Structure

Physi-Chem Properties

Molecular Weight:  231.1
Volume:  233.747
LogP:  0.467
LogD:  0.661
LogS:  -3.348
# Rotatable Bonds:  4
TPSA:  74.25
# H-Bond Aceptor:  5
# H-Bond Donor:  3
# Rings:  2
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.423
Synthetic Accessibility Score:  2.896
Fsp3:  0.167
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.726
MDCK Permeability:  3.7284264635673026e-06
Pgp-inhibitor:  0.0
Pgp-substrate:  0.335
Human Intestinal Absorption (HIA):  0.014
20% Bioavailability (F20%):  0.9
30% Bioavailability (F30%):  0.73

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.033
Plasma Protein Binding (PPB):  83.2188720703125%
Volume Distribution (VD):  1.41
Pgp-substrate:  12.923824310302734%

ADMET: Metabolism

CYP1A2-inhibitor:  0.56
CYP1A2-substrate:  0.681
CYP2C19-inhibitor:  0.087
CYP2C19-substrate:  0.065
CYP2C9-inhibitor:  0.142
CYP2C9-substrate:  0.587
CYP2D6-inhibitor:  0.009
CYP2D6-substrate:  0.509
CYP3A4-inhibitor:  0.436
CYP3A4-substrate:  0.091

ADMET: Excretion

Clearance (CL):  8.259
Half-life (T1/2):  0.803

ADMET: Toxicity

hERG Blockers:  0.037
Human Hepatotoxicity (H-HT):  0.292
Drug-inuced Liver Injury (DILI):  0.943
AMES Toxicity:  0.54
Rat Oral Acute Toxicity:  0.26
Maximum Recommended Daily Dose:  0.297
Skin Sensitization:  0.943
Carcinogencity:  0.139
Eye Corrosion:  0.006
Eye Irritation:  0.569
Respiratory Toxicity:  0.925

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

  Natural Product: NPC209355

Natural Product ID:  NPC209355
Common Name*:   3-(2-((1R,4As,5R,8Ar)-5-(Hydroxymethyl)-5,8A-Dimethyl-2-Methylene-6-Oxo-Decahydronaphthalen-1-Yl)Vinyl)Furan-2(5H)-One
IUPAC Name:   4-[(E)-2-[(1R,4aS,5R,8aR)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-6-oxo-1,3,4,4a,7,8-hexahydronaphthalen-1-yl]ethenyl]-2H-furan-5-one
Synonyms:  
Standard InCHIKey:  VZUQDSZLBXYRHS-WHCBKWPTSA-N
Standard InCHI:  InChI=1S/C20H26O4/c1-13-4-7-16-19(2,10-8-17(22)20(16,3)12-21)15(13)6-5-14-9-11-24-18(14)23/h5-6,9,15-16,21H,1,4,7-8,10-12H2,2-3H3/b6-5+/t15-,16+,19+,20+/m1/s1
SMILES:  OC[C@]1(C)C(=O)CC[C@@]2([C@@H]1CCC(=C)[C@H]2/C=C/C1=CCOC1=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL466153
PubChem CID:   44577191
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones
          • [CHEMONTID:0001538] Diterpene lactones

*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
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. leaf n.a. PMID[15894448]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. root n.a. PMID[15894448]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota aerial parts purchased in Juhuacun herbal market, Kunming, Yunnan Province, China 2002-Oct PMID[16562826]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. n.a. n.a. PMID[18357994]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. leaf n.a. PMID[21598983]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. leaf n.a. PMID[22026410]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. n.a. n.a. PMID[8377022]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO3578 Andrographis paniculata Species Acanthaceae 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
NPT116 Cell Line HL-60 Homo sapiens GI50 = 19170.0 nM PMID[501303]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 75260.0 nM PMID[501304]
NPT113 Cell Line RAW264.7 Mus musculus Activity = 103.5 % PMID[501304]

☑ 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 NPC209355 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
0.9545 High Similarity NPC51486
0.9011 High Similarity NPC177037
0.9011 High Similarity NPC472814
0.9 High Similarity NPC5509
0.8977 High Similarity NPC65661
0.8977 High Similarity NPC86316
0.8977 High Similarity NPC106416
0.8936 High Similarity NPC208094
0.8925 High Similarity NPC295347
0.8842 High Similarity NPC316598
0.883 High Similarity NPC242848
0.8791 High Similarity NPC174342
0.8737 High Similarity NPC475709
0.871 High Similarity NPC115021
0.871 High Similarity NPC162615
0.871 High Similarity NPC139692
0.871 High Similarity NPC205034
0.871 High Similarity NPC152778
0.8696 High Similarity NPC182136
0.8696 High Similarity NPC310479
0.8646 High Similarity NPC57079
0.8646 High Similarity NPC108368
0.8636 High Similarity NPC200513
0.8636 High Similarity NPC94200
0.8602 High Similarity NPC477783
0.8571 High Similarity NPC114540
0.8571 High Similarity NPC155332
0.8571 High Similarity NPC32577
0.8557 High Similarity NPC474012
0.8557 High Similarity NPC476299
0.8557 High Similarity NPC477720
0.8557 High Similarity NPC117685
0.8556 High Similarity NPC189311
0.8542 High Similarity NPC474343
0.8515 High Similarity NPC220155
0.8495 Intermediate Similarity NPC477782
0.8447 Intermediate Similarity NPC474315
0.8438 Intermediate Similarity NPC16967
0.8438 Intermediate Similarity NPC473153
0.8438 Intermediate Similarity NPC134072
0.8438 Intermediate Similarity NPC234993
0.8431 Intermediate Similarity NPC475065
0.8421 Intermediate Similarity NPC191521
0.8421 Intermediate Similarity NPC53685
0.8416 Intermediate Similarity NPC330011
0.8416 Intermediate Similarity NPC329048
0.8404 Intermediate Similarity NPC474018
0.8404 Intermediate Similarity NPC473986
0.8387 Intermediate Similarity NPC168131
0.8387 Intermediate Similarity NPC284561
0.8387 Intermediate Similarity NPC251528
0.837 Intermediate Similarity NPC312561
0.8367 Intermediate Similarity NPC54705
0.8367 Intermediate Similarity NPC266955
0.8351 Intermediate Similarity NPC53844
0.8351 Intermediate Similarity NPC2049
0.8333 Intermediate Similarity NPC318363
0.8333 Intermediate Similarity NPC473482
0.8333 Intermediate Similarity NPC118423
0.8333 Intermediate Similarity NPC475418
0.8317 Intermediate Similarity NPC266570
0.8316 Intermediate Similarity NPC469939
0.8316 Intermediate Similarity NPC242069
0.8315 Intermediate Similarity NPC14203
0.8315 Intermediate Similarity NPC40228
0.8315 Intermediate Similarity NPC229584
0.83 Intermediate Similarity NPC329345
0.83 Intermediate Similarity NPC475526
0.83 Intermediate Similarity NPC72151
0.83 Intermediate Similarity NPC473283
0.8298 Intermediate Similarity NPC280149
0.8298 Intermediate Similarity NPC8062
0.8298 Intermediate Similarity NPC281942
0.8298 Intermediate Similarity NPC221111
0.8298 Intermediate Similarity NPC232426
0.8283 Intermediate Similarity NPC115899
0.8283 Intermediate Similarity NPC469657
0.8283 Intermediate Similarity NPC244456
0.8283 Intermediate Similarity NPC282524
0.828 Intermediate Similarity NPC472302
0.8265 Intermediate Similarity NPC474440
0.8265 Intermediate Similarity NPC98868
0.8261 Intermediate Similarity NPC168248
0.8261 Intermediate Similarity NPC261721
0.8252 Intermediate Similarity NPC137911
0.8252 Intermediate Similarity NPC228477
0.8247 Intermediate Similarity NPC471153
0.8247 Intermediate Similarity NPC250757
0.8247 Intermediate Similarity NPC301534
0.8242 Intermediate Similarity NPC149869
0.8235 Intermediate Similarity NPC473284
0.8235 Intermediate Similarity NPC91034
0.8229 Intermediate Similarity NPC477130
0.8229 Intermediate Similarity NPC476415
0.8229 Intermediate Similarity NPC470255
0.8229 Intermediate Similarity NPC477129
0.8229 Intermediate Similarity NPC84893
0.8222 Intermediate Similarity NPC268122
0.8211 Intermediate Similarity NPC141831
0.8211 Intermediate Similarity NPC72845
0.8211 Intermediate Similarity NPC303697
0.82 Intermediate Similarity NPC320447
0.8191 Intermediate Similarity NPC474396
0.8191 Intermediate Similarity NPC36668
0.8191 Intermediate Similarity NPC118011
0.8191 Intermediate Similarity NPC50488
0.8182 Intermediate Similarity NPC35751
0.8163 Intermediate Similarity NPC110937
0.8163 Intermediate Similarity NPC73911
0.8163 Intermediate Similarity NPC253826
0.8163 Intermediate Similarity NPC202705
0.8152 Intermediate Similarity NPC30984
0.8144 Intermediate Similarity NPC293052
0.8144 Intermediate Similarity NPC88310
0.8144 Intermediate Similarity NPC171395
0.8144 Intermediate Similarity NPC183012
0.8137 Intermediate Similarity NPC189863
0.8132 Intermediate Similarity NPC311070
0.8132 Intermediate Similarity NPC193198
0.8132 Intermediate Similarity NPC16488
0.8125 Intermediate Similarity NPC472303
0.8119 Intermediate Similarity NPC475050
0.8119 Intermediate Similarity NPC476889
0.8111 Intermediate Similarity NPC282293
0.8111 Intermediate Similarity NPC90055
0.8105 Intermediate Similarity NPC476369
0.8105 Intermediate Similarity NPC476437
0.8105 Intermediate Similarity NPC469595
0.8105 Intermediate Similarity NPC220454
0.8105 Intermediate Similarity NPC212679
0.81 Intermediate Similarity NPC475099
0.81 Intermediate Similarity NPC303559
0.81 Intermediate Similarity NPC471412
0.809 Intermediate Similarity NPC150646
0.8085 Intermediate Similarity NPC226863
0.8085 Intermediate Similarity NPC72397
0.8081 Intermediate Similarity NPC159763
0.8081 Intermediate Similarity NPC124512
0.8081 Intermediate Similarity NPC278386
0.8065 Intermediate Similarity NPC131813
0.8065 Intermediate Similarity NPC316426
0.8065 Intermediate Similarity NPC194417
0.8065 Intermediate Similarity NPC315395
0.8061 Intermediate Similarity NPC29952
0.8061 Intermediate Similarity NPC184065
0.8061 Intermediate Similarity NPC29152
0.8058 Intermediate Similarity NPC475294
0.8043 Intermediate Similarity NPC475100
0.8041 Intermediate Similarity NPC470697
0.8041 Intermediate Similarity NPC38830
0.8041 Intermediate Similarity NPC57117
0.8039 Intermediate Similarity NPC472868
0.8021 Intermediate Similarity NPC289479
0.8021 Intermediate Similarity NPC472705
0.802 Intermediate Similarity NPC273005
0.802 Intermediate Similarity NPC476081
0.802 Intermediate Similarity NPC40918
0.802 Intermediate Similarity NPC469606
0.802 Intermediate Similarity NPC476890
0.802 Intermediate Similarity NPC31058
0.8 Intermediate Similarity NPC471413
0.8 Intermediate Similarity NPC179642
0.8 Intermediate Similarity NPC212598
0.8 Intermediate Similarity NPC29133
0.8 Intermediate Similarity NPC476767
0.8 Intermediate Similarity NPC472644
0.8 Intermediate Similarity NPC201406
0.8 Intermediate Similarity NPC474844
0.7981 Intermediate Similarity NPC89171
0.7981 Intermediate Similarity NPC476802
0.798 Intermediate Similarity NPC84335
0.798 Intermediate Similarity NPC38530
0.798 Intermediate Similarity NPC156546
0.7979 Intermediate Similarity NPC477228
0.7979 Intermediate Similarity NPC181327
0.7979 Intermediate Similarity NPC475678
0.7978 Intermediate Similarity NPC198240
0.7961 Intermediate Similarity NPC477125
0.7961 Intermediate Similarity NPC34768
0.7959 Intermediate Similarity NPC139459
0.7959 Intermediate Similarity NPC33473
0.7957 Intermediate Similarity NPC261380
0.7957 Intermediate Similarity NPC76333
0.7957 Intermediate Similarity NPC471795
0.7955 Intermediate Similarity NPC4509
0.7944 Intermediate Similarity NPC122056
0.7941 Intermediate Similarity NPC112009
0.7941 Intermediate Similarity NPC95899
0.7941 Intermediate Similarity NPC120321
0.7938 Intermediate Similarity NPC166346
0.7938 Intermediate Similarity NPC476416
0.7938 Intermediate Similarity NPC271652
0.7938 Intermediate Similarity NPC475657
0.7938 Intermediate Similarity NPC472871
0.7935 Intermediate Similarity NPC474790
0.7935 Intermediate Similarity NPC22611
0.7935 Intermediate Similarity NPC474976
0.7925 Intermediate Similarity NPC470961
0.7925 Intermediate Similarity NPC324683
0.7921 Intermediate Similarity NPC99411

  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 NPC209355 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
0.8636 High Similarity NPD4752 Clinical (unspecified phase)
0.8081 Intermediate Similarity NPD4225 Approved
0.7917 Intermediate Similarity NPD5785 Approved
0.7778 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD7115 Discovery
0.7653 Intermediate Similarity NPD6411 Approved
0.7653 Intermediate Similarity NPD7637 Suspended
0.7642 Intermediate Similarity NPD6686 Approved
0.7634 Intermediate Similarity NPD5209 Approved
0.7579 Intermediate Similarity NPD1694 Approved
0.7576 Intermediate Similarity NPD5779 Approved
0.7576 Intermediate Similarity NPD5778 Approved
0.7549 Intermediate Similarity NPD7638 Approved
0.7476 Intermediate Similarity NPD7640 Approved
0.7476 Intermediate Similarity NPD7639 Approved
0.7451 Intermediate Similarity NPD6083 Phase 2
0.7451 Intermediate Similarity NPD6084 Phase 2
0.7449 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.7449 Intermediate Similarity NPD6101 Approved
0.7419 Intermediate Similarity NPD4695 Discontinued
0.74 Intermediate Similarity NPD6399 Phase 3
0.7396 Intermediate Similarity NPD5363 Approved
0.7347 Intermediate Similarity NPD6672 Approved
0.7347 Intermediate Similarity NPD5737 Approved
0.7327 Intermediate Similarity NPD7748 Approved
0.732 Intermediate Similarity NPD6409 Approved
0.732 Intermediate Similarity NPD7521 Approved
0.732 Intermediate Similarity NPD6684 Approved
0.732 Intermediate Similarity NPD5279 Phase 3
0.732 Intermediate Similarity NPD5330 Approved
0.732 Intermediate Similarity NPD7334 Approved
0.732 Intermediate Similarity NPD7146 Approved
0.73 Intermediate Similarity NPD7515 Phase 2
0.73 Intermediate Similarity NPD5281 Approved
0.73 Intermediate Similarity NPD5693 Phase 1
0.73 Intermediate Similarity NPD5284 Approved
0.7292 Intermediate Similarity NPD3133 Approved
0.7292 Intermediate Similarity NPD3666 Approved
0.7292 Intermediate Similarity NPD3665 Phase 1
0.7273 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.7263 Intermediate Similarity NPD3667 Approved
0.7255 Intermediate Similarity NPD5695 Phase 3
0.7253 Intermediate Similarity NPD8039 Approved
0.7222 Intermediate Similarity NPD5697 Approved
0.7212 Intermediate Similarity NPD5696 Approved
0.7172 Intermediate Similarity NPD6903 Approved
0.7172 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7156 Intermediate Similarity NPD6881 Approved
0.7156 Intermediate Similarity NPD6899 Approved
0.7156 Intermediate Similarity NPD6011 Approved
0.7143 Intermediate Similarity NPD4519 Discontinued
0.7143 Intermediate Similarity NPD3618 Phase 1
0.7143 Intermediate Similarity NPD4623 Approved
0.7143 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7129 Intermediate Similarity NPD6079 Approved
0.7129 Intermediate Similarity NPD5694 Approved
0.7115 Intermediate Similarity NPD7902 Approved
0.7113 Intermediate Similarity NPD4786 Approved
0.71 Intermediate Similarity NPD4753 Phase 2
0.7091 Intermediate Similarity NPD6013 Approved
0.7091 Intermediate Similarity NPD6012 Approved
0.7091 Intermediate Similarity NPD6014 Approved
0.7087 Intermediate Similarity NPD5210 Approved
0.7087 Intermediate Similarity NPD4629 Approved
0.7083 Intermediate Similarity NPD4270 Approved
0.7083 Intermediate Similarity NPD4269 Approved
0.7071 Intermediate Similarity NPD3573 Approved
0.703 Intermediate Similarity NPD5207 Approved
0.703 Intermediate Similarity NPD5692 Phase 3
0.7027 Intermediate Similarity NPD6371 Approved
0.7027 Intermediate Similarity NPD7290 Approved
0.7027 Intermediate Similarity NPD6883 Approved
0.7027 Intermediate Similarity NPD7102 Approved
0.7021 Intermediate Similarity NPD5784 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD5222 Approved
0.7019 Intermediate Similarity NPD5221 Approved
0.7019 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.6979 Remote Similarity NPD5369 Approved
0.6972 Remote Similarity NPD7128 Approved
0.6972 Remote Similarity NPD6675 Approved
0.6972 Remote Similarity NPD6402 Approved
0.6972 Remote Similarity NPD5739 Approved
0.697 Remote Similarity NPD5786 Approved
0.6964 Remote Similarity NPD6617 Approved
0.6964 Remote Similarity NPD6869 Approved
0.6964 Remote Similarity NPD6649 Approved
0.6964 Remote Similarity NPD6847 Approved
0.6964 Remote Similarity NPD8130 Phase 1
0.6964 Remote Similarity NPD6650 Approved
0.6961 Remote Similarity NPD6050 Approved
0.6952 Remote Similarity NPD5173 Approved
0.6939 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6937 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6931 Remote Similarity NPD6673 Approved
0.6931 Remote Similarity NPD6904 Approved
0.6931 Remote Similarity NPD5328 Approved
0.6931 Remote Similarity NPD6080 Approved
0.6909 Remote Similarity NPD5701 Approved
0.6907 Remote Similarity NPD4221 Approved
0.6907 Remote Similarity NPD4223 Phase 3
0.6903 Remote Similarity NPD8297 Approved
0.6903 Remote Similarity NPD6882 Approved
0.6875 Remote Similarity NPD4252 Approved
0.6863 Remote Similarity NPD7838 Discovery
0.6863 Remote Similarity NPD46 Approved
0.6863 Remote Similarity NPD6698 Approved
0.6852 Remote Similarity NPD7632 Discontinued
0.6852 Remote Similarity NPD5211 Phase 2
0.6847 Remote Similarity NPD7320 Approved
0.6837 Remote Similarity NPD5362 Discontinued
0.6837 Remote Similarity NPD7154 Phase 3
0.6832 Remote Similarity NPD5208 Approved
0.6827 Remote Similarity NPD5282 Discontinued
0.6827 Remote Similarity NPD7900 Approved
0.6827 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6822 Remote Similarity NPD5285 Approved
0.6822 Remote Similarity NPD5286 Approved
0.6822 Remote Similarity NPD4696 Approved
0.68 Remote Similarity NPD5280 Approved
0.68 Remote Similarity NPD4694 Approved
0.68 Remote Similarity NPD5690 Phase 2
0.6796 Remote Similarity NPD7983 Approved
0.6786 Remote Similarity NPD6373 Approved
0.6786 Remote Similarity NPD6372 Approved
0.678 Remote Similarity NPD6319 Approved
0.6774 Remote Similarity NPD4058 Approved
0.6768 Remote Similarity NPD3668 Phase 3
0.6768 Remote Similarity NPD4197 Approved
0.6762 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6759 Remote Similarity NPD5223 Approved
0.6737 Remote Similarity NPD4756 Discovery
0.6731 Remote Similarity NPD4202 Approved
0.6729 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6727 Remote Similarity NPD5141 Approved
0.6726 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6724 Remote Similarity NPD6868 Approved
0.6701 Remote Similarity NPD8259 Clinical (unspecified phase)
0.67 Remote Similarity NPD5329 Approved
0.67 Remote Similarity NPD1696 Phase 3
0.6698 Remote Similarity NPD4697 Phase 3
0.6698 Remote Similarity NPD7839 Suspended
0.6697 Remote Similarity NPD5225 Approved
0.6697 Remote Similarity NPD5224 Approved
0.6697 Remote Similarity NPD5226 Approved
0.6697 Remote Similarity NPD4633 Approved
0.6696 Remote Similarity NPD4632 Approved
0.6667 Remote Similarity NPD3617 Approved
0.6667 Remote Similarity NPD6404 Discontinued
0.6667 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4788 Approved
0.6667 Remote Similarity NPD6317 Approved
0.6667 Remote Similarity NPD4518 Approved
0.6667 Remote Similarity NPD6695 Phase 3
0.6636 Remote Similarity NPD5174 Approved
0.6636 Remote Similarity NPD4755 Approved
0.6636 Remote Similarity NPD5175 Approved
0.6634 Remote Similarity NPD4689 Approved
0.6634 Remote Similarity NPD4138 Approved
0.6634 Remote Similarity NPD4693 Phase 3
0.6634 Remote Similarity NPD6098 Approved
0.6634 Remote Similarity NPD4688 Approved
0.6634 Remote Similarity NPD4690 Approved
0.6634 Remote Similarity NPD5205 Approved
0.6613 Remote Similarity NPD7319 Approved
0.661 Remote Similarity NPD6335 Approved
0.661 Remote Similarity NPD6313 Approved
0.661 Remote Similarity NPD6314 Approved
0.6609 Remote Similarity NPD6053 Discontinued
0.6607 Remote Similarity NPD6412 Phase 2
0.6607 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6604 Remote Similarity NPD5654 Approved
0.6602 Remote Similarity NPD6051 Approved
0.66 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6598 Remote Similarity NPD4195 Approved
0.6596 Remote Similarity NPD6926 Approved
0.6596 Remote Similarity NPD6924 Approved
0.6581 Remote Similarity NPD6274 Approved
0.6579 Remote Similarity NPD4634 Approved
0.6566 Remote Similarity NPD6435 Approved
0.6557 Remote Similarity NPD7492 Approved
0.6555 Remote Similarity NPD7101 Approved
0.6555 Remote Similarity NPD7100 Approved
0.6549 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6542 Remote Similarity NPD7614 Phase 1
0.6538 Remote Similarity NPD4096 Approved
0.6535 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6531 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6525 Remote Similarity NPD6009 Approved
0.6518 Remote Similarity NPD6008 Approved
0.6514 Remote Similarity NPD6648 Approved
0.6514 Remote Similarity NPD4700 Approved
0.6509 Remote Similarity NPD6001 Approved
0.6508 Remote Similarity NPD7260 Phase 2
0.6504 Remote Similarity NPD7507 Approved
0.6504 Remote Similarity NPD6616 Approved
0.65 Remote Similarity NPD6054 Approved
0.6495 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6486 Remote Similarity NPD6647 Phase 2
0.6481 Remote Similarity NPD5959 Approved
0.6476 Remote Similarity NPD4810 Clinical (unspecified phase)

  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