Structure

Physi-Chem Properties

Molecular Weight:  544.34
Volume:  570.231
LogP:  3.334
LogD:  2.731
LogS:  -4.167
# Rotatable Bonds:  4
TPSA:  113.29
# H-Bond Aceptor:  7
# H-Bond Donor:  3
# Rings:  5
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.358
Synthetic Accessibility Score:  5.53
Fsp3:  0.812
Lipinski Rule-of-5:  Accepted
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:  -5.13
MDCK Permeability:  2.518755354685709e-05
Pgp-inhibitor:  0.997
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.121
30% Bioavailability (F30%):  0.09

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.548
Plasma Protein Binding (PPB):  84.298583984375%
Volume Distribution (VD):  1.416
Pgp-substrate:  9.333158493041992%

ADMET: Metabolism

CYP1A2-inhibitor:  0.006
CYP1A2-substrate:  0.111
CYP2C19-inhibitor:  0.015
CYP2C19-substrate:  0.703
CYP2C9-inhibitor:  0.083
CYP2C9-substrate:  0.033
CYP2D6-inhibitor:  0.006
CYP2D6-substrate:  0.042
CYP3A4-inhibitor:  0.626
CYP3A4-substrate:  0.602

ADMET: Excretion

Clearance (CL):  2.358
Half-life (T1/2):  0.511

ADMET: Toxicity

hERG Blockers:  0.107
Human Hepatotoxicity (H-HT):  0.528
Drug-inuced Liver Injury (DILI):  0.098
AMES Toxicity:  0.017
Rat Oral Acute Toxicity:  0.828
Maximum Recommended Daily Dose:  0.979
Skin Sensitization:  0.911
Carcinogencity:  0.081
Eye Corrosion:  0.003
Eye Irritation:  0.013
Respiratory Toxicity:  0.977

Download Data

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

  Natural Product: NPC255017

Natural Product ID:  NPC255017
Common Name*:   Spicatin
IUPAC Name:   [(5R,7R,8R,9R,10R,13S,17S)-17-[(3S,5R)-5,6-dihydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-4,4,8,10,13-pentamethyl-3-oxo-5,6,7,9,11,12,16,17-octahydrocyclopenta[a]phenanthren-7-yl] acetate
Synonyms:   spicatin
Standard InCHIKey:  QMPWWBJWTUYRPO-HCEUJBAUSA-N
Standard InCHI:  InChI=1S/C32H48O7/c1-18(33)39-26-16-23-27(2,3)24(34)12-14-30(23,7)22-11-13-29(6)20(9-10-21(29)31(22,26)8)19-15-25(35)32(37,38-17-19)28(4,5)36/h10,12,14,19-20,22-23,25-26,35-37H,9,11,13,15-17H2,1-8H3/t19-,20+,22-,23+,25-,26-,29+,30-,31+,32?/m1/s1
SMILES:  CC(=O)O[C@@H]1C[C@H]2C(C)(C)C(=O)C=C[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](CC=C3[C@]12C)[C@@H]1C[C@H](C(C(C)(C)O)(O)OC1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1214756
PubChem CID:   49864005
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
NPO4406 Azadirachta indica Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[12193038]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[1593280]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[18816111]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota fruits n.a. n.a. PMID[20669933]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota n.a. seed n.a. PMID[21381696]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota Seeds n.a. n.a. PMID[21381696]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[2607354]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[2614419]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[26339153]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota Leaves n.a. n.a. PMID[28493718]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota n.a. fruit n.a. PMID[9134742]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota n.a. leaf n.a. PMID[9134742]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota n.a. bark n.a. PMID[9134742]
NPO17476 Austrotaxus spicata Species Taxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9289 Liatris squarrosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2267 Liatris tenuifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15736 Liatris spicata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15224 Liatris pycnostachya Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17476 Austrotaxus spicata Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15736 Liatris spicata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9289 Liatris squarrosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2267 Liatris tenuifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17476 Austrotaxus spicata Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9289 Liatris squarrosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2267 Liatris tenuifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15736 Liatris spicata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15224 Liatris pycnostachya Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4406 Azadirachta indica Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17476 Austrotaxus spicata Species Taxaceae 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
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 5400.0 nM PMID[530002]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 2740.0 nM PMID[530002]

☑ 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 NPC255017 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
0.9615 High Similarity NPC41405
0.9346 High Similarity NPC152117
0.9346 High Similarity NPC234042
0.934 High Similarity NPC5284
0.9018 High Similarity NPC161065
0.8938 High Similarity NPC241192
0.8774 High Similarity NPC264048
0.875 High Similarity NPC134869
0.875 High Similarity NPC152199
0.875 High Similarity NPC302471
0.875 High Similarity NPC235539
0.8727 High Similarity NPC201992
0.8716 High Similarity NPC218853
0.8696 High Similarity NPC202051
0.8661 High Similarity NPC243354
0.8661 High Similarity NPC474906
0.8661 High Similarity NPC18547
0.8649 High Similarity NPC11252
0.8649 High Similarity NPC289312
0.8636 High Similarity NPC197428
0.8636 High Similarity NPC250956
0.8624 High Similarity NPC469844
0.8598 High Similarity NPC239716
0.8596 High Similarity NPC297179
0.8585 High Similarity NPC470054
0.8584 High Similarity NPC243981
0.8571 High Similarity NPC51978
0.8571 High Similarity NPC194273
0.8571 High Similarity NPC194100
0.8559 High Similarity NPC471243
0.8545 High Similarity NPC246205
0.8522 High Similarity NPC476529
0.8522 High Similarity NPC469488
0.8522 High Similarity NPC475775
0.8512 High Similarity NPC471855
0.8509 High Similarity NPC473968
0.8505 High Similarity NPC473163
0.8505 High Similarity NPC470053
0.8496 Intermediate Similarity NPC471398
0.8496 Intermediate Similarity NPC473882
0.8496 Intermediate Similarity NPC165439
0.8496 Intermediate Similarity NPC74727
0.8482 Intermediate Similarity NPC205534
0.8468 Intermediate Similarity NPC52241
0.8468 Intermediate Similarity NPC474567
0.8468 Intermediate Similarity NPC475317
0.8468 Intermediate Similarity NPC239097
0.8468 Intermediate Similarity NPC154856
0.8468 Intermediate Similarity NPC470065
0.8455 Intermediate Similarity NPC272576
0.8455 Intermediate Similarity NPC293850
0.8455 Intermediate Similarity NPC258323
0.8455 Intermediate Similarity NPC295389
0.8448 Intermediate Similarity NPC107338
0.8448 Intermediate Similarity NPC109607
0.8448 Intermediate Similarity NPC476961
0.8435 Intermediate Similarity NPC188667
0.8435 Intermediate Similarity NPC204552
0.8421 Intermediate Similarity NPC328374
0.8421 Intermediate Similarity NPC96312
0.8421 Intermediate Similarity NPC251236
0.8421 Intermediate Similarity NPC176840
0.8421 Intermediate Similarity NPC270929
0.8421 Intermediate Similarity NPC40632
0.8417 Intermediate Similarity NPC473888
0.8417 Intermediate Similarity NPC245094
0.8411 Intermediate Similarity NPC469327
0.8407 Intermediate Similarity NPC178981
0.8407 Intermediate Similarity NPC49451
0.8407 Intermediate Similarity NPC320118
0.8407 Intermediate Similarity NPC260665
0.8407 Intermediate Similarity NPC471627
0.8407 Intermediate Similarity NPC471173
0.8407 Intermediate Similarity NPC62696
0.8407 Intermediate Similarity NPC293038
0.8403 Intermediate Similarity NPC174367
0.8403 Intermediate Similarity NPC47113
0.8396 Intermediate Similarity NPC470068
0.8396 Intermediate Similarity NPC114274
0.8393 Intermediate Similarity NPC263827
0.8393 Intermediate Similarity NPC250481
0.8393 Intermediate Similarity NPC285410
0.839 Intermediate Similarity NPC473979
0.839 Intermediate Similarity NPC469789
0.8378 Intermediate Similarity NPC472216
0.8378 Intermediate Similarity NPC143706
0.8378 Intermediate Similarity NPC284828
0.8378 Intermediate Similarity NPC5475
0.8378 Intermediate Similarity NPC118225
0.8378 Intermediate Similarity NPC472534
0.8378 Intermediate Similarity NPC173905
0.8378 Intermediate Similarity NPC477069
0.8378 Intermediate Similarity NPC477070
0.8365 Intermediate Similarity NPC240617
0.8362 Intermediate Similarity NPC473203
0.8362 Intermediate Similarity NPC61520
0.8349 Intermediate Similarity NPC255309
0.8349 Intermediate Similarity NPC471293
0.8348 Intermediate Similarity NPC309433
0.8348 Intermediate Similarity NPC284068
0.8348 Intermediate Similarity NPC470959
0.8348 Intermediate Similarity NPC477252
0.8348 Intermediate Similarity NPC476965
0.8347 Intermediate Similarity NPC476966
0.8347 Intermediate Similarity NPC471407
0.8333 Intermediate Similarity NPC287423
0.8333 Intermediate Similarity NPC472274
0.8333 Intermediate Similarity NPC102088
0.8333 Intermediate Similarity NPC477580
0.8333 Intermediate Similarity NPC473798
0.8319 Intermediate Similarity NPC477253
0.8319 Intermediate Similarity NPC177820
0.8319 Intermediate Similarity NPC473255
0.8319 Intermediate Similarity NPC474265
0.8319 Intermediate Similarity NPC470922
0.8319 Intermediate Similarity NPC30188
0.8319 Intermediate Similarity NPC130427
0.8319 Intermediate Similarity NPC470063
0.8319 Intermediate Similarity NPC90769
0.8319 Intermediate Similarity NPC471967
0.8319 Intermediate Similarity NPC210420
0.8319 Intermediate Similarity NPC71348
0.8318 Intermediate Similarity NPC167974
0.8305 Intermediate Similarity NPC28532
0.8304 Intermediate Similarity NPC129340
0.8304 Intermediate Similarity NPC101450
0.8302 Intermediate Similarity NPC108078
0.8291 Intermediate Similarity NPC79579
0.8291 Intermediate Similarity NPC308459
0.8291 Intermediate Similarity NPC48692
0.8291 Intermediate Similarity NPC471406
0.8291 Intermediate Similarity NPC112038
0.8288 Intermediate Similarity NPC472219
0.8288 Intermediate Similarity NPC472218
0.8288 Intermediate Similarity NPC472217
0.8286 Intermediate Similarity NPC473415
0.8286 Intermediate Similarity NPC473170
0.8286 Intermediate Similarity NPC30677
0.8286 Intermediate Similarity NPC180557
0.8286 Intermediate Similarity NPC37787
0.8286 Intermediate Similarity NPC469329
0.8279 Intermediate Similarity NPC173347
0.8276 Intermediate Similarity NPC239293
0.8276 Intermediate Similarity NPC153440
0.8276 Intermediate Similarity NPC329736
0.8273 Intermediate Similarity NPC210178
0.8273 Intermediate Similarity NPC102352
0.8273 Intermediate Similarity NPC96377
0.8273 Intermediate Similarity NPC231530
0.8273 Intermediate Similarity NPC470587
0.8273 Intermediate Similarity NPC278628
0.8269 Intermediate Similarity NPC79117
0.8264 Intermediate Similarity NPC311534
0.8264 Intermediate Similarity NPC473620
0.8261 Intermediate Similarity NPC474046
0.8261 Intermediate Similarity NPC190286
0.8261 Intermediate Similarity NPC259306
0.8261 Intermediate Similarity NPC470628
0.825 Intermediate Similarity NPC473635
0.825 Intermediate Similarity NPC293112
0.8246 Intermediate Similarity NPC25909
0.8246 Intermediate Similarity NPC208998
0.8246 Intermediate Similarity NPC251309
0.8246 Intermediate Similarity NPC7921
0.8246 Intermediate Similarity NPC250109
0.8235 Intermediate Similarity NPC11895
0.823 Intermediate Similarity NPC146945
0.823 Intermediate Similarity NPC477073
0.823 Intermediate Similarity NPC171888
0.823 Intermediate Similarity NPC474229
0.822 Intermediate Similarity NPC204731
0.822 Intermediate Similarity NPC46570
0.822 Intermediate Similarity NPC67569
0.822 Intermediate Similarity NPC102822
0.822 Intermediate Similarity NPC477046
0.8214 Intermediate Similarity NPC27814
0.8214 Intermediate Similarity NPC310546
0.8214 Intermediate Similarity NPC265655
0.8211 Intermediate Similarity NPC231240
0.8208 Intermediate Similarity NPC471822
0.8205 Intermediate Similarity NPC475041
0.8205 Intermediate Similarity NPC476960
0.8205 Intermediate Similarity NPC5292
0.8205 Intermediate Similarity NPC477071
0.8205 Intermediate Similarity NPC258592
0.8205 Intermediate Similarity NPC178548
0.8205 Intermediate Similarity NPC473401
0.8205 Intermediate Similarity NPC470777
0.8205 Intermediate Similarity NPC473636
0.8205 Intermediate Similarity NPC77689
0.8198 Intermediate Similarity NPC44063
0.8198 Intermediate Similarity NPC144854
0.8198 Intermediate Similarity NPC9457
0.8198 Intermediate Similarity NPC3316
0.8198 Intermediate Similarity NPC59530
0.8198 Intermediate Similarity NPC471783
0.819 Intermediate Similarity NPC287343
0.819 Intermediate Similarity NPC471854
0.819 Intermediate Similarity NPC97908
0.819 Intermediate Similarity NPC218970

  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 NPC255017 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
0.8482 Intermediate Similarity NPD8297 Approved
0.8319 Intermediate Similarity NPD6882 Approved
0.8288 Intermediate Similarity NPD6899 Approved
0.8288 Intermediate Similarity NPD6881 Approved
0.8264 Intermediate Similarity NPD7736 Approved
0.8246 Intermediate Similarity NPD4632 Approved
0.823 Intermediate Similarity NPD8130 Phase 1
0.8198 Intermediate Similarity NPD5697 Approved
0.819 Intermediate Similarity NPD6009 Approved
0.8167 Intermediate Similarity NPD7492 Approved
0.8142 Intermediate Similarity NPD6883 Approved
0.8142 Intermediate Similarity NPD7102 Approved
0.8142 Intermediate Similarity NPD7290 Approved
0.8136 Intermediate Similarity NPD6054 Approved
0.8136 Intermediate Similarity NPD6319 Approved
0.8108 Intermediate Similarity NPD6402 Approved
0.8108 Intermediate Similarity NPD7128 Approved
0.8108 Intermediate Similarity NPD5739 Approved
0.8108 Intermediate Similarity NPD6675 Approved
0.8099 Intermediate Similarity NPD6616 Approved
0.807 Intermediate Similarity NPD6847 Approved
0.807 Intermediate Similarity NPD6649 Approved
0.807 Intermediate Similarity NPD6650 Approved
0.807 Intermediate Similarity NPD6869 Approved
0.807 Intermediate Similarity NPD6617 Approved
0.8053 Intermediate Similarity NPD6013 Approved
0.8053 Intermediate Similarity NPD6014 Approved
0.8053 Intermediate Similarity NPD6012 Approved
0.8036 Intermediate Similarity NPD6412 Phase 2
0.8034 Intermediate Similarity NPD7115 Discovery
0.8033 Intermediate Similarity NPD7078 Approved
0.8 Intermediate Similarity NPD6370 Approved
0.7965 Intermediate Similarity NPD7320 Approved
0.7965 Intermediate Similarity NPD6011 Approved
0.7951 Intermediate Similarity NPD7507 Approved
0.7934 Intermediate Similarity NPD8328 Phase 3
0.7917 Intermediate Similarity NPD6016 Approved
0.7917 Intermediate Similarity NPD6015 Approved
0.7895 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7895 Intermediate Similarity NPD6372 Approved
0.7895 Intermediate Similarity NPD6373 Approved
0.7886 Intermediate Similarity NPD8293 Discontinued
0.7876 Intermediate Similarity NPD5701 Approved
0.7851 Intermediate Similarity NPD5988 Approved
0.7833 Intermediate Similarity NPD6059 Approved
0.783 Intermediate Similarity NPD6079 Approved
0.7826 Intermediate Similarity NPD4634 Approved
0.7818 Intermediate Similarity NPD5285 Approved
0.7818 Intermediate Similarity NPD5286 Approved
0.7818 Intermediate Similarity NPD4696 Approved
0.7787 Intermediate Similarity NPD7604 Phase 2
0.7769 Intermediate Similarity NPD5983 Phase 2
0.776 Intermediate Similarity NPD7319 Approved
0.7731 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7685 Intermediate Similarity NPD7748 Approved
0.7679 Intermediate Similarity NPD5211 Phase 2
0.7679 Intermediate Similarity NPD5225 Approved
0.7679 Intermediate Similarity NPD5226 Approved
0.7679 Intermediate Similarity NPD4633 Approved
0.7679 Intermediate Similarity NPD5224 Approved
0.7661 Intermediate Similarity NPD6336 Discontinued
0.7652 Intermediate Similarity NPD6686 Approved
0.7642 Intermediate Similarity NPD5328 Approved
0.7636 Intermediate Similarity NPD4755 Approved
0.7636 Intermediate Similarity NPD7902 Approved
0.7632 Intermediate Similarity NPD6008 Approved
0.7619 Intermediate Similarity NPD3573 Approved
0.7611 Intermediate Similarity NPD5175 Approved
0.7611 Intermediate Similarity NPD5174 Approved
0.7607 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7603 Intermediate Similarity NPD7101 Approved
0.7603 Intermediate Similarity NPD7100 Approved
0.7593 Intermediate Similarity NPD6399 Phase 3
0.7589 Intermediate Similarity NPD5223 Approved
0.7545 Intermediate Similarity NPD5222 Approved
0.7545 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7545 Intermediate Similarity NPD5221 Approved
0.7544 Intermediate Similarity NPD5141 Approved
0.7521 Intermediate Similarity NPD6335 Approved
0.75 Intermediate Similarity NPD7515 Phase 2
0.75 Intermediate Similarity NPD4700 Approved
0.75 Intermediate Similarity NPD6274 Approved
0.75 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.748 Intermediate Similarity NPD7503 Approved
0.748 Intermediate Similarity NPD8033 Approved
0.7477 Intermediate Similarity NPD6084 Phase 2
0.7477 Intermediate Similarity NPD6083 Phase 2
0.7477 Intermediate Similarity NPD5173 Approved
0.7438 Intermediate Similarity NPD6317 Approved
0.7436 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7398 Intermediate Similarity NPD8294 Approved
0.7398 Intermediate Similarity NPD8377 Approved
0.7377 Intermediate Similarity NPD6314 Approved
0.7377 Intermediate Similarity NPD7328 Approved
0.7377 Intermediate Similarity NPD7327 Approved
0.7377 Intermediate Similarity NPD6313 Approved
0.7364 Intermediate Similarity NPD7900 Approved
0.7364 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7355 Intermediate Similarity NPD6868 Approved
0.735 Intermediate Similarity NPD4729 Approved
0.735 Intermediate Similarity NPD4730 Approved
0.7339 Intermediate Similarity NPD8380 Approved
0.7339 Intermediate Similarity NPD8335 Approved
0.7339 Intermediate Similarity NPD8378 Approved
0.7339 Intermediate Similarity NPD8296 Approved
0.7339 Intermediate Similarity NPD8379 Approved
0.7333 Intermediate Similarity NPD8133 Approved
0.7317 Intermediate Similarity NPD7516 Approved
0.7273 Intermediate Similarity NPD4202 Approved
0.7266 Intermediate Similarity NPD6033 Approved
0.7257 Intermediate Similarity NPD7638 Approved
0.7232 Intermediate Similarity NPD4697 Phase 3
0.7227 Intermediate Similarity NPD5250 Approved
0.7227 Intermediate Similarity NPD5248 Approved
0.7227 Intermediate Similarity NPD5247 Approved
0.7227 Intermediate Similarity NPD5249 Phase 3
0.7227 Intermediate Similarity NPD5251 Approved
0.7203 Intermediate Similarity NPD5128 Approved
0.72 Intermediate Similarity NPD6909 Approved
0.72 Intermediate Similarity NPD8513 Phase 3
0.72 Intermediate Similarity NPD6291 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD6908 Approved
0.72 Intermediate Similarity NPD8516 Approved
0.72 Intermediate Similarity NPD8515 Approved
0.72 Intermediate Similarity NPD8517 Approved
0.7196 Intermediate Similarity NPD3618 Phase 1
0.7193 Intermediate Similarity NPD7640 Approved
0.7193 Intermediate Similarity NPD7639 Approved
0.7182 Intermediate Similarity NPD6411 Approved
0.7182 Intermediate Similarity NPD8035 Phase 2
0.7182 Intermediate Similarity NPD8034 Phase 2
0.7179 Intermediate Similarity NPD4767 Approved
0.7179 Intermediate Similarity NPD4768 Approved
0.717 Intermediate Similarity NPD4786 Approved
0.7167 Intermediate Similarity NPD5215 Approved
0.7167 Intermediate Similarity NPD5216 Approved
0.7167 Intermediate Similarity NPD5217 Approved
0.7155 Intermediate Similarity NPD4754 Approved
0.7143 Intermediate Similarity NPD5695 Phase 3
0.7105 Intermediate Similarity NPD5696 Approved
0.7105 Intermediate Similarity NPD4225 Approved
0.7083 Intermediate Similarity NPD5135 Approved
0.7083 Intermediate Similarity NPD5134 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD5169 Approved
0.7083 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7064 Intermediate Similarity NPD5737 Approved
0.7064 Intermediate Similarity NPD6672 Approved
0.7064 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD7146 Approved
0.7037 Intermediate Similarity NPD6684 Approved
0.7037 Intermediate Similarity NPD5330 Approved
0.7037 Intermediate Similarity NPD7521 Approved
0.7037 Intermediate Similarity NPD7334 Approved
0.7037 Intermediate Similarity NPD6409 Approved
0.7025 Intermediate Similarity NPD5127 Approved
0.7 Intermediate Similarity NPD4753 Phase 2
0.7 Intermediate Similarity NPD6101 Approved
0.7 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.6991 Remote Similarity NPD5210 Approved
0.6991 Remote Similarity NPD4629 Approved
0.6991 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6981 Remote Similarity NPD3667 Approved
0.6967 Remote Similarity NPD6053 Discontinued
0.6953 Remote Similarity NPD6067 Discontinued
0.6949 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6944 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6917 Remote Similarity NPD5168 Approved
0.6909 Remote Similarity NPD6903 Approved
0.6881 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6875 Remote Similarity NPD5284 Approved
0.6875 Remote Similarity NPD5281 Approved
0.6855 Remote Similarity NPD5167 Approved
0.6852 Remote Similarity NPD3665 Phase 1
0.6852 Remote Similarity NPD3666 Approved
0.6852 Remote Similarity NPD3133 Approved
0.6847 Remote Similarity NPD6673 Approved
0.6847 Remote Similarity NPD6904 Approved
0.6847 Remote Similarity NPD6080 Approved
0.6833 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6814 Remote Similarity NPD5778 Approved
0.6814 Remote Similarity NPD5779 Approved
0.6803 Remote Similarity NPD6371 Approved
0.6797 Remote Similarity NPD6921 Approved
0.6794 Remote Similarity NPD8074 Phase 3
0.678 Remote Similarity NPD7632 Discontinued
0.6767 Remote Similarity NPD5956 Approved
0.6748 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6716 Remote Similarity NPD7260 Phase 2
0.6696 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6696 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6695 Remote Similarity NPD5344 Discontinued
0.6667 Remote Similarity NPD4223 Phase 3
0.6667 Remote Similarity NPD4221 Approved
0.6641 Remote Similarity NPD4522 Approved
0.6637 Remote Similarity NPD6698 Approved
0.6637 Remote Similarity NPD46 Approved
0.6636 Remote Similarity NPD1694 Approved
0.6636 Remote Similarity NPD5329 Approved
0.6636 Remote Similarity NPD7525 Registered
0.6609 Remote Similarity NPD6001 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