Structure

Physi-Chem Properties

Molecular Weight:  606.39
Volume:  651.388
LogP:  6.086
LogD:  4.585
LogS:  -4.487
# Rotatable Bonds:  5
TPSA:  107.22
# H-Bond Aceptor:  6
# H-Bond Donor:  4
# Rings:  6
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.171
Synthetic Accessibility Score:  5.613
Fsp3:  0.711
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.341
MDCK Permeability:  2.757306174316909e-05
Pgp-inhibitor:  0.342
Pgp-substrate:  0.007
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.277
30% Bioavailability (F30%):  0.843

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.182
Plasma Protein Binding (PPB):  99.59297180175781%
Volume Distribution (VD):  1.102
Pgp-substrate:  2.9380314350128174%

ADMET: Metabolism

CYP1A2-inhibitor:  0.046
CYP1A2-substrate:  0.153
CYP2C19-inhibitor:  0.056
CYP2C19-substrate:  0.609
CYP2C9-inhibitor:  0.243
CYP2C9-substrate:  0.763
CYP2D6-inhibitor:  0.59
CYP2D6-substrate:  0.201
CYP3A4-inhibitor:  0.78
CYP3A4-substrate:  0.474

ADMET: Excretion

Clearance (CL):  3.26
Half-life (T1/2):  0.362

ADMET: Toxicity

hERG Blockers:  0.571
Human Hepatotoxicity (H-HT):  0.127
Drug-inuced Liver Injury (DILI):  0.036
AMES Toxicity:  0.011
Rat Oral Acute Toxicity:  0.376
Maximum Recommended Daily Dose:  0.99
Skin Sensitization:  0.906
Carcinogencity:  0.056
Eye Corrosion:  0.003
Eye Irritation:  0.04
Respiratory Toxicity:  0.959

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

  Natural Product: NPC13924

Natural Product ID:  NPC13924
Common Name*:   (2Z)-2-[(5R,6S,10R)-1,6-Dihydroxy-10-(3-Hydroxypropyl)-6-Methyl-3-[(1E,3E,5E)-2,6,10-Trimethylundeca-1,3,5,9-Tetraenyl]-2-Oxaspiro[4.5]Decan-9-Ylidene]Propanal
IUPAC Name:   (2Z)-2-[(5R,6S,10R)-1,6-dihydroxy-10-(3-hydroxypropyl)-6-methyl-3-[(1E,3E,5E)-2,6,10-trimethylundeca-1,3,5,9-tetraenyl]-2-oxaspiro[4.5]decan-9-ylidene]propanal
Synonyms:  
Standard InCHIKey:  UYSHRHKOHCLBCE-PHRMGERWSA-N
Standard InCHI:  InChI=1S/C30H46O5/c1-21(2)10-7-11-22(3)12-8-13-23(4)18-25-19-30(28(33)35-25)27(14-9-17-31)26(24(5)20-32)15-16-29(30,6)34/h8,10,12-13,18,20,25,27-28,31,33-34H,7,9,11,14-17,19H2,1-6H3/b13-8+,22-12+,23-18+,26-24-/t25?,27-,28?,29+,30+/m1/s1
SMILES:  OCCC[C@@H]1/C(=C(C=O)/C)/CC[C@]([C@]21CC(OC2O)/C=C(/C=C/C=C(/CCC=C(C)C)C)C)(C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1970520
PubChem CID:   11969877
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001552] Sesterterpenoids

*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
NPO14417 Iris tectorum Species Iridaceae Eukaryota n.a. n.a. n.a. PMID[10075762]
NPO14417 Iris tectorum Species Iridaceae Eukaryota n.a. n.a. n.a. PMID[24433009]
NPO14417 Iris tectorum Species Iridaceae Eukaryota n.a. n.a. n.a. PMID[28032759]
NPO20123 Actinidia polygama Species Actinidiaceae Eukaryota n.a. n.a. n.a. PMID[6061704]
NPO20123 Actinidia polygama Species Actinidiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14417 Iris tectorum Species Iridaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20123 Actinidia polygama Species Actinidiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14417 Iris tectorum Species Iridaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20123 Actinidia polygama Species Actinidiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14417 Iris tectorum Species Iridaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14417 Iris tectorum Species Iridaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14417 Iris tectorum Species Iridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20123 Actinidia polygama Species Actinidiaceae 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
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 15631.48 nM PMID[496854]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 10000.0 nM PMID[496854]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 11614.49 nM PMID[496854]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 10.0 nM PMID[496854]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 17258.38 nM PMID[496854]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 11142.95 nM PMID[496854]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 12189.9 nM PMID[496854]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 4591.98 nM PMID[496854]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 8892.01 nM PMID[496854]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 4954.5 nM PMID[496854]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 10000.0 nM PMID[496854]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 21978.6 nM PMID[496854]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 40831.94 nM PMID[496854]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 1389.95 nM PMID[496854]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 19098.53 nM PMID[496854]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 25527.01 nM PMID[496854]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 14588.14 nM PMID[496854]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 10447.2 nM PMID[496854]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 16180.8 nM PMID[496854]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 19453.6 nM PMID[496854]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 18323.14 nM PMID[496854]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 13520.73 nM PMID[496854]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 12531.41 nM PMID[496854]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 11748.98 nM PMID[496854]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 18620.87 nM PMID[496854]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 15310.87 nM PMID[496854]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 7798.3 nM PMID[496854]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 15031.42 nM PMID[496854]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 51880.0 nM PMID[496854]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 16255.49 nM PMID[496854]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 20230.19 nM PMID[496854]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 15205.48 nM PMID[496854]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 11857.69 nM PMID[496854]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 10000.0 nM PMID[496854]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 13273.94 nM PMID[496854]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 6637.43 nM PMID[496854]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 11614.49 nM PMID[496854]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 22284.35 nM PMID[496854]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 11350.11 nM PMID[496854]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 20464.45 nM PMID[496854]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 25409.73 nM PMID[496854]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 16443.72 nM PMID[496854]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 16405.9 nM PMID[496854]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 22438.82 nM PMID[496854]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 15922.09 nM PMID[496854]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 18620.87 nM PMID[496854]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 1083.93 nM PMID[496854]
NPT732 Cell Line HOP-18 Homo sapiens GI50 n.a. 19054.61 nM PMID[496854]

☑ 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 NPC13924 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
0.85 High Similarity NPC218158
0.8454 Intermediate Similarity NPC474440
0.8387 Intermediate Similarity NPC257485
0.83 Intermediate Similarity NPC134270
0.8265 Intermediate Similarity NPC473154
0.8235 Intermediate Similarity NPC109376
0.8235 Intermediate Similarity NPC475074
0.8229 Intermediate Similarity NPC470255
0.8218 Intermediate Similarity NPC201880
0.8218 Intermediate Similarity NPC264867
0.8218 Intermediate Similarity NPC470321
0.8218 Intermediate Similarity NPC473207
0.8218 Intermediate Similarity NPC81567
0.82 Intermediate Similarity NPC238397
0.82 Intermediate Similarity NPC471363
0.8155 Intermediate Similarity NPC224660
0.8155 Intermediate Similarity NPC470024
0.8152 Intermediate Similarity NPC280203
0.8137 Intermediate Similarity NPC252296
0.8137 Intermediate Similarity NPC172867
0.8125 Intermediate Similarity NPC162615
0.8125 Intermediate Similarity NPC205034
0.8125 Intermediate Similarity NPC472812
0.8125 Intermediate Similarity NPC152778
0.8119 Intermediate Similarity NPC475889
0.8119 Intermediate Similarity NPC7644
0.8119 Intermediate Similarity NPC127933
0.8119 Intermediate Similarity NPC7613
0.8085 Intermediate Similarity NPC472809
0.8085 Intermediate Similarity NPC472810
0.8061 Intermediate Similarity NPC16967
0.8058 Intermediate Similarity NPC184512
0.8043 Intermediate Similarity NPC471302
0.8021 Intermediate Similarity NPC472811
0.8 Intermediate Similarity NPC324841
0.8 Intermediate Similarity NPC470734
0.8 Intermediate Similarity NPC316708
0.7981 Intermediate Similarity NPC311223
0.798 Intermediate Similarity NPC98112
0.7961 Intermediate Similarity NPC239961
0.7959 Intermediate Similarity NPC472441
0.7941 Intermediate Similarity NPC120009
0.7925 Intermediate Similarity NPC470026
0.7925 Intermediate Similarity NPC17791
0.7917 Intermediate Similarity NPC253186
0.7917 Intermediate Similarity NPC310479
0.7917 Intermediate Similarity NPC469403
0.7905 Intermediate Similarity NPC316974
0.79 Intermediate Similarity NPC278673
0.7885 Intermediate Similarity NPC125423
0.7885 Intermediate Similarity NPC88013
0.7872 Intermediate Similarity NPC131813
0.7857 Intermediate Similarity NPC104925
0.7857 Intermediate Similarity NPC298973
0.7857 Intermediate Similarity NPC469697
0.7857 Intermediate Similarity NPC191521
0.785 Intermediate Similarity NPC328074
0.785 Intermediate Similarity NPC317460
0.785 Intermediate Similarity NPC321272
0.785 Intermediate Similarity NPC470025
0.7849 Intermediate Similarity NPC471301
0.7843 Intermediate Similarity NPC472815
0.7843 Intermediate Similarity NPC471889
0.7835 Intermediate Similarity NPC72845
0.783 Intermediate Similarity NPC119550
0.7826 Intermediate Similarity NPC109938
0.7826 Intermediate Similarity NPC122945
0.7822 Intermediate Similarity NPC473204
0.7812 Intermediate Similarity NPC470819
0.781 Intermediate Similarity NPC128795
0.781 Intermediate Similarity NPC217921
0.781 Intermediate Similarity NPC38948
0.781 Intermediate Similarity NPC135015
0.781 Intermediate Similarity NPC48548
0.7802 Intermediate Similarity NPC206062
0.78 Intermediate Similarity NPC472188
0.7789 Intermediate Similarity NPC166857
0.7788 Intermediate Similarity NPC82251
0.7778 Intermediate Similarity NPC471362
0.7778 Intermediate Similarity NPC276110
0.7778 Intermediate Similarity NPC471372
0.7778 Intermediate Similarity NPC472189
0.7778 Intermediate Similarity NPC470027
0.7767 Intermediate Similarity NPC132395
0.7767 Intermediate Similarity NPC471365
0.7767 Intermediate Similarity NPC471364
0.7767 Intermediate Similarity NPC471450
0.7767 Intermediate Similarity NPC45897
0.7745 Intermediate Similarity NPC198992
0.7742 Intermediate Similarity NPC471297
0.7736 Intermediate Similarity NPC40728
0.7736 Intermediate Similarity NPC206618
0.7732 Intermediate Similarity NPC221111
0.7732 Intermediate Similarity NPC470817
0.7732 Intermediate Similarity NPC280149
0.7732 Intermediate Similarity NPC78973
0.7732 Intermediate Similarity NPC182136
0.7727 Intermediate Similarity NPC78527
0.7723 Intermediate Similarity NPC472186
0.7723 Intermediate Similarity NPC318917
0.7723 Intermediate Similarity NPC476800
0.7723 Intermediate Similarity NPC471366
0.7714 Intermediate Similarity NPC179380
0.7708 Intermediate Similarity NPC474629
0.7706 Intermediate Similarity NPC475163
0.77 Intermediate Similarity NPC165632
0.77 Intermediate Similarity NPC473153
0.77 Intermediate Similarity NPC162346
0.77 Intermediate Similarity NPC171598
0.7677 Intermediate Similarity NPC105490
0.7677 Intermediate Similarity NPC88507
0.767 Intermediate Similarity NPC32577
0.767 Intermediate Similarity NPC114540
0.767 Intermediate Similarity NPC470571
0.767 Intermediate Similarity NPC155332
0.767 Intermediate Similarity NPC150463
0.7653 Intermediate Similarity NPC329842
0.7647 Intermediate Similarity NPC228251
0.7647 Intermediate Similarity NPC477971
0.7647 Intermediate Similarity NPC219285
0.7647 Intermediate Similarity NPC477720
0.7647 Intermediate Similarity NPC477972
0.7647 Intermediate Similarity NPC20113
0.7647 Intermediate Similarity NPC473545
0.7647 Intermediate Similarity NPC161527
0.7647 Intermediate Similarity NPC477968
0.7647 Intermediate Similarity NPC472187
0.7647 Intermediate Similarity NPC16601
0.7634 Intermediate Similarity NPC471298
0.7634 Intermediate Similarity NPC155521
0.7629 Intermediate Similarity NPC309310
0.7624 Intermediate Similarity NPC477719
0.7624 Intermediate Similarity NPC477718
0.7624 Intermediate Similarity NPC475709
0.7624 Intermediate Similarity NPC73911
0.7619 Intermediate Similarity NPC34768
0.7619 Intermediate Similarity NPC477125
0.76 Intermediate Similarity NPC135224
0.76 Intermediate Similarity NPC477969
0.7596 Intermediate Similarity NPC471938
0.7596 Intermediate Similarity NPC471888
0.7596 Intermediate Similarity NPC471886
0.7596 Intermediate Similarity NPC120321
0.7596 Intermediate Similarity NPC23584
0.7596 Intermediate Similarity NPC471885
0.7596 Intermediate Similarity NPC471887
0.7579 Intermediate Similarity NPC471795
0.7579 Intermediate Similarity NPC473251
0.7579 Intermediate Similarity NPC42586
0.7579 Intermediate Similarity NPC472442
0.7576 Intermediate Similarity NPC53555
0.7576 Intermediate Similarity NPC139692
0.7576 Intermediate Similarity NPC7349
0.7576 Intermediate Similarity NPC472641
0.7576 Intermediate Similarity NPC472640
0.7553 Intermediate Similarity NPC474809
0.7553 Intermediate Similarity NPC23748
0.7553 Intermediate Similarity NPC311070
0.7551 Intermediate Similarity NPC472642
0.7551 Intermediate Similarity NPC477782
0.7549 Intermediate Similarity NPC57079
0.7549 Intermediate Similarity NPC108368
0.7549 Intermediate Similarity NPC92275
0.7549 Intermediate Similarity NPC475068
0.7526 Intermediate Similarity NPC93411
0.7526 Intermediate Similarity NPC472378
0.7525 Intermediate Similarity NPC470801
0.7525 Intermediate Similarity NPC311166
0.7525 Intermediate Similarity NPC190713
0.7524 Intermediate Similarity NPC471937
0.7524 Intermediate Similarity NPC222161
0.7522 Intermediate Similarity NPC257610
0.75 Intermediate Similarity NPC471482
0.75 Intermediate Similarity NPC11956
0.75 Intermediate Similarity NPC177047
0.75 Intermediate Similarity NPC121423
0.75 Intermediate Similarity NPC476081
0.75 Intermediate Similarity NPC189513
0.75 Intermediate Similarity NPC471914
0.75 Intermediate Similarity NPC477129
0.75 Intermediate Similarity NPC473828
0.75 Intermediate Similarity NPC473617
0.75 Intermediate Similarity NPC469491
0.75 Intermediate Similarity NPC37207
0.75 Intermediate Similarity NPC109195
0.75 Intermediate Similarity NPC57117
0.75 Intermediate Similarity NPC17550
0.75 Intermediate Similarity NPC477130
0.75 Intermediate Similarity NPC474554
0.75 Intermediate Similarity NPC475038
0.75 Intermediate Similarity NPC300399
0.7476 Intermediate Similarity NPC38855
0.7476 Intermediate Similarity NPC477716
0.7476 Intermediate Similarity NPC227865
0.7476 Intermediate Similarity NPC477721
0.7475 Intermediate Similarity NPC473675
0.7475 Intermediate Similarity NPC477122
0.7475 Intermediate Similarity NPC477783
0.7475 Intermediate Similarity NPC78594
0.7455 Intermediate Similarity NPC264153

  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 NPC13924 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
0.7379 Intermediate Similarity NPD4225 Approved
0.7315 Intermediate Similarity NPD6686 Approved
0.7304 Intermediate Similarity NPD7503 Approved
0.7292 Intermediate Similarity NPD6400 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD7638 Approved
0.7143 Intermediate Similarity NPD7640 Approved
0.7143 Intermediate Similarity NPD7639 Approved
0.7059 Intermediate Similarity NPD7507 Approved
0.7043 Intermediate Similarity NPD7328 Approved
0.7043 Intermediate Similarity NPD7327 Approved
0.6983 Remote Similarity NPD7516 Approved
0.6981 Remote Similarity NPD6648 Approved
0.6939 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6923 Remote Similarity NPD8294 Approved
0.6923 Remote Similarity NPD8377 Approved
0.6916 Remote Similarity NPD5344 Discontinued
0.6885 Remote Similarity NPD7319 Approved
0.6864 Remote Similarity NPD8380 Approved
0.6864 Remote Similarity NPD8378 Approved
0.6864 Remote Similarity NPD8033 Approved
0.6864 Remote Similarity NPD8379 Approved
0.6864 Remote Similarity NPD8335 Approved
0.6864 Remote Similarity NPD8296 Approved
0.6863 Remote Similarity NPD7838 Discovery
0.6837 Remote Similarity NPD6695 Phase 3
0.6796 Remote Similarity NPD7637 Suspended
0.6757 Remote Similarity NPD6412 Phase 2
0.6754 Remote Similarity NPD6882 Approved
0.6735 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6729 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6701 Remote Similarity NPD7525 Registered
0.67 Remote Similarity NPD1694 Approved
0.6696 Remote Similarity NPD6899 Approved
0.6696 Remote Similarity NPD6881 Approved
0.6667 Remote Similarity NPD7128 Approved
0.6667 Remote Similarity NPD5739 Approved
0.6667 Remote Similarity NPD6675 Approved
0.6667 Remote Similarity NPD6370 Approved
0.6667 Remote Similarity NPD6402 Approved
0.6667 Remote Similarity NPD7115 Discovery
0.6635 Remote Similarity NPD6411 Approved
0.6607 Remote Similarity NPD5697 Approved
0.6604 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6596 Remote Similarity NPD6926 Approved
0.6596 Remote Similarity NPD6924 Approved
0.6579 Remote Similarity NPD6883 Approved
0.6579 Remote Similarity NPD7102 Approved
0.6579 Remote Similarity NPD7290 Approved
0.6571 Remote Similarity NPD5778 Approved
0.6571 Remote Similarity NPD5779 Approved
0.6569 Remote Similarity NPD7750 Discontinued
0.6569 Remote Similarity NPD7524 Approved
0.6549 Remote Similarity NPD7320 Approved
0.6545 Remote Similarity NPD7632 Discontinued
0.6545 Remote Similarity NPD5211 Phase 2
0.6531 Remote Similarity NPD6931 Approved
0.6531 Remote Similarity NPD7514 Phase 3
0.6531 Remote Similarity NPD6930 Phase 2
0.6531 Remote Similarity NPD7332 Phase 2
0.6531 Remote Similarity NPD7509 Discontinued
0.6526 Remote Similarity NPD8264 Approved
0.6522 Remote Similarity NPD6649 Approved
0.6522 Remote Similarity NPD6869 Approved
0.6522 Remote Similarity NPD8130 Phase 1
0.6522 Remote Similarity NPD6617 Approved
0.6522 Remote Similarity NPD6650 Approved
0.6522 Remote Similarity NPD6847 Approved
0.6514 Remote Similarity NPD5286 Approved
0.6514 Remote Similarity NPD4696 Approved
0.6514 Remote Similarity NPD5285 Approved
0.6509 Remote Similarity NPD7748 Approved
0.65 Remote Similarity NPD6054 Approved
0.6495 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6491 Remote Similarity NPD6373 Approved
0.6491 Remote Similarity NPD6372 Approved
0.6491 Remote Similarity NPD6012 Approved
0.6491 Remote Similarity NPD6013 Approved
0.6491 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6491 Remote Similarity NPD6014 Approved
0.6481 Remote Similarity NPD4755 Approved
0.6481 Remote Similarity NPD6084 Phase 2
0.6481 Remote Similarity NPD6083 Phase 2
0.6481 Remote Similarity NPD7902 Approved
0.6476 Remote Similarity NPD6079 Approved
0.6476 Remote Similarity NPD7515 Phase 2
0.6471 Remote Similarity NPD5279 Phase 3
0.6471 Remote Similarity NPD3618 Phase 1
0.6466 Remote Similarity NPD8297 Approved
0.646 Remote Similarity NPD5701 Approved
0.6458 Remote Similarity NPD6933 Approved
0.6446 Remote Similarity NPD8515 Approved
0.6446 Remote Similarity NPD8517 Approved
0.6446 Remote Similarity NPD8513 Phase 3
0.6446 Remote Similarity NPD8516 Approved
0.6442 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6442 Remote Similarity NPD6101 Approved
0.6442 Remote Similarity NPD6051 Approved
0.6442 Remote Similarity NPD5328 Approved
0.6429 Remote Similarity NPD5141 Approved
0.6429 Remote Similarity NPD6929 Approved
0.6429 Remote Similarity NPD7645 Phase 2
0.6415 Remote Similarity NPD4202 Approved
0.6404 Remote Similarity NPD6011 Approved
0.64 Remote Similarity NPD5209 Approved
0.64 Remote Similarity NPD7736 Approved
0.6396 Remote Similarity NPD5226 Approved
0.6396 Remote Similarity NPD5225 Approved
0.6396 Remote Similarity NPD4633 Approved
0.6396 Remote Similarity NPD5224 Approved
0.6392 Remote Similarity NPD6932 Approved
0.6389 Remote Similarity NPD4697 Phase 3
0.6381 Remote Similarity NPD6698 Approved
0.6381 Remote Similarity NPD46 Approved
0.6381 Remote Similarity NPD5785 Approved
0.6373 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6364 Remote Similarity NPD4821 Approved
0.6364 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6364 Remote Similarity NPD6059 Approved
0.6364 Remote Similarity NPD4822 Approved
0.6364 Remote Similarity NPD4700 Approved
0.6364 Remote Similarity NPD4820 Approved
0.6364 Remote Similarity NPD4819 Approved
0.6355 Remote Similarity NPD5282 Discontinued
0.6354 Remote Similarity NPD8039 Approved
0.6339 Remote Similarity NPD5175 Approved
0.6339 Remote Similarity NPD5174 Approved
0.6327 Remote Similarity NPD7145 Approved
0.6321 Remote Similarity NPD5281 Approved
0.6321 Remote Similarity NPD5284 Approved
0.6321 Remote Similarity NPD7087 Discontinued
0.632 Remote Similarity NPD8293 Discontinued
0.6311 Remote Similarity NPD6015 Approved
0.6311 Remote Similarity NPD6016 Approved
0.6306 Remote Similarity NPD5223 Approved
0.63 Remote Similarity NPD6902 Approved
0.6296 Remote Similarity NPD5695 Phase 3
0.6293 Remote Similarity NPD5955 Clinical (unspecified phase)
0.629 Remote Similarity NPD7492 Approved
0.6286 Remote Similarity NPD4753 Phase 2
0.6277 Remote Similarity NPD7143 Approved
0.6277 Remote Similarity NPD7144 Approved
0.6275 Remote Similarity NPD3665 Phase 1
0.6275 Remote Similarity NPD3133 Approved
0.6275 Remote Similarity NPD3666 Approved
0.6271 Remote Similarity NPD8133 Approved
0.6262 Remote Similarity NPD6399 Phase 3
0.626 Remote Similarity NPD5988 Approved
0.624 Remote Similarity NPD6616 Approved
0.6239 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6239 Remote Similarity NPD5222 Approved
0.6239 Remote Similarity NPD5221 Approved
0.6239 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6224 Remote Similarity NPD6925 Approved
0.6224 Remote Similarity NPD5776 Phase 2
0.6214 Remote Similarity NPD6893 Approved
0.6214 Remote Similarity NPD1696 Phase 3
0.6211 Remote Similarity NPD7152 Approved
0.6211 Remote Similarity NPD7150 Approved
0.6211 Remote Similarity NPD7151 Approved
0.621 Remote Similarity NPD6067 Discontinued
0.6204 Remote Similarity NPD7900 Approved
0.6204 Remote Similarity NPD7901 Clinical (unspecified phase)
0.62 Remote Similarity NPD8259 Clinical (unspecified phase)
0.619 Remote Similarity NPD7078 Approved
0.6186 Remote Similarity NPD6053 Discontinued
0.6182 Remote Similarity NPD5173 Approved
0.6176 Remote Similarity NPD7154 Phase 3
0.617 Remote Similarity NPD6922 Approved
0.617 Remote Similarity NPD6923 Approved
0.6162 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6162 Remote Similarity NPD4271 Approved
0.6162 Remote Similarity NPD4268 Approved
0.6154 Remote Similarity NPD4519 Discontinued
0.6154 Remote Similarity NPD7334 Approved
0.6154 Remote Similarity NPD6409 Approved
0.6154 Remote Similarity NPD4623 Approved
0.6154 Remote Similarity NPD5330 Approved
0.6154 Remote Similarity NPD6684 Approved
0.6154 Remote Similarity NPD6371 Approved
0.6154 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6154 Remote Similarity NPD7146 Approved
0.6154 Remote Similarity NPD7521 Approved
0.6148 Remote Similarity NPD7100 Approved
0.6148 Remote Similarity NPD7101 Approved
0.6147 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6147 Remote Similarity NPD4629 Approved
0.6147 Remote Similarity NPD5210 Approved
0.6139 Remote Similarity NPD6898 Phase 1
0.6126 Remote Similarity NPD5696 Approved
0.6121 Remote Similarity NPD4729 Approved
0.6121 Remote Similarity NPD4730 Approved
0.6117 Remote Similarity NPD4786 Approved
0.6116 Remote Similarity NPD6009 Approved
0.6102 Remote Similarity NPD8413 Clinical (unspecified phase)
0.61 Remote Similarity NPD6683 Phase 2
0.61 Remote Similarity NPD4195 Approved
0.6095 Remote Similarity NPD4250 Approved
0.6095 Remote Similarity NPD4251 Approved
0.6091 Remote Similarity NPD7839 Suspended
0.6087 Remote Similarity NPD4768 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