Structure

Physi-Chem Properties

Molecular Weight:  320.24
Volume:  343.985
LogP:  4.146
LogD:  4.125
LogS:  -3.617
# Rotatable Bonds:  1
TPSA:  49.69
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.73
Synthetic Accessibility Score:  4.835
Fsp3:  0.9
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.614
MDCK Permeability:  1.773846997821238e-05
Pgp-inhibitor:  0.414
Pgp-substrate:  0.978
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.93
30% Bioavailability (F30%):  0.079

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.463
Plasma Protein Binding (PPB):  62.87312316894531%
Volume Distribution (VD):  1.003
Pgp-substrate:  41.6572151184082%

ADMET: Metabolism

CYP1A2-inhibitor:  0.06
CYP1A2-substrate:  0.295
CYP2C19-inhibitor:  0.022
CYP2C19-substrate:  0.639
CYP2C9-inhibitor:  0.06
CYP2C9-substrate:  0.084
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.121
CYP3A4-inhibitor:  0.115
CYP3A4-substrate:  0.181

ADMET: Excretion

Clearance (CL):  10.348
Half-life (T1/2):  0.27

ADMET: Toxicity

hERG Blockers:  0.093
Human Hepatotoxicity (H-HT):  0.294
Drug-inuced Liver Injury (DILI):  0.322
AMES Toxicity:  0.017
Rat Oral Acute Toxicity:  0.829
Maximum Recommended Daily Dose:  0.451
Skin Sensitization:  0.741
Carcinogencity:  0.804
Eye Corrosion:  0.529
Eye Irritation:  0.762
Respiratory Toxicity:  0.969

Download Data

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

  Natural Product: NPC471952

Natural Product ID:  NPC471952
Common Name*:   YHUOVJRNTFTRNX-LSTAUHRDSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  YHUOVJRNTFTRNX-LSTAUHRDSA-N
Standard InCHI:  InChI=1S/C20H32O3/c1-19(2)6-4-7-20(3)15-9-13-12(11-21)5-8-23-17(13)14(15)10-16(22)18(19)20/h5,13-18,21-22H,4,6-11H2,1-3H3/t13-,14-,15-,16-,17-,18-,20+/m0/s1
SMILES:  OCC1=CCO[C@H]2[C@H]1C[C@H]1[C@@H]2C[C@@H]([C@@H]2[C@]1(C)CCCC2(C)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3309974
PubChem CID:   91810318
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000086] Pyrans

*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
NPO29798 Podocarpus imbricatus Species Podocarpaceae Eukaryota twigs and leaves n.a. n.a. PMID[24953598]
NPO29798 Podocarpus imbricatus Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[HerDing]

☑ 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
NPT81 Cell Line A549 Homo sapiens IC50 = 25200.0 nM PMID[484352]
NPT2452 Cell Line NCI-H292 IC50 = 19100.0 nM PMID[484352]

☑ 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 NPC471952 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
0.9036 High Similarity NPC470049
0.8941 High Similarity NPC274448
0.8941 High Similarity NPC266511
0.8916 High Similarity NPC474683
0.8916 High Similarity NPC474759
0.8916 High Similarity NPC82986
0.8916 High Similarity NPC7505
0.8916 High Similarity NPC474731
0.8916 High Similarity NPC474752
0.8824 High Similarity NPC470077
0.875 High Similarity NPC473647
0.8736 High Similarity NPC149224
0.8721 High Similarity NPC157257
0.8706 High Similarity NPC470558
0.8675 High Similarity NPC1319
0.8675 High Similarity NPC28862
0.8675 High Similarity NPC209430
0.8675 High Similarity NPC47982
0.8675 High Similarity NPC143182
0.8675 High Similarity NPC81306
0.8675 High Similarity NPC30986
0.8675 High Similarity NPC84694
0.8675 High Similarity NPC109546
0.8652 High Similarity NPC295668
0.8621 High Similarity NPC139724
0.8605 High Similarity NPC124172
0.8605 High Similarity NPC474047
0.8588 High Similarity NPC296701
0.8588 High Similarity NPC49964
0.8588 High Similarity NPC218616
0.8588 High Similarity NPC155521
0.8588 High Similarity NPC101462
0.8571 High Similarity NPC234193
0.8554 High Similarity NPC477522
0.8554 High Similarity NPC474216
0.8554 High Similarity NPC244385
0.8554 High Similarity NPC6978
0.8554 High Similarity NPC138621
0.8554 High Similarity NPC167037
0.8506 High Similarity NPC318390
0.8506 High Similarity NPC474349
0.8506 High Similarity NPC474189
0.8488 Intermediate Similarity NPC477818
0.8488 Intermediate Similarity NPC475789
0.8488 Intermediate Similarity NPC110778
0.8488 Intermediate Similarity NPC317458
0.8478 Intermediate Similarity NPC8774
0.8471 Intermediate Similarity NPC23852
0.8471 Intermediate Similarity NPC209620
0.8471 Intermediate Similarity NPC264245
0.8462 Intermediate Similarity NPC307776
0.8452 Intermediate Similarity NPC80530
0.8452 Intermediate Similarity NPC273410
0.8434 Intermediate Similarity NPC138502
0.8427 Intermediate Similarity NPC67872
0.8409 Intermediate Similarity NPC24277
0.8409 Intermediate Similarity NPC293287
0.8409 Intermediate Similarity NPC152808
0.8409 Intermediate Similarity NPC261266
0.8409 Intermediate Similarity NPC6391
0.8391 Intermediate Similarity NPC475798
0.8391 Intermediate Similarity NPC205845
0.8391 Intermediate Similarity NPC127606
0.8391 Intermediate Similarity NPC209802
0.8391 Intermediate Similarity NPC185568
0.8387 Intermediate Similarity NPC288970
0.8387 Intermediate Similarity NPC72204
0.8387 Intermediate Similarity NPC98457
0.8387 Intermediate Similarity NPC227583
0.8387 Intermediate Similarity NPC12103
0.8372 Intermediate Similarity NPC189972
0.8372 Intermediate Similarity NPC470614
0.8372 Intermediate Similarity NPC87489
0.8372 Intermediate Similarity NPC1272
0.8372 Intermediate Similarity NPC201852
0.8372 Intermediate Similarity NPC50964
0.8372 Intermediate Similarity NPC5985
0.8372 Intermediate Similarity NPC202389
0.837 Intermediate Similarity NPC144202
0.837 Intermediate Similarity NPC127718
0.837 Intermediate Similarity NPC65402
0.8353 Intermediate Similarity NPC26117
0.8353 Intermediate Similarity NPC322313
0.8353 Intermediate Similarity NPC236237
0.8353 Intermediate Similarity NPC102253
0.8353 Intermediate Similarity NPC241290
0.8353 Intermediate Similarity NPC164840
0.8353 Intermediate Similarity NPC209944
0.8353 Intermediate Similarity NPC47149
0.8333 Intermediate Similarity NPC477514
0.8333 Intermediate Similarity NPC275910
0.8333 Intermediate Similarity NPC285761
0.8333 Intermediate Similarity NPC470361
0.8333 Intermediate Similarity NPC473943
0.8313 Intermediate Similarity NPC237460
0.8313 Intermediate Similarity NPC240604
0.8313 Intermediate Similarity NPC96319
0.8313 Intermediate Similarity NPC244488
0.8313 Intermediate Similarity NPC321016
0.8313 Intermediate Similarity NPC107059
0.8313 Intermediate Similarity NPC189883
0.8313 Intermediate Similarity NPC300324
0.8313 Intermediate Similarity NPC247325
0.8313 Intermediate Similarity NPC38141
0.8313 Intermediate Similarity NPC321381
0.828 Intermediate Similarity NPC476894
0.8276 Intermediate Similarity NPC82623
0.8276 Intermediate Similarity NPC141941
0.8276 Intermediate Similarity NPC193870
0.8276 Intermediate Similarity NPC474634
0.8261 Intermediate Similarity NPC27531
0.8256 Intermediate Similarity NPC474531
0.8256 Intermediate Similarity NPC476646
0.8256 Intermediate Similarity NPC47761
0.8256 Intermediate Similarity NPC157655
0.8242 Intermediate Similarity NPC291484
0.8242 Intermediate Similarity NPC80561
0.8242 Intermediate Similarity NPC11216
0.8242 Intermediate Similarity NPC204188
0.8242 Intermediate Similarity NPC329596
0.8242 Intermediate Similarity NPC3345
0.8235 Intermediate Similarity NPC24504
0.8235 Intermediate Similarity NPC5604
0.8222 Intermediate Similarity NPC474668
0.8222 Intermediate Similarity NPC470542
0.8222 Intermediate Similarity NPC133588
0.8214 Intermediate Similarity NPC260301
0.8214 Intermediate Similarity NPC91594
0.8214 Intermediate Similarity NPC318495
0.8214 Intermediate Similarity NPC470758
0.8214 Intermediate Similarity NPC198968
0.8214 Intermediate Similarity NPC214570
0.8214 Intermediate Similarity NPC307336
0.8214 Intermediate Similarity NPC155986
0.8214 Intermediate Similarity NPC470711
0.8202 Intermediate Similarity NPC299068
0.8202 Intermediate Similarity NPC474970
0.8202 Intermediate Similarity NPC286153
0.8202 Intermediate Similarity NPC201273
0.8193 Intermediate Similarity NPC22105
0.8193 Intermediate Similarity NPC230301
0.8193 Intermediate Similarity NPC28657
0.8193 Intermediate Similarity NPC471723
0.8193 Intermediate Similarity NPC257347
0.8193 Intermediate Similarity NPC288035
0.8193 Intermediate Similarity NPC141071
0.8193 Intermediate Similarity NPC136188
0.8193 Intermediate Similarity NPC185536
0.8193 Intermediate Similarity NPC285893
0.8193 Intermediate Similarity NPC134847
0.8193 Intermediate Similarity NPC304309
0.8193 Intermediate Similarity NPC162742
0.8191 Intermediate Similarity NPC88009
0.8182 Intermediate Similarity NPC15534
0.8182 Intermediate Similarity NPC231310
0.8182 Intermediate Similarity NPC238485
0.8161 Intermediate Similarity NPC304285
0.8161 Intermediate Similarity NPC20853
0.8152 Intermediate Similarity NPC234335
0.8152 Intermediate Similarity NPC97404
0.8152 Intermediate Similarity NPC471453
0.8152 Intermediate Similarity NPC177641
0.8152 Intermediate Similarity NPC41554
0.814 Intermediate Similarity NPC96362
0.814 Intermediate Similarity NPC13554
0.814 Intermediate Similarity NPC78545
0.814 Intermediate Similarity NPC236112
0.814 Intermediate Similarity NPC71535
0.8132 Intermediate Similarity NPC105495
0.8132 Intermediate Similarity NPC101886
0.8125 Intermediate Similarity NPC473510
0.8118 Intermediate Similarity NPC472502
0.8118 Intermediate Similarity NPC477819
0.8118 Intermediate Similarity NPC472501
0.8118 Intermediate Similarity NPC476314
0.8118 Intermediate Similarity NPC11908
0.8118 Intermediate Similarity NPC477817
0.8118 Intermediate Similarity NPC475
0.8118 Intermediate Similarity NPC85346
0.8118 Intermediate Similarity NPC301707
0.8118 Intermediate Similarity NPC472500
0.8118 Intermediate Similarity NPC87604
0.8118 Intermediate Similarity NPC302041
0.8118 Intermediate Similarity NPC65897
0.8118 Intermediate Similarity NPC472499
0.8111 Intermediate Similarity NPC476948
0.8111 Intermediate Similarity NPC470620
0.8105 Intermediate Similarity NPC210337
0.8105 Intermediate Similarity NPC476893
0.8095 Intermediate Similarity NPC202642
0.8095 Intermediate Similarity NPC129165
0.8095 Intermediate Similarity NPC113733
0.8095 Intermediate Similarity NPC470749
0.8095 Intermediate Similarity NPC46160
0.8095 Intermediate Similarity NPC134330
0.8095 Intermediate Similarity NPC73875
0.809 Intermediate Similarity NPC470360
0.8081 Intermediate Similarity NPC220217
0.8081 Intermediate Similarity NPC119855
0.8072 Intermediate Similarity NPC469533

  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 NPC471952 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
0.8353 Intermediate Similarity NPD7525 Registered
0.8313 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.8193 Intermediate Similarity NPD6942 Approved
0.8193 Intermediate Similarity NPD7339 Approved
0.8111 Intermediate Similarity NPD4751 Clinical (unspecified phase)
0.7938 Intermediate Similarity NPD7640 Approved
0.7938 Intermediate Similarity NPD7639 Approved
0.7835 Intermediate Similarity NPD7638 Approved
0.7778 Intermediate Similarity NPD7338 Clinical (unspecified phase)
0.7667 Intermediate Similarity NPD6695 Phase 3
0.7647 Intermediate Similarity NPD4785 Approved
0.7647 Intermediate Similarity NPD4784 Approved
0.7647 Intermediate Similarity NPD6926 Approved
0.7647 Intermediate Similarity NPD6924 Approved
0.7619 Intermediate Similarity NPD4243 Approved
0.7614 Intermediate Similarity NPD7645 Phase 2
0.7614 Intermediate Similarity NPD6929 Approved
0.7582 Intermediate Similarity NPD4786 Approved
0.7553 Intermediate Similarity NPD6051 Approved
0.7528 Intermediate Similarity NPD6930 Phase 2
0.7528 Intermediate Similarity NPD6931 Approved
0.7528 Intermediate Similarity NPD4748 Discontinued
0.75 Intermediate Similarity NPD4202 Approved
0.7471 Intermediate Similarity NPD6933 Approved
0.7412 Intermediate Similarity NPD7150 Approved
0.7412 Intermediate Similarity NPD7152 Approved
0.7412 Intermediate Similarity NPD7151 Approved
0.7386 Intermediate Similarity NPD6925 Approved
0.7386 Intermediate Similarity NPD5776 Phase 2
0.7381 Intermediate Similarity NPD6923 Approved
0.7381 Intermediate Similarity NPD6922 Approved
0.7368 Intermediate Similarity NPD5328 Approved
0.7363 Intermediate Similarity NPD3667 Approved
0.734 Intermediate Similarity NPD7750 Discontinued
0.734 Intermediate Similarity NPD7524 Approved
0.7333 Intermediate Similarity NPD7509 Discontinued
0.7333 Intermediate Similarity NPD7514 Phase 3
0.7327 Intermediate Similarity NPD4159 Approved
0.732 Intermediate Similarity NPD6399 Phase 3
0.7303 Intermediate Similarity NPD7322 Clinical (unspecified phase)
0.7303 Intermediate Similarity NPD7145 Approved
0.7294 Intermediate Similarity NPD7143 Approved
0.7294 Intermediate Similarity NPD7144 Approved
0.7255 Intermediate Similarity NPD7632 Discontinued
0.7255 Intermediate Similarity NPD5211 Phase 2
0.7253 Intermediate Similarity NPD6902 Approved
0.7234 Intermediate Similarity NPD3618 Phase 1
0.7216 Intermediate Similarity NPD6079 Approved
0.7212 Intermediate Similarity NPD7128 Approved
0.7212 Intermediate Similarity NPD5739 Approved
0.7212 Intermediate Similarity NPD6675 Approved
0.7212 Intermediate Similarity NPD6402 Approved
0.7204 Intermediate Similarity NPD3133 Approved
0.7204 Intermediate Similarity NPD3666 Approved
0.7204 Intermediate Similarity NPD3665 Phase 1
0.72 Intermediate Similarity NPD4755 Approved
0.7182 Intermediate Similarity NPD7115 Discovery
0.7159 Intermediate Similarity NPD8264 Approved
0.7159 Intermediate Similarity NPD5275 Approved
0.7159 Intermediate Similarity NPD4190 Phase 3
0.7143 Intermediate Similarity NPD7332 Phase 2
0.7129 Intermediate Similarity NPD4225 Approved
0.7128 Intermediate Similarity NPD6893 Approved
0.7117 Intermediate Similarity NPD7328 Approved
0.7117 Intermediate Similarity NPD7327 Approved
0.7115 Intermediate Similarity NPD5141 Approved
0.708 Intermediate Similarity NPD8033 Approved
0.7075 Intermediate Similarity NPD7320 Approved
0.7075 Intermediate Similarity NPD6881 Approved
0.7075 Intermediate Similarity NPD6899 Approved
0.7059 Intermediate Similarity NPD5286 Approved
0.7059 Intermediate Similarity NPD4700 Approved
0.7059 Intermediate Similarity NPD5285 Approved
0.7059 Intermediate Similarity NPD4696 Approved
0.7054 Intermediate Similarity NPD7516 Approved
0.7041 Intermediate Similarity NPD7087 Discontinued
0.7033 Intermediate Similarity NPD4195 Approved
0.7009 Intermediate Similarity NPD6372 Approved
0.7009 Intermediate Similarity NPD6373 Approved
0.7 Intermediate Similarity NPD6932 Approved
0.6991 Remote Similarity NPD8377 Approved
0.6991 Remote Similarity NPD8294 Approved
0.699 Remote Similarity NPD5223 Approved
0.6981 Remote Similarity NPD5697 Approved
0.6981 Remote Similarity NPD5701 Approved
0.6947 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6944 Remote Similarity NPD7290 Approved
0.6944 Remote Similarity NPD7102 Approved
0.6944 Remote Similarity NPD6883 Approved
0.693 Remote Similarity NPD8380 Approved
0.693 Remote Similarity NPD8335 Approved
0.693 Remote Similarity NPD8379 Approved
0.693 Remote Similarity NPD8296 Approved
0.693 Remote Similarity NPD8378 Approved
0.693 Remote Similarity NPD7503 Approved
0.6923 Remote Similarity NPD5224 Approved
0.6923 Remote Similarity NPD5226 Approved
0.6923 Remote Similarity NPD5225 Approved
0.6923 Remote Similarity NPD4633 Approved
0.6916 Remote Similarity NPD6011 Approved
0.6882 Remote Similarity NPD6898 Phase 1
0.6881 Remote Similarity NPD6869 Approved
0.6881 Remote Similarity NPD8130 Phase 1
0.6881 Remote Similarity NPD6649 Approved
0.6881 Remote Similarity NPD6650 Approved
0.6881 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6881 Remote Similarity NPD6617 Approved
0.6881 Remote Similarity NPD6847 Approved
0.6875 Remote Similarity NPD6409 Approved
0.6875 Remote Similarity NPD7334 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
0.6869 Remote Similarity NPD8034 Phase 2
0.6869 Remote Similarity NPD7637 Suspended
0.6869 Remote Similarity NPD8035 Phase 2
0.6863 Remote Similarity NPD6083 Phase 2
0.6863 Remote Similarity NPD6084 Phase 2
0.6857 Remote Similarity NPD5175 Approved
0.6857 Remote Similarity NPD5174 Approved
0.6857 Remote Similarity NPD4754 Approved
0.6852 Remote Similarity NPD6013 Approved
0.6852 Remote Similarity NPD6014 Approved
0.6852 Remote Similarity NPD6012 Approved
0.6848 Remote Similarity NPD6683 Phase 2
0.6837 Remote Similarity NPD4753 Phase 2
0.6818 Remote Similarity NPD8297 Approved
0.6818 Remote Similarity NPD6882 Approved
0.6809 Remote Similarity NPD4223 Phase 3
0.6809 Remote Similarity NPD4221 Approved
0.6771 Remote Similarity NPD5329 Approved
0.6771 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6765 Remote Similarity NPD4697 Phase 3
0.6765 Remote Similarity NPD5221 Approved
0.6765 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6765 Remote Similarity NPD5222 Approved
0.6737 Remote Similarity NPD4788 Approved
0.6735 Remote Similarity NPD6903 Approved
0.6735 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6729 Remote Similarity NPD4767 Approved
0.6729 Remote Similarity NPD4768 Approved
0.6705 Remote Similarity NPD4787 Phase 1
0.6699 Remote Similarity NPD5173 Approved
0.6695 Remote Similarity NPD7507 Approved
0.6667 Remote Similarity NPD6053 Discontinued
0.6667 Remote Similarity NPD4197 Approved
0.6667 Remote Similarity NPD3668 Phase 3
0.6606 Remote Similarity NPD4730 Approved
0.6606 Remote Similarity NPD4729 Approved
0.6606 Remote Similarity NPD5128 Approved
0.6596 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6596 Remote Similarity NPD6928 Phase 2
0.6591 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6574 Remote Similarity NPD6008 Approved
0.6569 Remote Similarity NPD7748 Approved
0.6562 Remote Similarity NPD5362 Discontinued
0.6548 Remote Similarity NPD368 Approved
0.6538 Remote Similarity NPD7902 Approved
0.6535 Remote Similarity NPD7515 Phase 2
0.6535 Remote Similarity NPD5693 Phase 1
0.6531 Remote Similarity NPD5205 Approved
0.6531 Remote Similarity NPD6098 Approved
0.6531 Remote Similarity NPD4690 Approved
0.6531 Remote Similarity NPD4138 Approved
0.6531 Remote Similarity NPD5279 Phase 3
0.6531 Remote Similarity NPD4689 Approved
0.6531 Remote Similarity NPD4693 Phase 3
0.6531 Remote Similarity NPD4688 Approved
0.6529 Remote Similarity NPD7319 Approved
0.6522 Remote Similarity NPD6335 Approved
0.6514 Remote Similarity NPD6412 Phase 2
0.6505 Remote Similarity NPD4629 Approved
0.6505 Remote Similarity NPD5210 Approved
0.6505 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6505 Remote Similarity NPD5695 Phase 3
0.6495 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6491 Remote Similarity NPD6274 Approved
0.6486 Remote Similarity NPD5169 Approved
0.6486 Remote Similarity NPD5250 Approved
0.6486 Remote Similarity NPD5248 Approved
0.6486 Remote Similarity NPD5251 Approved
0.6486 Remote Similarity NPD5135 Approved
0.6486 Remote Similarity NPD5249 Phase 3
0.6486 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6486 Remote Similarity NPD4634 Approved
0.6486 Remote Similarity NPD5247 Approved
0.6476 Remote Similarity NPD5696 Approved
0.6476 Remote Similarity NPD5290 Discontinued
0.6466 Remote Similarity NPD7100 Approved
0.6466 Remote Similarity NPD7101 Approved
0.646 Remote Similarity NPD4632 Approved
0.6436 Remote Similarity NPD5785 Approved
0.6435 Remote Similarity NPD6317 Approved
0.6429 Remote Similarity NPD5215 Approved
0.6429 Remote Similarity NPD5127 Approved
0.6429 Remote Similarity NPD5216 Approved
0.6429 Remote Similarity NPD5217 Approved
0.6422 Remote Similarity NPD6640 Phase 3
0.6421 Remote Similarity NPD4819 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