Structure

Physi-Chem Properties

Molecular Weight:  318.22
Volume:  347.268
LogP:  2.613
LogD:  3.015
LogS:  -4.428
# Rotatable Bonds:  2
TPSA:  57.53
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.768
Synthetic Accessibility Score:  4.978
Fsp3:  0.75
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:  -4.858
MDCK Permeability:  2.5675995857454836e-05
Pgp-inhibitor:  0.028
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.742
Plasma Protein Binding (PPB):  91.02912139892578%
Volume Distribution (VD):  0.963
Pgp-substrate:  8.964301109313965%

ADMET: Metabolism

CYP1A2-inhibitor:  0.021
CYP1A2-substrate:  0.536
CYP2C19-inhibitor:  0.063
CYP2C19-substrate:  0.822
CYP2C9-inhibitor:  0.133
CYP2C9-substrate:  0.08
CYP2D6-inhibitor:  0.083
CYP2D6-substrate:  0.053
CYP3A4-inhibitor:  0.885
CYP3A4-substrate:  0.824

ADMET: Excretion

Clearance (CL):  3.944
Half-life (T1/2):  0.351

ADMET: Toxicity

hERG Blockers:  0.045
Human Hepatotoxicity (H-HT):  0.507
Drug-inuced Liver Injury (DILI):  0.032
AMES Toxicity:  0.037
Rat Oral Acute Toxicity:  0.235
Maximum Recommended Daily Dose:  0.743
Skin Sensitization:  0.944
Carcinogencity:  0.463
Eye Corrosion:  0.185
Eye Irritation:  0.758
Respiratory Toxicity:  0.953

Download Data

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

  Natural Product: NPC471791

Natural Product ID:  NPC471791
Common Name*:   (4S,5S,8R,9R,10R,13R)-10,19-Dihydroxy-1,15-Rosadien-3-One
IUPAC Name:   (1S,4aR,4bR,7R,8aR,10aS)-7-ethenyl-4a-hydroxy-1-(hydroxymethyl)-1,4b,7-trimethyl-6,8,8a,9,10,10a-hexahydro-5H-phenanthren-2-one
Synonyms:  
Standard InCHIKey:  DMNRNXPOMWACEA-WFDVMHAPSA-N
Standard InCHI:  InChI=1S/C20H30O3/c1-5-17(2)10-11-19(4)14(12-17)6-7-15-18(3,13-21)16(22)8-9-20(15,19)23/h5,8-9,14-15,21,23H,1,6-7,10-13H2,2-4H3/t14-,15+,17-,18-,19-,20-/m1/s1
SMILES:  CC1(CCC2(C(C1)CCC3C2(C=CC(=O)C3(C)CO)O)C)C=C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3234205
PubChem CID:   90670329
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0001295] Hydroxysteroids

*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
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota roots n.a. n.a. PMID[24660966]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota Roots n.a. n.a. PMID[29148766]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[31184480]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae 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
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 7320.0 nM PMID[507344]

☑ 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 NPC471791 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
1.0 High Similarity NPC471793
0.8795 High Similarity NPC469637
0.8721 High Similarity NPC476426
0.8621 High Similarity NPC194417
0.8621 High Similarity NPC470955
0.8605 High Similarity NPC476412
0.8539 High Similarity NPC472477
0.8539 High Similarity NPC472973
0.8539 High Similarity NPC472475
0.8523 High Similarity NPC471792
0.8462 Intermediate Similarity NPC474807
0.8427 Intermediate Similarity NPC58271
0.8427 Intermediate Similarity NPC48107
0.8409 Intermediate Similarity NPC472974
0.8409 Intermediate Similarity NPC472986
0.8409 Intermediate Similarity NPC472985
0.8404 Intermediate Similarity NPC316598
0.8353 Intermediate Similarity NPC104120
0.8353 Intermediate Similarity NPC148685
0.8353 Intermediate Similarity NPC172013
0.8353 Intermediate Similarity NPC157895
0.8353 Intermediate Similarity NPC476809
0.8352 Intermediate Similarity NPC472978
0.8352 Intermediate Similarity NPC73457
0.8352 Intermediate Similarity NPC475806
0.8333 Intermediate Similarity NPC472489
0.8333 Intermediate Similarity NPC472983
0.828 Intermediate Similarity NPC271195
0.8261 Intermediate Similarity NPC131840
0.8256 Intermediate Similarity NPC226068
0.8256 Intermediate Similarity NPC116797
0.8242 Intermediate Similarity NPC230332
0.8242 Intermediate Similarity NPC472476
0.8242 Intermediate Similarity NPC134321
0.8235 Intermediate Similarity NPC474113
0.8235 Intermediate Similarity NPC308038
0.8235 Intermediate Similarity NPC170394
0.8214 Intermediate Similarity NPC34110
0.8211 Intermediate Similarity NPC103051
0.8202 Intermediate Similarity NPC82979
0.8202 Intermediate Similarity NPC472479
0.8172 Intermediate Similarity NPC299100
0.8172 Intermediate Similarity NPC472976
0.8172 Intermediate Similarity NPC472977
0.8172 Intermediate Similarity NPC8993
0.8152 Intermediate Similarity NPC26865
0.8152 Intermediate Similarity NPC252433
0.8152 Intermediate Similarity NPC472975
0.814 Intermediate Similarity NPC472301
0.814 Intermediate Similarity NPC2482
0.8132 Intermediate Similarity NPC309603
0.8132 Intermediate Similarity NPC119416
0.8132 Intermediate Similarity NPC473999
0.8125 Intermediate Similarity NPC154072
0.8118 Intermediate Similarity NPC471409
0.8118 Intermediate Similarity NPC62336
0.8118 Intermediate Similarity NPC275494
0.8111 Intermediate Similarity NPC272039
0.8111 Intermediate Similarity NPC220930
0.8105 Intermediate Similarity NPC170131
0.8095 Intermediate Similarity NPC263582
0.809 Intermediate Similarity NPC255174
0.809 Intermediate Similarity NPC70685
0.8085 Intermediate Similarity NPC474602
0.8085 Intermediate Similarity NPC259286
0.8085 Intermediate Similarity NPC180950
0.8085 Intermediate Similarity NPC290481
0.8085 Intermediate Similarity NPC476245
0.8065 Intermediate Similarity NPC476416
0.8065 Intermediate Similarity NPC109305
0.8065 Intermediate Similarity NPC474736
0.8061 Intermediate Similarity NPC131366
0.8046 Intermediate Similarity NPC14151
0.8046 Intermediate Similarity NPC473217
0.8046 Intermediate Similarity NPC121984
0.8043 Intermediate Similarity NPC128672
0.8043 Intermediate Similarity NPC48010
0.8041 Intermediate Similarity NPC282524
0.8041 Intermediate Similarity NPC470184
0.8023 Intermediate Similarity NPC281138
0.8022 Intermediate Similarity NPC158778
0.8022 Intermediate Similarity NPC472802
0.8022 Intermediate Similarity NPC474677
0.8022 Intermediate Similarity NPC72397
0.8022 Intermediate Similarity NPC476796
0.8021 Intermediate Similarity NPC478056
0.8 Intermediate Similarity NPC149550
0.8 Intermediate Similarity NPC94666
0.8 Intermediate Similarity NPC257666
0.8 Intermediate Similarity NPC472488
0.8 Intermediate Similarity NPC197659
0.8 Intermediate Similarity NPC85105
0.8 Intermediate Similarity NPC266193
0.8 Intermediate Similarity NPC249954
0.8 Intermediate Similarity NPC117133
0.798 Intermediate Similarity NPC160843
0.7979 Intermediate Similarity NPC148964
0.7979 Intermediate Similarity NPC196227
0.7978 Intermediate Similarity NPC251170
0.7978 Intermediate Similarity NPC40687
0.7957 Intermediate Similarity NPC116726
0.7957 Intermediate Similarity NPC172101
0.7957 Intermediate Similarity NPC272746
0.7957 Intermediate Similarity NPC473998
0.7955 Intermediate Similarity NPC93590
0.7952 Intermediate Similarity NPC247586
0.7935 Intermediate Similarity NPC472970
0.7935 Intermediate Similarity NPC472971
0.7935 Intermediate Similarity NPC2983
0.7931 Intermediate Similarity NPC45495
0.7931 Intermediate Similarity NPC472478
0.7917 Intermediate Similarity NPC273269
0.7912 Intermediate Similarity NPC93778
0.7912 Intermediate Similarity NPC298904
0.7912 Intermediate Similarity NPC472484
0.7912 Intermediate Similarity NPC472482
0.7912 Intermediate Similarity NPC472481
0.7907 Intermediate Similarity NPC207772
0.7907 Intermediate Similarity NPC475994
0.79 Intermediate Similarity NPC166607
0.7895 Intermediate Similarity NPC280725
0.7895 Intermediate Similarity NPC53565
0.7895 Intermediate Similarity NPC472485
0.7895 Intermediate Similarity NPC272617
0.7889 Intermediate Similarity NPC470574
0.7889 Intermediate Similarity NPC179006
0.7889 Intermediate Similarity NPC471224
0.7889 Intermediate Similarity NPC274724
0.7889 Intermediate Similarity NPC474853
0.7882 Intermediate Similarity NPC151622
0.7882 Intermediate Similarity NPC186554
0.7882 Intermediate Similarity NPC472305
0.7882 Intermediate Similarity NPC76966
0.7882 Intermediate Similarity NPC7629
0.7879 Intermediate Similarity NPC478057
0.7879 Intermediate Similarity NPC247957
0.7879 Intermediate Similarity NPC95899
0.7879 Intermediate Similarity NPC311612
0.7879 Intermediate Similarity NPC249187
0.7872 Intermediate Similarity NPC69454
0.7872 Intermediate Similarity NPC134826
0.7865 Intermediate Similarity NPC169941
0.7865 Intermediate Similarity NPC105173
0.7865 Intermediate Similarity NPC297398
0.7865 Intermediate Similarity NPC64600
0.7865 Intermediate Similarity NPC251475
0.7857 Intermediate Similarity NPC115862
0.7857 Intermediate Similarity NPC81530
0.7857 Intermediate Similarity NPC38426
0.7849 Intermediate Similarity NPC85173
0.7843 Intermediate Similarity NPC87335
0.7841 Intermediate Similarity NPC6663
0.7835 Intermediate Similarity NPC174663
0.7826 Intermediate Similarity NPC206060
0.7826 Intermediate Similarity NPC104560
0.7826 Intermediate Similarity NPC328539
0.7826 Intermediate Similarity NPC471724
0.7816 Intermediate Similarity NPC7232
0.7816 Intermediate Similarity NPC19900
0.7812 Intermediate Similarity NPC235053
0.7812 Intermediate Similarity NPC167193
0.7812 Intermediate Similarity NPC472806
0.7812 Intermediate Similarity NPC29152
0.7812 Intermediate Similarity NPC473158
0.7812 Intermediate Similarity NPC301534
0.7812 Intermediate Similarity NPC250757
0.7802 Intermediate Similarity NPC74363
0.7802 Intermediate Similarity NPC476043
0.7802 Intermediate Similarity NPC198761
0.7802 Intermediate Similarity NPC322159
0.7802 Intermediate Similarity NPC179591
0.7802 Intermediate Similarity NPC158393
0.7802 Intermediate Similarity NPC473226
0.7802 Intermediate Similarity NPC475862
0.7791 Intermediate Similarity NPC472746
0.7791 Intermediate Similarity NPC74995
0.7789 Intermediate Similarity NPC474690
0.7789 Intermediate Similarity NPC103527
0.7789 Intermediate Similarity NPC471207
0.7789 Intermediate Similarity NPC292793
0.7789 Intermediate Similarity NPC476415
0.7778 Intermediate Similarity NPC58841
0.7778 Intermediate Similarity NPC321187
0.7778 Intermediate Similarity NPC136289
0.7778 Intermediate Similarity NPC85774
0.7778 Intermediate Similarity NPC477915
0.7778 Intermediate Similarity NPC329043
0.7778 Intermediate Similarity NPC237712
0.7778 Intermediate Similarity NPC227132
0.7778 Intermediate Similarity NPC470812
0.7778 Intermediate Similarity NPC214043
0.7778 Intermediate Similarity NPC161423
0.7778 Intermediate Similarity NPC87351
0.7778 Intermediate Similarity NPC227064
0.7766 Intermediate Similarity NPC63748
0.7766 Intermediate Similarity NPC233116
0.7755 Intermediate Similarity NPC198880
0.7755 Intermediate Similarity NPC144956
0.7753 Intermediate Similarity NPC48362
0.7753 Intermediate Similarity NPC92226

  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 NPC471791 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
0.8409 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.8202 Intermediate Similarity NPD3618 Phase 1
0.8 Intermediate Similarity NPD4519 Discontinued
0.8 Intermediate Similarity NPD4623 Approved
0.7959 Intermediate Similarity NPD5211 Phase 2
0.7957 Intermediate Similarity NPD6079 Approved
0.7872 Intermediate Similarity NPD4202 Approved
0.78 Intermediate Similarity NPD5141 Approved
0.7778 Intermediate Similarity NPD3665 Phase 1
0.7778 Intermediate Similarity NPD3666 Approved
0.7778 Intermediate Similarity NPD3133 Approved
0.7755 Intermediate Similarity NPD5286 Approved
0.7755 Intermediate Similarity NPD4696 Approved
0.7755 Intermediate Similarity NPD5285 Approved
0.7742 Intermediate Similarity NPD5328 Approved
0.7708 Intermediate Similarity NPD5210 Approved
0.7708 Intermediate Similarity NPD4629 Approved
0.7677 Intermediate Similarity NPD5223 Approved
0.7629 Intermediate Similarity NPD5221 Approved
0.7629 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7629 Intermediate Similarity NPD5222 Approved
0.76 Intermediate Similarity NPD5225 Approved
0.76 Intermediate Similarity NPD4633 Approved
0.76 Intermediate Similarity NPD5226 Approved
0.76 Intermediate Similarity NPD5224 Approved
0.7579 Intermediate Similarity NPD7515 Phase 2
0.7556 Intermediate Similarity NPD4223 Phase 3
0.7556 Intermediate Similarity NPD3667 Approved
0.7556 Intermediate Similarity NPD4221 Approved
0.7553 Intermediate Similarity NPD4753 Phase 2
0.7551 Intermediate Similarity NPD4755 Approved
0.7551 Intermediate Similarity NPD5173 Approved
0.7528 Intermediate Similarity NPD4695 Discontinued
0.7525 Intermediate Similarity NPD5175 Approved
0.7525 Intermediate Similarity NPD5174 Approved
0.75 Intermediate Similarity NPD7115 Discovery
0.7449 Intermediate Similarity NPD4697 Phase 3
0.7429 Intermediate Similarity NPD4634 Approved
0.7419 Intermediate Similarity NPD5690 Phase 2
0.74 Intermediate Similarity NPD4700 Approved
0.7391 Intermediate Similarity NPD4786 Approved
0.7391 Intermediate Similarity NPD4197 Approved
0.7374 Intermediate Similarity NPD7902 Approved
0.734 Intermediate Similarity NPD3573 Approved
0.7312 Intermediate Similarity NPD5329 Approved
0.7312 Intermediate Similarity NPD1694 Approved
0.7308 Intermediate Similarity NPD5697 Approved
0.7303 Intermediate Similarity NPD3617 Approved
0.7245 Intermediate Similarity NPD7748 Approved
0.7238 Intermediate Similarity NPD4729 Approved
0.7238 Intermediate Similarity NPD6881 Approved
0.7238 Intermediate Similarity NPD6011 Approved
0.7238 Intermediate Similarity NPD4730 Approved
0.7238 Intermediate Similarity NPD6899 Approved
0.7234 Intermediate Similarity NPD4689 Approved
0.7234 Intermediate Similarity NPD5205 Approved
0.7234 Intermediate Similarity NPD5279 Phase 3
0.7234 Intermediate Similarity NPD4693 Phase 3
0.7234 Intermediate Similarity NPD4690 Approved
0.7234 Intermediate Similarity NPD4688 Approved
0.7234 Intermediate Similarity NPD4138 Approved
0.7222 Intermediate Similarity NPD4195 Approved
0.7216 Intermediate Similarity NPD5281 Approved
0.7216 Intermediate Similarity NPD5284 Approved
0.7196 Intermediate Similarity NPD6649 Approved
0.7196 Intermediate Similarity NPD6650 Approved
0.7184 Intermediate Similarity NPD4754 Approved
0.717 Intermediate Similarity NPD6013 Approved
0.717 Intermediate Similarity NPD6012 Approved
0.717 Intermediate Similarity NPD6014 Approved
0.7129 Intermediate Similarity NPD4225 Approved
0.7128 Intermediate Similarity NPD1696 Phase 3
0.7103 Intermediate Similarity NPD5251 Approved
0.7103 Intermediate Similarity NPD5134 Clinical (unspecified phase)
0.7103 Intermediate Similarity NPD5247 Approved
0.7103 Intermediate Similarity NPD5135 Approved
0.7103 Intermediate Similarity NPD6883 Approved
0.7103 Intermediate Similarity NPD5248 Approved
0.7103 Intermediate Similarity NPD5250 Approved
0.7103 Intermediate Similarity NPD7290 Approved
0.7103 Intermediate Similarity NPD5249 Phase 3
0.7103 Intermediate Similarity NPD7102 Approved
0.7103 Intermediate Similarity NPD5169 Approved
0.7097 Intermediate Similarity NPD4788 Approved
0.7075 Intermediate Similarity NPD5128 Approved
0.7071 Intermediate Similarity NPD7900 Approved
0.7071 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7053 Intermediate Similarity NPD5280 Approved
0.7053 Intermediate Similarity NPD4694 Approved
0.7048 Intermediate Similarity NPD6675 Approved
0.7048 Intermediate Similarity NPD4768 Approved
0.7048 Intermediate Similarity NPD6402 Approved
0.7048 Intermediate Similarity NPD7128 Approved
0.7048 Intermediate Similarity NPD5739 Approved
0.7048 Intermediate Similarity NPD4767 Approved
0.7037 Intermediate Similarity NPD6869 Approved
0.7037 Intermediate Similarity NPD5215 Approved
0.7037 Intermediate Similarity NPD5127 Approved
0.7037 Intermediate Similarity NPD8130 Phase 1
0.7037 Intermediate Similarity NPD6847 Approved
0.7037 Intermediate Similarity NPD5217 Approved
0.7037 Intermediate Similarity NPD6617 Approved
0.7037 Intermediate Similarity NPD5216 Approved
0.703 Intermediate Similarity NPD6084 Phase 2
0.703 Intermediate Similarity NPD6083 Phase 2
0.7009 Intermediate Similarity NPD6372 Approved
0.7009 Intermediate Similarity NPD6373 Approved
0.6981 Remote Similarity NPD5701 Approved
0.6972 Remote Similarity NPD8297 Approved
0.6972 Remote Similarity NPD6882 Approved
0.697 Remote Similarity NPD6399 Phase 3
0.6961 Remote Similarity NPD5696 Approved
0.6947 Remote Similarity NPD5363 Approved
0.6939 Remote Similarity NPD5785 Approved
0.6916 Remote Similarity NPD7320 Approved
0.6916 Remote Similarity NPD5168 Approved
0.6909 Remote Similarity NPD4632 Approved
0.6897 Remote Similarity NPD4691 Approved
0.6893 Remote Similarity NPD7640 Approved
0.6893 Remote Similarity NPD7639 Approved
0.6875 Remote Similarity NPD7334 Approved
0.6875 Remote Similarity NPD6409 Approved
0.6875 Remote Similarity NPD7146 Approved
0.6875 Remote Similarity NPD5330 Approved
0.6875 Remote Similarity NPD6684 Approved
0.6875 Remote Similarity NPD7521 Approved
0.6854 Remote Similarity NPD4058 Approved
0.6847 Remote Similarity NPD5167 Approved
0.6842 Remote Similarity NPD3668 Phase 3
0.6842 Remote Similarity NPD6319 Approved
0.6842 Remote Similarity NPD6054 Approved
0.6837 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6832 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6832 Remote Similarity NPD5695 Phase 3
0.6809 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6796 Remote Similarity NPD7638 Approved
0.6783 Remote Similarity NPD6015 Approved
0.6783 Remote Similarity NPD6016 Approved
0.6782 Remote Similarity NPD4137 Phase 3
0.6774 Remote Similarity NPD7525 Registered
0.6762 Remote Similarity NPD5091 Approved
0.6759 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6735 Remote Similarity NPD5737 Approved
0.6735 Remote Similarity NPD6903 Approved
0.6735 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6735 Remote Similarity NPD6672 Approved
0.6733 Remote Similarity NPD6001 Approved
0.6727 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6726 Remote Similarity NPD6009 Approved
0.6726 Remote Similarity NPD6317 Approved
0.6724 Remote Similarity NPD5988 Approved
0.6724 Remote Similarity NPD6370 Approved
0.6705 Remote Similarity NPD4747 Approved
0.6702 Remote Similarity NPD4139 Approved
0.6702 Remote Similarity NPD4692 Approved
0.67 Remote Similarity NPD6411 Approved
0.6697 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6314 Approved
0.6667 Remote Similarity NPD6335 Approved
0.6667 Remote Similarity NPD7645 Phase 2
0.6667 Remote Similarity NPD6313 Approved
0.6638 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6637 Remote Similarity NPD6274 Approved
0.6636 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6635 Remote Similarity NPD5290 Discontinued
0.6634 Remote Similarity NPD5779 Approved
0.6634 Remote Similarity NPD5133 Approved
0.6634 Remote Similarity NPD5778 Approved
0.6632 Remote Similarity NPD4270 Approved
0.6632 Remote Similarity NPD4269 Approved
0.661 Remote Similarity NPD7492 Approved
0.6609 Remote Similarity NPD4522 Approved
0.6609 Remote Similarity NPD7101 Approved
0.6609 Remote Similarity NPD7100 Approved
0.6602 Remote Similarity NPD7614 Phase 1
0.66 Remote Similarity NPD5207 Approved
0.66 Remote Similarity NPD4096 Approved
0.6598 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6591 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6591 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6574 Remote Similarity NPD6008 Approved
0.6569 Remote Similarity NPD5282 Discontinued
0.6566 Remote Similarity NPD5208 Approved
0.6566 Remote Similarity NPD4518 Approved
0.6559 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6555 Remote Similarity NPD6616 Approved
0.6552 Remote Similarity NPD6059 Approved
0.6535 Remote Similarity NPD5693 Phase 1
0.6522 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6514 Remote Similarity NPD6412 Phase 2
0.6512 Remote Similarity NPD7341 Phase 2
0.6512 Remote Similarity NPD3171 Clinical (unspecified phase)
0.6505 Remote Similarity NPD1698 Clinical (unspecified phase)
0.65 Remote Similarity NPD6080 Approved
0.65 Remote Similarity NPD5764 Clinical (unspecified phase)
0.65 Remote Similarity NPD6673 Approved
0.65 Remote Similarity NPD6101 Approved
0.65 Remote Similarity NPD7078 Approved
0.65 Remote Similarity NPD6904 Approved
0.6496 Remote Similarity NPD5983 Phase 2

  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