Structure

Physi-Chem Properties

Molecular Weight:  470.34
Volume:  511.905
LogP:  4.963
LogD:  4.319
LogS:  -3.931
# Rotatable Bonds:  2
TPSA:  74.6
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.361
Synthetic Accessibility Score:  4.854
Fsp3:  0.867
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.447
MDCK Permeability:  1.1381226613593753e-05
Pgp-inhibitor:  0.017
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.228
30% Bioavailability (F30%):  0.954

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.986
Plasma Protein Binding (PPB):  77.91246795654297%
Volume Distribution (VD):  0.698
Pgp-substrate:  13.773690223693848%

ADMET: Metabolism

CYP1A2-inhibitor:  0.004
CYP1A2-substrate:  0.345
CYP2C19-inhibitor:  0.01
CYP2C19-substrate:  0.666
CYP2C9-inhibitor:  0.077
CYP2C9-substrate:  0.267
CYP2D6-inhibitor:  0.025
CYP2D6-substrate:  0.058
CYP3A4-inhibitor:  0.724
CYP3A4-substrate:  0.259

ADMET: Excretion

Clearance (CL):  3.106
Half-life (T1/2):  0.142

ADMET: Toxicity

hERG Blockers:  0.009
Human Hepatotoxicity (H-HT):  0.478
Drug-inuced Liver Injury (DILI):  0.013
AMES Toxicity:  0.008
Rat Oral Acute Toxicity:  0.476
Maximum Recommended Daily Dose:  0.845
Skin Sensitization:  0.315
Carcinogencity:  0.276
Eye Corrosion:  0.55
Eye Irritation:  0.065
Respiratory Toxicity:  0.984

Download Data

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

  Natural Product: NPC298554

Natural Product ID:  NPC298554
Common Name*:   (3Beta,4Alpha)-3-Hydroxy-23-Oxoolean-12-En-28-Oic Acid
IUPAC Name:   (4aS,6aR,6aS,6bR,8aR,9S,10S,12aR,14bS)-9-formyl-10-hydroxy-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms:  
Standard InCHIKey:  QMHCWDVPABYZMC-MYPRUECHSA-N
Standard InCHI:  InChI=1S/C30H46O4/c1-25(2)13-15-30(24(33)34)16-14-28(5)19(20(30)17-25)7-8-22-26(3)11-10-23(32)27(4,18-31)21(26)9-12-29(22,28)6/h7,18,20-23,32H,8-17H2,1-6H3,(H,33,34)/t20-,21+,22+,23-,26-,27-,28+,29+,30-/m0/s1
SMILES:  O=C[C@]1(C)[C@@H](O)CC[C@]2([C@H]1CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2CC(CC1)(C)C)C(=O)O)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2386825
PubChem CID:   92825
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
NPO25944 Streptomyces aureofaciens Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[14289338]
NPO25944 Streptomyces aureofaciens Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[Ann. N.Y. Acad. Sci., 1948, v51, 177]
NPO26555 Phytolacca icosandra Species Phytolaccaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26555 Phytolacca icosandra Species Phytolaccaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25944 Streptomyces aureofaciens Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO26555 Phytolacca icosandra Species Phytolaccaceae 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
NPT116 Cell Line HL-60 Homo sapiens IC50 = 10400.0 nM PMID[474919]
NPT139 Cell Line HT-29 Homo sapiens IC50 = 11900.0 nM PMID[474919]
NPT492 Cell Line Caco-2 Homo sapiens IC50 = 16670.0 nM PMID[474919]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 9020.0 nM PMID[474919]
NPT165 Cell Line HeLa Homo sapiens IC50 = 22480.0 nM PMID[474919]
NPT116 Cell Line HL-60 Homo sapiens Activity = 33.0 % PMID[474919]
NPT139 Cell Line HT-29 Homo sapiens Activity = 21.0 % PMID[474919]
NPT492 Cell Line Caco-2 Homo sapiens Activity = 20.0 % PMID[474919]
NPT2405 Cell Line SAOS-2 Homo sapiens Activity = 36.0 % PMID[474919]
NPT83 Cell Line MCF7 Homo sapiens Activity = 30.0 % PMID[474919]
NPT165 Cell Line HeLa Homo sapiens Activity = 29.0 % PMID[474919]
NPT116 Cell Line HL-60 Homo sapiens Activity = 4.0 % PMID[474919]
NPT139 Cell Line HT-29 Homo sapiens Activity = 2.0 % PMID[474919]
NPT492 Cell Line Caco-2 Homo sapiens Activity = 0.0 % PMID[474919]
NPT2405 Cell Line SAOS-2 Homo sapiens Activity = 2.0 % PMID[474919]
NPT83 Cell Line MCF7 Homo sapiens Activity = 4.0 % PMID[474919]
NPT165 Cell Line HeLa Homo sapiens Activity = 0.0 % PMID[474919]
NPT570 Individual Protein Arachidonate 5-lipoxygenase Homo sapiens Activity = 100.0 % PMID[474920]
NPT1139 Individual Protein Arachidonate 15-lipoxygenase, type II Homo sapiens Activity = 100.0 % PMID[474920]
NPT324 Individual Protein Cyclooxygenase-1 Ovis aries Activity = 100.0 % PMID[474920]
NPT31 Individual Protein Cyclooxygenase-2 Homo sapiens Activity = 100.0 % PMID[474920]
NPT113 Cell Line RAW264.7 Mus musculus ED50 = 36.6 uM PMID[474921]
NPT191 Organism Hepatitis C virus Hepatitis C virus Inhibition = 0.0 % PMID[474918]
NPT314 Organism Bacillus cereus Bacillus cereus IZ = 13.0 mm PMID[474919]
NPT79 Organism Bacillus subtilis Bacillus subtilis IZ = 13.0 mm PMID[474919]
NPT1261 Organism Bacillus thuringiensis Bacillus thuringiensis IZ = 13.0 mm PMID[474919]
NPT314 Organism Bacillus cereus Bacillus cereus MIC = 32.0 ug.mL-1 PMID[474919]
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 32.0 ug.mL-1 PMID[474919]
NPT1261 Organism Bacillus thuringiensis Bacillus thuringiensis MIC = 32.0 ug.mL-1 PMID[474919]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 7850.0 nM PMID[474919]
NPT2 Others Unspecified Ratio ED50 = 3.8 n.a. PMID[474921]
NPT842 Organism Leishmania mexicana Leishmania mexicana ED50 = 9.6 uM PMID[474921]
NPT842 Organism Leishmania mexicana Leishmania mexicana Inhibition >= 95.0 % PMID[474921]

☑ 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 NPC298554 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
0.9885 High Similarity NPC222047
0.9885 High Similarity NPC209868
0.9655 High Similarity NPC282616
0.9655 High Similarity NPC288833
0.9655 High Similarity NPC155120
0.9655 High Similarity NPC324341
0.9655 High Similarity NPC966
0.9655 High Similarity NPC228784
0.9556 High Similarity NPC187933
0.954 High Similarity NPC172361
0.954 High Similarity NPC86372
0.9535 High Similarity NPC182797
0.9535 High Similarity NPC52169
0.9451 High Similarity NPC188833
0.9438 High Similarity NPC474529
0.9432 High Similarity NPC471588
0.9432 High Similarity NPC6255
0.9425 High Similarity NPC127689
0.9425 High Similarity NPC293048
0.9425 High Similarity NPC130520
0.9425 High Similarity NPC274330
0.9425 High Similarity NPC25906
0.9425 High Similarity NPC234346
0.9425 High Similarity NPC143232
0.9425 High Similarity NPC290972
0.9425 High Similarity NPC64872
0.9425 High Similarity NPC121798
0.9425 High Similarity NPC61543
0.9425 High Similarity NPC263393
0.9425 High Similarity NPC270768
0.9425 High Similarity NPC198664
0.9425 High Similarity NPC225585
0.9425 High Similarity NPC59263
0.9419 High Similarity NPC51700
0.9419 High Similarity NPC242468
0.9419 High Similarity NPC307426
0.9419 High Similarity NPC88716
0.9419 High Similarity NPC18064
0.9419 High Similarity NPC68160
0.9419 High Similarity NPC102683
0.9419 High Similarity NPC130577
0.9419 High Similarity NPC98442
0.9419 High Similarity NPC171203
0.9419 High Similarity NPC293564
0.9419 High Similarity NPC142415
0.9341 High Similarity NPC21728
0.9333 High Similarity NPC148523
0.9318 High Similarity NPC227467
0.9318 High Similarity NPC210037
0.9318 High Similarity NPC290614
0.9318 High Similarity NPC291028
0.9318 High Similarity NPC477872
0.9318 High Similarity NPC126369
0.9318 High Similarity NPC7260
0.9318 High Similarity NPC18872
0.9318 High Similarity NPC273621
0.9318 High Similarity NPC120968
0.9318 High Similarity NPC470589
0.9318 High Similarity NPC130278
0.9318 High Similarity NPC111110
0.931 High Similarity NPC474512
0.931 High Similarity NPC473242
0.931 High Similarity NPC17733
0.931 High Similarity NPC246708
0.931 High Similarity NPC40552
0.931 High Similarity NPC290690
0.931 High Similarity NPC470629
0.931 High Similarity NPC181225
0.9302 High Similarity NPC95594
0.9302 High Similarity NPC72638
0.9302 High Similarity NPC235341
0.9302 High Similarity NPC477579
0.9231 High Similarity NPC132824
0.9231 High Similarity NPC98874
0.9231 High Similarity NPC201657
0.9222 High Similarity NPC78580
0.9222 High Similarity NPC184006
0.9222 High Similarity NPC23621
0.9213 High Similarity NPC235884
0.9213 High Similarity NPC71074
0.9213 High Similarity NPC306541
0.9213 High Similarity NPC105189
0.9213 High Similarity NPC84319
0.9213 High Similarity NPC52021
0.9213 High Similarity NPC145067
0.9213 High Similarity NPC233455
0.9213 High Similarity NPC472149
0.9213 High Similarity NPC25299
0.9213 High Similarity NPC300351
0.9213 High Similarity NPC158030
0.9213 High Similarity NPC187722
0.9213 High Similarity NPC4036
0.9213 High Similarity NPC65120
0.9213 High Similarity NPC474525
0.9205 High Similarity NPC95246
0.9205 High Similarity NPC474972
0.9205 High Similarity NPC161751
0.9205 High Similarity NPC470588
0.9195 High Similarity NPC158141
0.9195 High Similarity NPC173089
0.913 High Similarity NPC106112
0.913 High Similarity NPC261935
0.9121 High Similarity NPC195715
0.9121 High Similarity NPC23241
0.9111 High Similarity NPC118519
0.9111 High Similarity NPC202728
0.9111 High Similarity NPC295643
0.9111 High Similarity NPC214756
0.9111 High Similarity NPC136313
0.9111 High Similarity NPC275809
0.9111 High Similarity NPC272075
0.9111 High Similarity NPC307335
0.9111 High Similarity NPC229281
0.9111 High Similarity NPC86368
0.9111 High Similarity NPC158059
0.9111 High Similarity NPC74855
0.9101 High Similarity NPC49320
0.9101 High Similarity NPC120840
0.9101 High Similarity NPC113989
0.9101 High Similarity NPC46441
0.9101 High Similarity NPC193750
0.9101 High Similarity NPC474728
0.9091 High Similarity NPC474511
0.9091 High Similarity NPC1753
0.9032 High Similarity NPC111214
0.9032 High Similarity NPC271614
0.9032 High Similarity NPC174663
0.9032 High Similarity NPC29765
0.9032 High Similarity NPC164349
0.9032 High Similarity NPC471966
0.9011 High Similarity NPC32407
0.9011 High Similarity NPC191412
0.9011 High Similarity NPC91010
0.9011 High Similarity NPC231063
0.9011 High Similarity NPC145667
0.9011 High Similarity NPC114159
0.9011 High Similarity NPC299996
0.9011 High Similarity NPC88116
0.9011 High Similarity NPC20235
0.9011 High Similarity NPC148964
0.9011 High Similarity NPC263548
0.9011 High Similarity NPC159365
0.9011 High Similarity NPC6818
0.9011 High Similarity NPC282395
0.9 High Similarity NPC285184
0.9 High Similarity NPC38754
0.9 High Similarity NPC60755
0.9 High Similarity NPC77099
0.9 High Similarity NPC475708
0.9 High Similarity NPC470590
0.8989 High Similarity NPC30522
0.8989 High Similarity NPC69627
0.8989 High Similarity NPC474686
0.8977 High Similarity NPC71507
0.8966 High Similarity NPC133954
0.8936 High Similarity NPC35239
0.8925 High Similarity NPC26413
0.8913 High Similarity NPC473240
0.8913 High Similarity NPC139570
0.8913 High Similarity NPC474727
0.8913 High Similarity NPC198245
0.8913 High Similarity NPC96916
0.8901 High Similarity NPC133579
0.8901 High Similarity NPC63118
0.8901 High Similarity NPC118490
0.8901 High Similarity NPC474806
0.8901 High Similarity NPC474436
0.8901 High Similarity NPC49776
0.8889 High Similarity NPC169933
0.8876 High Similarity NPC224145
0.8876 High Similarity NPC474474
0.8866 High Similarity NPC80566
0.8864 High Similarity NPC74363
0.8864 High Similarity NPC475862
0.8864 High Similarity NPC213412
0.8864 High Similarity NPC73038
0.8851 High Similarity NPC171789
0.8817 High Similarity NPC25848
0.8817 High Similarity NPC476327
0.8817 High Similarity NPC173744
0.8817 High Similarity NPC167193
0.8817 High Similarity NPC62516
0.8817 High Similarity NPC19376
0.8817 High Similarity NPC230151
0.8817 High Similarity NPC305464
0.8817 High Similarity NPC73004
0.8817 High Similarity NPC472806
0.8817 High Similarity NPC157113
0.8817 High Similarity NPC116457
0.8817 High Similarity NPC204961
0.8817 High Similarity NPC307282
0.8817 High Similarity NPC207922
0.8817 High Similarity NPC158371
0.8817 High Similarity NPC259733
0.8817 High Similarity NPC327179
0.8817 High Similarity NPC476318
0.8804 High Similarity NPC296164
0.8804 High Similarity NPC80365
0.8804 High Similarity NPC60692
0.8804 High Similarity NPC87095

  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 NPC298554 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
0.9213 High Similarity NPD7515 Phase 2
0.8804 High Similarity NPD7748 Approved
0.8526 High Similarity NPD7902 Approved
0.8333 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.8211 Intermediate Similarity NPD7900 Approved
0.8211 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.8068 Intermediate Similarity NPD7645 Phase 2
0.7849 Intermediate Similarity NPD3618 Phase 1
0.7826 Intermediate Similarity NPD4786 Approved
0.7812 Intermediate Similarity NPD8035 Phase 2
0.7812 Intermediate Similarity NPD8034 Phase 2
0.7802 Intermediate Similarity NPD3667 Approved
0.7789 Intermediate Similarity NPD5328 Approved
0.7732 Intermediate Similarity NPD6399 Phase 3
0.7677 Intermediate Similarity NPD4697 Phase 3
0.7629 Intermediate Similarity NPD6079 Approved
0.7629 Intermediate Similarity NPD6411 Approved
0.7604 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.7525 Intermediate Similarity NPD7638 Approved
0.75 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7451 Intermediate Similarity NPD7639 Approved
0.7451 Intermediate Similarity NPD7640 Approved
0.7447 Intermediate Similarity NPD3665 Phase 1
0.7447 Intermediate Similarity NPD3666 Approved
0.7447 Intermediate Similarity NPD3133 Approved
0.7429 Intermediate Similarity NPD6675 Approved
0.7429 Intermediate Similarity NPD7128 Approved
0.7429 Intermediate Similarity NPD6402 Approved
0.7429 Intermediate Similarity NPD5739 Approved
0.7423 Intermediate Similarity NPD6101 Approved
0.7423 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD7525 Registered
0.7374 Intermediate Similarity NPD4202 Approved
0.7333 Intermediate Similarity NPD6117 Approved
0.7327 Intermediate Similarity NPD5222 Approved
0.7327 Intermediate Similarity NPD5221 Approved
0.7327 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7304 Intermediate Similarity NPD8328 Phase 3
0.7292 Intermediate Similarity NPD6684 Approved
0.7292 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7292 Intermediate Similarity NPD7146 Approved
0.7292 Intermediate Similarity NPD6409 Approved
0.7292 Intermediate Similarity NPD5330 Approved
0.7292 Intermediate Similarity NPD7521 Approved
0.7292 Intermediate Similarity NPD7334 Approved
0.729 Intermediate Similarity NPD6881 Approved
0.729 Intermediate Similarity NPD7320 Approved
0.729 Intermediate Similarity NPD6899 Approved
0.7263 Intermediate Similarity NPD3668 Phase 3
0.7255 Intermediate Similarity NPD6084 Phase 2
0.7255 Intermediate Similarity NPD5173 Approved
0.7255 Intermediate Similarity NPD4755 Approved
0.7255 Intermediate Similarity NPD6083 Phase 2
0.7253 Intermediate Similarity NPD6116 Phase 1
0.7232 Intermediate Similarity NPD7115 Discovery
0.7232 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD6372 Approved
0.7222 Intermediate Similarity NPD6373 Approved
0.7216 Intermediate Similarity NPD3573 Approved
0.7196 Intermediate Similarity NPD5697 Approved
0.7196 Intermediate Similarity NPD5701 Approved
0.7174 Intermediate Similarity NPD6118 Approved
0.7174 Intermediate Similarity NPD6115 Approved
0.7174 Intermediate Similarity NPD6114 Approved
0.7174 Intermediate Similarity NPD6697 Approved
0.7157 Intermediate Similarity NPD7614 Phase 1
0.7156 Intermediate Similarity NPD6883 Approved
0.7156 Intermediate Similarity NPD7290 Approved
0.7156 Intermediate Similarity NPD7102 Approved
0.7143 Intermediate Similarity NPD6903 Approved
0.7143 Intermediate Similarity NPD6672 Approved
0.7143 Intermediate Similarity NPD5737 Approved
0.713 Intermediate Similarity NPD6011 Approved
0.7115 Intermediate Similarity NPD5285 Approved
0.7115 Intermediate Similarity NPD4700 Approved
0.7115 Intermediate Similarity NPD5286 Approved
0.7115 Intermediate Similarity NPD4696 Approved
0.7111 Intermediate Similarity NPD6113 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD6650 Approved
0.7091 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD6869 Approved
0.7091 Intermediate Similarity NPD6847 Approved
0.7091 Intermediate Similarity NPD8130 Phase 1
0.7091 Intermediate Similarity NPD6649 Approved
0.7091 Intermediate Similarity NPD6617 Approved
0.7071 Intermediate Similarity NPD4753 Phase 2
0.7064 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7064 Intermediate Similarity NPD6012 Approved
0.7064 Intermediate Similarity NPD6014 Approved
0.7064 Intermediate Similarity NPD6013 Approved
0.7048 Intermediate Similarity NPD5223 Approved
0.7033 Intermediate Similarity NPD6942 Approved
0.7033 Intermediate Similarity NPD7339 Approved
0.703 Intermediate Similarity NPD5778 Approved
0.703 Intermediate Similarity NPD5779 Approved
0.7027 Intermediate Similarity NPD8297 Approved
0.7027 Intermediate Similarity NPD6882 Approved
0.7021 Intermediate Similarity NPD4695 Discontinued
0.7019 Intermediate Similarity NPD4225 Approved
0.6981 Remote Similarity NPD5211 Phase 2
0.6981 Remote Similarity NPD5226 Approved
0.6981 Remote Similarity NPD5225 Approved
0.6981 Remote Similarity NPD4633 Approved
0.6981 Remote Similarity NPD5224 Approved
0.6957 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6939 Remote Similarity NPD5279 Phase 3
0.6916 Remote Similarity NPD5175 Approved
0.6916 Remote Similarity NPD4754 Approved
0.6916 Remote Similarity NPD5174 Approved
0.6893 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6893 Remote Similarity NPD5695 Phase 3
0.6875 Remote Similarity NPD4221 Approved
0.6875 Remote Similarity NPD4223 Phase 3
0.686 Remote Similarity NPD7319 Approved
0.6857 Remote Similarity NPD5696 Approved
0.6852 Remote Similarity NPD5141 Approved
0.6847 Remote Similarity NPD4634 Approved
0.6842 Remote Similarity NPD6868 Approved
0.6837 Remote Similarity NPD5329 Approved
0.6827 Remote Similarity NPD7732 Phase 3
0.6822 Remote Similarity NPD7632 Discontinued
0.6814 Remote Similarity NPD4632 Approved
0.6804 Remote Similarity NPD4788 Approved
0.6789 Remote Similarity NPD4768 Approved
0.6789 Remote Similarity NPD4767 Approved
0.6777 Remote Similarity NPD7736 Approved
0.6768 Remote Similarity NPD6098 Approved
0.6765 Remote Similarity NPD5281 Approved
0.6765 Remote Similarity NPD5284 Approved
0.6752 Remote Similarity NPD6319 Approved
0.675 Remote Similarity NPD7507 Approved
0.6735 Remote Similarity NPD4197 Approved
0.6733 Remote Similarity NPD6904 Approved
0.6733 Remote Similarity NPD6673 Approved
0.6733 Remote Similarity NPD6080 Approved
0.6731 Remote Similarity NPD5210 Approved
0.6731 Remote Similarity NPD4629 Approved
0.6727 Remote Similarity NPD6412 Phase 2
0.6724 Remote Similarity NPD6335 Approved
0.6703 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6703 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6701 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6696 Remote Similarity NPD6274 Approved
0.6667 Remote Similarity NPD7100 Approved
0.6667 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7492 Approved
0.6667 Remote Similarity NPD4729 Approved
0.6667 Remote Similarity NPD4730 Approved
0.6667 Remote Similarity NPD5168 Approved
0.6667 Remote Similarity NPD5128 Approved
0.6667 Remote Similarity NPD7101 Approved
0.6667 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6638 Remote Similarity NPD6317 Approved
0.6638 Remote Similarity NPD6009 Approved
0.6636 Remote Similarity NPD6008 Approved
0.6632 Remote Similarity NPD3617 Approved
0.6632 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6612 Remote Similarity NPD6616 Approved
0.661 Remote Similarity NPD6059 Approved
0.661 Remote Similarity NPD6054 Approved
0.6607 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6602 Remote Similarity NPD7637 Suspended
0.66 Remote Similarity NPD4689 Approved
0.66 Remote Similarity NPD4519 Discontinued
0.66 Remote Similarity NPD4693 Phase 3
0.66 Remote Similarity NPD5205 Approved
0.66 Remote Similarity NPD4688 Approved
0.66 Remote Similarity NPD4138 Approved
0.66 Remote Similarity NPD4623 Approved
0.66 Remote Similarity NPD4690 Approved
0.6598 Remote Similarity NPD5369 Approved
0.6581 Remote Similarity NPD6314 Approved
0.6581 Remote Similarity NPD6313 Approved
0.6557 Remote Similarity NPD7078 Approved
0.6557 Remote Similarity NPD8293 Discontinued
0.6555 Remote Similarity NPD6909 Approved
0.6555 Remote Similarity NPD6908 Approved
0.6549 Remote Similarity NPD5169 Approved
0.6549 Remote Similarity NPD5250 Approved
0.6549 Remote Similarity NPD5251 Approved
0.6549 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6549 Remote Similarity NPD5247 Approved
0.6549 Remote Similarity NPD5135 Approved
0.6549 Remote Similarity NPD5249 Phase 3
0.6549 Remote Similarity NPD5248 Approved
0.6531 Remote Similarity NPD4269 Approved
0.6531 Remote Similarity NPD4270 Approved
0.6522 Remote Similarity NPD8133 Approved
0.6518 Remote Similarity NPD6686 Approved
0.65 Remote Similarity NPD1694 Approved
0.65 Remote Similarity NPD6370 Approved
0.6495 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6491 Remote Similarity NPD5127 Approved
0.6491 Remote Similarity NPD5217 Approved
0.6491 Remote Similarity NPD5216 Approved
0.6491 Remote Similarity NPD5215 Approved
0.6489 Remote Similarity NPD3703 Phase 2
0.6476 Remote Similarity NPD6001 Approved
0.6471 Remote Similarity NPD5208 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