Structure

Physi-Chem Properties

Molecular Weight:  321.21
Volume:  358.811
LogP:  4.571
LogD:  3.948
LogS:  -4.598
# Rotatable Bonds:  3
TPSA:  23.47
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.917
Synthetic Accessibility Score:  3.909
Fsp3:  0.455
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:  -4.819
MDCK Permeability:  1.3221178960520774e-05
Pgp-inhibitor:  0.981
Pgp-substrate:  0.929
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.973
30% Bioavailability (F30%):  0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.994
Plasma Protein Binding (PPB):  91.87355041503906%
Volume Distribution (VD):  2.542
Pgp-substrate:  6.119507312774658%

ADMET: Metabolism

CYP1A2-inhibitor:  0.199
CYP1A2-substrate:  0.801
CYP2C19-inhibitor:  0.179
CYP2C19-substrate:  0.937
CYP2C9-inhibitor:  0.036
CYP2C9-substrate:  0.104
CYP2D6-inhibitor:  0.992
CYP2D6-substrate:  0.919
CYP3A4-inhibitor:  0.138
CYP3A4-substrate:  0.755

ADMET: Excretion

Clearance (CL):  9.053
Half-life (T1/2):  0.476

ADMET: Toxicity

hERG Blockers:  0.899
Human Hepatotoxicity (H-HT):  0.356
Drug-inuced Liver Injury (DILI):  0.021
AMES Toxicity:  0.027
Rat Oral Acute Toxicity:  0.264
Maximum Recommended Daily Dose:  0.903
Skin Sensitization:  0.804
Carcinogencity:  0.077
Eye Corrosion:  0.008
Eye Irritation:  0.121
Respiratory Toxicity:  0.91

Download Data

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

  Natural Product: NPC126859

Natural Product ID:  NPC126859
Common Name*:   ZQHYKVKNPWDQSL-KNXBSLHKSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  ZQHYKVKNPWDQSL-KNXBSLHKSA-N
Standard InCHI:  InChI=1S/C22H27NO/c1-16-21-14-18-8-9-19(24)15-20(18)22(16,2)11-13-23(21)12-10-17-6-4-3-5-7-17/h3-9,15-16,21,24H,10-14H2,1-2H3/t16-,21+,22+/m0/s1
SMILES:  C[C@H]1[C@H]2Cc3ccc(cc3[C@]1(C)CCN2CCc1ccccc1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL316632
PubChem CID:   443405
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0004131] 6,7-benzomorphans
        • [CHEMONTID:0004823] 2,6-dimethyl-3-benzazocines

*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
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[15019787]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[22029392]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[23517479]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota Latex Exudate n.a. n.a. Database[FooDB]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. Database[FooDB]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. Database[FooDB]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9498 Papaver somniferum Species Papaveraceae 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
NPT1069 Individual Protein Mu opioid receptor Rattus norvegicus Ki = 0.2 nM PMID[550140]
NPT2 Others Unspecified Ki = 61.7 nM PMID[550140]
NPT2 Others Unspecified Ki = 1880.0 nM PMID[550140]
NPT2 Others Unspecified Ratio = 30.5 n.a. PMID[550140]

☑ 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 NPC126859 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 NPC89769
1.0 High Similarity NPC259665
0.9756 High Similarity NPC124802
0.9675 High Similarity NPC8305
0.9675 High Similarity NPC66177
0.9675 High Similarity NPC268763
0.937 High Similarity NPC149379
0.8855 High Similarity NPC325568
0.8168 Intermediate Similarity NPC307020
0.8143 Intermediate Similarity NPC470925
0.8049 Intermediate Similarity NPC11554
0.8 Intermediate Similarity NPC322753
0.7953 Intermediate Similarity NPC195922
0.792 Intermediate Similarity NPC141782
0.7857 Intermediate Similarity NPC260323
0.7857 Intermediate Similarity NPC176279
0.7829 Intermediate Similarity NPC166014
0.7829 Intermediate Similarity NPC27410
0.7795 Intermediate Similarity NPC250323
0.7785 Intermediate Similarity NPC26601
0.7778 Intermediate Similarity NPC13482
0.7746 Intermediate Similarity NPC211468
0.7746 Intermediate Similarity NPC219233
0.7746 Intermediate Similarity NPC170170
0.7734 Intermediate Similarity NPC715
0.7727 Intermediate Similarity NPC1229
0.7717 Intermediate Similarity NPC95716
0.7692 Intermediate Similarity NPC323123
0.7692 Intermediate Similarity NPC471668
0.7674 Intermediate Similarity NPC268160
0.7671 Intermediate Similarity NPC185838
0.7656 Intermediate Similarity NPC46940
0.7623 Intermediate Similarity NPC155847
0.7623 Intermediate Similarity NPC289381
0.7615 Intermediate Similarity NPC35797
0.7615 Intermediate Similarity NPC147179
0.7615 Intermediate Similarity NPC192948
0.7613 Intermediate Similarity NPC324144
0.76 Intermediate Similarity NPC81733
0.76 Intermediate Similarity NPC326316
0.758 Intermediate Similarity NPC81218
0.758 Intermediate Similarity NPC306555
0.758 Intermediate Similarity NPC12053
0.758 Intermediate Similarity NPC145832
0.758 Intermediate Similarity NPC158376
0.758 Intermediate Similarity NPC205421
0.758 Intermediate Similarity NPC117188
0.758 Intermediate Similarity NPC298979
0.758 Intermediate Similarity NPC474931
0.7578 Intermediate Similarity NPC77772
0.7576 Intermediate Similarity NPC164649
0.7576 Intermediate Similarity NPC48342
0.7568 Intermediate Similarity NPC476151
0.7568 Intermediate Similarity NPC321505
0.7568 Intermediate Similarity NPC179825
0.7568 Intermediate Similarity NPC191376
0.7564 Intermediate Similarity NPC78222
0.7564 Intermediate Similarity NPC13504
0.7564 Intermediate Similarity NPC96603
0.7564 Intermediate Similarity NPC136508
0.7564 Intermediate Similarity NPC253043
0.7564 Intermediate Similarity NPC477563
0.7564 Intermediate Similarity NPC306843
0.7564 Intermediate Similarity NPC212794
0.7564 Intermediate Similarity NPC196447
0.7559 Intermediate Similarity NPC58865
0.7557 Intermediate Similarity NPC219112
0.7557 Intermediate Similarity NPC308311
0.7557 Intermediate Similarity NPC308828
0.7557 Intermediate Similarity NPC477137
0.7557 Intermediate Similarity NPC38893
0.754 Intermediate Similarity NPC151477
0.7532 Intermediate Similarity NPC221864
0.7519 Intermediate Similarity NPC126002
0.7519 Intermediate Similarity NPC42657
0.7519 Intermediate Similarity NPC93071
0.7517 Intermediate Similarity NPC246587
0.7517 Intermediate Similarity NPC24233
0.7517 Intermediate Similarity NPC135538
0.7517 Intermediate Similarity NPC476571
0.7517 Intermediate Similarity NPC428
0.7517 Intermediate Similarity NPC147390
0.7516 Intermediate Similarity NPC81247
0.7516 Intermediate Similarity NPC35627
0.7516 Intermediate Similarity NPC476573
0.75 Intermediate Similarity NPC477136
0.75 Intermediate Similarity NPC257390
0.75 Intermediate Similarity NPC150712
0.75 Intermediate Similarity NPC16030
0.75 Intermediate Similarity NPC304510
0.75 Intermediate Similarity NPC172219
0.7484 Intermediate Similarity NPC235143
0.7484 Intermediate Similarity NPC226428
0.7484 Intermediate Similarity NPC271388
0.7484 Intermediate Similarity NPC119649
0.7484 Intermediate Similarity NPC205255
0.7484 Intermediate Similarity NPC230956
0.7481 Intermediate Similarity NPC109151
0.748 Intermediate Similarity NPC211885
0.7468 Intermediate Similarity NPC79328
0.7467 Intermediate Similarity NPC477565
0.7467 Intermediate Similarity NPC103379
0.7463 Intermediate Similarity NPC321133
0.7463 Intermediate Similarity NPC318552
0.7463 Intermediate Similarity NPC99734
0.7463 Intermediate Similarity NPC190501
0.7462 Intermediate Similarity NPC321589
0.7462 Intermediate Similarity NPC322239
0.746 Intermediate Similarity NPC271274
0.7459 Intermediate Similarity NPC225464
0.7453 Intermediate Similarity NPC329969
0.7452 Intermediate Similarity NPC3375
0.7452 Intermediate Similarity NPC255607
0.745 Intermediate Similarity NPC90844
0.745 Intermediate Similarity NPC253883
0.745 Intermediate Similarity NPC144863
0.745 Intermediate Similarity NPC95075
0.7444 Intermediate Similarity NPC471671
0.7444 Intermediate Similarity NPC469609
0.7442 Intermediate Similarity NPC470770
0.7442 Intermediate Similarity NPC266937
0.7436 Intermediate Similarity NPC80759
0.7436 Intermediate Similarity NPC79402
0.7431 Intermediate Similarity NPC193528
0.7424 Intermediate Similarity NPC469663
0.7424 Intermediate Similarity NPC82963
0.7424 Intermediate Similarity NPC92
0.7424 Intermediate Similarity NPC141001
0.7422 Intermediate Similarity NPC65855
0.7422 Intermediate Similarity NPC314187
0.7422 Intermediate Similarity NPC292758
0.7417 Intermediate Similarity NPC192768
0.7417 Intermediate Similarity NPC88249
0.7417 Intermediate Similarity NPC151895
0.7417 Intermediate Similarity NPC97221
0.7417 Intermediate Similarity NPC220858
0.7407 Intermediate Similarity NPC328504
0.7405 Intermediate Similarity NPC124657
0.7405 Intermediate Similarity NPC471534
0.7403 Intermediate Similarity NPC186063
0.7398 Intermediate Similarity NPC92730
0.7394 Intermediate Similarity NPC132847
0.7388 Intermediate Similarity NPC469644
0.7385 Intermediate Similarity NPC177962
0.7385 Intermediate Similarity NPC62867
0.7381 Intermediate Similarity NPC117115
0.7375 Intermediate Similarity NPC168753
0.7375 Intermediate Similarity NPC118274
0.7372 Intermediate Similarity NPC475780
0.7368 Intermediate Similarity NPC299180
0.7368 Intermediate Similarity NPC311737
0.7368 Intermediate Similarity NPC38458
0.7364 Intermediate Similarity NPC474149
0.7355 Intermediate Similarity NPC476572
0.7353 Intermediate Similarity NPC77569
0.7353 Intermediate Similarity NPC142198
0.7351 Intermediate Similarity NPC207824
0.7351 Intermediate Similarity NPC219162
0.7351 Intermediate Similarity NPC92541
0.7351 Intermediate Similarity NPC60538
0.7348 Intermediate Similarity NPC469719
0.7344 Intermediate Similarity NPC96224
0.7344 Intermediate Similarity NPC24101
0.7342 Intermediate Similarity NPC134858
0.7338 Intermediate Similarity NPC204828
0.7338 Intermediate Similarity NPC39701
0.7338 Intermediate Similarity NPC193949
0.7338 Intermediate Similarity NPC110416
0.7338 Intermediate Similarity NPC54379
0.7338 Intermediate Similarity NPC295691
0.7338 Intermediate Similarity NPC127674
0.7338 Intermediate Similarity NPC99659
0.7338 Intermediate Similarity NPC2413
0.7338 Intermediate Similarity NPC469817
0.7338 Intermediate Similarity NPC189266
0.7338 Intermediate Similarity NPC278799
0.7338 Intermediate Similarity NPC325871
0.7338 Intermediate Similarity NPC249797
0.7338 Intermediate Similarity NPC184026
0.7338 Intermediate Similarity NPC172765
0.7338 Intermediate Similarity NPC5238
0.7338 Intermediate Similarity NPC207757
0.7338 Intermediate Similarity NPC276588
0.7333 Intermediate Similarity NPC260832
0.7333 Intermediate Similarity NPC135467
0.7329 Intermediate Similarity NPC314682
0.7329 Intermediate Similarity NPC239775
0.7324 Intermediate Similarity NPC302171
0.7324 Intermediate Similarity NPC33338
0.7324 Intermediate Similarity NPC300020
0.7323 Intermediate Similarity NPC21594
0.7317 Intermediate Similarity NPC32674
0.7308 Intermediate Similarity NPC151537
0.7299 Intermediate Similarity NPC176208
0.7293 Intermediate Similarity NPC247858
0.7293 Intermediate Similarity NPC474358
0.7293 Intermediate Similarity NPC154511
0.7293 Intermediate Similarity NPC137496
0.7293 Intermediate Similarity NPC257540
0.7293 Intermediate Similarity NPC474387

  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 NPC126859 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
1.0 High Similarity NPD5156 Approved
1.0 High Similarity NPD5155 Approved
0.9918 High Similarity NPD2606 Approved
0.9918 High Similarity NPD2605 Approved
0.9756 High Similarity NPD3595 Approved
0.9756 High Similarity NPD3594 Approved
0.9675 High Similarity NPD3636 Approved
0.9675 High Similarity NPD3637 Approved
0.9675 High Similarity NPD3635 Approved
0.9098 High Similarity NPD4093 Discontinued
0.9023 High Similarity NPD4725 Approved
0.9023 High Similarity NPD4726 Approved
0.9023 High Similarity NPD4721 Approved
0.8855 High Similarity NPD3109 Approved
0.8855 High Similarity NPD3110 Approved
0.872 High Similarity NPD1751 Approved
0.856 High Similarity NPD2226 Clinical (unspecified phase)
0.8538 High Similarity NPD2195 Approved
0.8538 High Similarity NPD2194 Approved
0.85 High Similarity NPD2420 Approved
0.85 High Similarity NPD2421 Approved
0.8298 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.8295 Intermediate Similarity NPD5350 Clinical (unspecified phase)
0.8295 Intermediate Similarity NPD5351 Clinical (unspecified phase)
0.8279 Intermediate Similarity NPD1792 Phase 2
0.8273 Intermediate Similarity NPD4257 Approved
0.8273 Intermediate Similarity NPD4256 Phase 2
0.8268 Intermediate Similarity NPD5303 Approved
0.8268 Intermediate Similarity NPD5304 Approved
0.8168 Intermediate Similarity NPD4659 Approved
0.816 Intermediate Similarity NPD2229 Approved
0.816 Intermediate Similarity NPD2228 Approved
0.816 Intermediate Similarity NPD2234 Approved
0.8099 Intermediate Similarity NPD8131 Suspended
0.8045 Intermediate Similarity NPD4103 Phase 2
0.8045 Intermediate Similarity NPD4104 Clinical (unspecified phase)
0.8033 Intermediate Similarity NPD1445 Approved
0.8033 Intermediate Similarity NPD1444 Approved
0.8 Intermediate Similarity NPD3364 Phase 3
0.8 Intermediate Similarity NPD5238 Clinical (unspecified phase)
0.7986 Intermediate Similarity NPD7718 Clinical (unspecified phase)
0.7953 Intermediate Similarity NPD1791 Approved
0.7953 Intermediate Similarity NPD1793 Approved
0.7929 Intermediate Similarity NPD1753 Discontinued
0.7895 Intermediate Similarity NPD6025 Phase 1
0.7832 Intermediate Similarity NPD3638 Discontinued
0.7823 Intermediate Similarity NPD4727 Phase 1
0.7793 Intermediate Similarity NPD3845 Phase 1
0.777 Intermediate Similarity NPD6346 Approved
0.7724 Intermediate Similarity NPD7910 Clinical (unspecified phase)
0.766 Intermediate Similarity NPD4579 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD3053 Approved
0.7647 Intermediate Similarity NPD3055 Approved
0.7643 Intermediate Similarity NPD27 Approved
0.7643 Intermediate Similarity NPD2489 Approved
0.7639 Intermediate Similarity NPD7037 Approved
0.763 Intermediate Similarity NPD1755 Approved
0.7628 Intermediate Similarity NPD3051 Approved
0.7626 Intermediate Similarity NPD2028 Clinical (unspecified phase)
0.7626 Intermediate Similarity NPD6812 Clinical (unspecified phase)
0.7603 Intermediate Similarity NPD5241 Discontinued
0.7594 Intermediate Similarity NPD7725 Approved
0.758 Intermediate Similarity NPD2969 Approved
0.758 Intermediate Similarity NPD2970 Approved
0.7576 Intermediate Similarity NPD3091 Approved
0.75 Intermediate Similarity NPD4658 Approved
0.75 Intermediate Similarity NPD4656 Approved
0.75 Intermediate Similarity NPD4231 Approved
0.75 Intermediate Similarity NPD4229 Approved
0.7463 Intermediate Similarity NPD4059 Approved
0.7463 Intermediate Similarity NPD2668 Approved
0.7463 Intermediate Similarity NPD3019 Approved
0.7463 Intermediate Similarity NPD2667 Approved
0.745 Intermediate Similarity NPD3645 Discontinued
0.7426 Intermediate Similarity NPD2233 Approved
0.7426 Intermediate Similarity NPD2232 Approved
0.7426 Intermediate Similarity NPD2562 Approved
0.7426 Intermediate Similarity NPD2230 Approved
0.7426 Intermediate Similarity NPD2561 Approved
0.7424 Intermediate Similarity NPD6775 Clinical (unspecified phase)
0.7402 Intermediate Similarity NPD4095 Clinical (unspecified phase)
0.7398 Intermediate Similarity NPD3020 Approved
0.7379 Intermediate Similarity NPD1632 Clinical (unspecified phase)
0.7372 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7372 Intermediate Similarity NPD7831 Phase 2
0.7372 Intermediate Similarity NPD7833 Phase 2
0.7364 Intermediate Similarity NPD4253 Approved
0.7364 Intermediate Similarity NPD4254 Approved
0.7353 Intermediate Similarity NPD3092 Approved
0.7347 Intermediate Similarity NPD3599 Approved
0.7346 Intermediate Similarity NPD5190 Phase 2
0.7333 Intermediate Similarity NPD2932 Approved
0.7333 Intermediate Similarity NPD2286 Discontinued
0.7319 Intermediate Similarity NPD7258 Clinical (unspecified phase)
0.7319 Intermediate Similarity NPD5310 Approved
0.7319 Intermediate Similarity NPD5311 Approved
0.7302 Intermediate Similarity NPD9610 Approved
0.7302 Intermediate Similarity NPD9608 Approved
0.7297 Intermediate Similarity NPD5754 Discontinued
0.7284 Intermediate Similarity NPD4603 Phase 2
0.728 Intermediate Similarity NPD4818 Approved
0.728 Intermediate Similarity NPD4817 Approved
0.7279 Intermediate Similarity NPD2688 Clinical (unspecified phase)
0.7279 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD4577 Approved
0.7273 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD4578 Approved
0.7266 Intermediate Similarity NPD2342 Discontinued
0.7254 Intermediate Similarity NPD7294 Phase 1
0.7246 Intermediate Similarity NPD1669 Approved
0.7231 Intermediate Similarity NPD4025 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD2173 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD3683 Approved
0.7222 Intermediate Similarity NPD3681 Approved
0.7214 Intermediate Similarity NPD6584 Phase 3
0.7213 Intermediate Similarity NPD1432 Clinical (unspecified phase)
0.7206 Intermediate Similarity NPD3095 Discontinued
0.72 Intermediate Similarity NPD6884 Clinical (unspecified phase)
0.7185 Intermediate Similarity NPD2227 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD2568 Approved
0.7169 Intermediate Similarity NPD7313 Approved
0.7169 Intermediate Similarity NPD7311 Approved
0.7169 Intermediate Similarity NPD7310 Approved
0.7169 Intermediate Similarity NPD7312 Approved
0.7154 Intermediate Similarity NPD2860 Approved
0.7154 Intermediate Similarity NPD2859 Approved
0.7154 Intermediate Similarity NPD3021 Approved
0.7154 Intermediate Similarity NPD3022 Approved
0.7143 Intermediate Similarity NPD3094 Phase 2
0.7143 Intermediate Similarity NPD4663 Approved
0.7132 Intermediate Similarity NPD1710 Approved
0.7126 Intermediate Similarity NPD7309 Approved
0.7121 Intermediate Similarity NPD7635 Approved
0.7118 Intermediate Similarity NPD2490 Approved
0.7118 Intermediate Similarity NPD2488 Approved
0.7108 Intermediate Similarity NPD5522 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD4584 Approved
0.7101 Intermediate Similarity NPD7906 Approved
0.7099 Intermediate Similarity NPD4481 Phase 3
0.7092 Intermediate Similarity NPD7905 Discontinued
0.7092 Intermediate Similarity NPD7451 Discontinued
0.7087 Intermediate Similarity NPD3680 Approved
0.7087 Intermediate Similarity NPD3682 Approved
0.7083 Intermediate Similarity NPD4474 Approved
0.7083 Intermediate Similarity NPD4475 Approved
0.7077 Intermediate Similarity NPD4720 Approved
0.7077 Intermediate Similarity NPD4717 Approved
0.7077 Intermediate Similarity NPD4718 Approved
0.7075 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7075 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD2933 Approved
0.7073 Intermediate Similarity NPD2934 Approved
0.7063 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD817 Approved
0.7055 Intermediate Similarity NPD823 Approved
0.7042 Intermediate Similarity NPD5736 Approved
0.7039 Intermediate Similarity NPD7598 Phase 2
0.7039 Intermediate Similarity NPD3124 Discontinued
0.7037 Intermediate Similarity NPD3975 Discontinued
0.7034 Intermediate Similarity NPD2238 Phase 2
0.7025 Intermediate Similarity NPD7737 Approved
0.7025 Intermediate Similarity NPD7738 Approved
0.7014 Intermediate Similarity NPD5718 Phase 2
0.7013 Intermediate Similarity NPD7427 Discontinued
0.7008 Intermediate Similarity NPD4719 Phase 2
0.7007 Intermediate Similarity NPD3552 Approved
0.7007 Intermediate Similarity NPD6896 Approved
0.7007 Intermediate Similarity NPD3555 Approved
0.7007 Intermediate Similarity NPD4235 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD6895 Approved
0.7007 Intermediate Similarity NPD3554 Approved
0.7007 Intermediate Similarity NPD3553 Approved
0.7 Intermediate Similarity NPD2209 Approved
0.7 Intermediate Similarity NPD5177 Phase 3
0.7 Intermediate Similarity NPD2211 Approved
0.7 Intermediate Similarity NPD6038 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6583 Phase 3
0.7 Intermediate Similarity NPD4127 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6582 Phase 2
0.6985 Remote Similarity NPD318 Approved
0.6985 Remote Similarity NPD16 Approved
0.6985 Remote Similarity NPD856 Approved
0.6985 Remote Similarity NPD317 Approved
0.698 Remote Similarity NPD2174 Clinical (unspecified phase)
0.698 Remote Similarity NPD7030 Discontinued
0.698 Remote Similarity NPD6809 Clinical (unspecified phase)
0.6966 Remote Similarity NPD7714 Approved
0.6966 Remote Similarity NPD6405 Approved
0.6966 Remote Similarity NPD7715 Approved
0.6966 Remote Similarity NPD6407 Approved
0.6962 Remote Similarity NPD6818 Clinical (unspecified phase)
0.696 Remote Similarity NPD288 Approved
0.6954 Remote Similarity NPD7066 Clinical (unspecified phase)
0.6954 Remote Similarity NPD5819 Phase 2
0.6948 Remote Similarity NPD6090 Discontinued
0.6939 Remote Similarity NPD4097 Suspended
0.6934 Remote Similarity NPD316 Approved
0.6929 Remote Similarity NPD7249 Approved
0.6929 Remote Similarity NPD7250 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