Structure

Physi-Chem Properties

Molecular Weight:  370.18
Volume:  362.778
LogP:  2.085
LogD:  2.916
LogS:  -1.357
# Rotatable Bonds:  2
TPSA:  80.67
# H-Bond Aceptor:  5
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.748
Synthetic Accessibility Score:  4.139
Fsp3:  0.947
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.737
MDCK Permeability:  9.160190529655665e-06
Pgp-inhibitor:  0.683
Pgp-substrate:  0.014
Human Intestinal Absorption (HIA):  0.3
20% Bioavailability (F20%):  0.94
30% Bioavailability (F30%):  0.939

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.364
Plasma Protein Binding (PPB):  90.96048736572266%
Volume Distribution (VD):  0.912
Pgp-substrate:  3.233159303665161%

ADMET: Metabolism

CYP1A2-inhibitor:  0.012
CYP1A2-substrate:  0.905
CYP2C19-inhibitor:  0.017
CYP2C19-substrate:  0.851
CYP2C9-inhibitor:  0.033
CYP2C9-substrate:  0.122
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.115
CYP3A4-inhibitor:  0.031
CYP3A4-substrate:  0.11

ADMET: Excretion

Clearance (CL):  6.603
Half-life (T1/2):  0.249

ADMET: Toxicity

hERG Blockers:  0.204
Human Hepatotoxicity (H-HT):  0.701
Drug-inuced Liver Injury (DILI):  0.746
AMES Toxicity:  0.927
Rat Oral Acute Toxicity:  0.529
Maximum Recommended Daily Dose:  0.918
Skin Sensitization:  0.964
Carcinogencity:  0.902
Eye Corrosion:  0.979
Eye Irritation:  0.855
Respiratory Toxicity:  0.981

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

  Natural Product: NPC126642

Natural Product ID:  NPC126642
Common Name*:   Androsterone-3-Sulfate
IUPAC Name:   [(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl] hydrogen sulfate
Synonyms:  
Standard InCHIKey:  ZMITXKRGXGRMKS-HLUDHZFRSA-N
Standard InCHI:  InChI=1S/C19H30O5S/c1-18-9-7-13(24-25(21,22)23)11-12(18)3-4-14-15-5-6-17(20)19(15,2)10-8-16(14)18/h12-16H,3-11H2,1-2H3,(H,21,22,23)/t12-,13+,14-,15-,16-,18-,19-/m0/s1
SMILES:  O=C1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC[C@@H]2[C@]1(C)CC[C@H](C2)OS(=O)(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2074598
PubChem CID:   159663
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0001692] Sulfated steroids

*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

☑ 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
NPT752 Individual Protein Solute carrier organic anion transporter family member 1A1 Rattus norvegicus Ki = 2400.0 nM PMID[501565]

☑ 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 NPC126642 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
0.8904 High Similarity NPC329117
0.8841 High Similarity NPC6120
0.8841 High Similarity NPC327728
0.8841 High Similarity NPC131892
0.8841 High Similarity NPC213178
0.8649 High Similarity NPC478128
0.8592 High Similarity NPC89310
0.8592 High Similarity NPC151018
0.8592 High Similarity NPC156277
0.8592 High Similarity NPC320549
0.8592 High Similarity NPC58057
0.8472 Intermediate Similarity NPC232112
0.8356 Intermediate Similarity NPC254340
0.8356 Intermediate Similarity NPC133922
0.831 Intermediate Similarity NPC324607
0.831 Intermediate Similarity NPC321732
0.8289 Intermediate Similarity NPC52951
0.8243 Intermediate Similarity NPC174964
0.8243 Intermediate Similarity NPC195155
0.8243 Intermediate Similarity NPC273366
0.8243 Intermediate Similarity NPC97534
0.8243 Intermediate Similarity NPC159789
0.8158 Intermediate Similarity NPC185465
0.8133 Intermediate Similarity NPC4209
0.8133 Intermediate Similarity NPC475742
0.8133 Intermediate Similarity NPC472486
0.8133 Intermediate Similarity NPC472487
0.8133 Intermediate Similarity NPC5767
0.8108 Intermediate Similarity NPC167702
0.8108 Intermediate Similarity NPC280026
0.8052 Intermediate Similarity NPC320144
0.8026 Intermediate Similarity NPC23884
0.8026 Intermediate Similarity NPC221420
0.8026 Intermediate Similarity NPC207010
0.8026 Intermediate Similarity NPC475031
0.8026 Intermediate Similarity NPC317913
0.8 Intermediate Similarity NPC477603
0.8 Intermediate Similarity NPC125767
0.8 Intermediate Similarity NPC25833
0.8 Intermediate Similarity NPC21220
0.8 Intermediate Similarity NPC212733
0.7973 Intermediate Similarity NPC310766
0.7949 Intermediate Similarity NPC470609
0.7922 Intermediate Similarity NPC80089
0.7922 Intermediate Similarity NPC324700
0.7922 Intermediate Similarity NPC224802
0.7922 Intermediate Similarity NPC34046
0.7922 Intermediate Similarity NPC171426
0.7875 Intermediate Similarity NPC15821
0.7848 Intermediate Similarity NPC469745
0.7838 Intermediate Similarity NPC473267
0.7821 Intermediate Similarity NPC80891
0.7821 Intermediate Similarity NPC201276
0.7792 Intermediate Similarity NPC264602
0.7792 Intermediate Similarity NPC143133
0.7792 Intermediate Similarity NPC298168
0.7778 Intermediate Similarity NPC475172
0.7763 Intermediate Similarity NPC472311
0.775 Intermediate Similarity NPC30583
0.775 Intermediate Similarity NPC61107
0.775 Intermediate Similarity NPC317066
0.775 Intermediate Similarity NPC328351
0.775 Intermediate Similarity NPC289486
0.775 Intermediate Similarity NPC328007
0.7738 Intermediate Similarity NPC271974
0.7738 Intermediate Similarity NPC247312
0.7733 Intermediate Similarity NPC282905
0.7733 Intermediate Similarity NPC477229
0.7733 Intermediate Similarity NPC68426
0.7733 Intermediate Similarity NPC474123
0.7722 Intermediate Similarity NPC261616
0.7703 Intermediate Similarity NPC476731
0.7671 Intermediate Similarity NPC473225
0.7662 Intermediate Similarity NPC471046
0.7662 Intermediate Similarity NPC108840
0.7654 Intermediate Similarity NPC327451
0.7639 Intermediate Similarity NPC268736
0.7639 Intermediate Similarity NPC477931
0.7632 Intermediate Similarity NPC472854
0.7632 Intermediate Similarity NPC168511
0.7632 Intermediate Similarity NPC130011
0.7632 Intermediate Similarity NPC159325
0.7625 Intermediate Similarity NPC12933
0.76 Intermediate Similarity NPC469940
0.76 Intermediate Similarity NPC478103
0.7576 Intermediate Similarity NPC288296
0.7576 Intermediate Similarity NPC53245
0.7568 Intermediate Similarity NPC252032
0.7568 Intermediate Similarity NPC469941
0.7568 Intermediate Similarity NPC64466
0.7568 Intermediate Similarity NPC319671
0.7568 Intermediate Similarity NPC476734
0.7568 Intermediate Similarity NPC196197
0.7564 Intermediate Similarity NPC471151
0.7564 Intermediate Similarity NPC477918
0.7561 Intermediate Similarity NPC473336
0.7561 Intermediate Similarity NPC50438
0.7561 Intermediate Similarity NPC471044
0.7561 Intermediate Similarity NPC319909
0.7534 Intermediate Similarity NPC472984
0.7532 Intermediate Similarity NPC478105
0.7532 Intermediate Similarity NPC267753
0.7531 Intermediate Similarity NPC268040
0.7531 Intermediate Similarity NPC121121
0.75 Intermediate Similarity NPC477851
0.75 Intermediate Similarity NPC81759
0.747 Intermediate Similarity NPC478127
0.7468 Intermediate Similarity NPC26029
0.7467 Intermediate Similarity NPC477850
0.7467 Intermediate Similarity NPC477929
0.7467 Intermediate Similarity NPC108131
0.7465 Intermediate Similarity NPC114891
0.7439 Intermediate Similarity NPC472743
0.7439 Intermediate Similarity NPC475726
0.7432 Intermediate Similarity NPC2568
0.7432 Intermediate Similarity NPC260319
0.7432 Intermediate Similarity NPC474954
0.7432 Intermediate Similarity NPC103647
0.7432 Intermediate Similarity NPC180777
0.7432 Intermediate Similarity NPC475977
0.7407 Intermediate Similarity NPC58631
0.7403 Intermediate Similarity NPC478130
0.7403 Intermediate Similarity NPC477930
0.7397 Intermediate Similarity NPC42060
0.7381 Intermediate Similarity NPC80700
0.7381 Intermediate Similarity NPC476726
0.7381 Intermediate Similarity NPC476727
0.7375 Intermediate Similarity NPC245029
0.7375 Intermediate Similarity NPC31302
0.7375 Intermediate Similarity NPC472310
0.7368 Intermediate Similarity NPC472309
0.7368 Intermediate Similarity NPC477822
0.7368 Intermediate Similarity NPC473552
0.7368 Intermediate Similarity NPC323900
0.7368 Intermediate Similarity NPC477823
0.7368 Intermediate Similarity NPC324984
0.7368 Intermediate Similarity NPC477821
0.7361 Intermediate Similarity NPC159654
0.7361 Intermediate Similarity NPC118937
0.7361 Intermediate Similarity NPC167995
0.7361 Intermediate Similarity NPC281540
0.7353 Intermediate Similarity NPC143597
0.7353 Intermediate Similarity NPC151464
0.7349 Intermediate Similarity NPC474233
0.7349 Intermediate Similarity NPC474996
0.7349 Intermediate Similarity NPC474482
0.7349 Intermediate Similarity NPC475745
0.7342 Intermediate Similarity NPC477919
0.7342 Intermediate Similarity NPC472746
0.7342 Intermediate Similarity NPC180199
0.7342 Intermediate Similarity NPC474404
0.7333 Intermediate Similarity NPC474962
0.7324 Intermediate Similarity NPC71460
0.7324 Intermediate Similarity NPC218585
0.7324 Intermediate Similarity NPC148174
0.7317 Intermediate Similarity NPC13494
0.7308 Intermediate Similarity NPC72444
0.7308 Intermediate Similarity NPC27349
0.7308 Intermediate Similarity NPC24014
0.7308 Intermediate Similarity NPC477934
0.7297 Intermediate Similarity NPC130459
0.7297 Intermediate Similarity NPC474221
0.7297 Intermediate Similarity NPC478180
0.7294 Intermediate Similarity NPC263802
0.7294 Intermediate Similarity NPC202937
0.7284 Intermediate Similarity NPC472853
0.7284 Intermediate Similarity NPC164999
0.7273 Intermediate Similarity NPC478129
0.7273 Intermediate Similarity NPC109510
0.7273 Intermediate Similarity NPC475255
0.7262 Intermediate Similarity NPC292553
0.7262 Intermediate Similarity NPC76518
0.725 Intermediate Similarity NPC243594
0.725 Intermediate Similarity NPC472608
0.725 Intermediate Similarity NPC31031
0.725 Intermediate Similarity NPC199965
0.725 Intermediate Similarity NPC476732
0.7229 Intermediate Similarity NPC471036
0.7229 Intermediate Similarity NPC291320
0.7229 Intermediate Similarity NPC217559
0.7229 Intermediate Similarity NPC472744
0.7229 Intermediate Similarity NPC292458
0.7229 Intermediate Similarity NPC268578
0.7215 Intermediate Similarity NPC477932
0.7215 Intermediate Similarity NPC473916
0.7215 Intermediate Similarity NPC477601
0.7215 Intermediate Similarity NPC477602
0.7215 Intermediate Similarity NPC477933
0.7209 Intermediate Similarity NPC474719
0.7206 Intermediate Similarity NPC184819
0.72 Intermediate Similarity NPC470956
0.7195 Intermediate Similarity NPC77311
0.7195 Intermediate Similarity NPC50658
0.7179 Intermediate Similarity NPC55508
0.7176 Intermediate Similarity NPC2783
0.7176 Intermediate Similarity NPC472738
0.7176 Intermediate Similarity NPC302111
0.7176 Intermediate Similarity NPC472272
0.7162 Intermediate Similarity NPC142712
0.7162 Intermediate Similarity NPC44122

  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 NPC126642 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
0.8841 High Similarity NPD3700 Clinical (unspecified phase)
0.8841 High Similarity NPD3699 Clinical (unspecified phase)
0.8592 High Similarity NPD4809 Clinical (unspecified phase)
0.8592 High Similarity NPD4808 Clinical (unspecified phase)
0.831 Intermediate Similarity NPD3698 Phase 2
0.8243 Intermediate Similarity NPD3703 Phase 2
0.8194 Intermediate Similarity NPD4244 Approved
0.8194 Intermediate Similarity NPD4245 Approved
0.8169 Intermediate Similarity NPD5361 Clinical (unspecified phase)
0.8169 Intermediate Similarity NPD5360 Phase 3
0.8158 Intermediate Similarity NPD5364 Discontinued
0.8133 Intermediate Similarity NPD6117 Approved
0.8108 Intermediate Similarity NPD6113 Clinical (unspecified phase)
0.8026 Intermediate Similarity NPD6116 Phase 1
0.8 Intermediate Similarity NPD3668 Phase 3
0.8 Intermediate Similarity NPD3171 Clinical (unspecified phase)
0.7945 Intermediate Similarity NPD4789 Approved
0.7922 Intermediate Similarity NPD6115 Approved
0.7922 Intermediate Similarity NPD6697 Approved
0.7922 Intermediate Similarity NPD3671 Phase 1
0.7922 Intermediate Similarity NPD6118 Approved
0.7922 Intermediate Similarity NPD6114 Approved
0.7838 Intermediate Similarity NPD4758 Discontinued
0.7838 Intermediate Similarity NPD5777 Approved
0.7639 Intermediate Similarity NPD4224 Phase 2
0.76 Intermediate Similarity NPD6081 Approved
0.7108 Intermediate Similarity NPD3667 Approved
0.7105 Intermediate Similarity NPD4267 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD3702 Approved
0.7059 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.6977 Remote Similarity NPD3618 Phase 1
0.6941 Remote Similarity NPD4786 Approved
0.6824 Remote Similarity NPD4788 Approved
0.6795 Remote Similarity NPD4787 Phase 1
0.6778 Remote Similarity NPD8034 Phase 2
0.6778 Remote Similarity NPD8035 Phase 2
0.6744 Remote Similarity NPD3133 Approved
0.6744 Remote Similarity NPD3666 Approved
0.6744 Remote Similarity NPD3665 Phase 1
0.6742 Remote Similarity NPD5328 Approved
0.6627 Remote Similarity NPD3617 Approved
0.6593 Remote Similarity NPD6079 Approved
0.6522 Remote Similarity NPD6399 Phase 3
0.6522 Remote Similarity NPD4202 Approved
0.6489 Remote Similarity NPD5222 Approved
0.6489 Remote Similarity NPD5221 Approved
0.6489 Remote Similarity NPD4697 Phase 3
0.6489 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6444 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6421 Remote Similarity NPD5173 Approved
0.6421 Remote Similarity NPD4755 Approved
0.6413 Remote Similarity NPD7515 Phase 2
0.6404 Remote Similarity NPD7146 Approved
0.6404 Remote Similarity NPD6409 Approved
0.6404 Remote Similarity NPD6684 Approved
0.6404 Remote Similarity NPD7521 Approved
0.6404 Remote Similarity NPD7334 Approved
0.6404 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6404 Remote Similarity NPD5330 Approved
0.6374 Remote Similarity NPD4753 Phase 2
0.6322 Remote Similarity NPD4223 Phase 3
0.6322 Remote Similarity NPD4221 Approved
0.6304 Remote Similarity NPD6701 Clinical (unspecified phase)
0.6304 Remote Similarity NPD6700 Approved
0.6289 Remote Similarity NPD5286 Approved
0.6289 Remote Similarity NPD8418 Phase 2
0.6289 Remote Similarity NPD4700 Approved
0.6289 Remote Similarity NPD4696 Approved
0.6289 Remote Similarity NPD5285 Approved
0.6279 Remote Similarity NPD7525 Registered
0.6277 Remote Similarity NPD7748 Approved
0.6264 Remote Similarity NPD6672 Approved
0.6264 Remote Similarity NPD6903 Approved
0.6264 Remote Similarity NPD5737 Approved
0.6263 Remote Similarity NPD4754 Approved
0.6237 Remote Similarity NPD6702 Approved
0.6237 Remote Similarity NPD6703 Approved
0.6224 Remote Similarity NPD5223 Approved
0.6222 Remote Similarity NPD5279 Phase 3
0.6207 Remote Similarity NPD4139 Approved
0.6207 Remote Similarity NPD4692 Approved
0.62 Remote Similarity NPD8170 Clinical (unspecified phase)
0.618 Remote Similarity NPD4197 Approved
0.6162 Remote Similarity NPD5211 Phase 2
0.6162 Remote Similarity NPD5226 Approved
0.6162 Remote Similarity NPD4633 Approved
0.6162 Remote Similarity NPD5225 Approved
0.6162 Remote Similarity NPD5224 Approved
0.6139 Remote Similarity NPD6920 Discontinued
0.6133 Remote Similarity NPD3198 Approved
0.6111 Remote Similarity NPD5329 Approved
0.6105 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6105 Remote Similarity NPD7900 Approved
0.61 Remote Similarity NPD5174 Approved
0.61 Remote Similarity NPD5175 Approved
0.6092 Remote Similarity NPD6928 Phase 2
0.6082 Remote Similarity NPD7902 Approved
0.6049 Remote Similarity NPD4137 Phase 3
0.6047 Remote Similarity NPD4776 Phase 2
0.6047 Remote Similarity NPD4777 Suspended
0.6044 Remote Similarity NPD4138 Approved
0.6044 Remote Similarity NPD4693 Phase 3
0.6044 Remote Similarity NPD5205 Approved
0.6044 Remote Similarity NPD4688 Approved
0.6044 Remote Similarity NPD4689 Approved
0.6044 Remote Similarity NPD4690 Approved
0.6042 Remote Similarity NPD5210 Approved
0.6042 Remote Similarity NPD4629 Approved
0.604 Remote Similarity NPD5141 Approved
0.602 Remote Similarity NPD7638 Approved
0.6 Remote Similarity NPD3701 Clinical (unspecified phase)
0.598 Remote Similarity NPD7128 Approved
0.598 Remote Similarity NPD5739 Approved
0.598 Remote Similarity NPD4768 Approved
0.598 Remote Similarity NPD6675 Approved
0.598 Remote Similarity NPD6402 Approved
0.598 Remote Similarity NPD4767 Approved
0.5976 Remote Similarity NPD4691 Approved
0.5976 Remote Similarity NPD4747 Approved
0.596 Remote Similarity NPD7639 Approved
0.596 Remote Similarity NPD7640 Approved
0.5926 Remote Similarity NPD3621 Clinical (unspecified phase)
0.5922 Remote Similarity NPD5701 Approved
0.5922 Remote Similarity NPD5697 Approved
0.5918 Remote Similarity NPD7919 Phase 3
0.5918 Remote Similarity NPD7920 Phase 3
0.5918 Remote Similarity NPD6084 Phase 2
0.5918 Remote Similarity NPD6083 Phase 2
0.5909 Remote Similarity NPD1462 Approved
0.5909 Remote Similarity NPD4695 Discontinued
0.5905 Remote Similarity NPD5135 Approved
0.5905 Remote Similarity NPD5134 Clinical (unspecified phase)
0.589 Remote Similarity NPD615 Clinical (unspecified phase)
0.589 Remote Similarity NPD3729 Clinical (unspecified phase)
0.5882 Remote Similarity NPD6942 Approved
0.5882 Remote Similarity NPD7339 Approved
0.5876 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5876 Remote Similarity NPD5695 Phase 3
0.587 Remote Similarity NPD5690 Phase 2
0.587 Remote Similarity NPD5280 Approved
0.587 Remote Similarity NPD4694 Approved
0.587 Remote Similarity NPD6098 Approved
0.5865 Remote Similarity NPD6899 Approved
0.5865 Remote Similarity NPD7320 Approved
0.5865 Remote Similarity NPD5128 Approved
0.5865 Remote Similarity NPD6011 Approved
0.5865 Remote Similarity NPD4730 Approved
0.5865 Remote Similarity NPD4729 Approved
0.5865 Remote Similarity NPD5168 Approved
0.5865 Remote Similarity NPD6415 Discontinued
0.5865 Remote Similarity NPD6881 Approved
0.5859 Remote Similarity NPD8088 Phase 1
0.5859 Remote Similarity NPD5696 Approved
0.5851 Remote Similarity NPD6080 Approved
0.5851 Remote Similarity NPD6673 Approved
0.5851 Remote Similarity NPD6904 Approved
0.5849 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5842 Remote Similarity NPD7632 Discontinued
0.5825 Remote Similarity NPD6008 Approved
0.581 Remote Similarity NPD6373 Approved
0.581 Remote Similarity NPD6012 Approved
0.581 Remote Similarity NPD6372 Approved
0.581 Remote Similarity NPD6014 Approved
0.581 Remote Similarity NPD6013 Approved
0.5797 Remote Similarity NPD344 Approved
0.5797 Remote Similarity NPD343 Approved
0.5797 Remote Similarity NPD345 Approved
0.5765 Remote Similarity NPD4058 Approved
0.5755 Remote Similarity NPD7102 Approved
0.5755 Remote Similarity NPD5169 Approved
0.5755 Remote Similarity NPD4634 Approved
0.5755 Remote Similarity NPD5249 Phase 3
0.5755 Remote Similarity NPD5250 Approved
0.5755 Remote Similarity NPD5247 Approved
0.5755 Remote Similarity NPD5251 Approved
0.5755 Remote Similarity NPD5248 Approved
0.5755 Remote Similarity NPD6883 Approved
0.5755 Remote Similarity NPD7290 Approved
0.5745 Remote Similarity NPD5208 Approved
0.5732 Remote Similarity NPD6705 Phase 1
0.573 Remote Similarity NPD4748 Discontinued
0.5729 Remote Similarity NPD5281 Approved
0.5729 Remote Similarity NPD5693 Phase 1
0.5729 Remote Similarity NPD5284 Approved
0.5701 Remote Similarity NPD6847 Approved
0.5701 Remote Similarity NPD5215 Approved
0.5701 Remote Similarity NPD6649 Approved
0.5701 Remote Similarity NPD8130 Phase 1
0.5701 Remote Similarity NPD5127 Approved
0.5701 Remote Similarity NPD6650 Approved
0.5701 Remote Similarity NPD6617 Approved
0.5701 Remote Similarity NPD5216 Approved
0.5701 Remote Similarity NPD5217 Approved
0.5701 Remote Similarity NPD6869 Approved
0.5699 Remote Similarity NPD4519 Discontinued
0.5699 Remote Similarity NPD4623 Approved
0.5684 Remote Similarity NPD7285 Clinical (unspecified phase)
0.5682 Remote Similarity NPD4802 Phase 2
0.5682 Remote Similarity NPD4238 Approved
0.5648 Remote Similarity NPD6882 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