Structure

Physi-Chem Properties

Molecular Weight:  500.35
Volume:  543.911
LogP:  4.167
LogD:  2.715
LogS:  -3.948
# Rotatable Bonds:  6
TPSA:  97.99
# H-Bond Aceptor:  5
# H-Bond Donor:  4
# Rings:  4
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.353
Synthetic Accessibility Score:  5.287
Fsp3:  0.774
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:  -5.224
MDCK Permeability:  2.1945370463072322e-05
Pgp-inhibitor:  0.341
Pgp-substrate:  0.004
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.009
30% Bioavailability (F30%):  0.023

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.028
Plasma Protein Binding (PPB):  85.10465240478516%
Volume Distribution (VD):  0.709
Pgp-substrate:  7.222644329071045%

ADMET: Metabolism

CYP1A2-inhibitor:  0.004
CYP1A2-substrate:  0.139
CYP2C19-inhibitor:  0.009
CYP2C19-substrate:  0.896
CYP2C9-inhibitor:  0.029
CYP2C9-substrate:  0.944
CYP2D6-inhibitor:  0.001
CYP2D6-substrate:  0.212
CYP3A4-inhibitor:  0.048
CYP3A4-substrate:  0.214

ADMET: Excretion

Clearance (CL):  2.349
Half-life (T1/2):  0.39

ADMET: Toxicity

hERG Blockers:  0.037
Human Hepatotoxicity (H-HT):  0.661
Drug-inuced Liver Injury (DILI):  0.012
AMES Toxicity:  0.015
Rat Oral Acute Toxicity:  0.291
Maximum Recommended Daily Dose:  0.926
Skin Sensitization:  0.881
Carcinogencity:  0.104
Eye Corrosion:  0.004
Eye Irritation:  0.024
Respiratory Toxicity:  0.979

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

  Natural Product: NPC186810

Natural Product ID:  NPC186810
Common Name*:   25-Hydroxy-3-Epidehydrotumulosic Acid
IUPAC Name:   (2R)-2-[(3R,5R,10S,13R,14R,16R,17R)-3,16-dihydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-6-methyl-5-methylideneheptanoic acid
Synonyms:  
Standard InCHIKey:  GDIGQYHXIOMOQU-NEAGZGJDSA-N
Standard InCHI:  InChI=1S/C31H48O5/c1-18(28(4,5)36)9-10-19(26(34)35)25-22(32)17-31(8)21-11-12-23-27(2,3)24(33)14-15-29(23,6)20(21)13-16-30(25,31)7/h11,13,19,22-25,32-33,36H,1,9-10,12,14-17H2,2-8H3,(H,34,35)/t19-,22-,23+,24-,25+,29-,30-,31+/m1/s1
SMILES:  C=C(CC[C@H]([C@H]1[C@@H](C[C@@]2(C)C3=CC[C@H]4C(C)(C)[C@@H](CC[C@]4(C)C3=CC[C@]12C)O)O)C(=O)O)C(C)(C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL465660
PubChem CID:   10368709
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0001445] Bile acids, alcohols and derivatives
          • [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives
            • [CHEMONTID:0001104] Trihydroxy bile acids, alcohols and derivatives

*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
NPO23577 Wolfiporia cocos Species Coriolaceae Eukaryota n.a. n.a. n.a. PMID[11975480]
NPO23577 Wolfiporia cocos Species Coriolaceae Eukaryota epidermis of the sclerotia n.a. n.a. PMID[19746919]
NPO30645 Poria cocos Species Coriolaceae Eukaryota n.a. sclerotium n.a. PMID[21250700]
NPO23577 Wolfiporia cocos Species Coriolaceae Eukaryota n.a. n.a. n.a. PMID[27808511]
NPO23577 Wolfiporia cocos Species Coriolaceae Eukaryota n.a. n.a. n.a. PMID[8984162]
NPO30645 Poria cocos Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10608 Exodermis poria n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO10608 Exodermis poria n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO23577 Wolfiporia cocos Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO30645 Poria cocos Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23577 Wolfiporia cocos Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO23577 Wolfiporia cocos Species Coriolaceae 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
NPT80 Cell Line Raji Homo sapiens Activity = 70.0 % PMID[512630]
NPT116 Cell Line HL-60 Homo sapiens IC50 = 29400.0 nM PMID[512631]
NPT81 Cell Line A549 Homo sapiens IC50 = 4000.0 nM PMID[512632]
NPT377 Cell Line OVCAR-3 Homo sapiens IC50 = 9500.0 nM PMID[512632]
NPT116 Cell Line HL-60 Homo sapiens IC50 = 29400.0 nM PMID[512632]
NPT134 Cell Line SK-BR-3 Homo sapiens IC50 = 62300.0 nM PMID[512632]
NPT461 Cell Line PANC-1 Homo sapiens IC50 = 67400.0 nM PMID[512632]
NPT90 Cell Line DU-145 Homo sapiens IC50 > 100000.0 nM PMID[512632]
NPT2 Others Unspecified Activity = 0.0 % PMID[512630]
NPT2 Others Unspecified Activity = 13.2 % PMID[512630]
NPT2 Others Unspecified Activity = 51.6 % PMID[512630]
NPT2 Others Unspecified Activity = 79.4 % PMID[512630]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 84000.0 nM PMID[512631]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 51500.0 nM PMID[512632]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 84000.0 nM PMID[512632]

☑ 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 NPC186810 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
0.9783 High Similarity NPC48647
0.967 High Similarity NPC162001
0.967 High Similarity NPC45324
0.967 High Similarity NPC222845
0.9565 High Similarity NPC155676
0.9362 High Similarity NPC477813
0.9348 High Similarity NPC469406
0.9341 High Similarity NPC45269
0.9341 High Similarity NPC23434
0.9239 High Similarity NPC152897
0.9239 High Similarity NPC66429
0.9239 High Similarity NPC470376
0.9239 High Similarity NPC243866
0.9239 High Similarity NPC470375
0.9231 High Similarity NPC469400
0.914 High Similarity NPC7165
0.9121 High Similarity NPC84271
0.9121 High Similarity NPC102414
0.9121 High Similarity NPC77168
0.9121 High Similarity NPC155479
0.9043 High Similarity NPC184848
0.9043 High Similarity NPC69548
0.9043 High Similarity NPC263347
0.9022 High Similarity NPC46281
0.9011 High Similarity NPC48866
0.9011 High Similarity NPC247406
0.8913 High Similarity NPC54689
0.8901 High Similarity NPC187376
0.8901 High Similarity NPC312215
0.8901 High Similarity NPC159046
0.8901 High Similarity NPC233836
0.8889 High Similarity NPC477812
0.8854 High Similarity NPC469432
0.8854 High Similarity NPC107243
0.8842 High Similarity NPC20546
0.8817 High Similarity NPC123854
0.8804 High Similarity NPC242864
0.8804 High Similarity NPC294480
0.8791 High Similarity NPC28252
0.8791 High Similarity NPC212843
0.8791 High Similarity NPC55309
0.8763 High Similarity NPC166745
0.8763 High Similarity NPC235464
0.875 High Similarity NPC173272
0.8737 High Similarity NPC49670
0.8723 High Similarity NPC154101
0.8723 High Similarity NPC297265
0.871 High Similarity NPC474704
0.871 High Similarity NPC475921
0.8696 High Similarity NPC474684
0.8696 High Similarity NPC142361
0.8687 High Similarity NPC195290
0.8687 High Similarity NPC204450
0.8673 High Similarity NPC154072
0.866 High Similarity NPC57416
0.8646 High Similarity NPC48330
0.8632 High Similarity NPC472942
0.8632 High Similarity NPC214697
0.8617 High Similarity NPC148414
0.8617 High Similarity NPC69622
0.8617 High Similarity NPC175628
0.8617 High Similarity NPC111585
0.8602 High Similarity NPC183546
0.86 High Similarity NPC236390
0.8571 High Similarity NPC165064
0.8557 High Similarity NPC235053
0.8529 High Similarity NPC64844
0.8529 High Similarity NPC42847
0.8526 High Similarity NPC189520
0.8526 High Similarity NPC86266
0.8526 High Similarity NPC212301
0.8526 High Similarity NPC110657
0.8526 High Similarity NPC26888
0.8526 High Similarity NPC212948
0.8515 High Similarity NPC472228
0.8515 High Similarity NPC472227
0.8511 High Similarity NPC474889
0.85 High Similarity NPC234892
0.85 High Similarity NPC293753
0.8485 Intermediate Similarity NPC218383
0.8469 Intermediate Similarity NPC475894
0.8469 Intermediate Similarity NPC320306
0.8462 Intermediate Similarity NPC310470
0.8454 Intermediate Similarity NPC53565
0.8454 Intermediate Similarity NPC469599
0.8438 Intermediate Similarity NPC107674
0.8438 Intermediate Similarity NPC170220
0.8438 Intermediate Similarity NPC470224
0.8438 Intermediate Similarity NPC141497
0.8421 Intermediate Similarity NPC471896
0.8416 Intermediate Similarity NPC55872
0.84 Intermediate Similarity NPC302537
0.84 Intermediate Similarity NPC99411
0.84 Intermediate Similarity NPC163372
0.8387 Intermediate Similarity NPC73038
0.8387 Intermediate Similarity NPC94755
0.8387 Intermediate Similarity NPC469994
0.8387 Intermediate Similarity NPC155011
0.8387 Intermediate Similarity NPC473226
0.8384 Intermediate Similarity NPC471717
0.8384 Intermediate Similarity NPC197386
0.8384 Intermediate Similarity NPC477854
0.8384 Intermediate Similarity NPC10364
0.8367 Intermediate Similarity NPC116457
0.8367 Intermediate Similarity NPC250757
0.8367 Intermediate Similarity NPC249954
0.8367 Intermediate Similarity NPC472941
0.8367 Intermediate Similarity NPC301534
0.8367 Intermediate Similarity NPC95565
0.8367 Intermediate Similarity NPC477853
0.8367 Intermediate Similarity NPC456
0.8351 Intermediate Similarity NPC166906
0.8351 Intermediate Similarity NPC111015
0.8351 Intermediate Similarity NPC292793
0.8333 Intermediate Similarity NPC150383
0.8333 Intermediate Similarity NPC107690
0.8333 Intermediate Similarity NPC204341
0.8333 Intermediate Similarity NPC28656
0.8317 Intermediate Similarity NPC308726
0.8317 Intermediate Similarity NPC119601
0.8317 Intermediate Similarity NPC473424
0.8317 Intermediate Similarity NPC22388
0.8317 Intermediate Similarity NPC477915
0.8317 Intermediate Similarity NPC136289
0.8316 Intermediate Similarity NPC476733
0.8316 Intermediate Similarity NPC215029
0.8316 Intermediate Similarity NPC214387
0.8316 Intermediate Similarity NPC472971
0.8316 Intermediate Similarity NPC472970
0.8316 Intermediate Similarity NPC2983
0.83 Intermediate Similarity NPC316964
0.83 Intermediate Similarity NPC51370
0.83 Intermediate Similarity NPC287833
0.83 Intermediate Similarity NPC205899
0.83 Intermediate Similarity NPC327431
0.83 Intermediate Similarity NPC476274
0.8298 Intermediate Similarity NPC317590
0.8283 Intermediate Similarity NPC141401
0.8283 Intermediate Similarity NPC18319
0.8283 Intermediate Similarity NPC122294
0.828 Intermediate Similarity NPC474083
0.828 Intermediate Similarity NPC474218
0.8265 Intermediate Similarity NPC290481
0.8265 Intermediate Similarity NPC127063
0.8265 Intermediate Similarity NPC174948
0.8265 Intermediate Similarity NPC469995
0.8265 Intermediate Similarity NPC470016
0.8265 Intermediate Similarity NPC472485
0.8265 Intermediate Similarity NPC318282
0.8265 Intermediate Similarity NPC259286
0.8265 Intermediate Similarity NPC271195
0.8265 Intermediate Similarity NPC173875
0.8265 Intermediate Similarity NPC279974
0.8265 Intermediate Similarity NPC317586
0.8261 Intermediate Similarity NPC69279
0.8261 Intermediate Similarity NPC83569
0.8252 Intermediate Similarity NPC48733
0.8252 Intermediate Similarity NPC319077
0.8252 Intermediate Similarity NPC150531
0.8252 Intermediate Similarity NPC97202
0.8252 Intermediate Similarity NPC202167
0.8252 Intermediate Similarity NPC296945
0.8252 Intermediate Similarity NPC49958
0.8252 Intermediate Similarity NPC323834
0.8252 Intermediate Similarity NPC214264
0.8252 Intermediate Similarity NPC302607
0.8252 Intermediate Similarity NPC50692
0.8252 Intermediate Similarity NPC476027
0.8252 Intermediate Similarity NPC260268
0.8252 Intermediate Similarity NPC85829
0.8252 Intermediate Similarity NPC152695
0.8252 Intermediate Similarity NPC171137
0.8247 Intermediate Similarity NPC158059
0.8247 Intermediate Similarity NPC202728
0.8247 Intermediate Similarity NPC470254
0.8247 Intermediate Similarity NPC118519
0.8247 Intermediate Similarity NPC69454
0.8247 Intermediate Similarity NPC206810
0.8235 Intermediate Similarity NPC140723
0.8229 Intermediate Similarity NPC44240
0.8229 Intermediate Similarity NPC18872
0.8229 Intermediate Similarity NPC210037
0.8229 Intermediate Similarity NPC290614
0.8229 Intermediate Similarity NPC477147
0.8229 Intermediate Similarity NPC477872
0.8229 Intermediate Similarity NPC7260
0.8229 Intermediate Similarity NPC227467
0.8229 Intermediate Similarity NPC477149
0.8229 Intermediate Similarity NPC171441
0.8229 Intermediate Similarity NPC273621
0.8229 Intermediate Similarity NPC120968
0.8229 Intermediate Similarity NPC320026
0.8224 Intermediate Similarity NPC962
0.8224 Intermediate Similarity NPC250109
0.8218 Intermediate Similarity NPC476223
0.8218 Intermediate Similarity NPC474327
0.8218 Intermediate Similarity NPC224720
0.8218 Intermediate Similarity NPC476240
0.8218 Intermediate Similarity NPC282524
0.8218 Intermediate Similarity NPC81530

  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 NPC186810 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
0.8526 High Similarity NPD5281 Approved
0.8526 High Similarity NPD5284 Approved
0.8252 Intermediate Similarity NPD6675 Approved
0.8252 Intermediate Similarity NPD7128 Approved
0.8252 Intermediate Similarity NPD6402 Approved
0.8252 Intermediate Similarity NPD5739 Approved
0.8247 Intermediate Similarity NPD4202 Approved
0.8247 Intermediate Similarity NPD6399 Phase 3
0.819 Intermediate Similarity NPD6372 Approved
0.819 Intermediate Similarity NPD6373 Approved
0.8137 Intermediate Similarity NPD5211 Phase 2
0.81 Intermediate Similarity NPD4755 Approved
0.8095 Intermediate Similarity NPD6899 Approved
0.8095 Intermediate Similarity NPD7320 Approved
0.8095 Intermediate Similarity NPD6881 Approved
0.8037 Intermediate Similarity NPD6649 Approved
0.8037 Intermediate Similarity NPD6650 Approved
0.8 Intermediate Similarity NPD3618 Phase 1
0.8 Intermediate Similarity NPD5701 Approved
0.8 Intermediate Similarity NPD5697 Approved
0.7981 Intermediate Similarity NPD5141 Approved
0.7979 Intermediate Similarity NPD4786 Approved
0.7944 Intermediate Similarity NPD7290 Approved
0.7944 Intermediate Similarity NPD7102 Approved
0.7944 Intermediate Similarity NPD6883 Approved
0.7941 Intermediate Similarity NPD4700 Approved
0.7941 Intermediate Similarity NPD4696 Approved
0.7941 Intermediate Similarity NPD5285 Approved
0.7941 Intermediate Similarity NPD5286 Approved
0.7938 Intermediate Similarity NPD5328 Approved
0.7925 Intermediate Similarity NPD6011 Approved
0.7921 Intermediate Similarity NPD6084 Phase 2
0.7921 Intermediate Similarity NPD6083 Phase 2
0.79 Intermediate Similarity NPD5695 Phase 3
0.7895 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.787 Intermediate Similarity NPD6869 Approved
0.787 Intermediate Similarity NPD6617 Approved
0.787 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.787 Intermediate Similarity NPD8130 Phase 1
0.787 Intermediate Similarity NPD6847 Approved
0.7864 Intermediate Similarity NPD5223 Approved
0.785 Intermediate Similarity NPD6013 Approved
0.785 Intermediate Similarity NPD6012 Approved
0.785 Intermediate Similarity NPD6014 Approved
0.7812 Intermediate Similarity NPD4694 Approved
0.7812 Intermediate Similarity NPD5280 Approved
0.7812 Intermediate Similarity NPD5279 Phase 3
0.7798 Intermediate Similarity NPD8297 Approved
0.7798 Intermediate Similarity NPD6882 Approved
0.7789 Intermediate Similarity NPD3133 Approved
0.7789 Intermediate Similarity NPD3666 Approved
0.7789 Intermediate Similarity NPD3665 Phase 1
0.7788 Intermediate Similarity NPD5224 Approved
0.7788 Intermediate Similarity NPD5226 Approved
0.7788 Intermediate Similarity NPD5225 Approved
0.7788 Intermediate Similarity NPD4633 Approved
0.7778 Intermediate Similarity NPD8035 Phase 2
0.7778 Intermediate Similarity NPD6050 Approved
0.7778 Intermediate Similarity NPD8034 Phase 2
0.7778 Intermediate Similarity NPD6079 Approved
0.7778 Intermediate Similarity NPD7515 Phase 2
0.7767 Intermediate Similarity NPD7640 Approved
0.7767 Intermediate Similarity NPD7639 Approved
0.7766 Intermediate Similarity NPD3667 Approved
0.7755 Intermediate Similarity NPD4753 Phase 2
0.7742 Intermediate Similarity NPD7525 Registered
0.7723 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7714 Intermediate Similarity NPD4754 Approved
0.7714 Intermediate Similarity NPD5175 Approved
0.7714 Intermediate Similarity NPD5174 Approved
0.7677 Intermediate Similarity NPD5207 Approved
0.7677 Intermediate Similarity NPD5692 Phase 3
0.767 Intermediate Similarity NPD5696 Approved
0.767 Intermediate Similarity NPD7638 Approved
0.7647 Intermediate Similarity NPD4697 Phase 3
0.7629 Intermediate Similarity NPD7521 Approved
0.7629 Intermediate Similarity NPD5330 Approved
0.7629 Intermediate Similarity NPD7146 Approved
0.7629 Intermediate Similarity NPD6409 Approved
0.7629 Intermediate Similarity NPD7334 Approved
0.7629 Intermediate Similarity NPD6684 Approved
0.76 Intermediate Similarity NPD5694 Approved
0.7579 Intermediate Similarity NPD4221 Approved
0.7579 Intermediate Similarity NPD4223 Phase 3
0.7573 Intermediate Similarity NPD7902 Approved
0.757 Intermediate Similarity NPD6008 Approved
0.757 Intermediate Similarity NPD4767 Approved
0.757 Intermediate Similarity NPD4768 Approved
0.7568 Intermediate Similarity NPD4632 Approved
0.7549 Intermediate Similarity NPD4629 Approved
0.7549 Intermediate Similarity NPD5210 Approved
0.7526 Intermediate Similarity NPD5329 Approved
0.7522 Intermediate Similarity NPD7115 Discovery
0.7476 Intermediate Similarity NPD5221 Approved
0.7476 Intermediate Similarity NPD5222 Approved
0.7476 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7475 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7475 Intermediate Similarity NPD6903 Approved
0.7456 Intermediate Similarity NPD6335 Approved
0.7451 Intermediate Similarity NPD7748 Approved
0.7449 Intermediate Similarity NPD6098 Approved
0.7449 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7449 Intermediate Similarity NPD5690 Phase 2
0.7434 Intermediate Similarity NPD6274 Approved
0.7431 Intermediate Similarity NPD4729 Approved
0.7431 Intermediate Similarity NPD5128 Approved
0.7431 Intermediate Similarity NPD4730 Approved
0.7426 Intermediate Similarity NPD6411 Approved
0.7423 Intermediate Similarity NPD4197 Approved
0.7419 Intermediate Similarity NPD6116 Phase 1
0.7404 Intermediate Similarity NPD5173 Approved
0.74 Intermediate Similarity NPD6904 Approved
0.74 Intermediate Similarity NPD6080 Approved
0.74 Intermediate Similarity NPD6673 Approved
0.7391 Intermediate Similarity NPD7101 Approved
0.7391 Intermediate Similarity NPD7100 Approved
0.7368 Intermediate Similarity NPD6009 Approved
0.7368 Intermediate Similarity NPD6317 Approved
0.734 Intermediate Similarity NPD5784 Clinical (unspecified phase)
0.7327 Intermediate Similarity NPD4096 Approved
0.732 Intermediate Similarity NPD4788 Approved
0.732 Intermediate Similarity NPD5362 Discontinued
0.7312 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7312 Intermediate Similarity NPD6117 Approved
0.7304 Intermediate Similarity NPD6313 Approved
0.7304 Intermediate Similarity NPD6314 Approved
0.73 Intermediate Similarity NPD6672 Approved
0.73 Intermediate Similarity NPD5737 Approved
0.7297 Intermediate Similarity NPD5247 Approved
0.7297 Intermediate Similarity NPD5250 Approved
0.7297 Intermediate Similarity NPD5134 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD5169 Approved
0.7297 Intermediate Similarity NPD5135 Approved
0.7297 Intermediate Similarity NPD5251 Approved
0.7297 Intermediate Similarity NPD5248 Approved
0.7297 Intermediate Similarity NPD5249 Phase 3
0.7297 Intermediate Similarity NPD4634 Approved
0.7292 Intermediate Similarity NPD4139 Approved
0.7292 Intermediate Similarity NPD4692 Approved
0.7282 Intermediate Similarity NPD7900 Approved
0.7282 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7282 Intermediate Similarity NPD6001 Approved
0.7273 Intermediate Similarity NPD4138 Approved
0.7273 Intermediate Similarity NPD5205 Approved
0.7273 Intermediate Similarity NPD4690 Approved
0.7273 Intermediate Similarity NPD4693 Phase 3
0.7273 Intermediate Similarity NPD4688 Approved
0.7273 Intermediate Similarity NPD4689 Approved
0.7265 Intermediate Similarity NPD6291 Clinical (unspecified phase)
0.7265 Intermediate Similarity NPD6908 Approved
0.7265 Intermediate Similarity NPD6909 Approved
0.7264 Intermediate Similarity NPD6404 Discontinued
0.7255 Intermediate Similarity NPD5693 Phase 1
0.7245 Intermediate Similarity NPD3668 Phase 3
0.7232 Intermediate Similarity NPD5216 Approved
0.7232 Intermediate Similarity NPD5217 Approved
0.7232 Intermediate Similarity NPD5215 Approved
0.7232 Intermediate Similarity NPD5127 Approved
0.7228 Intermediate Similarity NPD6051 Approved
0.7228 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.7228 Intermediate Similarity NPD6101 Approved
0.7216 Intermediate Similarity NPD4269 Approved
0.7216 Intermediate Similarity NPD4270 Approved
0.7212 Intermediate Similarity NPD5654 Approved
0.7204 Intermediate Similarity NPD7339 Approved
0.7204 Intermediate Similarity NPD6942 Approved
0.72 Intermediate Similarity NPD4751 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD4748 Discontinued
0.7188 Intermediate Similarity NPD4820 Approved
0.7188 Intermediate Similarity NPD4822 Approved
0.7188 Intermediate Similarity NPD4821 Approved
0.7188 Intermediate Similarity NPD4819 Approved
0.7184 Intermediate Similarity NPD5779 Approved
0.7184 Intermediate Similarity NPD5133 Approved
0.7184 Intermediate Similarity NPD5778 Approved
0.7179 Intermediate Similarity NPD6319 Approved
0.7158 Intermediate Similarity NPD6697 Approved
0.7158 Intermediate Similarity NPD6118 Approved
0.7158 Intermediate Similarity NPD6115 Approved
0.7158 Intermediate Similarity NPD6114 Approved
0.7143 Intermediate Similarity NPD7604 Phase 2
0.713 Intermediate Similarity NPD7632 Discontinued
0.7129 Intermediate Similarity NPD4518 Approved
0.7129 Intermediate Similarity NPD5208 Approved
0.7119 Intermediate Similarity NPD5983 Phase 2
0.7113 Intermediate Similarity NPD5369 Approved
0.7097 Intermediate Similarity NPD6926 Approved
0.7097 Intermediate Similarity NPD6924 Approved
0.7097 Intermediate Similarity NPD6113 Clinical (unspecified phase)
0.7087 Intermediate Similarity NPD7637 Suspended
0.7083 Intermediate Similarity NPD7492 Approved
0.7075 Intermediate Similarity NPD5959 Approved
0.7071 Intermediate Similarity NPD7338 Clinical (unspecified phase)
0.7065 Intermediate Similarity NPD4243 Approved
0.7059 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.7043 Intermediate Similarity NPD5167 Approved
0.7034 Intermediate Similarity NPD6054 Approved
0.7034 Intermediate Similarity NPD6059 Approved
0.7027 Intermediate Similarity NPD6412 Phase 2
0.7025 Intermediate Similarity NPD6336 Discontinued

  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