Structure

Physi-Chem Properties

Molecular Weight:  218.17
Volume:  251.764
LogP:  3.815
LogD:  3.693
LogS:  -3.667
# Rotatable Bonds:  0
TPSA:  17.07
# H-Bond Aceptor:  1
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.566
Synthetic Accessibility Score:  4.813
Fsp3:  0.667
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.554
MDCK Permeability:  2.795259206322953e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.197
30% Bioavailability (F30%):  0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.681
Plasma Protein Binding (PPB):  84.2209701538086%
Volume Distribution (VD):  0.86
Pgp-substrate:  27.010610580444336%

ADMET: Metabolism

CYP1A2-inhibitor:  0.224
CYP1A2-substrate:  0.309
CYP2C19-inhibitor:  0.132
CYP2C19-substrate:  0.782
CYP2C9-inhibitor:  0.194
CYP2C9-substrate:  0.395
CYP2D6-inhibitor:  0.014
CYP2D6-substrate:  0.555
CYP3A4-inhibitor:  0.258
CYP3A4-substrate:  0.319

ADMET: Excretion

Clearance (CL):  12.778
Half-life (T1/2):  0.39

ADMET: Toxicity

hERG Blockers:  0.004
Human Hepatotoxicity (H-HT):  0.144
Drug-inuced Liver Injury (DILI):  0.264
AMES Toxicity:  0.015
Rat Oral Acute Toxicity:  0.158
Maximum Recommended Daily Dose:  0.292
Skin Sensitization:  0.06
Carcinogencity:  0.656
Eye Corrosion:  0.274
Eye Irritation:  0.247
Respiratory Toxicity:  0.813

Download Data

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

  Natural Product: NPC285594

Natural Product ID:  NPC285594
Common Name*:   Buddledin C
IUPAC Name:   (1R,4E,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-en-3-one
Synonyms:   Buddledin C
Standard InCHIKey:  KXSUIPOSVGSLQP-PGJRDNSLSA-N
Standard InCHI:  InChI=1S/C15H22O/c1-10-6-5-7-11(2)14(16)8-13-12(10)9-15(13,3)4/h7,12-13H,1,5-6,8-9H2,2-4H3/b11-7+/t12-,13-/m1/s1
SMILES:  C=C1CC/C=C(C)/C(=O)C[C@@H]2[C@@H]1CC2(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL465682
PubChem CID:   5352042
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO27625 Buddleja globosa Species Scrophulariaceae Eukaryota Roots London n.a. PMID[10514305]
NPO27625 Buddleja globosa Species Scrophulariaceae Eukaryota n.a. n.a. n.a. PMID[11000021]
NPO11745 Subergorgia suberosa Species Subergorgiidae Eukaryota n.a. Taiwanese gorgonian coral n.a. PMID[12088433]
NPO11745 Subergorgia suberosa Species Subergorgiidae Eukaryota n.a. Taiwanese Gorgonian coral n.a. PMID[12141868]
NPO11745 Subergorgia suberosa Species Subergorgiidae Eukaryota n.a. n.a. n.a. PMID[16124781]
NPO11745 Subergorgia suberosa Species Subergorgiidae Eukaryota n.a. n.a. n.a. PMID[18290631]
NPO27625 Buddleja globosa Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27625 Buddleja globosa Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11745 Subergorgia suberosa Species Subergorgiidae 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
NPT168 Cell Line P388 Mus musculus ED50 = 4.6 ug ml-1 PMID[512024]
NPT81 Cell Line A549 Homo sapiens ED50 = 3.8 ug ml-1 PMID[512024]
NPT139 Cell Line HT-29 Homo sapiens ED50 = 3.6 ug ml-1 PMID[512024]
NPT183 Individual Protein Arachidonate 5-lipoxygenase Rattus norvegicus Inhibition = 16.4 % PMID[512025]
NPT183 Individual Protein Arachidonate 5-lipoxygenase Rattus norvegicus IC50 > 200000.0 nM PMID[512025]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 1588.55 nM PMID[512026]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 1202.26 nM PMID[512026]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 2182.73 nM PMID[512026]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 5199.96 nM PMID[512026]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 1972.42 nM PMID[512026]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 2624.22 nM PMID[512026]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 128.82 nM PMID[512026]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 3162.28 nM PMID[512026]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 2312.06 nM PMID[512026]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 2837.92 nM PMID[512026]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 2483.13 nM PMID[512026]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 1815.52 nM PMID[512026]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 8590.14 nM PMID[512026]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 6338.7 nM PMID[512026]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 184.5 nM PMID[512026]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 4528.98 nM PMID[512026]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 15346.17 nM PMID[512026]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 6792.04 nM PMID[512026]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 4698.94 nM PMID[512026]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 9462.37 nM PMID[512026]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 7533.56 nM PMID[512026]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 12589.25 nM PMID[512026]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 57.81 nM PMID[512026]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 3126.08 nM PMID[512026]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 1104.08 nM PMID[512026]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 14962.36 nM PMID[512026]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 438.53 nM PMID[512026]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 3689.78 nM PMID[512026]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 21183.61 nM PMID[512026]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 2023.02 nM PMID[512026]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 743.02 nM PMID[512026]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 1174.9 nM PMID[512026]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 2449.06 nM PMID[512026]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 17498.47 nM PMID[512026]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 13899.53 nM PMID[512026]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 3396.25 nM PMID[512026]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 10568.18 nM PMID[512026]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 688.65 nM PMID[512026]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 1166.81 nM PMID[512026]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 14092.89 nM PMID[512026]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 7447.32 nM PMID[512026]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 561.05 nM PMID[512026]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 9141.13 nM PMID[512026]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 20276.83 nM PMID[512026]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 2618.18 nM PMID[512026]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 2306.75 nM PMID[512026]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 1380.38 nM PMID[512026]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 5956.62 nM PMID[512026]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 1425.61 nM PMID[512026]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 3258.37 nM PMID[512026]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 15523.87 nM PMID[512026]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 974.99 nM PMID[512026]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 4655.86 nM PMID[512026]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 94.41 nM PMID[512026]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 2443.43 nM PMID[512026]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 14791.08 nM PMID[512026]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 2747.89 nM PMID[512026]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 1845.02 nM PMID[512026]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 1803.02 nM PMID[512026]
NPT2 Others Unspecified Inhibition = 9.5 % PMID[512025]
NPT2 Others Unspecified IC50 > 200000.0 nM PMID[512025]

☑ 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 NPC285594 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 NPC96551
0.85 High Similarity NPC25853
0.8475 Intermediate Similarity NPC266295
0.8475 Intermediate Similarity NPC94991
0.8475 Intermediate Similarity NPC30215
0.8387 Intermediate Similarity NPC6697
0.8387 Intermediate Similarity NPC475124
0.8333 Intermediate Similarity NPC259261
0.8305 Intermediate Similarity NPC115385
0.8226 Intermediate Similarity NPC165695
0.8197 Intermediate Similarity NPC127582
0.8167 Intermediate Similarity NPC308108
0.8167 Intermediate Similarity NPC170799
0.8095 Intermediate Similarity NPC212210
0.8065 Intermediate Similarity NPC475795
0.8065 Intermediate Similarity NPC213152
0.8065 Intermediate Similarity NPC97322
0.8 Intermediate Similarity NPC267626
0.8 Intermediate Similarity NPC193695
0.8 Intermediate Similarity NPC49575
0.8 Intermediate Similarity NPC55004
0.8 Intermediate Similarity NPC230823
0.7969 Intermediate Similarity NPC251118
0.7966 Intermediate Similarity NPC275472
0.7937 Intermediate Similarity NPC167256
0.7937 Intermediate Similarity NPC288253
0.7937 Intermediate Similarity NPC32285
0.7931 Intermediate Similarity NPC268564
0.7931 Intermediate Similarity NPC296311
0.7931 Intermediate Similarity NPC474141
0.7895 Intermediate Similarity NPC27438
0.7869 Intermediate Similarity NPC56905
0.7869 Intermediate Similarity NPC311852
0.7869 Intermediate Similarity NPC27610
0.7833 Intermediate Similarity NPC20603
0.7812 Intermediate Similarity NPC473902
0.7812 Intermediate Similarity NPC285371
0.7797 Intermediate Similarity NPC63396
0.7797 Intermediate Similarity NPC202850
0.7746 Intermediate Similarity NPC211279
0.7742 Intermediate Similarity NPC472304
0.7742 Intermediate Similarity NPC143834
0.7742 Intermediate Similarity NPC276764
0.7727 Intermediate Similarity NPC475523
0.7719 Intermediate Similarity NPC32351
0.7705 Intermediate Similarity NPC192427
0.7692 Intermediate Similarity NPC470329
0.7627 Intermediate Similarity NPC23117
0.7612 Intermediate Similarity NPC87141
0.7612 Intermediate Similarity NPC310992
0.7612 Intermediate Similarity NPC188292
0.7612 Intermediate Similarity NPC260474
0.7612 Intermediate Similarity NPC155198
0.7586 Intermediate Similarity NPC64866
0.7586 Intermediate Similarity NPC236623
0.7544 Intermediate Similarity NPC145311
0.75 Intermediate Similarity NPC61702
0.75 Intermediate Similarity NPC162867
0.75 Intermediate Similarity NPC60565
0.75 Intermediate Similarity NPC256846
0.7458 Intermediate Similarity NPC471751
0.7432 Intermediate Similarity NPC304795
0.7414 Intermediate Similarity NPC228776
0.7414 Intermediate Similarity NPC176819
0.7414 Intermediate Similarity NPC116906
0.7414 Intermediate Similarity NPC163984
0.7414 Intermediate Similarity NPC58970
0.7397 Intermediate Similarity NPC321180
0.7391 Intermediate Similarity NPC265782
0.7391 Intermediate Similarity NPC2634
0.7391 Intermediate Similarity NPC251929
0.7385 Intermediate Similarity NPC197238
0.7385 Intermediate Similarity NPC202118
0.7377 Intermediate Similarity NPC200258
0.7333 Intermediate Similarity NPC14002
0.7333 Intermediate Similarity NPC45283
0.7333 Intermediate Similarity NPC37644
0.7302 Intermediate Similarity NPC60772
0.7286 Intermediate Similarity NPC54123
0.7286 Intermediate Similarity NPC21944
0.7286 Intermediate Similarity NPC474562
0.7273 Intermediate Similarity NPC150162
0.7273 Intermediate Similarity NPC109813
0.7273 Intermediate Similarity NPC469662
0.7273 Intermediate Similarity NPC60556
0.7258 Intermediate Similarity NPC473733
0.7246 Intermediate Similarity NPC139397
0.7213 Intermediate Similarity NPC5626
0.7206 Intermediate Similarity NPC290350
0.7206 Intermediate Similarity NPC4370
0.7193 Intermediate Similarity NPC236355
0.7193 Intermediate Similarity NPC4079
0.7193 Intermediate Similarity NPC14917
0.7193 Intermediate Similarity NPC262558
0.7193 Intermediate Similarity NPC8610
0.7183 Intermediate Similarity NPC303613
0.7183 Intermediate Similarity NPC251705
0.7183 Intermediate Similarity NPC470044
0.7183 Intermediate Similarity NPC474228
0.7183 Intermediate Similarity NPC470045
0.7143 Intermediate Similarity NPC260040
0.7143 Intermediate Similarity NPC307176
0.7143 Intermediate Similarity NPC282593
0.7143 Intermediate Similarity NPC159577
0.7143 Intermediate Similarity NPC35734
0.7121 Intermediate Similarity NPC472306
0.7101 Intermediate Similarity NPC469688
0.7097 Intermediate Similarity NPC188789
0.7083 Intermediate Similarity NPC474796
0.7083 Intermediate Similarity NPC309852
0.7083 Intermediate Similarity NPC20025
0.7083 Intermediate Similarity NPC329866
0.7083 Intermediate Similarity NPC474797
0.7069 Intermediate Similarity NPC91962
0.7059 Intermediate Similarity NPC197089
0.7049 Intermediate Similarity NPC69898
0.7049 Intermediate Similarity NPC295777
0.7042 Intermediate Similarity NPC225467
0.7042 Intermediate Similarity NPC234707
0.7042 Intermediate Similarity NPC190035
0.7042 Intermediate Similarity NPC181204
0.7042 Intermediate Similarity NPC115023
0.7042 Intermediate Similarity NPC5701
0.7042 Intermediate Similarity NPC133253
0.7015 Intermediate Similarity NPC4638
0.7013 Intermediate Similarity NPC145963
0.6986 Remote Similarity NPC251435
0.6986 Remote Similarity NPC476346
0.6986 Remote Similarity NPC293803
0.697 Remote Similarity NPC260573
0.6964 Remote Similarity NPC216921
0.6944 Remote Similarity NPC109576
0.6944 Remote Similarity NPC56747
0.6944 Remote Similarity NPC130016
0.6944 Remote Similarity NPC470237
0.6944 Remote Similarity NPC180015
0.6935 Remote Similarity NPC250539
0.6935 Remote Similarity NPC209431
0.6935 Remote Similarity NPC100809
0.6901 Remote Similarity NPC246722
0.6901 Remote Similarity NPC151045
0.6897 Remote Similarity NPC100380
0.6892 Remote Similarity NPC469793
0.6892 Remote Similarity NPC1254
0.6892 Remote Similarity NPC469796
0.6892 Remote Similarity NPC69408
0.6892 Remote Similarity NPC470525
0.6857 Remote Similarity NPC39157
0.6857 Remote Similarity NPC476614
0.6857 Remote Similarity NPC20610
0.6857 Remote Similarity NPC82477
0.6857 Remote Similarity NPC469679
0.6857 Remote Similarity NPC142754
0.6857 Remote Similarity NPC296697
0.6849 Remote Similarity NPC167049
0.6849 Remote Similarity NPC255021
0.6849 Remote Similarity NPC469691
0.6842 Remote Similarity NPC25771
0.6833 Remote Similarity NPC118788
0.6818 Remote Similarity NPC40206
0.6818 Remote Similarity NPC270042
0.6812 Remote Similarity NPC323005
0.6806 Remote Similarity NPC304983
0.6806 Remote Similarity NPC305501
0.68 Remote Similarity NPC97377
0.6765 Remote Similarity NPC52449
0.6765 Remote Similarity NPC169275
0.6761 Remote Similarity NPC10758
0.6761 Remote Similarity NPC469677
0.6761 Remote Similarity NPC286814
0.6761 Remote Similarity NPC182815
0.6761 Remote Similarity NPC469914
0.6761 Remote Similarity NPC250928
0.6757 Remote Similarity NPC469678
0.6757 Remote Similarity NPC473171
0.6757 Remote Similarity NPC255650
0.6757 Remote Similarity NPC65650
0.6757 Remote Similarity NPC472256
0.6757 Remote Similarity NPC114236
0.6757 Remote Similarity NPC469669
0.6757 Remote Similarity NPC475771
0.6757 Remote Similarity NPC77501
0.6724 Remote Similarity NPC166788
0.6721 Remote Similarity NPC234829
0.6716 Remote Similarity NPC294304
0.6716 Remote Similarity NPC228574
0.6714 Remote Similarity NPC20181
0.6714 Remote Similarity NPC220210
0.6711 Remote Similarity NPC475994
0.6711 Remote Similarity NPC189485
0.6711 Remote Similarity NPC228911
0.6711 Remote Similarity NPC62336
0.6711 Remote Similarity NPC74410
0.6711 Remote Similarity NPC115515
0.6667 Remote Similarity NPC469646
0.6667 Remote Similarity NPC95581
0.6667 Remote Similarity NPC268039
0.6667 Remote Similarity NPC474527
0.6667 Remote Similarity NPC474304
0.6667 Remote Similarity NPC471726

  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 NPC285594 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
0.8167 Intermediate Similarity NPD287 Approved
0.7391 Intermediate Similarity NPD4691 Approved
0.7246 Intermediate Similarity NPD4137 Phase 3
0.7143 Intermediate Similarity NPD4747 Approved
0.7083 Intermediate Similarity NPD4058 Approved
0.7042 Intermediate Similarity NPD5276 Approved
0.6857 Remote Similarity NPD3621 Clinical (unspecified phase)
0.6849 Remote Similarity NPD4687 Approved
0.6849 Remote Similarity NPD5733 Approved
0.6571 Remote Similarity NPD7331 Phase 2
0.6538 Remote Similarity NPD4695 Discontinued
0.6296 Remote Similarity NPD3527 Clinical (unspecified phase)
0.625 Remote Similarity NPD8028 Phase 2
0.6197 Remote Similarity NPD7341 Phase 2
0.6173 Remote Similarity NPD4223 Phase 3
0.6173 Remote Similarity NPD4221 Approved
0.6071 Remote Similarity NPD5690 Phase 2
0.6024 Remote Similarity NPD3665 Phase 1
0.6024 Remote Similarity NPD3133 Approved
0.6024 Remote Similarity NPD3666 Approved
0.6024 Remote Similarity NPD4197 Approved
0.6 Remote Similarity NPD3573 Approved
0.5976 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5965 Remote Similarity NPD5783 Phase 3
0.5952 Remote Similarity NPD1694 Approved
0.5952 Remote Similarity NPD5329 Approved
0.5915 Remote Similarity NPD2664 Clinical (unspecified phase)
0.589 Remote Similarity NPD6108 Clinical (unspecified phase)
0.5882 Remote Similarity NPD5205 Approved
0.5882 Remote Similarity NPD5330 Approved
0.5882 Remote Similarity NPD7146 Approved
0.5882 Remote Similarity NPD3574 Clinical (unspecified phase)
0.5882 Remote Similarity NPD4138 Approved
0.5882 Remote Similarity NPD7521 Approved
0.5882 Remote Similarity NPD3618 Phase 1
0.5882 Remote Similarity NPD7334 Approved
0.5882 Remote Similarity NPD4694 Approved
0.5882 Remote Similarity NPD4623 Approved
0.5882 Remote Similarity NPD6409 Approved
0.5882 Remote Similarity NPD5280 Approved
0.5882 Remote Similarity NPD5279 Phase 3
0.5882 Remote Similarity NPD4693 Phase 3
0.5882 Remote Similarity NPD4690 Approved
0.5882 Remote Similarity NPD6684 Approved
0.5882 Remote Similarity NPD4689 Approved
0.5882 Remote Similarity NPD4688 Approved
0.5882 Remote Similarity NPD4519 Discontinued
0.5875 Remote Similarity NPD3617 Approved
0.5875 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5854 Remote Similarity NPD857 Phase 3
0.5821 Remote Similarity NPD4627 Clinical (unspecified phase)
0.5806 Remote Similarity NPD344 Approved
0.5806 Remote Similarity NPD345 Approved
0.5806 Remote Similarity NPD343 Approved
0.5783 Remote Similarity NPD3667 Approved
0.5783 Remote Similarity NPD5209 Approved
0.5775 Remote Similarity NPD4191 Approved
0.5775 Remote Similarity NPD4193 Approved
0.5775 Remote Similarity NPD4192 Approved
0.5775 Remote Similarity NPD4194 Approved
0.5747 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5747 Remote Similarity NPD6672 Approved
0.5747 Remote Similarity NPD4518 Approved
0.5747 Remote Similarity NPD6903 Approved
0.5747 Remote Similarity NPD5208 Approved
0.5747 Remote Similarity NPD5737 Approved
0.5732 Remote Similarity NPD8259 Clinical (unspecified phase)
0.573 Remote Similarity NPD6079 Approved
0.5682 Remote Similarity NPD5328 Approved
0.5682 Remote Similarity NPD6904 Approved
0.5682 Remote Similarity NPD4753 Phase 2
0.5682 Remote Similarity NPD6080 Approved
0.5682 Remote Similarity NPD6673 Approved
0.5647 Remote Similarity NPD3668 Phase 3
0.5647 Remote Similarity NPD4786 Approved
0.5618 Remote Similarity NPD5207 Approved
0.5618 Remote Similarity NPD5785 Approved
0.5618 Remote Similarity NPD4096 Approved
0.5618 Remote Similarity NPD5692 Phase 3
0.561 Remote Similarity NPD4195 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