Structure

Physi-Chem Properties

Molecular Weight:  428.37
Volume:  482.302
LogP:  6.449
LogD:  5.165
LogS:  -5.388
# Rotatable Bonds:  0
TPSA:  40.46
# H-Bond Aceptor:  2
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.419
Synthetic Accessibility Score:  4.833
Fsp3:  0.931
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.912
MDCK Permeability:  1.5065821571624838e-05
Pgp-inhibitor:  0.292
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.47
30% Bioavailability (F30%):  0.794

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.626
Plasma Protein Binding (PPB):  97.74022674560547%
Volume Distribution (VD):  1.156
Pgp-substrate:  2.08725643157959%

ADMET: Metabolism

CYP1A2-inhibitor:  0.035
CYP1A2-substrate:  0.441
CYP2C19-inhibitor:  0.07
CYP2C19-substrate:  0.918
CYP2C9-inhibitor:  0.21
CYP2C9-substrate:  0.086
CYP2D6-inhibitor:  0.019
CYP2D6-substrate:  0.181
CYP3A4-inhibitor:  0.757
CYP3A4-substrate:  0.743

ADMET: Excretion

Clearance (CL):  8.307
Half-life (T1/2):  0.045

ADMET: Toxicity

hERG Blockers:  0.025
Human Hepatotoxicity (H-HT):  0.341
Drug-inuced Liver Injury (DILI):  0.016
AMES Toxicity:  0.001
Rat Oral Acute Toxicity:  0.918
Maximum Recommended Daily Dose:  0.957
Skin Sensitization:  0.292
Carcinogencity:  0.05
Eye Corrosion:  0.634
Eye Irritation:  0.222
Respiratory Toxicity:  0.988

Download Data

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

  Natural Product: NPC291379

Natural Product ID:  NPC291379
Common Name*:   28-Nor-Urs-12-Ene-3Beta,17Beta-Diol
IUPAC Name:   (3S,4aR,6aR,6bS,8aS,11R,12S,12aS,14aR,14bR)-4,4,6a,6b,11,12,14b-heptamethyl-2,3,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydro-1H-picene-3,8a-diol
Synonyms:  
Standard InCHIKey:  OHURLQYFJBUGGV-SQPCZADNSA-N
Standard InCHI:  InChI=1S/C29H48O2/c1-18-10-15-29(31)17-16-27(6)20(24(29)19(18)2)8-9-22-26(5)13-12-23(30)25(3,4)21(26)11-14-28(22,27)7/h8,18-19,21-24,30-31H,9-17H2,1-7H3/t18-,19+,21+,22-,23+,24+,26+,27-,28-,29+/m1/s1
SMILES:  C[C@@H]1CC[C@]2([C@@H]([C@H]1C)C1=CC[C@H]3[C@@]([C@@]1(CC2)C)(C)CC[C@@H]1[C@]3(C)CC[C@@H](C1(C)C)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL497269
PubChem CID:   21580512
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
NPO26266 Isodon japonicus Species Lamiaceae Eukaryota n.a. n.a. n.a. DOI[10.1039/C39730000707]
NPO1071 Parerythropodium fulvum Species n.a. n.a. n.a. n.a. n.a. PMID[11277760]
NPO10021 Nerium oleander Species Apocynaceae Eukaryota leaves Niigata City, Niigata Province, Japan 2000-Nov PMID[15730243]
NPO10021 Nerium oleander Species Apocynaceae Eukaryota leaves n.a. n.a. PMID[16933868]
NPO10021 Nerium oleander Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[17253842]
NPO10021 Nerium oleander Species Apocynaceae Eukaryota stems and twigs Niigata City, Niigata Province, Japan 2001-NOV PMID[17595134]
NPO10021 Nerium oleander Species Apocynaceae Eukaryota stems and twigs n.a. n.a. PMID[17595134]
NPO26266 Isodon japonicus Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[18491868]
NPO3936 Malva sylvestris Species Malvaceae Eukaryota n.a. n.a. n.a. PMID[19731587]
NPO10021 Nerium oleander Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[29693393]
NPO10021 Nerium oleander Species Apocynaceae Eukaryota Leaves; Stems n.a. n.a. PMID[9214727]
NPO13325 Plantago lanceolata Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10021 Nerium oleander Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3664 Mesembryanthemum anatomicum Species Aizoaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3936 Malva sylvestris Species Malvaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6520 Myrica multiflora Species Myricaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2342 Cytisus scoparius Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2747 Hypericum triquetrifolium Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2518 Crinum kirkii Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2342 Cytisus scoparius Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2747 Hypericum triquetrifolium Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10021 Nerium oleander Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6520 Myrica multiflora Species Myricaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3664 Mesembryanthemum anatomicum Species Aizoaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13325 Plantago lanceolata Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3936 Malva sylvestris Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2342 Cytisus scoparius Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7097 Rhynchosporium orthosporum Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6776 Trifolium apertum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6974 Solanum racemigerum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2361 Aconitum brevicalcaratum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13325 Plantago lanceolata Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4082 Ophiarthrum elegans Species Ophiocomidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1607 Croton rhamnifolius Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2342 Cytisus scoparius Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6520 Myrica multiflora Species Myricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8840 Ptilidium ciliare Species Ptilidiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26266 Isodon japonicus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5591 Fucus spiralis Species Fucaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20132 Scutellaria seleriana Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5980 Eria subsessilis Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2747 Hypericum triquetrifolium Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3146 Ammodendron conollyi Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO715 Teucrium pestalozzae Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2518 Crinum kirkii Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8472 Knightia deplanchei Species Proteaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4253 Viguiera annua Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3936 Malva sylvestris Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1308 Veronica pectinata Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15583 Tripodanthus acutifolius Species Loranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3664 Mesembryanthemum anatomicum Species Aizoaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1071 Parerythropodium fulvum Species n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO10021 Nerium oleander Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8585 Verpa digitaliformis Species Morchellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO351 Cirsium dipsacolepis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6377 Cocculus diversifolius Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5197 Streptomyces eurythermus Species Streptomycetaceae Bacteria 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
NPT1475 Cell Line WI-38 VA13 Homo sapiens IC50 = 108000.0 nM PMID[537955]
NPT81 Cell Line A549 Homo sapiens IC50 > 316000.0 nM PMID[537955]
NPT27 Others Unspecified IC50 = 20100.0 nM PMID[537955]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 21100.0 nM PMID[537955]

☑ 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 NPC291379 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
0.9863 High Similarity NPC22955
0.9863 High Similarity NPC470396
0.9863 High Similarity NPC99168
0.9863 High Similarity NPC474989
0.973 High Similarity NPC53744
0.9726 High Similarity NPC101475
0.9726 High Similarity NPC40394
0.9726 High Similarity NPC157996
0.9726 High Similarity NPC34177
0.9595 High Similarity NPC253807
0.9595 High Similarity NPC230295
0.9595 High Similarity NPC158662
0.9595 High Similarity NPC300499
0.9595 High Similarity NPC98386
0.9595 High Similarity NPC196753
0.9589 High Similarity NPC27765
0.9589 High Similarity NPC122418
0.9589 High Similarity NPC265328
0.9589 High Similarity NPC106364
0.9589 High Similarity NPC120098
0.9589 High Similarity NPC30590
0.9589 High Similarity NPC290598
0.9452 High Similarity NPC138374
0.9452 High Similarity NPC34700
0.9342 High Similarity NPC295131
0.9315 High Similarity NPC100334
0.9221 High Similarity NPC242350
0.9221 High Similarity NPC116202
0.92 High Similarity NPC472805
0.92 High Similarity NPC90979
0.9114 High Similarity NPC238992
0.9103 High Similarity NPC47763
0.9103 High Similarity NPC304285
0.9079 High Similarity NPC72507
0.9054 High Similarity NPC477138
0.9054 High Similarity NPC243342
0.9041 High Similarity NPC167706
0.8987 High Similarity NPC82538
0.8987 High Similarity NPC159168
0.8987 High Similarity NPC237795
0.8987 High Similarity NPC253402
0.8947 High Similarity NPC471798
0.8947 High Similarity NPC470711
0.8947 High Similarity NPC470758
0.8933 High Similarity NPC66566
0.8933 High Similarity NPC477923
0.8933 High Similarity NPC291503
0.8919 High Similarity NPC211009
0.8919 High Similarity NPC182717
0.8919 High Similarity NPC471799
0.8889 High Similarity NPC237344
0.8861 High Similarity NPC248886
0.8831 High Similarity NPC285761
0.8816 High Similarity NPC470749
0.8816 High Similarity NPC265588
0.88 High Similarity NPC91858
0.88 High Similarity NPC471797
0.8784 High Similarity NPC242001
0.8784 High Similarity NPC301226
0.878 High Similarity NPC73064
0.8765 High Similarity NPC133954
0.8765 High Similarity NPC477578
0.8765 High Similarity NPC191965
0.8718 High Similarity NPC472463
0.8718 High Similarity NPC273410
0.8718 High Similarity NPC80530
0.8701 High Similarity NPC198968
0.8701 High Similarity NPC318495
0.8701 High Similarity NPC155986
0.8701 High Similarity NPC477924
0.8701 High Similarity NPC91594
0.8684 High Similarity NPC144075
0.8675 High Similarity NPC474512
0.8675 High Similarity NPC181225
0.8675 High Similarity NPC17733
0.8675 High Similarity NPC473242
0.8675 High Similarity NPC470629
0.8675 High Similarity NPC290690
0.8659 High Similarity NPC74363
0.8659 High Similarity NPC477579
0.8659 High Similarity NPC84121
0.8659 High Similarity NPC235341
0.8659 High Similarity NPC137306
0.8659 High Similarity NPC475862
0.8659 High Similarity NPC95594
0.8659 High Similarity NPC213412
0.8649 High Similarity NPC145498
0.8649 High Similarity NPC92801
0.8642 High Similarity NPC180834
0.8642 High Similarity NPC209802
0.863 High Similarity NPC94192
0.863 High Similarity NPC208999
0.8608 High Similarity NPC236237
0.8608 High Similarity NPC13554
0.8608 High Similarity NPC322313
0.8608 High Similarity NPC102253
0.859 High Similarity NPC167037
0.859 High Similarity NPC244385
0.859 High Similarity NPC138621
0.859 High Similarity NPC6978
0.859 High Similarity NPC275910
0.8571 High Similarity NPC321016
0.8571 High Similarity NPC240604
0.8571 High Similarity NPC237460
0.8571 High Similarity NPC274330
0.8571 High Similarity NPC470588
0.8571 High Similarity NPC198664
0.8571 High Similarity NPC274079
0.8571 High Similarity NPC321381
0.8571 High Similarity NPC106432
0.8571 High Similarity NPC477925
0.8571 High Similarity NPC107059
0.8571 High Similarity NPC189883
0.8571 High Similarity NPC143232
0.8571 High Similarity NPC300324
0.8554 High Similarity NPC242468
0.8554 High Similarity NPC98442
0.8554 High Similarity NPC171203
0.8554 High Similarity NPC88716
0.8554 High Similarity NPC293564
0.8554 High Similarity NPC307426
0.8554 High Similarity NPC102683
0.8554 High Similarity NPC68160
0.8554 High Similarity NPC18064
0.8554 High Similarity NPC130577
0.8554 High Similarity NPC51700
0.8554 High Similarity NPC142415
0.8553 High Similarity NPC476366
0.8553 High Similarity NPC201048
0.8533 High Similarity NPC110799
0.8533 High Similarity NPC164022
0.8514 High Similarity NPC210323
0.85 High Similarity NPC476646
0.85 High Similarity NPC474531
0.8488 Intermediate Similarity NPC202728
0.8488 Intermediate Similarity NPC158059
0.8488 Intermediate Similarity NPC118519
0.8481 Intermediate Similarity NPC1319
0.8481 Intermediate Similarity NPC328714
0.8471 Intermediate Similarity NPC126369
0.8471 Intermediate Similarity NPC111110
0.8471 Intermediate Similarity NPC470589
0.8462 Intermediate Similarity NPC130136
0.8462 Intermediate Similarity NPC214570
0.8452 Intermediate Similarity NPC40552
0.8452 Intermediate Similarity NPC246708
0.8452 Intermediate Similarity NPC182797
0.8452 Intermediate Similarity NPC52169
0.8442 Intermediate Similarity NPC231256
0.8442 Intermediate Similarity NPC22105
0.8442 Intermediate Similarity NPC136188
0.8442 Intermediate Similarity NPC471723
0.8442 Intermediate Similarity NPC240235
0.8442 Intermediate Similarity NPC134847
0.8442 Intermediate Similarity NPC257347
0.8442 Intermediate Similarity NPC28657
0.8442 Intermediate Similarity NPC178383
0.8442 Intermediate Similarity NPC230301
0.8442 Intermediate Similarity NPC304309
0.8442 Intermediate Similarity NPC285893
0.8442 Intermediate Similarity NPC162742
0.8442 Intermediate Similarity NPC288035
0.8442 Intermediate Similarity NPC212879
0.8442 Intermediate Similarity NPC141071
0.8442 Intermediate Similarity NPC104387
0.8434 Intermediate Similarity NPC72638
0.8434 Intermediate Similarity NPC24277
0.8415 Intermediate Similarity NPC474493
0.8395 Intermediate Similarity NPC310989
0.8395 Intermediate Similarity NPC296701
0.8395 Intermediate Similarity NPC49964
0.8395 Intermediate Similarity NPC30166
0.8395 Intermediate Similarity NPC218616
0.8391 Intermediate Similarity NPC6818
0.8391 Intermediate Similarity NPC191412
0.8391 Intermediate Similarity NPC114159
0.8378 Intermediate Similarity NPC2648
0.8375 Intermediate Similarity NPC241290
0.8375 Intermediate Similarity NPC287749
0.8375 Intermediate Similarity NPC236112
0.8375 Intermediate Similarity NPC164840
0.8375 Intermediate Similarity NPC209944
0.8375 Intermediate Similarity NPC96362
0.8372 Intermediate Similarity NPC187722
0.8354 Intermediate Similarity NPC83351
0.8354 Intermediate Similarity NPC148977
0.8354 Intermediate Similarity NPC85346
0.8354 Intermediate Similarity NPC42853
0.8354 Intermediate Similarity NPC65897
0.8354 Intermediate Similarity NPC167891
0.8354 Intermediate Similarity NPC474216
0.8354 Intermediate Similarity NPC302041
0.8354 Intermediate Similarity NPC312328
0.8354 Intermediate Similarity NPC476314
0.8354 Intermediate Similarity NPC477522
0.8354 Intermediate Similarity NPC473943
0.8354 Intermediate Similarity NPC87604
0.8354 Intermediate Similarity NPC11908
0.8353 Intermediate Similarity NPC290972
0.8353 Intermediate Similarity NPC130520

  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 NPC291379 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
0.9467 High Similarity NPD7645 Phase 2
0.8608 High Similarity NPD7525 Registered
0.8442 Intermediate Similarity NPD6942 Approved
0.8442 Intermediate Similarity NPD7339 Approved
0.8333 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.8161 Intermediate Similarity NPD7515 Phase 2
0.7848 Intermediate Similarity NPD6924 Approved
0.7848 Intermediate Similarity NPD6926 Approved
0.7778 Intermediate Similarity NPD7748 Approved
0.7765 Intermediate Similarity NPD4786 Approved
0.7738 Intermediate Similarity NPD3667 Approved
0.7654 Intermediate Similarity NPD6933 Approved
0.7625 Intermediate Similarity NPD4784 Approved
0.7625 Intermediate Similarity NPD4785 Approved
0.7595 Intermediate Similarity NPD4243 Approved
0.7586 Intermediate Similarity NPD3618 Phase 1
0.7531 Intermediate Similarity NPD8264 Approved
0.7528 Intermediate Similarity NPD5328 Approved
0.7527 Intermediate Similarity NPD7902 Approved
0.75 Intermediate Similarity NPD7509 Discontinued
0.75 Intermediate Similarity NPD4748 Discontinued
0.75 Intermediate Similarity NPD4751 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7375 Intermediate Similarity NPD7150 Approved
0.7375 Intermediate Similarity NPD7151 Approved
0.7375 Intermediate Similarity NPD7152 Approved
0.7363 Intermediate Similarity NPD6079 Approved
0.7342 Intermediate Similarity NPD6923 Approved
0.7342 Intermediate Similarity NPD6922 Approved
0.7294 Intermediate Similarity NPD6930 Phase 2
0.7294 Intermediate Similarity NPD6931 Approved
0.7283 Intermediate Similarity NPD4202 Approved
0.725 Intermediate Similarity NPD7143 Approved
0.725 Intermediate Similarity NPD7144 Approved
0.7204 Intermediate Similarity NPD7900 Approved
0.7204 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD6929 Approved
0.7159 Intermediate Similarity NPD3666 Approved
0.7159 Intermediate Similarity NPD3133 Approved
0.7159 Intermediate Similarity NPD3665 Phase 1
0.7143 Intermediate Similarity NPD6932 Approved
0.7108 Intermediate Similarity NPD5275 Approved
0.7108 Intermediate Similarity NPD4190 Phase 3
0.7059 Intermediate Similarity NPD7322 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD6695 Phase 3
0.6979 Remote Similarity NPD4755 Approved
0.6977 Remote Similarity NPD4195 Approved
0.6977 Remote Similarity NPD6683 Phase 2
0.6966 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6966 Remote Similarity NPD3668 Phase 3
0.6941 Remote Similarity NPD6925 Approved
0.6941 Remote Similarity NPD5776 Phase 2
0.6915 Remote Similarity NPD6399 Phase 3
0.6914 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6907 Remote Similarity NPD7638 Approved
0.6897 Remote Similarity NPD7332 Phase 2
0.6897 Remote Similarity NPD7514 Phase 3
0.6889 Remote Similarity NPD6893 Approved
0.6883 Remote Similarity NPD368 Approved
0.6875 Remote Similarity NPD5222 Approved
0.6875 Remote Similarity NPD4697 Phase 3
0.6875 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6875 Remote Similarity NPD5221 Approved
0.686 Remote Similarity NPD7145 Approved
0.6837 Remote Similarity NPD4696 Approved
0.6837 Remote Similarity NPD7640 Approved
0.6837 Remote Similarity NPD7639 Approved
0.6837 Remote Similarity NPD4700 Approved
0.6837 Remote Similarity NPD5286 Approved
0.6837 Remote Similarity NPD5285 Approved
0.6818 Remote Similarity NPD6898 Phase 1
0.6809 Remote Similarity NPD8034 Phase 2
0.6809 Remote Similarity NPD8035 Phase 2
0.6804 Remote Similarity NPD5173 Approved
0.6774 Remote Similarity NPD4753 Phase 2
0.6774 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6768 Remote Similarity NPD5223 Approved
0.6742 Remote Similarity NPD4223 Phase 3
0.6742 Remote Similarity NPD4221 Approved
0.6739 Remote Similarity NPD7524 Approved
0.6739 Remote Similarity NPD7750 Discontinued
0.6735 Remote Similarity NPD5290 Discontinued
0.6705 Remote Similarity NPD4695 Discontinued
0.6703 Remote Similarity NPD5329 Approved
0.67 Remote Similarity NPD5225 Approved
0.67 Remote Similarity NPD5226 Approved
0.67 Remote Similarity NPD5211 Phase 2
0.67 Remote Similarity NPD5224 Approved
0.67 Remote Similarity NPD4633 Approved
0.6667 Remote Similarity NPD6402 Approved
0.6667 Remote Similarity NPD7128 Approved
0.6667 Remote Similarity NPD5739 Approved
0.6667 Remote Similarity NPD4788 Approved
0.6667 Remote Similarity NPD6675 Approved
0.6667 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6634 Remote Similarity NPD5174 Approved
0.6634 Remote Similarity NPD5175 Approved
0.6634 Remote Similarity NPD4754 Approved
0.663 Remote Similarity NPD3574 Clinical (unspecified phase)
0.663 Remote Similarity NPD5279 Phase 3
0.6629 Remote Similarity NPD6902 Approved
0.6627 Remote Similarity NPD4787 Phase 1
0.6593 Remote Similarity NPD4197 Approved
0.6569 Remote Similarity NPD5141 Approved
0.6559 Remote Similarity NPD3573 Approved
0.6538 Remote Similarity NPD6899 Approved
0.6538 Remote Similarity NPD7320 Approved
0.6538 Remote Similarity NPD6881 Approved
0.6505 Remote Similarity NPD4767 Approved
0.6505 Remote Similarity NPD4768 Approved
0.6476 Remote Similarity NPD6372 Approved
0.6476 Remote Similarity NPD6373 Approved
0.6465 Remote Similarity NPD6083 Phase 2
0.6465 Remote Similarity NPD6084 Phase 2
0.6458 Remote Similarity NPD6411 Approved
0.6458 Remote Similarity NPD7087 Discontinued
0.6452 Remote Similarity NPD4519 Discontinued
0.6452 Remote Similarity NPD7334 Approved
0.6452 Remote Similarity NPD6409 Approved
0.6452 Remote Similarity NPD5330 Approved
0.6452 Remote Similarity NPD4688 Approved
0.6452 Remote Similarity NPD6684 Approved
0.6452 Remote Similarity NPD4623 Approved
0.6452 Remote Similarity NPD7146 Approved
0.6452 Remote Similarity NPD5205 Approved
0.6452 Remote Similarity NPD7521 Approved
0.6452 Remote Similarity NPD4689 Approved
0.6452 Remote Similarity NPD4690 Approved
0.6452 Remote Similarity NPD4693 Phase 3
0.6452 Remote Similarity NPD4138 Approved
0.6442 Remote Similarity NPD5697 Approved
0.6442 Remote Similarity NPD5701 Approved
0.6436 Remote Similarity NPD4159 Approved
0.6429 Remote Similarity NPD5210 Approved
0.6429 Remote Similarity NPD4629 Approved
0.6421 Remote Similarity NPD6051 Approved
0.6415 Remote Similarity NPD7102 Approved
0.6415 Remote Similarity NPD7290 Approved
0.6415 Remote Similarity NPD6883 Approved
0.64 Remote Similarity NPD4225 Approved
0.6381 Remote Similarity NPD5128 Approved
0.6381 Remote Similarity NPD4729 Approved
0.6381 Remote Similarity NPD4730 Approved
0.6381 Remote Similarity NPD6011 Approved
0.6364 Remote Similarity NPD7115 Discovery
0.6355 Remote Similarity NPD6847 Approved
0.6355 Remote Similarity NPD6869 Approved
0.6355 Remote Similarity NPD6649 Approved
0.6355 Remote Similarity NPD6617 Approved
0.6355 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6355 Remote Similarity NPD6650 Approved
0.6355 Remote Similarity NPD8130 Phase 1
0.6353 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6353 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6333 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6321 Remote Similarity NPD6014 Approved
0.6321 Remote Similarity NPD6013 Approved
0.6321 Remote Similarity NPD6012 Approved
0.6316 Remote Similarity NPD342 Phase 1
0.6316 Remote Similarity NPD4723 Approved
0.6316 Remote Similarity NPD6903 Approved
0.6316 Remote Similarity NPD4722 Approved
0.631 Remote Similarity NPD3699 Clinical (unspecified phase)
0.631 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6296 Remote Similarity NPD6882 Approved
0.6296 Remote Similarity NPD8297 Approved
0.6292 Remote Similarity NPD3617 Approved
0.6283 Remote Similarity NPD8033 Approved
0.6277 Remote Similarity NPD5280 Approved
0.6277 Remote Similarity NPD4694 Approved
0.6277 Remote Similarity NPD5690 Phase 2
0.6262 Remote Similarity NPD5251 Approved
0.6262 Remote Similarity NPD5250 Approved
0.6262 Remote Similarity NPD4634 Approved
0.6262 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6262 Remote Similarity NPD5247 Approved
0.6262 Remote Similarity NPD5248 Approved
0.6262 Remote Similarity NPD5249 Phase 3
0.6262 Remote Similarity NPD5169 Approved
0.6262 Remote Similarity NPD5135 Approved
0.625 Remote Similarity NPD6117 Approved
0.625 Remote Similarity NPD6101 Approved
0.625 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6226 Remote Similarity NPD5168 Approved
0.6216 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6214 Remote Similarity NPD7632 Discontinued
0.6207 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6204 Remote Similarity NPD5215 Approved
0.6204 Remote Similarity NPD5127 Approved
0.6204 Remote Similarity NPD5217 Approved
0.6204 Remote Similarity NPD5216 Approved
0.62 Remote Similarity NPD7614 Phase 1
0.6195 Remote Similarity NPD8377 Approved
0.6195 Remote Similarity NPD8294 Approved
0.618 Remote Similarity NPD6116 Phase 1
0.6174 Remote Similarity NPD8328 Phase 3
0.617 Remote Similarity NPD1696 Phase 3
0.6168 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6161 Remote Similarity NPD7328 Approved
0.6161 Remote Similarity NPD7327 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