125 Intermediate Similarity NPC193645
0.8119 Intermediate Similarity NPC44004
0.8111 Intermediate Similarity NPC128246
0.8111 Intermediate Similarity NPC111409
0.8105 Intermediate Similarity NPC475788
0.81 Intermediate Similarity NPC110989
0.8085 Intermediate Similarity NPC301969
0.8085 Intermediate Similarity NPC37607
0.8081 Intermediate Similarity NPC474742
0.8081 Intermediate Similarity NPC477950
0.8065 Intermediate Similarity NPC91248
0.8065 Intermediate Similarity NPC53158
0.8061 Intermediate Similarity NPC45125
0.8061 Intermediate Similarity NPC141191
0.8046 Intermediate Similarity NPC208223
0.8043 Intermediate Similarity NPC162071
0.8043 Intermediate Similarity NPC64153
0.8041 Intermediate Similarity NPC185553
0.8021 Intermediate Similarity NPC262133
0.8021 Intermediate Similarity NPC470013
0.8021 Intermediate Similarity NPC470010
0.8021 Intermediate Similarity NPC323008
0.802 Intermediate Similarity NPC100487
0.8 Intermediate Similarity NPC150978
0.8 Intermediate Similarity NPC474747
0.8 Intermediate Similarity NPC123177
0.8 Intermediate Similarity NPC70595
0.8 Intermediate Similarity NPC74103
0.798 Intermediate Similarity NPC280963
0.7979 Intermediate Similarity NPC32922
0.7978 Intermediate Similarity NPC51507
0.7961 Intermediate Similarity NPC255082
0.7959 Intermediate Similarity NPC181151
0.7957 Intermediate Similarity NPC186148
0.7941 Intermediate Similarity NPC54737
0.7938 Intermediate Similarity NPC304886
0.7921 Intermediate Similarity NPC475945
0.7921 Intermediate Similarity NPC475873
0.7921 Intermediate Similarity NPC475871
0.7917 Intermediate Similarity NPC472874
0.7912 Intermediate Similarity NPC215294
0.7907 Intermediate Similarity NPC320537
0.7907 Intermediate Similarity NPC143979
0.79 Intermediate Similarity NPC150923
0.79 Intermediate Similarity NPC475099
0.7895 Intermediate Similarity NPC71533
0.7895 Intermediate Similarity NPC106510
0.7895 Intermediate Similarity NPC253144
0.7889 Intermediate Similarity NPC126248
0.7879 Intermediate Similarity NPC221615
0.7872 Intermediate Similarity NPC224652
0.7872 Intermediate Similarity NPC58219
0.7872 Intermediate Similarity NPC177629
0.7865 Intermediate Similarity NPC19841
0.7864 Intermediate Similarity NPC26617
0.7857 Intermediate Similarity NPC39859
0.7857 Intermediate Similarity NPC76862
0.7857 Intermediate Similarity NPC158416
0.7857 Intermediate Similarity NPC470883
0.7843 Intermediate Similarity NPC474741
0.7812 Intermediate Similarity NPC472705
0.7812 Intermediate Similarity NPC261607
0.7812 Intermediate Similarity NPC284185
0.7812 Intermediate Similarity NPC300312
0.7812 Intermediate Similarity NPC111114
0.781 Intermediate Similarity NPC471884
0.781 Intermediate Similarity NPC477103
0.7789 Intermediate Similarity NPC92974
0.7789 Intermediate Similarity NPC173926
0.7789 Intermediate Similarity NPC474951
0.7767 Intermediate Similarity NPC223450
0.7767 Intermediate Similarity NPC243998
0.7757 Intermediate Similarity NPC209058
0.7755 Intermediate Similarity NPC469873
0.7745 Intermediate Similarity NPC221421
0.7742 Intermediate Similarity NPC21471
0.7742 Intermediate Similarity NPC329749
0.7742 Intermediate Similarity NPC33570
0.7723 Intermediate Similarity NPC116139
0.7717 Intermediate Similarity NPC318468
0.7717 Intermediate Similarity NPC128429
0.7714 Intermediate Similarity NPC59489
0.7714 Intermediate Similarity NPC139838
0.7714 Intermediate Similarity NPC477102
0.7708 Intermediate Similarity NPC206614
0.7708 Intermediate Similarity NPC246173
0.7708 Intermediate Similarity NPC474323
0.77 Intermediate Similarity NPC249171
0.77 Intermediate Similarity NPC49833
0.7684 Intermediate Similarity NPC202672
0.7677 Intermediate Similarity NPC473964
0.767 Intermediate Similarity NPC309190
0.766 Intermediate Similarity NPC469676
0.766 Intermediate Similarity NPC475019

  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 NPC473273 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
0.8125 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7864 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7642 Intermediate Similarity NPD6371 Approved
0.7604 Intermediate Similarity NPD1695 Approved
0.7526 Intermediate Similarity NPD5785 Approved
0.73 Intermediate Similarity NPD5282 Discontinued
0.7128 Intermediate Similarity NPD5369 Approved
0.701 Intermediate Similarity NPD5363 Approved
0.701 Intermediate Similarity NPD1733 Clinical (unspecified phase)
0.6939 Remote Similarity NPD5786 Approved
0.6875 Remote Similarity NPD4270 Approved
0.6875 Remote Similarity NPD6053 Discontinued
0.6875 Remote Similarity NPD4269 Approved
0.6789 Remote Similarity NPD6008 Approved
0.6768 Remote Similarity NPD4249 Approved
0.6701 Remote Similarity NPD6435 Approved
0.67 Remote Similarity NPD4251 Approved
0.67 Remote Similarity NPD4250 Approved
0.6698 Remote Similarity NPD4225 Approved
0.6667 Remote Similarity NPD4252 Approved
0.6638 Remote Similarity NPD7115 Discovery
0.6633 Remote Similarity NPD5362 Discontinued
0.6571 Remote Similarity NPD5695 Phase 3
0.6542 Remote Similarity NPD5696 Approved
0.6542 Remote Similarity NPD7638 Approved
0.6538 Remote Similarity NPD6399 Phase 3
0.6538 Remote Similarity NPD5778 Approved
0.6538 Remote Similarity NPD5779 Approved
0.6531 Remote Similarity NPD5209 Approved
0.6529 Remote Similarity NPD7492 Approved
0.6518 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6505 Remote Similarity NPD6698 Approved
0.6505 Remote Similarity NPD46 Approved
0.65 Remote Similarity NPD6082 Clinical (unspecified phase)
0.65 Remote Similarity NPD1694 Approved
0.6495 Remote Similarity NPD5368 Approved
0.6481 Remote Similarity NPD7640 Approved
0.6481 Remote Similarity NPD7639 Approved
0.6475 Remote Similarity NPD6616 Approved
0.6471 Remote Similarity NPD6319 Approved
0.6471 Remote Similarity NPD6054 Approved
0.6458 Remote Similarity NPD4802 Phase 2
0.6458 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6458 Remote Similarity NPD4238 Approved
0.6449 Remote Similarity NPD6083 Phase 2
0.6449 Remote Similarity NPD6084 Phase 2
0.6442 Remote Similarity NPD6411 Approved
0.6442 Remote Similarity NPD7637 Suspended
0.6442 Remote Similarity NPD7983 Approved
0.6429 Remote Similarity NPD5697 Approved
0.6423 Remote Similarity NPD7078 Approved
0.6417 Remote Similarity NPD6016 Approved
0.6417 Remote Similarity NPD6015 Approved
0.6372 Remote Similarity NPD6881 Approved
0.6372 Remote Similarity NPD6686 Approved
0.6372 Remote Similarity NPD6899 Approved
0.6372 Remote Similarity NPD7320 Approved
0.6371 Remote Similarity NPD7736 Approved
0.6364 Remote Similarity NPD5988 Approved
0.6364 Remote Similarity NPD6370 Approved
0.6364 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6348 Remote Similarity NPD6649 Approved
0.6348 Remote Similarity NPD6650 Approved
0.6339 Remote Similarity NPD6675 Approved
0.6339 Remote Similarity NPD5739 Approved
0.6339 Remote Similarity NPD6402 Approved
0.6339 Remote Similarity NPD7128 Approved
0.6333 Remote Similarity NPD6059 Approved
0.6327 Remote Similarity NPD4820 Approved
0.6327 Remote Similarity NPD4819 Approved
0.6327 Remote Similarity NPD4821 Approved
0.6327 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6327 Remote Similarity NPD4822 Approved
0.632 Remote Similarity NPD7319 Approved
0.6316 Remote Similarity NPD6012 Approved
0.6316 Remote Similarity NPD6373 Approved
0.6316 Remote Similarity NPD6013 Approved
0.6316 Remote Similarity NPD6372 Approved
0.6316 Remote Similarity NPD6014 Approved
0.6311 Remote Similarity NPD6903 Approved
0.63 Remote Similarity NPD4788 Approved
0.63 Remote Similarity NPD7154 Phase 3
0.629 Remote Similarity NPD8293 Discontinued
0.6286 Remote Similarity NPD5693 Phase 1
0.6286 Remote Similarity NPD8035 Phase 2
0.6286 Remote Similarity NPD8034 Phase 2
0.6283 Remote Similarity NPD5701 Approved
0.6275 Remote Similarity NPD7146 Approved
0.6275 Remote Similarity NPD6409 Approved
0.6275 Remote Similarity NPD5330 Approved
0.6275 Remote Similarity NPD7521 Approved
0.6275 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6275 Remote Similarity NPD6684 Approved
0.6275 Remote Similarity NPD7334 Approved
0.6262 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6261 Remote Similarity NPD7102 Approved
0.6261 Remote Similarity NPD6883 Approved
0.6261 Remote Similarity NPD7290 Approved
0.625 Remote Similarity NPD6101 Approved
0.625 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6239 Remote Similarity NPD4632 Approved
0.6228 Remote Similarity NPD6011 Approved
0.621 Remote Similarity NPD7507 Approved
0.6207 Remote Similarity NPD6847 Approved
0.6207 Remote Similarity NPD6869 Approved
0.6207 Remote Similarity NPD8130 Phase 1
0.6207 Remote Similarity NPD6617 Approved
0.619 Remote Similarity NPD5207 Approved
0.619 Remote Similarity NPD7838 Discovery
0.6154 Remote Similarity NPD8297 Approved
0.6154 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6154 Remote Similarity NPD6882 Approved
0.614 Remote Similarity NPD6412 Phase 2
0.6139 Remote Similarity NPD5331 Approved
0.6139 Remote Similarity NPD5332 Approved
0.6132 Remote Similarity NPD5284 Approved
0.6132 Remote Similarity NPD5281 Approved
0.6126 Remote Similarity NPD1700 Approved
0.6122 Remote Similarity NPD4268 Approved
0.6122 Remote Similarity NPD4271 Approved
0.6121 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6121 Remote Similarity NPD4634 Approved
0.6111 Remote Similarity NPD5210 Approved
0.6111 Remote Similarity NPD4629 Approved
0.6106 Remote Similarity NPD4056 Clinical (unspecified phase)
0.6106 Remote Similarity NPD4057 Clinical (unspecified phase)
0.6102 Remote Similarity NPD8133 Approved
0.61 Remote Similarity NPD4790 Discontinued
0.6095 Remote Similarity NPD4753 Phase 2
0.6083 Remote Similarity NPD6009 Approved
0.6078 Remote Similarity NPD3133 Approved
0.6078 Remote Similarity NPD3665 Phase 1
0.6078 Remote Similarity NPD3666 Approved
0.6071 Remote Similarity NPD5211 Phase 2
0.6071 Remote Similarity NPD7632 Discontinued
0.6068 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6055 Remote Similarity NPD7839 Suspended
0.6047 Remote Similarity NPD6845 Suspended
0.604 Remote Similarity NPD3667 Approved
0.6036 Remote Similarity NPD4696 Approved
0.6036 Remote Similarity NPD5285 Approved
0.6036 Remote Similarity NPD5286 Approved
0.6034 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6019 Remote Similarity NPD6001 Approved
0.6019 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6016 Remote Similarity NPD8517 Approved
0.6016 Remote Similarity NPD8266 Approved
0.6016 Remote Similarity NPD8267 Approved
0.6016 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6016 Remote Similarity NPD8513 Phase 3
0.6016 Remote Similarity NPD8515 Approved
0.6016 Remote Similarity NPD8516 Approved
0.6016 Remote Similarity NPD8268 Approved
0.6016 Remote Similarity NPD5983 Phase 2
0.6016 Remote Similarity NPD8269 Approved
0.6 Remote Similarity NPD5737 Approved
0.6 Remote Similarity NPD6274 Approved
0.6 Remote Similarity NPD6672 Approved
0.6 Remote Similarity NPD4755 Approved
0.598 Remote Similarity NPD6695 Phase 3
0.5979 Remote Similarity NPD3702 Approved
0.5969 Remote Similarity NPD7260 Phase 2
0.5965 Remote Similarity NPD5141 Approved
0.5962 Remote Similarity NPD3618 Phase 1
0.5946 Remote Similarity NPD8029 Clinical (unspecified phase)
0.5943 Remote Similarity NPD6904 Approved
0.5943 Remote Similarity NPD6673 Approved
0.5943 Remote Similarity NPD6080 Approved
0.5943 Remote Similarity NPD5370 Suspended
0.5932 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5929 Remote Similarity NPD5226 Approved
0.5929 Remote Similarity NPD5224 Approved
0.5929 Remote Similarity NPD5225 Approved
0.5929 Remote Similarity NPD4633 Approved
0.5922 Remote Similarity NPD7338 Clinical (unspecified phase)
0.5922 Remote Similarity NPD4786 Approved
0.592 Remote Similarity NPD7604 Phase 2
0.5893 Remote Similarity NPD4700 Approved
0.5891 Remote Similarity NPD5956 Approved
0.5888 Remote Similarity NPD5692 Phase 3
0.5887 Remote Similarity NPD6921 Approved
0.5882 Remote Similarity NPD4221 Approved
0.5882 Remote Similarity NPD4223 Phase 3
0.5877 Remote Similarity NPD5175 Approved
0.5877 Remote Similarity NPD5174 Approved
0.5872 Remote Similarity NPD7748 Approved
0.5862 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5859 Remote Similarity NPD6033 Approved
0.5856 Remote Similarity NPD7902 Approved
0.5854 Remote Similarity NPD7100 Approved
0.5854 Remote Similarity NPD7101 Approved
0.5851 Remote Similarity NPD229 Approved
0.5849 Remote Similarity NPD5208 Approved
0.5843 Remote Similarity NPD3198 Approved
0.5841 Remote Similarity NPD5344 Discontinued
0.5841 Remote Similarity NPD5223 Approved
0.5833 Remote Similarity NPD4810 Clinical (unspecified phase)
0.5833 Remote Similarity NPD5694 Approved
0.5833 Remote Similarity NPD6079 Approved
0.5833 Remote Similarity NPD6050 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