Structure

Physi-Chem Properties

Molecular Weight:  782.48
Volume:  792.649
LogP:  3.268
LogD:  3.517
LogS:  -3.003
# Rotatable Bonds:  10
TPSA:  218.99
# H-Bond Aceptor:  13
# H-Bond Donor:  9
# Rings:  6
# Heavy Atoms:  13

MedChem Properties

QED Drug-Likeness Score:  0.115
Synthetic Accessibility Score:  5.944
Fsp3:  0.905
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.584
MDCK Permeability:  3.6534256651066244e-05
Pgp-inhibitor:  0.984
Pgp-substrate:  0.004
Human Intestinal Absorption (HIA):  0.856
20% Bioavailability (F20%):  0.91
30% Bioavailability (F30%):  0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.001
Plasma Protein Binding (PPB):  82.29325103759766%
Volume Distribution (VD):  0.425
Pgp-substrate:  8.546296119689941%

ADMET: Metabolism

CYP1A2-inhibitor:  0.002
CYP1A2-substrate:  0.057
CYP2C19-inhibitor:  0.002
CYP2C19-substrate:  0.222
CYP2C9-inhibitor:  0.003
CYP2C9-substrate:  0.052
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.07
CYP3A4-inhibitor:  0.023
CYP3A4-substrate:  0.05

ADMET: Excretion

Clearance (CL):  0.694
Half-life (T1/2):  0.647

ADMET: Toxicity

hERG Blockers:  0.094
Human Hepatotoxicity (H-HT):  0.237
Drug-inuced Liver Injury (DILI):  0.017
AMES Toxicity:  0.064
Rat Oral Acute Toxicity:  0.089
Maximum Recommended Daily Dose:  0.007
Skin Sensitization:  0.161
Carcinogencity:  0.005
Eye Corrosion:  0.003
Eye Irritation:  0.011
Respiratory Toxicity:  0.217

Download Data

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

  Natural Product: NPC16573

Natural Product ID:  NPC16573
Common Name*:   Damulin B
IUPAC Name:   (2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-2-[[(2R,3R,5R,8R,9R,10R,12R,13R,14R,17S)-2,12-dihydroxy-4,4,8,10,14-pentamethyl-17-(6-methylhepta-1,5-dien-2-yl)-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:   damulin B
Standard InCHIKey:  YHVZKDRAJHNHJX-UDBICBSZSA-N
Standard InCHI:  InChI=1S/C42H70O13/c1-20(2)10-9-11-21(3)22-12-14-42(8)29(22)23(45)16-28-40(6)17-24(46)36(39(4,5)27(40)13-15-41(28,42)7)55-38-35(33(50)31(48)26(19-44)53-38)54-37-34(51)32(49)30(47)25(18-43)52-37/h10,22-38,43-51H,3,9,11-19H2,1-2,4-8H3/t22-,23-,24-,25-,26-,27+,28-,29+,30-,31-,32+,33+,34-,35-,36+,37+,38+,40+,41-,42-/m1/s1
SMILES:  CC(=CCCC(=C)[C@H]1CC[C@]2(C)[C@@H]1[C@@H](C[C@@H]1[C@@]3(C)C[C@H]([C@@H](C(C)(C)[C@@H]3CC[C@@]21C)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1915129
PubChem CID:   57390324
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001553] Triterpenoids

*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
NPO12934 Gynostemma pentaphyllum Species Cucurbitaceae Eukaryota Stems n.a. n.a. PMID[20104880]
NPO12934 Gynostemma pentaphyllum Species Cucurbitaceae Eukaryota n.a. n.a. n.a. PMID[22342101]
NPO12934 Gynostemma pentaphyllum Species Cucurbitaceae Eukaryota aerial parts n.a. n.a. PMID[25895106]
NPO11990 Coleostephus myconis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO918 Dahlia pinnata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12934 Gynostemma pentaphyllum Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO918 Dahlia pinnata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12934 Gynostemma pentaphyllum Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11990 Coleostephus myconis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11990 Coleostephus myconis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12934 Gynostemma pentaphyllum Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12934 Gynostemma pentaphyllum Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16506 Synotis alata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO918 Dahlia pinnata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11990 Coleostephus myconis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4305 Pertusaria wulfenii Species Pertusariaceae 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
NPT81 Cell Line A549 Homo sapiens IC50 = 23.8 ug.mL-1 PMID[494143]

☑ 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 NPC16573 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
0.9896 High Similarity NPC273879
0.9896 High Similarity NPC165033
0.9895 High Similarity NPC312553
0.9895 High Similarity NPC288694
0.9895 High Similarity NPC159036
0.9792 High Similarity NPC31907
0.9792 High Similarity NPC472252
0.9792 High Similarity NPC120123
0.9792 High Similarity NPC114874
0.9792 High Similarity NPC155010
0.9792 High Similarity NPC473020
0.9792 High Similarity NPC131479
0.9792 High Similarity NPC211879
0.9792 High Similarity NPC189852
0.9792 High Similarity NPC16520
0.9792 High Similarity NPC8039
0.9792 High Similarity NPC245280
0.9792 High Similarity NPC157659
0.9792 High Similarity NPC286969
0.9694 High Similarity NPC181467
0.9684 High Similarity NPC473200
0.9684 High Similarity NPC7341
0.9596 High Similarity NPC246124
0.9596 High Similarity NPC180183
0.9592 High Similarity NPC208477
0.9592 High Similarity NPC127801
0.9592 High Similarity NPC69737
0.9592 High Similarity NPC194842
0.9592 High Similarity NPC208594
0.9592 High Similarity NPC269627
0.9592 High Similarity NPC152584
0.9592 High Similarity NPC160816
0.9583 High Similarity NPC47566
0.9583 High Similarity NPC4831
0.9583 High Similarity NPC309425
0.9583 High Similarity NPC88000
0.9583 High Similarity NPC160734
0.9583 High Similarity NPC472023
0.9583 High Similarity NPC129372
0.9579 High Similarity NPC280825
0.9579 High Similarity NPC234287
0.95 High Similarity NPC296761
0.95 High Similarity NPC154085
0.95 High Similarity NPC125361
0.95 High Similarity NPC51925
0.95 High Similarity NPC43976
0.9495 High Similarity NPC473469
0.9495 High Similarity NPC63368
0.9495 High Similarity NPC208650
0.9495 High Similarity NPC14946
0.9495 High Similarity NPC231340
0.9495 High Similarity NPC234160
0.949 High Similarity NPC470885
0.949 High Similarity NPC187400
0.949 High Similarity NPC221562
0.9485 High Similarity NPC136816
0.94 High Similarity NPC472988
0.94 High Similarity NPC38217
0.94 High Similarity NPC159005
0.94 High Similarity NPC7213
0.94 High Similarity NPC6931
0.94 High Similarity NPC220427
0.9394 High Similarity NPC242748
0.9388 High Similarity NPC473198
0.9388 High Similarity NPC213190
0.9314 High Similarity NPC65167
0.93 High Similarity NPC190395
0.9293 High Similarity NPC312774
0.9286 High Similarity NPC272015
0.9278 High Similarity NPC282669
0.9216 High Similarity NPC472717
0.9208 High Similarity NPC472897
0.9208 High Similarity NPC472896
0.92 High Similarity NPC472900
0.92 High Similarity NPC472898
0.92 High Similarity NPC472899
0.92 High Similarity NPC473923
0.92 High Similarity NPC473476
0.92 High Similarity NPC473199
0.92 High Similarity NPC309448
0.9184 High Similarity NPC117714
0.9184 High Similarity NPC263756
0.9167 High Similarity NPC472989
0.9126 High Similarity NPC473021
0.9126 High Similarity NPC472715
0.9126 High Similarity NPC114188
0.9126 High Similarity NPC472987
0.9118 High Similarity NPC157530
0.9118 High Similarity NPC14630
0.9118 High Similarity NPC250089
0.9118 High Similarity NPC302057
0.91 High Similarity NPC75608
0.91 High Similarity NPC148603
0.91 High Similarity NPC475365
0.91 High Similarity NPC475521
0.9091 High Similarity NPC76497
0.9091 High Similarity NPC256133
0.9091 High Similarity NPC213674
0.9091 High Similarity NPC30289
0.9072 High Similarity NPC243728
0.9072 High Similarity NPC473890
0.9038 High Similarity NPC475312
0.9038 High Similarity NPC472716
0.902 High Similarity NPC235824
0.902 High Similarity NPC476539
0.902 High Similarity NPC476538
0.902 High Similarity NPC476541
0.902 High Similarity NPC476540
0.901 High Similarity NPC173859
0.901 High Similarity NPC474569
0.901 High Similarity NPC181845
0.901 High Similarity NPC470512
0.9 High Similarity NPC162354
0.9 High Similarity NPC123796
0.899 High Similarity NPC31346
0.898 High Similarity NPC158088
0.8952 High Similarity NPC144068
0.8952 High Similarity NPC476693
0.8942 High Similarity NPC476547
0.8942 High Similarity NPC197231
0.8932 High Similarity NPC472901
0.8932 High Similarity NPC476835
0.8932 High Similarity NPC477027
0.8932 High Similarity NPC70204
0.8932 High Similarity NPC477026
0.8932 High Similarity NPC475670
0.8932 High Similarity NPC306131
0.8922 High Similarity NPC14704
0.8922 High Similarity NPC230507
0.8922 High Similarity NPC113044
0.8922 High Similarity NPC161676
0.8922 High Similarity NPC470432
0.8922 High Similarity NPC94272
0.8922 High Similarity NPC305423
0.8922 High Similarity NPC283829
0.8911 High Similarity NPC203354
0.8911 High Similarity NPC54521
0.8911 High Similarity NPC230948
0.8911 High Similarity NPC93352
0.8911 High Similarity NPC473734
0.8911 High Similarity NPC476360
0.8911 High Similarity NPC476361
0.8911 High Similarity NPC471434
0.8911 High Similarity NPC173583
0.8911 High Similarity NPC473127
0.8911 High Similarity NPC57065
0.8911 High Similarity NPC471435
0.8911 High Similarity NPC109792
0.8911 High Similarity NPC110656
0.8889 High Similarity NPC473790
0.8878 High Similarity NPC76486
0.8857 High Similarity NPC19888
0.8857 High Similarity NPC263359
0.8857 High Similarity NPC244431
0.8857 High Similarity NPC210569
0.8857 High Similarity NPC31896
0.8857 High Similarity NPC32361
0.8835 High Similarity NPC98696
0.8835 High Similarity NPC295980
0.8824 High Similarity NPC26798
0.8824 High Similarity NPC138057
0.8812 High Similarity NPC473124
0.8812 High Similarity NPC99627
0.8812 High Similarity NPC473123
0.8812 High Similarity NPC473129
0.88 High Similarity NPC267510
0.88 High Similarity NPC470434
0.8788 High Similarity NPC216260
0.8788 High Similarity NPC5358
0.8776 High Similarity NPC207617
0.8774 High Similarity NPC79900
0.8774 High Similarity NPC476671
0.8774 High Similarity NPC307642
0.8774 High Similarity NPC476546
0.8763 High Similarity NPC72817
0.8763 High Similarity NPC477927
0.8763 High Similarity NPC305160
0.8762 High Similarity NPC285410
0.8762 High Similarity NPC294129
0.8762 High Similarity NPC263827
0.8762 High Similarity NPC13190
0.8762 High Similarity NPC250481
0.8762 High Similarity NPC475247
0.875 High Similarity NPC244086
0.875 High Similarity NPC475550
0.875 High Similarity NPC224098
0.875 High Similarity NPC150372
0.875 High Similarity NPC249265
0.875 High Similarity NPC248746
0.875 High Similarity NPC475333
0.875 High Similarity NPC171073
0.875 High Similarity NPC6806
0.875 High Similarity NPC48463
0.875 High Similarity NPC218571
0.875 High Similarity NPC232054
0.875 High Similarity NPC40440
0.875 High Similarity NPC474573
0.875 High Similarity NPC84956
0.875 High Similarity NPC300557
0.875 High Similarity NPC102016

  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 NPC16573 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
0.8468 Intermediate Similarity NPD8377 Approved
0.8468 Intermediate Similarity NPD8294 Approved
0.8393 Intermediate Similarity NPD8335 Approved
0.8393 Intermediate Similarity NPD8296 Approved
0.8393 Intermediate Similarity NPD8033 Approved
0.8393 Intermediate Similarity NPD8378 Approved
0.8393 Intermediate Similarity NPD8380 Approved
0.8393 Intermediate Similarity NPD8379 Approved
0.8214 Intermediate Similarity NPD7516 Approved
0.8125 Intermediate Similarity NPD7327 Approved
0.8125 Intermediate Similarity NPD7328 Approved
0.81 Intermediate Similarity NPD8171 Discontinued
0.7928 Intermediate Similarity NPD8133 Approved
0.789 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.787 Intermediate Similarity NPD6412 Phase 2
0.7759 Intermediate Similarity NPD7503 Approved
0.7647 Intermediate Similarity NPD7507 Approved
0.7627 Intermediate Similarity NPD8328 Phase 3
0.7604 Intermediate Similarity NPD7525 Registered
0.7565 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7459 Intermediate Similarity NPD7319 Approved
0.7364 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD6686 Approved
0.732 Intermediate Similarity NPD7645 Phase 2
0.728 Intermediate Similarity NPD8449 Approved
0.7255 Intermediate Similarity NPD7524 Approved
0.7236 Intermediate Similarity NPD7736 Approved
0.7222 Intermediate Similarity NPD8450 Suspended
0.7107 Intermediate Similarity NPD6370 Approved
0.7071 Intermediate Similarity NPD6928 Phase 2
0.7064 Intermediate Similarity NPD7638 Approved
0.7016 Intermediate Similarity NPD8293 Discontinued
0.7 Intermediate Similarity NPD7640 Approved
0.7 Intermediate Similarity NPD7639 Approved
0.6961 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6942 Remote Similarity NPD6059 Approved
0.6942 Remote Similarity NPD6054 Approved
0.6907 Remote Similarity NPD7339 Approved
0.6907 Remote Similarity NPD6942 Approved
0.6863 Remote Similarity NPD6695 Phase 3
0.6838 Remote Similarity NPD7625 Phase 1
0.6822 Remote Similarity NPD8034 Phase 2
0.6822 Remote Similarity NPD8035 Phase 2
0.678 Remote Similarity NPD8297 Approved
0.678 Remote Similarity NPD6882 Approved
0.6774 Remote Similarity NPD6067 Discontinued
0.6762 Remote Similarity NPD7750 Discontinued
0.6748 Remote Similarity NPD8513 Phase 3
0.6748 Remote Similarity NPD8516 Approved
0.6748 Remote Similarity NPD6015 Approved
0.6748 Remote Similarity NPD8515 Approved
0.6748 Remote Similarity NPD8517 Approved
0.6748 Remote Similarity NPD6016 Approved
0.672 Remote Similarity NPD7492 Approved
0.6697 Remote Similarity NPD7748 Approved
0.6694 Remote Similarity NPD5988 Approved
0.6694 Remote Similarity NPD6009 Approved
0.6667 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6616 Approved
0.6667 Remote Similarity NPD6933 Approved
0.6667 Remote Similarity NPD7902 Approved
0.6667 Remote Similarity NPD6319 Approved
0.6634 Remote Similarity NPD6929 Approved
0.6614 Remote Similarity NPD7078 Approved
0.6606 Remote Similarity NPD6399 Phase 3
0.6583 Remote Similarity NPD4632 Approved
0.6571 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6569 Remote Similarity NPD6930 Phase 2
0.6569 Remote Similarity NPD6931 Approved
0.6562 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6552 Remote Similarity NPD6402 Approved
0.6552 Remote Similarity NPD5739 Approved
0.6552 Remote Similarity NPD6675 Approved
0.6552 Remote Similarity NPD7128 Approved
0.6525 Remote Similarity NPD6373 Approved
0.6525 Remote Similarity NPD6372 Approved
0.6514 Remote Similarity NPD7515 Phase 2
0.6481 Remote Similarity NPD5328 Approved
0.6476 Remote Similarity NPD4786 Approved
0.6465 Remote Similarity NPD6924 Approved
0.6465 Remote Similarity NPD1811 Approved
0.6465 Remote Similarity NPD6926 Approved
0.6465 Remote Similarity NPD1810 Approved
0.6449 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6441 Remote Similarity NPD7320 Approved
0.6441 Remote Similarity NPD6881 Approved
0.6441 Remote Similarity NPD6899 Approved
0.6436 Remote Similarity NPD5776 Phase 2
0.6436 Remote Similarity NPD6932 Approved
0.6436 Remote Similarity NPD6925 Approved
0.6435 Remote Similarity NPD7632 Discontinued
0.6434 Remote Similarity NPD6033 Approved
0.6423 Remote Similarity NPD7115 Discovery
0.6422 Remote Similarity NPD3168 Discontinued
0.6417 Remote Similarity NPD8130 Phase 1
0.6417 Remote Similarity NPD6649 Approved
0.6417 Remote Similarity NPD6650 Approved
0.6417 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6396 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6396 Remote Similarity NPD7900 Approved
0.6387 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6373 Remote Similarity NPD7145 Approved
0.6372 Remote Similarity NPD4755 Approved
0.6364 Remote Similarity NPD6079 Approved
0.6364 Remote Similarity NPD7087 Discontinued
0.6356 Remote Similarity NPD5697 Approved
0.6356 Remote Similarity NPD5701 Approved
0.6355 Remote Similarity NPD3618 Phase 1
0.6339 Remote Similarity NPD7991 Discontinued
0.6333 Remote Similarity NPD7290 Approved
0.6333 Remote Similarity NPD6883 Approved
0.6333 Remote Similarity NPD4634 Approved
0.6333 Remote Similarity NPD7102 Approved
0.6316 Remote Similarity NPD4225 Approved
0.6311 Remote Similarity NPD6683 Phase 2
0.6306 Remote Similarity NPD4202 Approved
0.6303 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6286 Remote Similarity NPD3667 Approved
0.6281 Remote Similarity NPD6847 Approved
0.6281 Remote Similarity NPD6869 Approved
0.6281 Remote Similarity NPD6617 Approved
0.6263 Remote Similarity NPD4243 Approved
0.6263 Remote Similarity NPD7150 Approved
0.6263 Remote Similarity NPD7151 Approved
0.6263 Remote Similarity NPD7152 Approved
0.6262 Remote Similarity NPD6893 Approved
0.6261 Remote Similarity NPD5286 Approved
0.6261 Remote Similarity NPD5285 Approved
0.6261 Remote Similarity NPD4700 Approved
0.6261 Remote Similarity NPD4696 Approved
0.625 Remote Similarity NPD6012 Approved
0.625 Remote Similarity NPD7509 Discontinued
0.625 Remote Similarity NPD6014 Approved
0.625 Remote Similarity NPD7514 Phase 3
0.625 Remote Similarity NPD7604 Phase 2
0.625 Remote Similarity NPD6013 Approved
0.6228 Remote Similarity NPD6083 Phase 2
0.6228 Remote Similarity NPD6084 Phase 2
0.6224 Remote Similarity NPD6922 Approved
0.6224 Remote Similarity NPD6923 Approved
0.622 Remote Similarity NPD5983 Phase 2
0.6216 Remote Similarity NPD7637 Suspended
0.621 Remote Similarity NPD6940 Discontinued
0.6207 Remote Similarity NPD5344 Discontinued
0.6207 Remote Similarity NPD4159 Approved
0.6198 Remote Similarity NPD5955 Clinical (unspecified phase)
0.619 Remote Similarity NPD6902 Approved
0.6167 Remote Similarity NPD8174 Phase 2
0.6167 Remote Similarity NPD6011 Approved
0.6162 Remote Similarity NPD7144 Approved
0.6162 Remote Similarity NPD7143 Approved
0.6162 Remote Similarity NPD2686 Approved
0.6162 Remote Similarity NPD2254 Approved
0.6162 Remote Similarity NPD2687 Approved
0.6162 Remote Similarity NPD7532 Clinical (unspecified phase)
0.6154 Remote Similarity NPD5225 Approved
0.6154 Remote Similarity NPD5226 Approved
0.6154 Remote Similarity NPD4633 Approved
0.6154 Remote Similarity NPD5224 Approved
0.6154 Remote Similarity NPD5211 Phase 2
0.6154 Remote Similarity NPD6336 Discontinued
0.6148 Remote Similarity NPD6401 Clinical (unspecified phase)
0.614 Remote Similarity NPD5220 Clinical (unspecified phase)
0.614 Remote Similarity NPD4697 Phase 3
0.614 Remote Similarity NPD5221 Approved
0.614 Remote Similarity NPD5222 Approved
0.6139 Remote Similarity NPD4784 Approved
0.6139 Remote Similarity NPD4785 Approved
0.6134 Remote Similarity NPD4768 Approved
0.6134 Remote Similarity NPD4767 Approved
0.6134 Remote Similarity NPD6008 Approved
0.6102 Remote Similarity NPD5174 Approved
0.6102 Remote Similarity NPD5175 Approved
0.6095 Remote Similarity NPD7332 Phase 2
0.6095 Remote Similarity NPD4748 Discontinued
0.6091 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6087 Remote Similarity NPD5173 Approved
0.6075 Remote Similarity NPD3669 Approved
0.6075 Remote Similarity NPD3670 Clinical (unspecified phase)
0.6068 Remote Similarity NPD5223 Approved
0.6058 Remote Similarity NPD6114 Approved
0.6058 Remote Similarity NPD6697 Approved
0.6058 Remote Similarity NPD6115 Approved
0.6058 Remote Similarity NPD6118 Approved
0.605 Remote Similarity NPD5141 Approved
0.6038 Remote Similarity NPD6898 Phase 1
0.6036 Remote Similarity NPD6051 Approved
0.6036 Remote Similarity NPD4753 Phase 2
0.6034 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6033 Remote Similarity NPD4729 Approved
0.6033 Remote Similarity NPD4730 Approved
0.6019 Remote Similarity NPD3666 Approved
0.6019 Remote Similarity NPD3665 Phase 1
0.6019 Remote Similarity NPD3133 Approved
0.6 Remote Similarity NPD5357 Phase 1
0.5985 Remote Similarity NPD8074 Phase 3
0.597 Remote Similarity NPD5956 Approved
0.5966 Remote Similarity NPD4754 Approved
0.5962 Remote Similarity NPD6116 Phase 1
0.5952 Remote Similarity NPD6274 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