Structure

Physi-Chem Properties

Molecular Weight:  594.27
Volume:  614.414
LogP:  5.882
LogD:  3.761
LogS:  -4.805
# Rotatable Bonds:  3
TPSA:  81.65
# H-Bond Aceptor:  8
# H-Bond Donor:  2
# Rings:  8
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.278
Synthetic Accessibility Score:  5.776
Fsp3:  0.333
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.862
MDCK Permeability:  2.04901607503416e-05
Pgp-inhibitor:  0.999
Pgp-substrate:  0.907
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.109
30% Bioavailability (F30%):  0.954

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.078
Plasma Protein Binding (PPB):  71.62682342529297%
Volume Distribution (VD):  0.702
Pgp-substrate:  15.61724853515625%

ADMET: Metabolism

CYP1A2-inhibitor:  0.07
CYP1A2-substrate:  0.954
CYP2C19-inhibitor:  0.183
CYP2C19-substrate:  0.949
CYP2C9-inhibitor:  0.049
CYP2C9-substrate:  0.486
CYP2D6-inhibitor:  0.023
CYP2D6-substrate:  0.956
CYP3A4-inhibitor:  0.114
CYP3A4-substrate:  0.948

ADMET: Excretion

Clearance (CL):  6.586
Half-life (T1/2):  0.306

ADMET: Toxicity

hERG Blockers:  0.954
Human Hepatotoxicity (H-HT):  0.062
Drug-inuced Liver Injury (DILI):  0.633
AMES Toxicity:  0.121
Rat Oral Acute Toxicity:  0.379
Maximum Recommended Daily Dose:  0.995
Skin Sensitization:  0.835
Carcinogencity:  0.03
Eye Corrosion:  0.003
Eye Irritation:  0.004
Respiratory Toxicity:  0.312

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

  Natural Product: NPC11296

Natural Product ID:  NPC11296
Common Name*:   REKCBEFSIKOPTD-IZLXSDGUSA-N
IUPAC Name:   n.a.
Synonyms:   (+)-Daphandrine
Standard InCHIKey:  REKCBEFSIKOPTD-IZLXSDGUSA-N
Standard InCHI:  InChI=1S/C36H38N2O6/c1-38-14-12-24-19-33(42-4)35(39)36-34(24)28(38)16-21-5-8-25(9-6-21)43-31-17-22(7-10-29(31)40-2)15-27-26-20-32(44-36)30(41-3)18-23(26)11-13-37-27/h5-10,17-20,27-28,37,39H,11-16H2,1-4H3/t27-,28+/m1/s1
SMILES:  COc1cc2CCN[C@H]3c2cc1Oc1c2c(CCN([C@H]2Cc2ccc(Oc4cc(C3)ccc4OC)cc2)C)cc(c1O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL510612
PubChem CID:   442214
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO26964 Stephania erecta Species Menispermaceae Eukaryota n.a. n.a. n.a. PMID[8450319]
NPO26964 Stephania erecta Species Menispermaceae Eukaryota tubers n.a. n.a. PMID[8450319]
NPO26964 Stephania erecta Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26964 Stephania erecta Species Menispermaceae Eukaryota tubers n.a. n.a. Database[PMID; Title]
NPO26964 Stephania erecta Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26964 Stephania erecta Species Menispermaceae 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
NPT453 Cell Line HT-1080 Homo sapiens ED50 = 6.9 ug ml-1 PMID[469297]
NPT147 Cell Line SK-MEL-2 Homo sapiens ED50 = 13.4 ug ml-1 PMID[469297]
NPT91 Cell Line KB Homo sapiens ED50 = 5.8 ug ml-1 PMID[469297]
NPT168 Cell Line P388 Mus musculus ED50 = 2.0 ug ml-1 PMID[469297]
NPT762 Cell Line A-431 Homo sapiens ED50 = 8.3 ug ml-1 PMID[469297]
NPT858 Cell Line LNCaP Homo sapiens ED50 = 5.8 ug ml-1 PMID[469297]
NPT133 Cell Line ZR-75-1 Homo sapiens ED50 = 1.2 ug ml-1 PMID[469297]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum ED50 = 63.0 ng/ml PMID[469297]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum ED50 = 223.2 ng/ml PMID[469297]
NPT27 Others Unspecified ED50 = 4.6 ug ml-1 PMID[469297]
NPT2 Others Unspecified Ratio ED50 = 73.0 n.a. PMID[469297]
NPT2 Others Unspecified Ratio ED50 = 21.0 n.a. PMID[469297]
NPT2 Others Unspecified Ratio ED50 = 110.0 n.a. PMID[469297]
NPT2 Others Unspecified Ratio ED50 = 31.0 n.a. PMID[469297]
NPT27 Others Unspecified ED50 = 2.0 ug ml-1 PMID[469297]
NPT2 Others Unspecified Ratio ED50 = 143.0 n.a. PMID[469297]
NPT2 Others Unspecified Ratio ED50 = 40.0 n.a. PMID[469297]
NPT2 Others Unspecified Ratio ED50 = 213.0 n.a. PMID[469297]
NPT2 Others Unspecified Ratio ED50 = 60.0 n.a. PMID[469297]
NPT27 Others Unspecified ED50 = 10.3 ug ml-1 PMID[469297]
NPT2 Others Unspecified Ratio ED50 = 164.0 n.a. PMID[469297]
NPT2 Others Unspecified Ratio ED50 = 46.0 n.a. PMID[469297]
NPT2 Others Unspecified Ratio ED50 = 92.0 n.a. PMID[469297]
NPT2 Others Unspecified Ratio ED50 = 26.0 n.a. PMID[469297]
NPT27 Others Unspecified ED50 = 2.2 ug ml-1 PMID[469297]
NPT2 Others Unspecified Ratio ED50 = 35.0 n.a. PMID[469297]
NPT2 Others Unspecified Ratio ED50 = 10.0 n.a. PMID[469297]
NPT2 Others Unspecified Ratio ED50 = 32.0 n.a. PMID[469297]
NPT2 Others Unspecified Ratio ED50 = 9.0 n.a. PMID[469297]
NPT2 Others Unspecified Ratio ED50 = 132.0 n.a. PMID[469297]
NPT2 Others Unspecified Ratio ED50 = 37.0 n.a. PMID[469297]
NPT2 Others Unspecified Ratio ED50 = 29.0 n.a. PMID[469297]
NPT2 Others Unspecified Ratio ED50 = 8.0 n.a. PMID[469297]

☑ 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 NPC11296 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 NPC82457
1.0 High Similarity NPC48490
1.0 High Similarity NPC274661
1.0 High Similarity NPC175890
0.9941 High Similarity NPC191132
0.9941 High Similarity NPC60295
0.9704 High Similarity NPC185639
0.9704 High Similarity NPC251735
0.9704 High Similarity NPC328155
0.9704 High Similarity NPC271013
0.9704 High Similarity NPC104196
0.9704 High Similarity NPC290582
0.9704 High Similarity NPC222661
0.9704 High Similarity NPC311973
0.9704 High Similarity NPC279228
0.9704 High Similarity NPC7715
0.9704 High Similarity NPC54654
0.9704 High Similarity NPC49075
0.9704 High Similarity NPC182052
0.9704 High Similarity NPC42663
0.9704 High Similarity NPC239824
0.9704 High Similarity NPC90998
0.9704 High Similarity NPC229373
0.9704 High Similarity NPC223690
0.9704 High Similarity NPC217748
0.9704 High Similarity NPC15414
0.9704 High Similarity NPC290005
0.9704 High Similarity NPC181796
0.9704 High Similarity NPC285931
0.9704 High Similarity NPC8836
0.9704 High Similarity NPC258657
0.9647 High Similarity NPC167116
0.9647 High Similarity NPC274716
0.9647 High Similarity NPC254441
0.9645 High Similarity NPC286119
0.9598 High Similarity NPC256124
0.9588 High Similarity NPC30779
0.9586 High Similarity NPC475479
0.9586 High Similarity NPC243454
0.9535 High Similarity NPC116465
0.9535 High Similarity NPC212237
0.9529 High Similarity NPC239584
0.948 High Similarity NPC22115
0.948 High Similarity NPC275680
0.9425 High Similarity NPC206900
0.9364 High Similarity NPC302245
0.9364 High Similarity NPC95426
0.9364 High Similarity NPC16357
0.9318 High Similarity NPC24260
0.931 High Similarity NPC139783
0.931 High Similarity NPC65312
0.929 High Similarity NPC115284
0.929 High Similarity NPC317439
0.929 High Similarity NPC63646
0.929 High Similarity NPC108434
0.929 High Similarity NPC475215
0.929 High Similarity NPC76682
0.929 High Similarity NPC227060
0.929 High Similarity NPC276890
0.929 High Similarity NPC10908
0.929 High Similarity NPC317145
0.929 High Similarity NPC198498
0.9235 High Similarity NPC129518
0.9235 High Similarity NPC41376
0.9235 High Similarity NPC12424
0.9235 High Similarity NPC251580
0.9209 High Similarity NPC478093
0.9205 High Similarity NPC281581
0.9157 High Similarity NPC30182
0.9157 High Similarity NPC473589
0.9157 High Similarity NPC478092
0.9157 High Similarity NPC478091
0.9128 High Similarity NPC293093
0.9053 High Similarity NPC250846
0.9053 High Similarity NPC268503
0.9053 High Similarity NPC256012
0.9053 High Similarity NPC264850
0.9053 High Similarity NPC42549
0.9053 High Similarity NPC13916
0.9053 High Similarity NPC317272
0.9053 High Similarity NPC240841
0.905 High Similarity NPC85381
0.9045 High Similarity NPC41122
0.9045 High Similarity NPC318805
0.9011 High Similarity NPC475654
0.8994 High Similarity NPC24465
0.895 High Similarity NPC234318
0.8947 High Similarity NPC204908
0.8947 High Similarity NPC83198
0.8935 High Similarity NPC475393
0.892 High Similarity NPC299990
0.892 High Similarity NPC73492
0.8807 High Similarity NPC474507
0.8793 High Similarity NPC232386
0.8793 High Similarity NPC152680
0.8793 High Similarity NPC190783
0.8764 High Similarity NPC302275
0.8757 High Similarity NPC257269
0.8757 High Similarity NPC230276
0.8715 High Similarity NPC249996
0.8701 High Similarity NPC40496
0.8701 High Similarity NPC119068
0.8693 High Similarity NPC173416
0.8693 High Similarity NPC148709
0.8693 High Similarity NPC476577
0.8678 High Similarity NPC109925
0.8663 High Similarity NPC4138
0.8663 High Similarity NPC121275
0.8663 High Similarity NPC254581
0.8663 High Similarity NPC284183
0.8652 High Similarity NPC195538
0.8639 High Similarity NPC247639
0.8639 High Similarity NPC25084
0.8626 High Similarity NPC475597
0.8626 High Similarity NPC473716
0.8603 High Similarity NPC476202
0.858 High Similarity NPC469817
0.858 High Similarity NPC172765
0.858 High Similarity NPC39701
0.858 High Similarity NPC276588
0.858 High Similarity NPC2413
0.858 High Similarity NPC193949
0.858 High Similarity NPC249797
0.858 High Similarity NPC127674
0.858 High Similarity NPC110416
0.858 High Similarity NPC184026
0.858 High Similarity NPC54379
0.858 High Similarity NPC189266
0.858 High Similarity NPC295691
0.858 High Similarity NPC5238
0.858 High Similarity NPC207757
0.858 High Similarity NPC204828
0.858 High Similarity NPC278799
0.8564 High Similarity NPC14507
0.8564 High Similarity NPC47077
0.8523 High Similarity NPC239775
0.8521 High Similarity NPC2295
0.8521 High Similarity NPC477564
0.8506 High Similarity NPC193853
0.8506 High Similarity NPC223077
0.8506 High Similarity NPC56887
0.8475 Intermediate Similarity NPC477020
0.8475 Intermediate Similarity NPC66341
0.8475 Intermediate Similarity NPC192135
0.8466 Intermediate Similarity NPC69712
0.8466 Intermediate Similarity NPC26240
0.8466 Intermediate Similarity NPC118274
0.8466 Intermediate Similarity NPC477562
0.8466 Intermediate Similarity NPC168753
0.8448 Intermediate Similarity NPC209377
0.8418 Intermediate Similarity NPC10871
0.8415 Intermediate Similarity NPC186546
0.8415 Intermediate Similarity NPC476576
0.8402 Intermediate Similarity NPC76213
0.8402 Intermediate Similarity NPC277669
0.8352 Intermediate Similarity NPC204947
0.8343 Intermediate Similarity NPC151895
0.8343 Intermediate Similarity NPC220858
0.8343 Intermediate Similarity NPC88249
0.8343 Intermediate Similarity NPC192768
0.8343 Intermediate Similarity NPC97221
0.8333 Intermediate Similarity NPC60186
0.8295 Intermediate Similarity NPC81247
0.8295 Intermediate Similarity NPC476573
0.8295 Intermediate Similarity NPC35627
0.8284 Intermediate Similarity NPC477565
0.8284 Intermediate Similarity NPC103379
0.8284 Intermediate Similarity NPC60538
0.8284 Intermediate Similarity NPC207824
0.8283 Intermediate Similarity NPC82056
0.828 Intermediate Similarity NPC476565
0.8276 Intermediate Similarity NPC205255
0.8276 Intermediate Similarity NPC230956
0.8276 Intermediate Similarity NPC119649
0.8276 Intermediate Similarity NPC235143
0.8276 Intermediate Similarity NPC271388
0.8261 Intermediate Similarity NPC57036
0.8256 Intermediate Similarity NPC187022
0.8256 Intermediate Similarity NPC80129
0.8249 Intermediate Similarity NPC12053
0.8249 Intermediate Similarity NPC474931
0.8249 Intermediate Similarity NPC205421
0.8249 Intermediate Similarity NPC81218
0.8249 Intermediate Similarity NPC158376
0.8249 Intermediate Similarity NPC145832
0.8249 Intermediate Similarity NPC306555
0.8249 Intermediate Similarity NPC117188
0.8239 Intermediate Similarity NPC253043
0.8239 Intermediate Similarity NPC276944
0.8239 Intermediate Similarity NPC196447
0.8239 Intermediate Similarity NPC306843
0.8239 Intermediate Similarity NPC232514
0.8239 Intermediate Similarity NPC212794
0.8239 Intermediate Similarity NPC96603
0.8239 Intermediate Similarity NPC136508
0.8239 Intermediate Similarity NPC238530
0.8239 Intermediate Similarity NPC13504
0.8239 Intermediate Similarity NPC477563
0.8239 Intermediate Similarity NPC78222
0.8229 Intermediate Similarity NPC79402

  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 NPC11296 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
0.9704 High Similarity NPD8053 Approved
0.9704 High Similarity NPD8054 Approved
0.929 High Similarity NPD8099 Discontinued
0.929 High Similarity NPD8251 Approved
0.929 High Similarity NPD8252 Approved
0.9235 High Similarity NPD8156 Discontinued
0.8701 High Similarity NPD8453 Clinical (unspecified phase)
0.8351 Intermediate Similarity NPD8095 Phase 1
0.8256 Intermediate Similarity NPD7298 Approved
0.8166 Intermediate Similarity NPD4584 Approved
0.8114 Intermediate Similarity NPD6788 Approved
0.7968 Intermediate Similarity NPD7906 Approved
0.7953 Intermediate Similarity NPD1424 Approved
0.7886 Intermediate Similarity NPD4772 Phase 2
0.7886 Intermediate Similarity NPD4773 Phase 2
0.7861 Intermediate Similarity NPD6031 Approved
0.7861 Intermediate Similarity NPD6030 Approved
0.7812 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7811 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.7797 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.779 Intermediate Similarity NPD6071 Discontinued
0.7765 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7765 Intermediate Similarity NPD7831 Phase 2
0.7765 Intermediate Similarity NPD7833 Phase 2
0.7754 Intermediate Similarity NPD7311 Approved
0.7754 Intermediate Similarity NPD7310 Approved
0.7754 Intermediate Similarity NPD7313 Approved
0.7754 Intermediate Similarity NPD7312 Approved
0.7733 Intermediate Similarity NPD3845 Phase 1
0.7713 Intermediate Similarity NPD7309 Approved
0.7709 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7705 Intermediate Similarity NPD2489 Approved
0.7705 Intermediate Similarity NPD27 Approved
0.7692 Intermediate Similarity NPD3051 Approved
0.767 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.766 Intermediate Similarity NPD4578 Approved
0.766 Intermediate Similarity NPD4577 Approved
0.765 Intermediate Similarity NPD2969 Approved
0.765 Intermediate Similarity NPD2970 Approved
0.7644 Intermediate Similarity NPD7447 Phase 1
0.7644 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7637 Intermediate Similarity NPD6107 Approved
0.7632 Intermediate Similarity NPD4663 Approved
0.7588 Intermediate Similarity NPD1632 Clinical (unspecified phase)
0.7586 Intermediate Similarity NPD7598 Phase 2
0.7582 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7556 Intermediate Similarity NPD2560 Approved
0.7556 Intermediate Similarity NPD2563 Approved
0.7529 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.7513 Intermediate Similarity NPD7549 Discontinued
0.75 Intermediate Similarity NPD7045 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD4010 Discontinued
0.7486 Intermediate Similarity NPD7213 Phase 3
0.7486 Intermediate Similarity NPD7212 Phase 2
0.7477 Intermediate Similarity NPD8152 Approved
0.7477 Intermediate Similarity NPD8153 Approved
0.7435 Intermediate Similarity NPD6851 Approved
0.7435 Intermediate Similarity NPD6853 Approved
0.7427 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7427 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD2898 Approved
0.7415 Intermediate Similarity NPD7827 Phase 1
0.7407 Intermediate Similarity NPD6297 Approved
0.7394 Intermediate Similarity NPD6042 Phase 2
0.7394 Intermediate Similarity NPD42 Phase 2
0.7386 Intermediate Similarity NPD2420 Approved
0.7386 Intermediate Similarity NPD2421 Approved
0.7377 Intermediate Similarity NPD4055 Discovery
0.7371 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7356 Intermediate Similarity NPD3060 Approved
0.7356 Intermediate Similarity NPD4162 Approved
0.7337 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD4675 Approved
0.7333 Intermediate Similarity NPD4678 Approved
0.733 Intermediate Similarity NPD7124 Phase 2
0.7308 Intermediate Similarity NPD4585 Approved
0.7308 Intermediate Similarity NPD2977 Approved
0.7308 Intermediate Similarity NPD2978 Approved
0.7297 Intermediate Similarity NPD5677 Discontinued
0.7293 Intermediate Similarity NPD6072 Discontinued
0.7278 Intermediate Similarity NPD4017 Approved
0.7273 Intermediate Similarity NPD5160 Discontinued
0.7273 Intermediate Similarity NPD5241 Discontinued
0.7273 Intermediate Similarity NPD2677 Approved
0.7264 Intermediate Similarity NPD2494 Approved
0.7264 Intermediate Similarity NPD3452 Approved
0.7264 Intermediate Similarity NPD3450 Approved
0.7264 Intermediate Similarity NPD2493 Approved
0.7263 Intermediate Similarity NPD3641 Approved
0.7263 Intermediate Similarity NPD7479 Phase 2
0.7263 Intermediate Similarity NPD3639 Approved
0.7263 Intermediate Similarity NPD3640 Phase 3
0.7258 Intermediate Similarity NPD7802 Discontinued
0.7247 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7245 Intermediate Similarity NPD2488 Approved
0.7245 Intermediate Similarity NPD2490 Approved
0.7241 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7234 Intermediate Similarity NPD4481 Phase 3
0.7219 Intermediate Similarity NPD4166 Phase 2
0.7213 Intermediate Similarity NPD7046 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD4873 Discontinued
0.7207 Intermediate Similarity NPD3647 Clinical (unspecified phase)
0.7204 Intermediate Similarity NPD4666 Phase 3
0.7183 Intermediate Similarity NPD6997 Phase 2
0.7182 Intermediate Similarity NPD4005 Discontinued
0.7167 Intermediate Similarity NPD5976 Discontinued
0.7165 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD5940 Clinical (unspecified phase)
0.7157 Intermediate Similarity NPD4582 Approved
0.7157 Intermediate Similarity NPD4583 Approved
0.7157 Intermediate Similarity NPD4040 Phase 1
0.7151 Intermediate Similarity NPD5709 Phase 3
0.7143 Intermediate Similarity NPD7047 Phase 3
0.7135 Intermediate Similarity NPD4475 Approved
0.7135 Intermediate Similarity NPD4474 Approved
0.7123 Intermediate Similarity NPD6723 Discontinued
0.712 Intermediate Similarity NPD5773 Approved
0.712 Intermediate Similarity NPD5772 Approved
0.7119 Intermediate Similarity NPD6748 Discontinued
0.7108 Intermediate Similarity NPD4002 Approved
0.7108 Intermediate Similarity NPD4004 Approved
0.7097 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD1774 Approved
0.7088 Intermediate Similarity NPD6523 Clinical (unspecified phase)
0.7077 Intermediate Similarity NPD6618 Phase 2
0.7076 Intermediate Similarity NPD5718 Phase 2
0.7072 Intermediate Similarity NPD2122 Discontinued
0.7069 Intermediate Similarity NPD2200 Suspended
0.7065 Intermediate Similarity NPD3384 Approved
0.7065 Intermediate Similarity NPD2973 Approved
0.7065 Intermediate Similarity NPD2974 Approved
0.7065 Intermediate Similarity NPD2975 Approved
0.7065 Intermediate Similarity NPD3383 Approved
0.7065 Intermediate Similarity NPD3382 Approved
0.7065 Intermediate Similarity NPD5722 Discontinued
0.7062 Intermediate Similarity NPD5177 Phase 3
0.7059 Intermediate Similarity NPD5006 Approved
0.7059 Intermediate Similarity NPD5005 Approved
0.7059 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7056 Intermediate Similarity NPD4123 Phase 3
0.7047 Intermediate Similarity NPD6996 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7031 Intermediate Similarity NPD5313 Approved
0.7031 Intermediate Similarity NPD5312 Approved
0.7029 Intermediate Similarity NPD2155 Approved
0.7029 Intermediate Similarity NPD2156 Approved
0.7029 Intermediate Similarity NPD2154 Approved
0.7022 Intermediate Similarity NPD3977 Clinical (unspecified phase)
0.7022 Intermediate Similarity NPD7466 Approved
0.7017 Intermediate Similarity NPD7526 Approved
0.7017 Intermediate Similarity NPD6090 Discontinued
0.7017 Intermediate Similarity NPD52 Approved
0.7017 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.7017 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD7153 Discontinued
0.7 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD3124 Discontinued
0.7 Intermediate Similarity NPD6087 Phase 1
0.6995 Remote Similarity NPD8158 Clinical (unspecified phase)
0.6994 Remote Similarity NPD1613 Approved
0.6994 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6982 Remote Similarity NPD3053 Approved
0.6982 Remote Similarity NPD3055 Approved
0.6974 Remote Similarity NPD7132 Clinical (unspecified phase)
0.6973 Remote Similarity NPD5720 Discontinued
0.6973 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6966 Remote Similarity NPD5061 Approved
0.6966 Remote Similarity NPD5062 Approved
0.6961 Remote Similarity NPD4580 Approved
0.6959 Remote Similarity NPD4908 Phase 1
0.6944 Remote Similarity NPD3122 Phase 3
0.694 Remote Similarity NPD3686 Approved
0.694 Remote Similarity NPD3687 Approved
0.6939 Remote Similarity NPD2971 Approved
0.6939 Remote Similarity NPD2968 Approved
0.6939 Remote Similarity NPD3534 Clinical (unspecified phase)
0.6935 Remote Similarity NPD2843 Phase 2
0.6935 Remote Similarity NPD6377 Clinical (unspecified phase)
0.6935 Remote Similarity NPD2845 Phase 2
0.6927 Remote Similarity NPD5602 Clinical (unspecified phase)
0.6923 Remote Similarity NPD7039 Approved
0.6923 Remote Similarity NPD5310 Approved
0.6923 Remote Similarity NPD5311 Approved
0.6923 Remote Similarity NPD7038 Approved
0.6914 Remote Similarity NPD3052 Approved
0.6914 Remote Similarity NPD2568 Approved
0.6914 Remote Similarity NPD817 Approved
0.6914 Remote Similarity NPD3054 Approved
0.6914 Remote Similarity NPD823 Approved
0.6914 Remote Similarity NPD5314 Approved
0.69 Remote Similarity NPD5525 Clinical (unspecified phase)
0.6898 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6897 Remote Similarity NPD6621 Clinical (unspecified phase)
0.6897 Remote Similarity NPD6284 Clinical (unspecified phase)
0.6897 Remote Similarity NPD4605 Approved
0.6897 Remote Similarity NPD4604 Approved
0.6891 Remote Similarity NPD7493 Clinical (unspecified phase)
0.6889 Remote Similarity NPD3692 Discontinued
0.6888 Remote Similarity NPD3936 Clinical (unspecified phase)

  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