Structure

Physi-Chem Properties

Molecular Weight:  311.15
Volume:  318.583
LogP:  2.786
LogD:  2.036
LogS:  -3.056
# Rotatable Bonds:  2
TPSA:  30.93
# H-Bond Aceptor:  4
# H-Bond Donor:  0
# Rings:  5
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.839
Synthetic Accessibility Score:  5.126
Fsp3:  0.474
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
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:  -4.759
MDCK Permeability:  1.8554603229858913e-05
Pgp-inhibitor:  0.628
Pgp-substrate:  0.452
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.99
30% Bioavailability (F30%):  0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.997
Plasma Protein Binding (PPB):  59.14893341064453%
Volume Distribution (VD):  2.69
Pgp-substrate:  39.028568267822266%

ADMET: Metabolism

CYP1A2-inhibitor:  0.109
CYP1A2-substrate:  0.639
CYP2C19-inhibitor:  0.061
CYP2C19-substrate:  0.952
CYP2C9-inhibitor:  0.028
CYP2C9-substrate:  0.202
CYP2D6-inhibitor:  0.474
CYP2D6-substrate:  0.916
CYP3A4-inhibitor:  0.019
CYP3A4-substrate:  0.932

ADMET: Excretion

Clearance (CL):  8.871
Half-life (T1/2):  0.523

ADMET: Toxicity

hERG Blockers:  0.873
Human Hepatotoxicity (H-HT):  0.834
Drug-inuced Liver Injury (DILI):  0.155
AMES Toxicity:  0.241
Rat Oral Acute Toxicity:  0.96
Maximum Recommended Daily Dose:  0.914
Skin Sensitization:  0.605
Carcinogencity:  0.817
Eye Corrosion:  0.003
Eye Irritation:  0.011
Respiratory Toxicity:  0.965

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

  Natural Product: NPC180756

Natural Product ID:  NPC180756
Common Name*:   Thebaine
IUPAC Name:   (4R,7aR,12bS)-7,9-dimethoxy-3-methyl-2,4,7a,13-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline
Synonyms:   Thebaine
Standard InCHIKey:  FQXXSQDCDRQNQE-VMDGZTHMSA-N
Standard InCHI:  InChI=1S/C19H21NO3/c1-20-9-8-19-12-5-7-15(22-3)18(19)23-17-14(21-2)6-4-11(16(17)19)10-13(12)20/h4-7,13,18H,8-10H2,1-3H3/t13-,18+,19+/m1/s1
SMILES:  CN1CC[C@]23C4=CC=C([C@@H]3Oc3c(ccc(C[C@@H]14)c23)OC)OC
Synthetic Gene Cluster:   BGC0001799;
ChEMBL Identifier:   CHEMBL403893
PubChem CID:   5324289
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0000058] Morphinans

*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]
NPO41658 Corynebacterium glutamicum Sorn2 [n.a.] Strain Corynebacteriaceae Bacteria n.a. n.a. n.a. PMID[28938890]
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 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. 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]
NPO7312 Aplidium multiplicatum Species Polyclinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2466 Aloe microstigma Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10176 Chrozophora prostrata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
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
NPT145 Individual Protein Mu opioid receptor Homo sapiens Emax = 76.3 % PMID[496458]
NPT145 Individual Protein Mu opioid receptor Homo sapiens EC50 = 5600.0 nM PMID[496458]
NPT145 Individual Protein Mu opioid receptor Homo sapiens Ki = 7400.0 nM PMID[496458]
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 61426.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 50118.7 nM PMID[496459]
NPT2 Others Unspecified Potency n.a. 44668.4 nM PMID[496459]
NPT2 Others Unspecified Potency n.a. 68310.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 19424.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 54261.1 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 38413.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 60882 nM PubChem BioAssay data set

☑ 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 NPC180756 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 NPC323443
0.9542 High Similarity NPC124657
0.8727 High Similarity NPC115906
0.8727 High Similarity NPC305847
0.8683 High Similarity NPC214629
0.8675 High Similarity NPC302449
0.8662 High Similarity NPC476572
0.8654 High Similarity NPC325871
0.8654 High Similarity NPC99659
0.8625 High Similarity NPC225774
0.8581 High Similarity NPC326316
0.8581 High Similarity NPC81733
0.8571 High Similarity NPC219341
0.8571 High Similarity NPC24264
0.8571 High Similarity NPC476432
0.8544 High Similarity NPC148014
0.8544 High Similarity NPC78359
0.8544 High Similarity NPC129603
0.8544 High Similarity NPC65490
0.8544 High Similarity NPC40389
0.8544 High Similarity NPC315707
0.8519 High Similarity NPC247389
0.8509 High Similarity NPC16805
0.8509 High Similarity NPC167546
0.8509 High Similarity NPC302527
0.8467 Intermediate Similarity NPC314682
0.8462 Intermediate Similarity NPC8337
0.8462 Intermediate Similarity NPC85747
0.8442 Intermediate Similarity NPC476144
0.8442 Intermediate Similarity NPC106295
0.8442 Intermediate Similarity NPC210437
0.8442 Intermediate Similarity NPC51957
0.8442 Intermediate Similarity NPC16107
0.8438 Intermediate Similarity NPC160298
0.8438 Intermediate Similarity NPC306902
0.8438 Intermediate Similarity NPC266753
0.8438 Intermediate Similarity NPC232924
0.8438 Intermediate Similarity NPC477559
0.8431 Intermediate Similarity NPC130926
0.8418 Intermediate Similarity NPC244112
0.8418 Intermediate Similarity NPC78733
0.8415 Intermediate Similarity NPC75958
0.8411 Intermediate Similarity NPC213206
0.8411 Intermediate Similarity NPC474915
0.8411 Intermediate Similarity NPC188163
0.8411 Intermediate Similarity NPC328750
0.8405 Intermediate Similarity NPC210918
0.8395 Intermediate Similarity NPC247972
0.8387 Intermediate Similarity NPC7467
0.8365 Intermediate Similarity NPC147091
0.8333 Intermediate Similarity NPC126284
0.8323 Intermediate Similarity NPC18402
0.8323 Intermediate Similarity NPC249274
0.8302 Intermediate Similarity NPC216459
0.8302 Intermediate Similarity NPC138487
0.8302 Intermediate Similarity NPC41178
0.8301 Intermediate Similarity NPC136860
0.8301 Intermediate Similarity NPC476567
0.8301 Intermediate Similarity NPC128019
0.8293 Intermediate Similarity NPC306555
0.8293 Intermediate Similarity NPC145832
0.8293 Intermediate Similarity NPC117188
0.8293 Intermediate Similarity NPC205421
0.8293 Intermediate Similarity NPC12053
0.8293 Intermediate Similarity NPC81218
0.8293 Intermediate Similarity NPC474931
0.8293 Intermediate Similarity NPC158376
0.8291 Intermediate Similarity NPC470924
0.8282 Intermediate Similarity NPC96603
0.8282 Intermediate Similarity NPC136508
0.8282 Intermediate Similarity NPC78222
0.8282 Intermediate Similarity NPC212794
0.8282 Intermediate Similarity NPC180306
0.8282 Intermediate Similarity NPC477563
0.8282 Intermediate Similarity NPC3375
0.8282 Intermediate Similarity NPC306843
0.8282 Intermediate Similarity NPC13504
0.8282 Intermediate Similarity NPC196447
0.8282 Intermediate Similarity NPC253043
0.8282 Intermediate Similarity NPC255607
0.8274 Intermediate Similarity NPC294790
0.8274 Intermediate Similarity NPC118633
0.8274 Intermediate Similarity NPC148693
0.8269 Intermediate Similarity NPC475959
0.8263 Intermediate Similarity NPC329969
0.8261 Intermediate Similarity NPC118804
0.8253 Intermediate Similarity NPC149090
0.8253 Intermediate Similarity NPC19520
0.8253 Intermediate Similarity NPC65403
0.825 Intermediate Similarity NPC146288
0.825 Intermediate Similarity NPC126519
0.825 Intermediate Similarity NPC203784
0.825 Intermediate Similarity NPC170503
0.8242 Intermediate Similarity NPC290759
0.8242 Intermediate Similarity NPC158148
0.8242 Intermediate Similarity NPC266176
0.8242 Intermediate Similarity NPC82533
0.8235 Intermediate Similarity NPC248642
0.8225 Intermediate Similarity NPC99179
0.8225 Intermediate Similarity NPC220961
0.8225 Intermediate Similarity NPC267408
0.8221 Intermediate Similarity NPC324144
0.8221 Intermediate Similarity NPC293871
0.8221 Intermediate Similarity NPC218614
0.8221 Intermediate Similarity NPC124433
0.8221 Intermediate Similarity NPC1229
0.8217 Intermediate Similarity NPC219162
0.821 Intermediate Similarity NPC166014
0.821 Intermediate Similarity NPC205167
0.821 Intermediate Similarity NPC4304
0.821 Intermediate Similarity NPC27410
0.8205 Intermediate Similarity NPC476151
0.8204 Intermediate Similarity NPC2314
0.8194 Intermediate Similarity NPC185838
0.8193 Intermediate Similarity NPC6152
0.8187 Intermediate Similarity NPC156576
0.8182 Intermediate Similarity NPC284842
0.8182 Intermediate Similarity NPC66909
0.8182 Intermediate Similarity NPC298979
0.8182 Intermediate Similarity NPC474324
0.8182 Intermediate Similarity NPC150879
0.8182 Intermediate Similarity NPC57812
0.8176 Intermediate Similarity NPC148898
0.8166 Intermediate Similarity NPC114364
0.8166 Intermediate Similarity NPC320223
0.8165 Intermediate Similarity NPC274026
0.8155 Intermediate Similarity NPC128560
0.8155 Intermediate Similarity NPC229166
0.8155 Intermediate Similarity NPC199465
0.815 Intermediate Similarity NPC237579
0.8148 Intermediate Similarity NPC59028
0.8148 Intermediate Similarity NPC92191
0.8148 Intermediate Similarity NPC477080
0.8144 Intermediate Similarity NPC10908
0.8144 Intermediate Similarity NPC227060
0.8144 Intermediate Similarity NPC198498
0.8144 Intermediate Similarity NPC477640
0.8144 Intermediate Similarity NPC317439
0.8144 Intermediate Similarity NPC63646
0.8144 Intermediate Similarity NPC225597
0.8144 Intermediate Similarity NPC276890
0.8144 Intermediate Similarity NPC76682
0.8144 Intermediate Similarity NPC317145
0.8144 Intermediate Similarity NPC115284
0.8144 Intermediate Similarity NPC470739
0.8137 Intermediate Similarity NPC31311
0.8137 Intermediate Similarity NPC234392
0.8137 Intermediate Similarity NPC247639
0.8137 Intermediate Similarity NPC25084
0.8133 Intermediate Similarity NPC204908
0.8133 Intermediate Similarity NPC58766
0.8133 Intermediate Similarity NPC475686
0.8133 Intermediate Similarity NPC241055
0.8133 Intermediate Similarity NPC83198
0.8133 Intermediate Similarity NPC475845
0.8121 Intermediate Similarity NPC86144
0.8121 Intermediate Similarity NPC304659
0.8118 Intermediate Similarity NPC244554
0.811 Intermediate Similarity NPC320104
0.8107 Intermediate Similarity NPC241704
0.8107 Intermediate Similarity NPC474470
0.8101 Intermediate Similarity NPC477565
0.8101 Intermediate Similarity NPC103379
0.8098 Intermediate Similarity NPC226428
0.8098 Intermediate Similarity NPC475780
0.8098 Intermediate Similarity NPC215829
0.8098 Intermediate Similarity NPC97072
0.8095 Intermediate Similarity NPC12424
0.8095 Intermediate Similarity NPC251580
0.8095 Intermediate Similarity NPC129518
0.8095 Intermediate Similarity NPC41376
0.8089 Intermediate Similarity NPC95075
0.8089 Intermediate Similarity NPC90844
0.8089 Intermediate Similarity NPC321505
0.8089 Intermediate Similarity NPC179825
0.8089 Intermediate Similarity NPC253883
0.8089 Intermediate Similarity NPC191376
0.8084 Intermediate Similarity NPC118274
0.8084 Intermediate Similarity NPC168753
0.8084 Intermediate Similarity NPC474708
0.8084 Intermediate Similarity NPC311991
0.8084 Intermediate Similarity NPC474475
0.8081 Intermediate Similarity NPC302275
0.8079 Intermediate Similarity NPC11147
0.8075 Intermediate Similarity NPC127674
0.8075 Intermediate Similarity NPC295691
0.8075 Intermediate Similarity NPC184026
0.8075 Intermediate Similarity NPC54379
0.8075 Intermediate Similarity NPC276588
0.8075 Intermediate Similarity NPC207757
0.8075 Intermediate Similarity NPC2413
0.8075 Intermediate Similarity NPC39701
0.8075 Intermediate Similarity NPC278799
0.8075 Intermediate Similarity NPC189266
0.8075 Intermediate Similarity NPC110416
0.8075 Intermediate Similarity NPC204828
0.8075 Intermediate Similarity NPC469817
0.8075 Intermediate Similarity NPC5238
0.8075 Intermediate Similarity NPC249797
0.8075 Intermediate Similarity NPC193949

  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 NPC180756 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
0.9355 High Similarity NPD2969 Approved
0.9355 High Similarity NPD2970 Approved
0.9295 High Similarity NPD4481 Phase 3
0.929 High Similarity NPD3051 Approved
0.9172 High Similarity NPD2489 Approved
0.9172 High Similarity NPD27 Approved
0.8727 High Similarity NPD7311 Approved
0.8727 High Similarity NPD2971 Approved
0.8727 High Similarity NPD7313 Approved
0.8727 High Similarity NPD7312 Approved
0.8727 High Similarity NPD7310 Approved
0.8727 High Similarity NPD2968 Approved
0.8675 High Similarity NPD7309 Approved
0.8631 High Similarity NPD7906 Approved
0.8614 High Similarity NPD4578 Approved
0.8614 High Similarity NPD4577 Approved
0.8571 High Similarity NPD6071 Discontinued
0.8544 High Similarity NPD2563 Approved
0.8544 High Similarity NPD2560 Approved
0.8462 Intermediate Similarity NPD4663 Approved
0.8456 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.8456 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.8442 Intermediate Similarity NPD4584 Approved
0.8411 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.8314 Intermediate Similarity NPD2490 Approved
0.8314 Intermediate Similarity NPD2488 Approved
0.8204 Intermediate Similarity NPD8156 Discontinued
0.8182 Intermediate Similarity NPD2974 Approved
0.8182 Intermediate Similarity NPD2973 Approved
0.8182 Intermediate Similarity NPD2975 Approved
0.8144 Intermediate Similarity NPD8251 Approved
0.8144 Intermediate Similarity NPD8252 Approved
0.8144 Intermediate Similarity NPD8099 Discontinued
0.8129 Intermediate Similarity NPD5241 Discontinued
0.8125 Intermediate Similarity NPD4773 Phase 2
0.8125 Intermediate Similarity NPD4772 Phase 2
0.8067 Intermediate Similarity NPD3109 Approved
0.8067 Intermediate Similarity NPD3110 Approved
0.8045 Intermediate Similarity NPD4580 Approved
0.8041 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD2494 Approved
0.8 Intermediate Similarity NPD3450 Approved
0.8 Intermediate Similarity NPD2493 Approved
0.8 Intermediate Similarity NPD3452 Approved
0.7988 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7988 Intermediate Similarity NPD7833 Phase 2
0.7988 Intermediate Similarity NPD7831 Phase 2
0.7987 Intermediate Similarity NPD6030 Approved
0.7987 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7987 Intermediate Similarity NPD6031 Approved
0.7975 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7962 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7944 Intermediate Similarity NPD4107 Approved
0.7917 Intermediate Similarity NPD2898 Approved
0.7898 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7888 Intermediate Similarity NPD4017 Approved
0.7869 Intermediate Similarity NPD4583 Approved
0.7869 Intermediate Similarity NPD4582 Approved
0.7857 Intermediate Similarity NPD3057 Approved
0.7818 Intermediate Similarity NPD6788 Approved
0.7816 Intermediate Similarity NPD8053 Approved
0.7816 Intermediate Similarity NPD8054 Approved
0.7815 Intermediate Similarity NPD5718 Phase 2
0.7814 Intermediate Similarity NPD4002 Approved
0.7814 Intermediate Similarity NPD4004 Approved
0.7812 Intermediate Similarity NPD3647 Clinical (unspecified phase)
0.7805 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7802 Intermediate Similarity NPD4482 Phase 3
0.7771 Intermediate Similarity NPD4236 Phase 3
0.7771 Intermediate Similarity NPD4237 Approved
0.7764 Intermediate Similarity NPD3640 Phase 3
0.7764 Intermediate Similarity NPD3639 Approved
0.7764 Intermediate Similarity NPD3641 Approved
0.776 Intermediate Similarity NPD3533 Approved
0.776 Intermediate Similarity NPD2972 Approved
0.7744 Intermediate Similarity NPD7298 Approved
0.7716 Intermediate Similarity NPD4210 Discontinued
0.7697 Intermediate Similarity NPD5773 Approved
0.7697 Intermediate Similarity NPD5772 Approved
0.7677 Intermediate Similarity NPD6895 Approved
0.7677 Intermediate Similarity NPD6896 Approved
0.7676 Intermediate Similarity NPD4040 Phase 1
0.7663 Intermediate Similarity NPD2491 Approved
0.7663 Intermediate Similarity NPD3448 Approved
0.7657 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7654 Intermediate Similarity NPD5976 Discontinued
0.7628 Intermediate Similarity NPD1753 Discontinued
0.7625 Intermediate Similarity NPD7124 Phase 2
0.761 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.761 Intermediate Similarity NPD5754 Discontinued
0.7574 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7564 Intermediate Similarity NPD2200 Suspended
0.7552 Intermediate Similarity NPD7047 Phase 3
0.7547 Intermediate Similarity NPD5177 Phase 3
0.7546 Intermediate Similarity NPD4727 Phase 1
0.7532 Intermediate Similarity NPD4474 Approved
0.7532 Intermediate Similarity NPD4475 Approved
0.7529 Intermediate Similarity NPD6107 Approved
0.7527 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6331 Phase 2
0.7484 Intermediate Similarity NPD1372 Clinical (unspecified phase)
0.7469 Intermediate Similarity NPD2420 Approved
0.7469 Intermediate Similarity NPD2421 Approved
0.7468 Intermediate Similarity NPD6812 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD3692 Discontinued
0.7446 Intermediate Similarity NPD4420 Approved
0.7439 Intermediate Similarity NPD2122 Discontinued
0.7438 Intermediate Similarity NPD4162 Approved
0.7435 Intermediate Similarity NPD5676 Approved
0.7423 Intermediate Similarity NPD1424 Approved
0.7423 Intermediate Similarity NPD7020 Approved
0.7423 Intermediate Similarity NPD7019 Approved
0.7417 Intermediate Similarity NPD7258 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD6667 Approved
0.7407 Intermediate Similarity NPD6666 Approved
0.7391 Intermediate Similarity NPD6748 Discontinued
0.7391 Intermediate Similarity NPD7466 Approved
0.7384 Intermediate Similarity NPD4166 Phase 2
0.7371 Intermediate Similarity NPD42 Phase 2
0.7371 Intermediate Similarity NPD6042 Phase 2
0.7368 Intermediate Similarity NPD4098 Discontinued
0.7365 Intermediate Similarity NPD6072 Discontinued
0.7365 Intermediate Similarity NPD1757 Discontinued
0.7362 Intermediate Similarity NPD3124 Discontinued
0.7358 Intermediate Similarity NPD2161 Phase 2
0.7356 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.7355 Intermediate Similarity NPD7294 Phase 1
0.7349 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7346 Intermediate Similarity NPD2677 Approved
0.7342 Intermediate Similarity NPD6111 Discontinued
0.7341 Intermediate Similarity NPD6688 Approved
0.7341 Intermediate Similarity NPD6687 Approved
0.7333 Intermediate Similarity NPD5980 Discovery
0.7329 Intermediate Similarity NPD3060 Approved
0.7317 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7312 Intermediate Similarity NPD1375 Discontinued
0.7312 Intermediate Similarity NPD8095 Phase 1
0.7308 Intermediate Similarity NPD3530 Approved
0.7308 Intermediate Similarity NPD3532 Approved
0.7308 Intermediate Similarity NPD3531 Approved
0.7308 Intermediate Similarity NPD554 Clinical (unspecified phase)
0.7287 Intermediate Similarity NPD5006 Approved
0.7287 Intermediate Similarity NPD5005 Approved
0.7283 Intermediate Similarity NPD4010 Discontinued
0.7278 Intermediate Similarity NPD5087 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD2977 Approved
0.7278 Intermediate Similarity NPD2978 Approved
0.7273 Intermediate Similarity NPD5312 Approved
0.7273 Intermediate Similarity NPD3636 Approved
0.7273 Intermediate Similarity NPD5313 Approved
0.7273 Intermediate Similarity NPD3635 Approved
0.7273 Intermediate Similarity NPD7907 Approved
0.7273 Intermediate Similarity NPD3637 Approved
0.7273 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD7037 Approved
0.7261 Intermediate Similarity NPD2238 Phase 2
0.7251 Intermediate Similarity NPD4055 Discovery
0.7248 Intermediate Similarity NPD3445 Approved
0.7248 Intermediate Similarity NPD3443 Approved
0.7248 Intermediate Similarity NPD3444 Approved
0.7246 Intermediate Similarity NPD4005 Discontinued
0.7244 Intermediate Similarity NPD1336 Approved
0.7236 Intermediate Similarity NPD6997 Phase 2
0.7226 Intermediate Similarity NPD2606 Approved
0.7226 Intermediate Similarity NPD3594 Approved
0.7226 Intermediate Similarity NPD2605 Approved
0.7226 Intermediate Similarity NPD3595 Approved
0.7225 Intermediate Similarity NPD7802 Discontinued
0.7219 Intermediate Similarity NPD5720 Discontinued
0.7212 Intermediate Similarity NPD4123 Phase 3
0.7209 Intermediate Similarity NPD5709 Phase 3
0.7208 Intermediate Similarity NPD7905 Discontinued
0.7205 Intermediate Similarity NPD4721 Approved
0.7205 Intermediate Similarity NPD4725 Approved
0.7205 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD4726 Approved
0.7198 Intermediate Similarity NPD7291 Discontinued
0.7193 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD2154 Approved
0.7188 Intermediate Similarity NPD2156 Approved
0.7188 Intermediate Similarity NPD2155 Approved
0.7186 Intermediate Similarity NPD3687 Approved
0.7186 Intermediate Similarity NPD3686 Approved
0.7179 Intermediate Similarity NPD5156 Approved
0.7179 Intermediate Similarity NPD5155 Approved
0.7176 Intermediate Similarity NPD4585 Approved
0.7172 Intermediate Similarity NPD4111 Phase 1
0.7172 Intermediate Similarity NPD4665 Approved
0.7168 Intermediate Similarity NPD5677 Discontinued
0.7168 Intermediate Similarity NPD4666 Phase 3
0.7168 Intermediate Similarity NPD6037 Discontinued
0.716 Intermediate Similarity NPD7109 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD6386 Approved
0.716 Intermediate Similarity NPD6385 Approved
0.716 Intermediate Similarity NPD7110 Phase 1
0.7152 Intermediate Similarity NPD7213 Phase 3
0.7152 Intermediate Similarity NPD7212 Phase 2
0.7152 Intermediate Similarity NPD1774 Approved
0.7135 Intermediate Similarity NPD5978 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