Structure

Physi-Chem Properties

Molecular Weight:  664.38
Volume:  668.656
LogP:  2.609
LogD:  2.096
LogS:  -3.624
# Rotatable Bonds:  6
TPSA:  183.21
# H-Bond Aceptor:  11
# H-Bond Donor:  6
# Rings:  6
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.144
Synthetic Accessibility Score:  5.558
Fsp3:  0.889
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.663
MDCK Permeability:  6.503020358650247e-06
Pgp-inhibitor:  0.853
Pgp-substrate:  0.021
Human Intestinal Absorption (HIA):  0.107
20% Bioavailability (F20%):  0.766
30% Bioavailability (F30%):  0.904

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.136
Plasma Protein Binding (PPB):  76.74182891845703%
Volume Distribution (VD):  0.351
Pgp-substrate:  13.584564208984375%

ADMET: Metabolism

CYP1A2-inhibitor:  0.001
CYP1A2-substrate:  0.941
CYP2C19-inhibitor:  0.002
CYP2C19-substrate:  0.63
CYP2C9-inhibitor:  0.008
CYP2C9-substrate:  0.026
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.051
CYP3A4-inhibitor:  0.301
CYP3A4-substrate:  0.089

ADMET: Excretion

Clearance (CL):  1.13
Half-life (T1/2):  0.651

ADMET: Toxicity

hERG Blockers:  0.047
Human Hepatotoxicity (H-HT):  0.236
Drug-inuced Liver Injury (DILI):  0.035
AMES Toxicity:  0.075
Rat Oral Acute Toxicity:  0.111
Maximum Recommended Daily Dose:  0.913
Skin Sensitization:  0.035
Carcinogencity:  0.099
Eye Corrosion:  0.003
Eye Irritation:  0.011
Respiratory Toxicity:  0.937

Download Data

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

  Natural Product: NPC127853

Natural Product ID:  NPC127853
Common Name*:   Phytolaccoside B
IUPAC Name:   (2S,4aR,6aR,6aS,6bR,8aR,9R,10R,11S,12aR,14bS)-11-hydroxy-9-(hydroxymethyl)-2-methoxycarbonyl-2,6a,6b,9,12a-pentamethyl-10-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms:   phytolaccoside B
Standard InCHIKey:  SFZVDNKTWPZIJG-ACNZYQHGSA-N
Standard InCHI:  InChI=1S/C36H56O11/c1-31(30(44)45-6)11-13-36(29(42)43)14-12-34(4)19(20(36)15-31)7-8-24-32(2)16-21(38)27(47-28-26(41)25(40)22(39)17-46-28)33(3,18-37)23(32)9-10-35(24,34)5/h7,20-28,37-41H,8-18H2,1-6H3,(H,42,43)/t20-,21-,22+,23+,24+,25-,26+,27-,28-,31-,32-,33-,34+,35+,36-/m0/s1
SMILES:  C[C@@]1(CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@@H]([C@@H]([C@@](C)(CO)[C@@H]5CC[C@@]34C)O[C@H]3[C@@H]([C@H]([C@@H](CO3)O)O)O)O)[C@@H]2C1)C(=O)O)C(=O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL258392
PubChem CID:   441939
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
NPO20652 Phytolacca acinosa Species Phytolaccaceae Eukaryota n.a. n.a. n.a. PMID[12932140]
NPO17551 Phytolacca americana Species Phytolaccaceae Eukaryota roots n.a. n.a. PMID[18177012]
NPO11619 Phytolacca tetramera hauman Strain Phytolaccaceae Eukaryota n.a. n.a. n.a. PMID[18816139]
NPO17551 Phytolacca americana Species Phytolaccaceae Eukaryota Seeds n.a. n.a. PMID[26595875]
NPO17551 Phytolacca americana Species Phytolaccaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO17551 Phytolacca americana Species Phytolaccaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO17551 Phytolacca americana Species Phytolaccaceae Eukaryota n.a. n.a. Database[FooDB]
NPO17551 Phytolacca americana Species Phytolaccaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17957 Solanum sodomeum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17551 Phytolacca americana Species Phytolaccaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17957 Solanum sodomeum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20652 Phytolacca acinosa Species Phytolaccaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5114 Canis lupus familiaris Species Canidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17551 Phytolacca americana Species Phytolaccaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20652 Phytolacca acinosa Species Phytolaccaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20652 Phytolacca acinosa Species Phytolaccaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO17551 Phytolacca americana Species Phytolaccaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22716 Petalostemon gattingeri Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5114 Canis lupus familiaris Species Canidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20652 Phytolacca acinosa Species Phytolaccaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19056 Allium nutans Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17551 Phytolacca americana Species Phytolaccaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17957 Solanum sodomeum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11619 Phytolacca tetramera hauman Strain Phytolaccaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18517 Phthorimaea operculella Species Gelechiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15872 Stachys mucronata Species Lamiaceae 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 Activity = 265.0 uM PMID[511518]
NPT81 Cell Line A549 Homo sapiens Activity = 253.0 uM PMID[511518]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 74700.0 nM PMID[511518]
NPT1475 Cell Line WI-38 VA13 Homo sapiens IC50 = 68900.0 nM PMID[511518]
NPT1374 Cell Line WI-38 Homo sapiens IC50 = 36200.0 nM PMID[511518]
NPT4438 Individual Protein Chitin synthase 1 Saccharomyces cerevisiae S288c Activity = 189.7 % PMID[511519]
NPT4438 Individual Protein Chitin synthase 1 Saccharomyces cerevisiae S288c IC50 > 400.0 nM PMID[511519]
NPT4438 Individual Protein Chitin synthase 1 Saccharomyces cerevisiae S288c Activity = 165.77 % PMID[511519]
NPT4438 Individual Protein Chitin synthase 1 Saccharomyces cerevisiae S288c Activity = 23.0 % PMID[511519]
NPT4439 Individual Protein Chitin synthase 1 Neurospora crassa OR74A Activity = 400.0 nm PMID[511519]
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Activity = 123.0 % PMID[511518]
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Activity = 117.0 % PMID[511518]
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Activity = 128.0 % PMID[511518]
NPT20 Organism Candida albicans Candida albicans MIC100 = 74.0 uM PMID[511519]
NPT20 Organism Candida albicans Candida albicans MIC80 = 74000.0 nM PMID[511519]
NPT20 Organism Candida albicans Candida albicans MIC50 = 74000.0 nM PMID[511519]
NPT20 Organism Candida albicans Candida albicans MFC = 150.0 uM PMID[511519]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae MIC100 = 74.0 uM PMID[511519]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae MIC80 = 37000.0 nM PMID[511519]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae MIC50 = 18000.0 nM PMID[511519]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae MFC = 150.0 uM PMID[511519]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans MIC100 = 112.0 uM PMID[511519]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans MIC80 = 74000.0 nM PMID[511519]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans MIC50 = 9000.0 nM PMID[511519]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans MFC = 112.0 uM PMID[511519]
NPT3644 Organism Neurospora crassa Neurospora crassa MIC100 = 74.0 uM PMID[511519]
NPT21 Organism Aspergillus niger Aspergillus niger MIC = 188000.0 nM PMID[511519]
NPT87 Organism Aspergillus fumigatus Aspergillus fumigatus MIC100 = 188.0 uM PMID[511519]
NPT185 Organism Aspergillus flavus Aspergillus flavus MIC100 = 74.0 uM PMID[511519]
NPT2 Others Unspecified Activity = 93.36 % PMID[511519]
NPT2 Others Unspecified IC50 > 0.5 ug.mL-1 PMID[511519]
NPT27 Others Unspecified LC100 > 188.0 uM PMID[511519]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae Activity = 17.0 % PMID[511519]

☑ 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 NPC127853 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
0.9901 High Similarity NPC102914
0.9901 High Similarity NPC199457
0.9901 High Similarity NPC108709
0.9901 High Similarity NPC68419
0.9901 High Similarity NPC110139
0.9901 High Similarity NPC7870
0.9901 High Similarity NPC75747
0.99 High Similarity NPC177246
0.99 High Similarity NPC476123
0.99 High Similarity NPC28198
0.99 High Similarity NPC284807
0.9804 High Similarity NPC179434
0.9802 High Similarity NPC306746
0.9802 High Similarity NPC167383
0.9802 High Similarity NPC237503
0.9802 High Similarity NPC57362
0.9802 High Similarity NPC204407
0.98 High Similarity NPC473538
0.98 High Similarity NPC283849
0.9709 High Similarity NPC139894
0.9709 High Similarity NPC116794
0.9709 High Similarity NPC473383
0.9709 High Similarity NPC48249
0.9706 High Similarity NPC475296
0.9706 High Similarity NPC174679
0.9706 High Similarity NPC476880
0.9706 High Similarity NPC274507
0.9706 High Similarity NPC59804
0.9706 High Similarity NPC476884
0.9706 High Similarity NPC136877
0.9706 High Similarity NPC56713
0.9706 High Similarity NPC476887
0.9706 High Similarity NPC476882
0.9706 High Similarity NPC474589
0.9706 High Similarity NPC476881
0.9706 High Similarity NPC29069
0.9706 High Similarity NPC279554
0.9706 High Similarity NPC164194
0.9706 High Similarity NPC476885
0.9706 High Similarity NPC476883
0.9706 High Similarity NPC90856
0.9706 High Similarity NPC127056
0.9706 High Similarity NPC270667
0.9706 High Similarity NPC242611
0.9706 High Similarity NPC220984
0.9706 High Similarity NPC476886
0.97 High Similarity NPC475611
0.9615 High Similarity NPC163183
0.9615 High Similarity NPC238935
0.9615 High Similarity NPC96641
0.9615 High Similarity NPC271138
0.9615 High Similarity NPC473343
0.9615 High Similarity NPC73318
0.9615 High Similarity NPC269315
0.9615 High Similarity NPC475208
0.9615 High Similarity NPC150400
0.9615 High Similarity NPC134835
0.9612 High Similarity NPC164419
0.9612 High Similarity NPC235841
0.9612 High Similarity NPC191763
0.9612 High Similarity NPC211798
0.9612 High Similarity NPC108748
0.9612 High Similarity NPC473481
0.9612 High Similarity NPC297208
0.9612 High Similarity NPC30397
0.9612 High Similarity NPC31839
0.9608 High Similarity NPC137917
0.9524 High Similarity NPC475633
0.9519 High Similarity NPC469946
0.9519 High Similarity NPC100383
0.9519 High Similarity NPC292677
0.9519 High Similarity NPC471383
0.9519 High Similarity NPC101744
0.9519 High Similarity NPC473373
0.9519 High Similarity NPC102439
0.9519 High Similarity NPC257468
0.9519 High Similarity NPC104071
0.9519 High Similarity NPC10320
0.9519 High Similarity NPC128925
0.9519 High Similarity NPC79718
0.9519 High Similarity NPC256798
0.9519 High Similarity NPC80843
0.9519 High Similarity NPC471967
0.9519 High Similarity NPC475516
0.9519 High Similarity NPC139044
0.9519 High Similarity NPC324875
0.9519 High Similarity NPC46388
0.9519 High Similarity NPC475504
0.9519 High Similarity NPC1046
0.9519 High Similarity NPC104400
0.9519 High Similarity NPC109079
0.9519 High Similarity NPC37739
0.9519 High Similarity NPC276093
0.9515 High Similarity NPC78046
0.9515 High Similarity NPC269095
0.951 High Similarity NPC285576
0.9429 High Similarity NPC219180
0.9429 High Similarity NPC251263
0.9429 High Similarity NPC241909
0.9429 High Similarity NPC309714
0.9429 High Similarity NPC114287
0.9429 High Similarity NPC473826
0.9429 High Similarity NPC174720
0.9429 High Similarity NPC295823
0.9429 High Similarity NPC166422
0.9429 High Similarity NPC138334
0.9429 High Similarity NPC47063
0.9429 High Similarity NPC258885
0.9429 High Similarity NPC133818
0.9429 High Similarity NPC189884
0.9429 High Similarity NPC323341
0.9429 High Similarity NPC204458
0.9429 High Similarity NPC192600
0.9429 High Similarity NPC114304
0.9429 High Similarity NPC475287
0.9429 High Similarity NPC46665
0.9429 High Similarity NPC151543
0.9429 High Similarity NPC475467
0.9429 High Similarity NPC155410
0.9429 High Similarity NPC124296
0.9346 High Similarity NPC300419
0.9346 High Similarity NPC471547
0.9346 High Similarity NPC473405
0.934 High Similarity NPC298034
0.934 High Similarity NPC224381
0.934 High Similarity NPC309907
0.934 High Similarity NPC227551
0.934 High Similarity NPC473714
0.934 High Similarity NPC261506
0.934 High Similarity NPC475160
0.934 High Similarity NPC236638
0.934 High Similarity NPC305981
0.934 High Similarity NPC164389
0.934 High Similarity NPC119592
0.934 High Similarity NPC76972
0.934 High Similarity NPC71065
0.934 High Similarity NPC123199
0.934 High Similarity NPC202828
0.934 High Similarity NPC43550
0.934 High Similarity NPC65105
0.934 High Similarity NPC293330
0.934 High Similarity NPC475140
0.934 High Similarity NPC41061
0.934 High Similarity NPC70809
0.934 High Similarity NPC79643
0.934 High Similarity NPC204414
0.934 High Similarity NPC67857
0.934 High Similarity NPC471385
0.934 High Similarity NPC161717
0.934 High Similarity NPC469782
0.934 High Similarity NPC294453
0.934 High Similarity NPC54636
0.934 High Similarity NPC250247
0.934 High Similarity NPC100639
0.934 High Similarity NPC476068
0.934 High Similarity NPC475486
0.934 High Similarity NPC471550
0.934 High Similarity NPC60557
0.934 High Similarity NPC57484
0.934 High Similarity NPC4328
0.9333 High Similarity NPC125923
0.9333 High Similarity NPC64106
0.9333 High Similarity NPC65590
0.9333 High Similarity NPC212968
0.9259 High Similarity NPC475899
0.9259 High Similarity NPC471548
0.9259 High Similarity NPC237191
0.9252 High Similarity NPC160415
0.9252 High Similarity NPC75287
0.9252 High Similarity NPC288205
0.9252 High Similarity NPC161674
0.9252 High Similarity NPC305267
0.9252 High Similarity NPC471384
0.9252 High Similarity NPC58448
0.9252 High Similarity NPC26626
0.9252 High Similarity NPC51465
0.9252 High Similarity NPC37134
0.9252 High Similarity NPC291903
0.9252 High Similarity NPC476992
0.9238 High Similarity NPC263827
0.9238 High Similarity NPC285410
0.9238 High Similarity NPC190837
0.9238 High Similarity NPC250481
0.9216 High Similarity NPC173583
0.9174 High Similarity NPC477464
0.9174 High Similarity NPC473401
0.9174 High Similarity NPC471577
0.9167 High Similarity NPC475514
0.9167 High Similarity NPC191827
0.9167 High Similarity NPC69811
0.9167 High Similarity NPC123522
0.9167 High Similarity NPC475119
0.9167 High Similarity NPC473452
0.9167 High Similarity NPC8524
0.9167 High Similarity NPC148417
0.9167 High Similarity NPC470876
0.9167 High Similarity NPC475209
0.9167 High Similarity NPC110633
0.9167 High Similarity NPC136768
0.9167 High Similarity NPC286457

  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 NPC127853 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
0.9048 High Similarity NPD8132 Clinical (unspecified phase)
0.8684 High Similarity NPD8328 Phase 3
0.8649 High Similarity NPD8295 Clinical (unspecified phase)
0.8214 Intermediate Similarity NPD8133 Approved
0.8165 Intermediate Similarity NPD6412 Phase 2
0.8155 Intermediate Similarity NPD7748 Approved
0.8095 Intermediate Similarity NPD7902 Approved
0.8091 Intermediate Similarity NPD6686 Approved
0.7961 Intermediate Similarity NPD7515 Phase 2
0.7917 Intermediate Similarity NPD7507 Approved
0.781 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.781 Intermediate Similarity NPD7900 Approved
0.7797 Intermediate Similarity NPD8294 Approved
0.7797 Intermediate Similarity NPD8377 Approved
0.7731 Intermediate Similarity NPD8380 Approved
0.7731 Intermediate Similarity NPD8335 Approved
0.7731 Intermediate Similarity NPD8378 Approved
0.7731 Intermediate Similarity NPD8379 Approved
0.7731 Intermediate Similarity NPD8033 Approved
0.7731 Intermediate Similarity NPD8296 Approved
0.7724 Intermediate Similarity NPD7319 Approved
0.7712 Intermediate Similarity NPD7516 Approved
0.7642 Intermediate Similarity NPD7736 Approved
0.7627 Intermediate Similarity NPD7327 Approved
0.7627 Intermediate Similarity NPD7328 Approved
0.7453 Intermediate Similarity NPD8035 Phase 2
0.7453 Intermediate Similarity NPD8034 Phase 2
0.7438 Intermediate Similarity NPD8513 Phase 3
0.7438 Intermediate Similarity NPD8516 Approved
0.7438 Intermediate Similarity NPD8517 Approved
0.7438 Intermediate Similarity NPD7503 Approved
0.7438 Intermediate Similarity NPD8515 Approved
0.7419 Intermediate Similarity NPD8293 Discontinued
0.735 Intermediate Similarity NPD8297 Approved
0.735 Intermediate Similarity NPD6882 Approved
0.73 Intermediate Similarity NPD7645 Phase 2
0.7241 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7236 Intermediate Similarity NPD6370 Approved
0.7222 Intermediate Similarity NPD6399 Phase 3
0.7212 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7207 Intermediate Similarity NPD7638 Approved
0.7193 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.7155 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7640 Approved
0.7143 Intermediate Similarity NPD7639 Approved
0.713 Intermediate Similarity NPD7128 Approved
0.713 Intermediate Similarity NPD6402 Approved
0.713 Intermediate Similarity NPD6675 Approved
0.713 Intermediate Similarity NPD5739 Approved
0.712 Intermediate Similarity NPD7492 Approved
0.7107 Intermediate Similarity NPD6009 Approved
0.7094 Intermediate Similarity NPD6373 Approved
0.7094 Intermediate Similarity NPD6372 Approved
0.7073 Intermediate Similarity NPD6059 Approved
0.7073 Intermediate Similarity NPD6319 Approved
0.7073 Intermediate Similarity NPD6054 Approved
0.7063 Intermediate Similarity NPD6616 Approved
0.704 Intermediate Similarity NPD6067 Discontinued
0.7034 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD7320 Approved
0.7009 Intermediate Similarity NPD6881 Approved
0.7009 Intermediate Similarity NPD6899 Approved
0.7008 Intermediate Similarity NPD7078 Approved
0.7 Intermediate Similarity NPD4632 Approved
0.6975 Remote Similarity NPD8130 Phase 1
0.6975 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6975 Remote Similarity NPD6650 Approved
0.6975 Remote Similarity NPD6649 Approved
0.6972 Remote Similarity NPD6411 Approved
0.6967 Remote Similarity NPD7115 Discovery
0.6923 Remote Similarity NPD5701 Approved
0.6923 Remote Similarity NPD5697 Approved
0.6891 Remote Similarity NPD6883 Approved
0.6891 Remote Similarity NPD7102 Approved
0.6891 Remote Similarity NPD7290 Approved
0.688 Remote Similarity NPD6015 Approved
0.688 Remote Similarity NPD6016 Approved
0.6852 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6833 Remote Similarity NPD6869 Approved
0.6833 Remote Similarity NPD6847 Approved
0.6833 Remote Similarity NPD6617 Approved
0.6825 Remote Similarity NPD5988 Approved
0.6822 Remote Similarity NPD3618 Phase 1
0.6814 Remote Similarity NPD6084 Phase 2
0.6814 Remote Similarity NPD6083 Phase 2
0.6807 Remote Similarity NPD6014 Approved
0.6807 Remote Similarity NPD6013 Approved
0.6807 Remote Similarity NPD6012 Approved
0.6792 Remote Similarity NPD4786 Approved
0.6789 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6789 Remote Similarity NPD6101 Approved
0.6789 Remote Similarity NPD5328 Approved
0.678 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6762 Remote Similarity NPD3667 Approved
0.6759 Remote Similarity NPD3573 Approved
0.6757 Remote Similarity NPD8171 Discontinued
0.6754 Remote Similarity NPD4225 Approved
0.6727 Remote Similarity NPD46 Approved
0.6727 Remote Similarity NPD6698 Approved
0.6723 Remote Similarity NPD6011 Approved
0.6694 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7521 Approved
0.6667 Remote Similarity NPD4755 Approved
0.6667 Remote Similarity NPD7146 Approved
0.6667 Remote Similarity NPD5330 Approved
0.6667 Remote Similarity NPD7334 Approved
0.6667 Remote Similarity NPD6684 Approved
0.6667 Remote Similarity NPD6409 Approved
0.6667 Remote Similarity NPD6079 Approved
0.6641 Remote Similarity NPD7604 Phase 2
0.6636 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6615 Remote Similarity NPD8074 Phase 3
0.6614 Remote Similarity NPD6921 Approved
0.6614 Remote Similarity NPD5983 Phase 2
0.6607 Remote Similarity NPD4202 Approved
0.6581 Remote Similarity NPD7632 Discontinued
0.6571 Remote Similarity NPD7525 Registered
0.6565 Remote Similarity NPD6033 Approved
0.6555 Remote Similarity NPD6008 Approved
0.6552 Remote Similarity NPD5286 Approved
0.6552 Remote Similarity NPD4700 Approved
0.6552 Remote Similarity NPD4696 Approved
0.6552 Remote Similarity NPD5285 Approved
0.6545 Remote Similarity NPD5737 Approved
0.6545 Remote Similarity NPD6903 Approved
0.6545 Remote Similarity NPD6672 Approved
0.6538 Remote Similarity NPD6336 Discontinued
0.6518 Remote Similarity NPD7983 Approved
0.6491 Remote Similarity NPD5695 Phase 3
0.6481 Remote Similarity NPD3133 Approved
0.6481 Remote Similarity NPD3665 Phase 1
0.6481 Remote Similarity NPD3666 Approved
0.648 Remote Similarity NPD6940 Discontinued
0.648 Remote Similarity NPD6274 Approved
0.6475 Remote Similarity NPD4634 Approved
0.6466 Remote Similarity NPD5696 Approved
0.646 Remote Similarity NPD5779 Approved
0.646 Remote Similarity NPD5778 Approved
0.6457 Remote Similarity NPD7101 Approved
0.6457 Remote Similarity NPD7100 Approved
0.6442 Remote Similarity NPD6116 Phase 1
0.6441 Remote Similarity NPD5225 Approved
0.6441 Remote Similarity NPD5224 Approved
0.6441 Remote Similarity NPD5211 Phase 2
0.6441 Remote Similarity NPD5226 Approved
0.6441 Remote Similarity NPD4633 Approved
0.6435 Remote Similarity NPD5222 Approved
0.6435 Remote Similarity NPD5221 Approved
0.6435 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6435 Remote Similarity NPD4697 Phase 3
0.6417 Remote Similarity NPD4768 Approved
0.6417 Remote Similarity NPD4767 Approved
0.6389 Remote Similarity NPD3669 Approved
0.6389 Remote Similarity NPD3670 Clinical (unspecified phase)
0.6387 Remote Similarity NPD5174 Approved
0.6387 Remote Similarity NPD5175 Approved
0.6381 Remote Similarity NPD6115 Approved
0.6381 Remote Similarity NPD6118 Approved
0.6381 Remote Similarity NPD6114 Approved
0.6381 Remote Similarity NPD6697 Approved
0.6379 Remote Similarity NPD5173 Approved
0.6378 Remote Similarity NPD6335 Approved
0.637 Remote Similarity NPD8449 Approved
0.6364 Remote Similarity NPD7625 Phase 1
0.6357 Remote Similarity NPD6908 Approved
0.6357 Remote Similarity NPD6909 Approved
0.6356 Remote Similarity NPD5344 Discontinued
0.6356 Remote Similarity NPD5223 Approved
0.6349 Remote Similarity NPD6868 Approved
0.6348 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6346 Remote Similarity NPD6117 Approved
0.6339 Remote Similarity NPD4753 Phase 2
0.6333 Remote Similarity NPD5141 Approved
0.633 Remote Similarity NPD3668 Phase 3
0.6325 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6324 Remote Similarity NPD8450 Suspended
0.6311 Remote Similarity NPD4729 Approved
0.6311 Remote Similarity NPD4730 Approved
0.6299 Remote Similarity NPD6317 Approved
0.6293 Remote Similarity NPD7614 Phase 1
0.6293 Remote Similarity NPD7732 Phase 3
0.625 Remote Similarity NPD8338 Approved
0.625 Remote Similarity NPD4754 Approved
0.625 Remote Similarity NPD6313 Approved
0.625 Remote Similarity NPD6314 Approved
0.6216 Remote Similarity NPD6098 Approved
0.621 Remote Similarity NPD5251 Approved
0.621 Remote Similarity NPD5250 Approved
0.621 Remote Similarity NPD5247 Approved
0.621 Remote Similarity NPD5248 Approved
0.621 Remote Similarity NPD5249 Phase 3
0.6204 Remote Similarity NPD1779 Approved
0.6204 Remote Similarity NPD1780 Approved
0.6195 Remote Similarity NPD6080 Approved
0.6195 Remote Similarity NPD6673 Approved
0.6195 Remote Similarity NPD6904 Approved
0.6194 Remote Similarity NPD8337 Approved
0.6194 Remote Similarity NPD8336 Approved
0.6179 Remote Similarity NPD5128 Approved
0.6172 Remote Similarity NPD8137 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