Structure

Physi-Chem Properties

Molecular Weight:  262.12
Volume:  266.942
LogP:  0.682
LogD:  0.873
LogS:  -1.857
# Rotatable Bonds:  0
TPSA:  63.6
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.405
Synthetic Accessibility Score:  4.743
Fsp3:  0.6
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:  -4.724
MDCK Permeability:  0.00011434835323598236
Pgp-inhibitor:  0.0
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.359
20% Bioavailability (F20%):  0.244
30% Bioavailability (F30%):  0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.946
Plasma Protein Binding (PPB):  60.62278747558594%
Volume Distribution (VD):  0.799
Pgp-substrate:  40.29068374633789%

ADMET: Metabolism

CYP1A2-inhibitor:  0.039
CYP1A2-substrate:  0.212
CYP2C19-inhibitor:  0.015
CYP2C19-substrate:  0.448
CYP2C9-inhibitor:  0.013
CYP2C9-substrate:  0.12
CYP2D6-inhibitor:  0.006
CYP2D6-substrate:  0.184
CYP3A4-inhibitor:  0.021
CYP3A4-substrate:  0.266

ADMET: Excretion

Clearance (CL):  14.156
Half-life (T1/2):  0.239

ADMET: Toxicity

hERG Blockers:  0.006
Human Hepatotoxicity (H-HT):  0.242
Drug-inuced Liver Injury (DILI):  0.657
AMES Toxicity:  0.008
Rat Oral Acute Toxicity:  0.942
Maximum Recommended Daily Dose:  0.671
Skin Sensitization:  0.045
Carcinogencity:  0.661
Eye Corrosion:  0.004
Eye Irritation:  0.023
Respiratory Toxicity:  0.914

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

  Natural Product: NPC236692

Natural Product ID:  NPC236692
Common Name*:   4-Hydroxy-9-Methyl-3,6-Dimethylidene-3A,4,5,6A,7,9,9A,9B-Octahydroazuleno[4,5-B]Furan-2,8-Dione
IUPAC Name:   4-hydroxy-9-methyl-3,6-dimethylidene-3a,4,5,6a,7,9,9a,9b-octahydroazuleno[4,5-b]furan-2,8-dione
Synonyms:  
Standard InCHIKey:  YGMIBVIKXJJQQJ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C15H18O4/c1-6-4-11(17)13-8(3)15(18)19-14(13)12-7(2)10(16)5-9(6)12/h7,9,11-14,17H,1,3-5H2,2H3
SMILES:  CC1C(=O)CC2C1C1OC(=O)C(=C)C1C(CC2=C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1968792
PubChem CID:   99967
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:0001770] Guaianolides and derivatives

*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
NPO26001 Carlina acaulis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26001 Carlina acaulis Species Asteraceae 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
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 15523.87 nM PMID[571160]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 6870.68 nM PMID[571160]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 5321.08 nM PMID[571160]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 15958.79 nM PMID[571160]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 14689.26 nM PMID[571160]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 13001.7 nM PMID[571160]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 15275.66 nM PMID[571160]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 3006.08 nM PMID[571160]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 19678.86 nM PMID[571160]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 20701.41 nM PMID[571160]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 12022.64 nM PMID[571160]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 5984.12 nM PMID[571160]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 29444.22 nM PMID[571160]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 11614.49 nM PMID[571160]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 7030.72 nM PMID[571160]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 19769.7 nM PMID[571160]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 18365.38 nM PMID[571160]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 22961.49 nM PMID[571160]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 21330.45 nM PMID[571160]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 16143.59 nM PMID[571160]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 20370.42 nM PMID[571160]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 18793.17 nM PMID[571160]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 9141.13 nM PMID[571160]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 4819.48 nM PMID[571160]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 5116.82 nM PMID[571160]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 5164.16 nM PMID[571160]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 24660.39 nM PMID[571160]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 11830.42 nM PMID[571160]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 13963.68 nM PMID[571160]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 64416.93 nM PMID[571160]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 17619.76 nM PMID[571160]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 19998.62 nM PMID[571160]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 7870.46 nM PMID[571160]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 18879.91 nM PMID[571160]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 20323.57 nM PMID[571160]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 19998.62 nM PMID[571160]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 15066.07 nM PMID[571160]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 4819.48 nM PMID[571160]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 10046.16 nM PMID[571160]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 22181.96 nM PMID[571160]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 15381.55 nM PMID[571160]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 36559.48 nM PMID[571160]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 9397.23 nM PMID[571160]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 33036.95 nM PMID[571160]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 16904.41 nM PMID[571160]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 24490.63 nM PMID[571160]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 4570.88 nM PMID[571160]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 15275.66 nM PMID[571160]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 27605.78 nM PMID[571160]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 11324.0 nM PMID[571160]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 18365.38 nM PMID[571160]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 19098.53 nM PMID[571160]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 10000.0 nM PMID[571160]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 12589.25 nM PMID[571160]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 4083.19 nM PMID[571160]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 18663.8 nM PMID[571160]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 14321.88 nM PMID[571160]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 4731.51 nM PMID[571160]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 7328.25 nM PMID[571160]

☑ 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 NPC236692 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 NPC309757
0.9405 High Similarity NPC12872
0.9405 High Similarity NPC168679
0.9286 High Similarity NPC178875
0.925 High Similarity NPC51507
0.9167 High Similarity NPC118601
0.8953 High Similarity NPC215556
0.8916 High Similarity NPC245665
0.8916 High Similarity NPC54468
0.8876 High Similarity NPC163228
0.8875 High Similarity NPC208223
0.8851 High Similarity NPC216284
0.8837 High Similarity NPC79549
0.8837 High Similarity NPC217983
0.8837 High Similarity NPC207114
0.8824 High Similarity NPC187661
0.8824 High Similarity NPC238593
0.878 High Similarity NPC73052
0.878 High Similarity NPC290508
0.878 High Similarity NPC293418
0.8778 High Similarity NPC142529
0.8778 High Similarity NPC91771
0.8736 High Similarity NPC155935
0.8721 High Similarity NPC201658
0.8652 High Similarity NPC200237
0.8652 High Similarity NPC153590
0.8636 High Similarity NPC35809
0.8636 High Similarity NPC297474
0.8636 High Similarity NPC19087
0.8636 High Similarity NPC54065
0.8605 High Similarity NPC470242
0.8588 High Similarity NPC194859
0.8588 High Similarity NPC224386
0.8556 High Similarity NPC473331
0.8539 High Similarity NPC57304
0.8539 High Similarity NPC133888
0.8539 High Similarity NPC35959
0.8539 High Similarity NPC29821
0.8539 High Similarity NPC293001
0.8539 High Similarity NPC155215
0.8539 High Similarity NPC171360
0.8539 High Similarity NPC63193
0.8539 High Similarity NPC184063
0.8539 High Similarity NPC131209
0.8523 High Similarity NPC38392
0.8506 High Similarity NPC190753
0.85 High Similarity NPC320537
0.85 High Similarity NPC143979
0.8495 Intermediate Similarity NPC471381
0.8488 Intermediate Similarity NPC284534
0.8488 Intermediate Similarity NPC300082
0.8488 Intermediate Similarity NPC204105
0.8478 Intermediate Similarity NPC471150
0.8471 Intermediate Similarity NPC128246
0.8471 Intermediate Similarity NPC111409
0.8462 Intermediate Similarity NPC472873
0.8462 Intermediate Similarity NPC476053
0.8462 Intermediate Similarity NPC48803
0.8462 Intermediate Similarity NPC90121
0.8462 Intermediate Similarity NPC193645
0.8462 Intermediate Similarity NPC275960
0.8444 Intermediate Similarity NPC308656
0.8444 Intermediate Similarity NPC60386
0.8444 Intermediate Similarity NPC473263
0.8444 Intermediate Similarity NPC135776
0.8444 Intermediate Similarity NPC473234
0.8444 Intermediate Similarity NPC473273
0.8444 Intermediate Similarity NPC258216
0.8427 Intermediate Similarity NPC129419
0.8404 Intermediate Similarity NPC171759
0.8391 Intermediate Similarity NPC56593
0.8372 Intermediate Similarity NPC156485
0.8353 Intermediate Similarity NPC246076
0.8333 Intermediate Similarity NPC133698
0.8333 Intermediate Similarity NPC286341
0.8333 Intermediate Similarity NPC191339
0.8333 Intermediate Similarity NPC475925
0.8333 Intermediate Similarity NPC6823
0.8315 Intermediate Similarity NPC268298
0.8298 Intermediate Similarity NPC186861
0.8295 Intermediate Similarity NPC270270
0.828 Intermediate Similarity NPC311904
0.828 Intermediate Similarity NPC169205
0.8276 Intermediate Similarity NPC165162
0.8261 Intermediate Similarity NPC52044
0.8235 Intermediate Similarity NPC126248
0.8191 Intermediate Similarity NPC141191
0.8182 Intermediate Similarity NPC304558
0.8172 Intermediate Similarity NPC18019
0.8172 Intermediate Similarity NPC476009
0.8172 Intermediate Similarity NPC185553
0.8172 Intermediate Similarity NPC24956
0.8161 Intermediate Similarity NPC165287
0.8152 Intermediate Similarity NPC323008
0.8152 Intermediate Similarity NPC470010
0.8152 Intermediate Similarity NPC470013
0.8152 Intermediate Similarity NPC477131
0.8152 Intermediate Similarity NPC262133
0.8152 Intermediate Similarity NPC198853
0.814 Intermediate Similarity NPC89555
0.8118 Intermediate Similarity NPC69271
0.8118 Intermediate Similarity NPC74673
0.8118 Intermediate Similarity NPC276356
0.8111 Intermediate Similarity NPC472872
0.8111 Intermediate Similarity NPC32922
0.809 Intermediate Similarity NPC24728
0.809 Intermediate Similarity NPC237540
0.809 Intermediate Similarity NPC186148
0.8085 Intermediate Similarity NPC474313
0.8085 Intermediate Similarity NPC161493
0.8085 Intermediate Similarity NPC170143
0.8085 Intermediate Similarity NPC213947
0.8085 Intermediate Similarity NPC108475
0.8065 Intermediate Similarity NPC67584
0.8065 Intermediate Similarity NPC475900
0.8065 Intermediate Similarity NPC213698
0.8065 Intermediate Similarity NPC170120
0.8061 Intermediate Similarity NPC54737
0.8046 Intermediate Similarity NPC39588
0.8023 Intermediate Similarity NPC35089
0.8023 Intermediate Similarity NPC10276
0.8021 Intermediate Similarity NPC477950
0.8 Intermediate Similarity NPC177629
0.8 Intermediate Similarity NPC45125
0.8 Intermediate Similarity NPC471149
0.8 Intermediate Similarity NPC58219
0.8 Intermediate Similarity NPC470239
0.8 Intermediate Similarity NPC53158
0.8 Intermediate Similarity NPC470244
0.8 Intermediate Similarity NPC5714
0.8 Intermediate Similarity NPC91248
0.8 Intermediate Similarity NPC182550
0.8 Intermediate Similarity NPC19841
0.7979 Intermediate Similarity NPC126156
0.7979 Intermediate Similarity NPC213078
0.7978 Intermediate Similarity NPC107787
0.7978 Intermediate Similarity NPC67493
0.7978 Intermediate Similarity NPC64153
0.7957 Intermediate Similarity NPC127019
0.7955 Intermediate Similarity NPC141193
0.7955 Intermediate Similarity NPC114979
0.7955 Intermediate Similarity NPC96259
0.7955 Intermediate Similarity NPC115786
0.7955 Intermediate Similarity NPC191476
0.7938 Intermediate Similarity NPC80144
0.7935 Intermediate Similarity NPC150978
0.7935 Intermediate Similarity NPC261607
0.7935 Intermediate Similarity NPC123177
0.7935 Intermediate Similarity NPC74103
0.7935 Intermediate Similarity NPC300312
0.7935 Intermediate Similarity NPC111114
0.7935 Intermediate Similarity NPC70595
0.7912 Intermediate Similarity NPC92974
0.7912 Intermediate Similarity NPC283409
0.7912 Intermediate Similarity NPC52198
0.7912 Intermediate Similarity NPC212664
0.7912 Intermediate Similarity NPC117405
0.7907 Intermediate Similarity NPC258965
0.7907 Intermediate Similarity NPC156658
0.7895 Intermediate Similarity NPC181151
0.7879 Intermediate Similarity NPC243998
0.7872 Intermediate Similarity NPC304886
0.7865 Intermediate Similarity NPC255307
0.7865 Intermediate Similarity NPC161957
0.7865 Intermediate Similarity NPC78089
0.7835 Intermediate Similarity NPC67296
0.7831 Intermediate Similarity NPC48641
0.7826 Intermediate Similarity NPC253144
0.7826 Intermediate Similarity NPC301969
0.7826 Intermediate Similarity NPC37607
0.7822 Intermediate Similarity NPC139838
0.7822 Intermediate Similarity NPC59489
0.7816 Intermediate Similarity NPC470241
0.7816 Intermediate Similarity NPC25684
0.7816 Intermediate Similarity NPC301477
0.7816 Intermediate Similarity NPC47635
0.7816 Intermediate Similarity NPC281949
0.7812 Intermediate Similarity NPC221615
0.7812 Intermediate Similarity NPC49833
0.7812 Intermediate Similarity NPC249171
0.7802 Intermediate Similarity NPC202672
0.7778 Intermediate Similarity NPC203659
0.7778 Intermediate Similarity NPC474949
0.7778 Intermediate Similarity NPC150755
0.7778 Intermediate Similarity NPC475461
0.7778 Intermediate Similarity NPC475019
0.7778 Intermediate Similarity NPC305475
0.7778 Intermediate Similarity NPC162071
0.7766 Intermediate Similarity NPC167219
0.7766 Intermediate Similarity NPC190294
0.7755 Intermediate Similarity NPC225353
0.7755 Intermediate Similarity NPC86077
0.7755 Intermediate Similarity NPC474747
0.7753 Intermediate Similarity NPC476804
0.7742 Intermediate Similarity NPC12172
0.7742 Intermediate Similarity NPC284185
0.7742 Intermediate Similarity NPC184463
0.7742 Intermediate Similarity NPC208886
0.7742 Intermediate Similarity NPC70251
0.7742 Intermediate Similarity NPC475881

  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 NPC236692 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
0.8462 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7717 Intermediate Similarity NPD1695 Approved
0.7333 Intermediate Similarity NPD6435 Approved
0.7115 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7111 Intermediate Similarity NPD5368 Approved
0.7097 Intermediate Similarity NPD6082 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD5785 Approved
0.7065 Intermediate Similarity NPD5362 Discontinued
0.7021 Intermediate Similarity NPD5786 Approved
0.6944 Remote Similarity NPD6053 Discontinued
0.6916 Remote Similarity NPD6371 Approved
0.6915 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6915 Remote Similarity NPD5363 Approved
0.6848 Remote Similarity NPD5369 Approved
0.6774 Remote Similarity NPD4270 Approved
0.6774 Remote Similarity NPD4269 Approved
0.6768 Remote Similarity NPD6399 Phase 3
0.6739 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6703 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6702 Remote Similarity NPD7154 Phase 3
0.6667 Remote Similarity NPD4249 Approved
0.6636 Remote Similarity NPD5697 Approved
0.6598 Remote Similarity NPD4251 Approved
0.6598 Remote Similarity NPD4250 Approved
0.6574 Remote Similarity NPD6899 Approved
0.6574 Remote Similarity NPD7320 Approved
0.6574 Remote Similarity NPD6881 Approved
0.6566 Remote Similarity NPD46 Approved
0.6566 Remote Similarity NPD6698 Approved
0.6562 Remote Similarity NPD1694 Approved
0.6559 Remote Similarity NPD4820 Approved
0.6559 Remote Similarity NPD4821 Approved
0.6559 Remote Similarity NPD4252 Approved
0.6559 Remote Similarity NPD4822 Approved
0.6559 Remote Similarity NPD4819 Approved
0.6545 Remote Similarity NPD6650 Approved
0.6545 Remote Similarity NPD6649 Approved
0.6542 Remote Similarity NPD7128 Approved
0.6542 Remote Similarity NPD5739 Approved
0.6542 Remote Similarity NPD6675 Approved
0.6542 Remote Similarity NPD6402 Approved
0.6526 Remote Similarity NPD5332 Approved
0.6526 Remote Similarity NPD5331 Approved
0.6522 Remote Similarity NPD4268 Approved
0.6522 Remote Similarity NPD4271 Approved
0.6514 Remote Similarity NPD6014 Approved
0.6514 Remote Similarity NPD6372 Approved
0.6514 Remote Similarity NPD6013 Approved
0.6514 Remote Similarity NPD6012 Approved
0.6514 Remote Similarity NPD6373 Approved
0.65 Remote Similarity NPD8034 Phase 2
0.65 Remote Similarity NPD8035 Phase 2
0.6489 Remote Similarity NPD4790 Discontinued
0.6481 Remote Similarity NPD5701 Approved
0.6465 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6465 Remote Similarity NPD6101 Approved
0.6455 Remote Similarity NPD6883 Approved
0.6455 Remote Similarity NPD7290 Approved
0.6455 Remote Similarity NPD7102 Approved
0.6442 Remote Similarity NPD4225 Approved
0.6436 Remote Similarity NPD5778 Approved
0.6436 Remote Similarity NPD5779 Approved
0.6422 Remote Similarity NPD6011 Approved
0.6404 Remote Similarity NPD7115 Discovery
0.6396 Remote Similarity NPD6617 Approved
0.6396 Remote Similarity NPD8130 Phase 1
0.6396 Remote Similarity NPD6869 Approved
0.6396 Remote Similarity NPD6847 Approved
0.6389 Remote Similarity NPD6008 Approved
0.6373 Remote Similarity NPD5282 Discontinued
0.6346 Remote Similarity NPD6083 Phase 2
0.6346 Remote Similarity NPD6084 Phase 2
0.6339 Remote Similarity NPD6882 Approved
0.6339 Remote Similarity NPD8297 Approved
0.6337 Remote Similarity NPD7983 Approved
0.6337 Remote Similarity NPD6411 Approved
0.6311 Remote Similarity NPD5695 Phase 3
0.6286 Remote Similarity NPD5696 Approved
0.6262 Remote Similarity NPD5211 Phase 2
0.625 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6238 Remote Similarity NPD7838 Discovery
0.6226 Remote Similarity NPD5286 Approved
0.6226 Remote Similarity NPD5285 Approved
0.6226 Remote Similarity NPD4696 Approved
0.6224 Remote Similarity NPD7520 Clinical (unspecified phase)
0.619 Remote Similarity NPD4755 Approved
0.6186 Remote Similarity NPD4788 Approved
0.6186 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6176 Remote Similarity NPD6079 Approved
0.6174 Remote Similarity NPD6274 Approved
0.6147 Remote Similarity NPD5141 Approved
0.6139 Remote Similarity NPD5328 Approved
0.6132 Remote Similarity NPD7638 Approved
0.6126 Remote Similarity NPD6686 Approved
0.6122 Remote Similarity NPD4786 Approved
0.6111 Remote Similarity NPD5224 Approved
0.6111 Remote Similarity NPD5225 Approved
0.6111 Remote Similarity NPD5226 Approved
0.6111 Remote Similarity NPD4633 Approved
0.6106 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6095 Remote Similarity NPD5222 Approved
0.6095 Remote Similarity NPD4697 Phase 3
0.6095 Remote Similarity NPD5221 Approved
0.6095 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6082 Remote Similarity NPD3667 Approved
0.6075 Remote Similarity NPD7639 Approved
0.6075 Remote Similarity NPD4700 Approved
0.6075 Remote Similarity NPD7640 Approved
0.6071 Remote Similarity NPD3198 Approved
0.6055 Remote Similarity NPD5175 Approved
0.6055 Remote Similarity NPD5174 Approved
0.604 Remote Similarity NPD6903 Approved
0.604 Remote Similarity NPD6672 Approved
0.604 Remote Similarity NPD5737 Approved
0.6038 Remote Similarity NPD5173 Approved
0.6033 Remote Similarity NPD7492 Approved
0.6019 Remote Similarity NPD5693 Phase 1
0.6019 Remote Similarity NPD7637 Suspended
0.6019 Remote Similarity NPD5223 Approved
0.6019 Remote Similarity NPD5281 Approved
0.6019 Remote Similarity NPD5284 Approved
0.6017 Remote Similarity NPD7100 Approved
0.6017 Remote Similarity NPD7101 Approved
0.6 Remote Similarity NPD5330 Approved
0.6 Remote Similarity NPD5279 Phase 3
0.6 Remote Similarity NPD5210 Approved
0.6 Remote Similarity NPD3618 Phase 1
0.6 Remote Similarity NPD4632 Approved
0.6 Remote Similarity NPD4629 Approved
0.6 Remote Similarity NPD6409 Approved
0.6 Remote Similarity NPD7334 Approved
0.6 Remote Similarity NPD7146 Approved
0.6 Remote Similarity NPD6684 Approved
0.6 Remote Similarity NPD7521 Approved
0.6 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5984 Remote Similarity NPD6616 Approved
0.5984 Remote Similarity NPD7507 Approved
0.5983 Remote Similarity NPD6317 Approved
0.5982 Remote Similarity NPD5345 Clinical (unspecified phase)
0.598 Remote Similarity NPD4753 Phase 2
0.5966 Remote Similarity NPD6319 Approved
0.5966 Remote Similarity NPD6054 Approved
0.5965 Remote Similarity NPD8413 Clinical (unspecified phase)
0.596 Remote Similarity NPD3665 Phase 1
0.596 Remote Similarity NPD3666 Approved
0.596 Remote Similarity NPD3133 Approved
0.5943 Remote Similarity NPD7839 Suspended
0.5935 Remote Similarity NPD7078 Approved
0.5932 Remote Similarity NPD6313 Approved
0.5932 Remote Similarity NPD6314 Approved
0.5932 Remote Similarity NPD6335 Approved
0.5922 Remote Similarity NPD5207 Approved
0.5918 Remote Similarity NPD5209 Approved
0.5917 Remote Similarity NPD6015 Approved
0.5917 Remote Similarity NPD6016 Approved
0.5917 Remote Similarity NPD8267 Approved
0.5917 Remote Similarity NPD8268 Approved
0.5917 Remote Similarity NPD8269 Approved
0.5917 Remote Similarity NPD8266 Approved
0.5897 Remote Similarity NPD6868 Approved
0.5888 Remote Similarity NPD7902 Approved
0.5887 Remote Similarity NPD7736 Approved
0.5882 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5868 Remote Similarity NPD5988 Approved
0.5868 Remote Similarity NPD6370 Approved
0.5862 Remote Similarity NPD8133 Approved
0.5847 Remote Similarity NPD6009 Approved
0.5841 Remote Similarity NPD4729 Approved
0.5841 Remote Similarity NPD5128 Approved
0.5841 Remote Similarity NPD4730 Approved
0.584 Remote Similarity NPD7319 Approved
0.5833 Remote Similarity NPD6059 Approved
0.5833 Remote Similarity NPD4238 Approved
0.5833 Remote Similarity NPD4802 Phase 2
0.5833 Remote Similarity NPD8029 Clinical (unspecified phase)
0.5827 Remote Similarity NPD6845 Suspended
0.5825 Remote Similarity NPD5370 Suspended
0.581 Remote Similarity NPD4202 Approved
0.5806 Remote Similarity NPD8293 Discontinued
0.5804 Remote Similarity NPD4768 Approved
0.5804 Remote Similarity NPD4767 Approved
0.58 Remote Similarity NPD7338 Clinical (unspecified phase)
0.5785 Remote Similarity NPD8516 Approved
0.5785 Remote Similarity NPD6908 Approved
0.5785 Remote Similarity NPD5983 Phase 2
0.5785 Remote Similarity NPD8517 Approved
0.5785 Remote Similarity NPD8515 Approved
0.5785 Remote Similarity NPD8513 Phase 3
0.5785 Remote Similarity NPD6909 Approved
0.5766 Remote Similarity NPD4754 Approved
0.5758 Remote Similarity NPD4800 Clinical (unspecified phase)
0.5755 Remote Similarity NPD6001 Approved
0.5755 Remote Similarity NPD7748 Approved
0.5752 Remote Similarity NPD6412 Phase 2
0.575 Remote Similarity NPD7519 Approved
0.575 Remote Similarity NPD7517 Approved
0.575 Remote Similarity NPD7518 Approved
0.5748 Remote Similarity NPD7260 Phase 2
0.5739 Remote Similarity NPD4634 Approved
0.5739 Remote Similarity NPD5250 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