Structure

Physi-Chem Properties

Molecular Weight:  560.23
Volume:  577.135
LogP:  7.111
LogD:  3.733
LogS:  -8.563
# Rotatable Bonds:  2
TPSA:  61.75
# H-Bond Aceptor:  7
# H-Bond Donor:  0
# Rings:  9
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.23
Synthetic Accessibility Score:  5.738
Fsp3:  0.286
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.879
MDCK Permeability:  2.0746283553307876e-05
Pgp-inhibitor:  0.999
Pgp-substrate:  0.981
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.67
30% Bioavailability (F30%):  0.929

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.162
Plasma Protein Binding (PPB):  87.19019317626953%
Volume Distribution (VD):  0.622
Pgp-substrate:  3.492551326751709%

ADMET: Metabolism

CYP1A2-inhibitor:  0.091
CYP1A2-substrate:  0.958
CYP2C19-inhibitor:  0.141
CYP2C19-substrate:  0.916
CYP2C9-inhibitor:  0.101
CYP2C9-substrate:  0.752
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.927
CYP3A4-inhibitor:  0.102
CYP3A4-substrate:  0.945

ADMET: Excretion

Clearance (CL):  8.342
Half-life (T1/2):  0.075

ADMET: Toxicity

hERG Blockers:  0.93
Human Hepatotoxicity (H-HT):  0.019
Drug-inuced Liver Injury (DILI):  0.815
AMES Toxicity:  0.146
Rat Oral Acute Toxicity:  0.81
Maximum Recommended Daily Dose:  0.989
Skin Sensitization:  0.719
Carcinogencity:  0.067
Eye Corrosion:  0.003
Eye Irritation:  0.005
Respiratory Toxicity:  0.568

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Similar NPs/Drugs  

  Natural Product: NPC249996

Natural Product ID:  NPC249996
Common Name*:   KRRIBHWRCGOGAF-MHZLTWQESA-N
IUPAC Name:   n.a.
Synonyms:   (+)-1,2-Dehydrotelobine
Standard InCHIKey:  KRRIBHWRCGOGAF-MHZLTWQESA-N
Standard InCHI:  InChI=1S/C35H32N2O5/c1-37-13-11-23-18-32(39-3)34-35-33(23)27(37)15-20-4-7-24(8-5-20)40-29-16-21(6-9-28(29)38-2)14-26-25-19-31(42-35)30(41-34)17-22(25)10-12-36-26/h4-9,16-19,27H,10-15H2,1-3H3/t27-/m0/s1
SMILES:  COc1ccc2cc1Oc1ccc(cc1)C[C@@H]1N(C)CCc3c1c1Oc4cc5C(=NCCc5cc4Oc1c(c3)OC)C2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL452663
PubChem CID:   10415402
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 = 2.1 ug ml-1 PMID[460845]
NPT147 Cell Line SK-MEL-2 Homo sapiens ED50 = 9.9 ug ml-1 PMID[460845]
NPT91 Cell Line KB Homo sapiens ED50 = 2.8 ug ml-1 PMID[460845]
NPT168 Cell Line P388 Mus musculus ED50 = 3.1 ug ml-1 PMID[460845]
NPT762 Cell Line A-431 Homo sapiens ED50 = 6.0 ug ml-1 PMID[460845]
NPT858 Cell Line LNCaP Homo sapiens ED50 = 2.0 ug ml-1 PMID[460845]
NPT133 Cell Line ZR-75-1 Homo sapiens ED50 = 0.7 ug ml-1 PMID[460845]
NPT91 Cell Line KB Homo sapiens ED50 = 5000.0 nM PMID[460846]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum ED50 = 306.7 ng/ml PMID[460845]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum ED50 = 256.4 ng/ml PMID[460845]
NPT27 Others Unspecified ED50 = 4.6 ug ml-1 PMID[460845]
NPT2 Others Unspecified Ratio ED50 = 15.0 n.a. PMID[460845]
NPT2 Others Unspecified Ratio ED50 = 18.0 n.a. PMID[460845]
NPT2 Others Unspecified Ratio ED50 = 7.0 n.a. PMID[460845]
NPT2 Others Unspecified Ratio ED50 = 8.0 n.a. PMID[460845]
NPT27 Others Unspecified ED50 = 1.7 ug ml-1 PMID[460845]
NPT2 Others Unspecified Ratio ED50 = 6.0 n.a. PMID[460845]
NPT2 Others Unspecified Ratio ED50 = 32.0 n.a. PMID[460845]
NPT2 Others Unspecified Ratio ED50 = 39.0 n.a. PMID[460845]
NPT27 Others Unspecified ED50 = 5.0 ug ml-1 PMID[460845]
NPT2 Others Unspecified Ratio ED50 = 16.0 n.a. PMID[460845]
NPT2 Others Unspecified Ratio ED50 = 20.0 n.a. PMID[460845]
NPT2 Others Unspecified Ratio ED50 = 9.0 n.a. PMID[460845]
NPT2 Others Unspecified Ratio ED50 = 11.0 n.a. PMID[460845]
NPT27 Others Unspecified ED50 = 6.8 ug ml-1 PMID[460845]
NPT2 Others Unspecified Ratio ED50 = 22.0 n.a. PMID[460845]
NPT2 Others Unspecified Ratio ED50 = 27.0 n.a. PMID[460845]
NPT2 Others Unspecified Ratio ED50 = 10.0 n.a. PMID[460845]
NPT2 Others Unspecified Ratio ED50 = 12.0 n.a. PMID[460845]
NPT2 Others Unspecified Ratio ED50 = 23.0 n.a. PMID[460845]
NPT2 Others Unspecified Ratio ED50 = 2.0 n.a. PMID[460845]
NPT2 Others Unspecified Ratio ED50 = 3.0 n.a. PMID[460845]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 554.0 nM PMID[460846]
NPT2 Others Unspecified Selectivity Index = 11.0 n.a. PMID[460846]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 464.0 nM PMID[460846]

☑ 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 NPC249996 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.988 High Similarity NPC476202
0.9819 High Similarity NPC195538
0.9538 High Similarity NPC85381
0.9422 High Similarity NPC318805
0.9422 High Similarity NPC41122
0.9341 High Similarity NPC63646
0.9341 High Similarity NPC317145
0.9341 High Similarity NPC115284
0.9341 High Similarity NPC227060
0.9341 High Similarity NPC317439
0.9341 High Similarity NPC276890
0.9341 High Similarity NPC198498
0.9341 High Similarity NPC76682
0.9341 High Similarity NPC10908
0.9318 High Similarity NPC234318
0.9286 High Similarity NPC12424
0.9286 High Similarity NPC251580
0.9286 High Similarity NPC129518
0.9286 High Similarity NPC41376
0.9176 High Similarity NPC293093
0.907 High Similarity NPC243454
0.907 High Similarity NPC475479
0.9017 High Similarity NPC239584
0.8966 High Similarity NPC185639
0.8966 High Similarity NPC182052
0.8966 High Similarity NPC54654
0.8966 High Similarity NPC290582
0.8966 High Similarity NPC285931
0.8966 High Similarity NPC217748
0.8966 High Similarity NPC279228
0.8966 High Similarity NPC8836
0.8966 High Similarity NPC223690
0.8966 High Similarity NPC271013
0.8966 High Similarity NPC42663
0.8966 High Similarity NPC258657
0.8966 High Similarity NPC104196
0.8966 High Similarity NPC222661
0.8966 High Similarity NPC90998
0.8966 High Similarity NPC311973
0.8966 High Similarity NPC181796
0.8966 High Similarity NPC251735
0.8966 High Similarity NPC7715
0.8966 High Similarity NPC229373
0.8966 High Similarity NPC15414
0.8966 High Similarity NPC49075
0.8966 High Similarity NPC73492
0.8966 High Similarity NPC290005
0.8966 High Similarity NPC239824
0.8966 High Similarity NPC299990
0.8966 High Similarity NPC328155
0.8914 High Similarity NPC254441
0.8914 High Similarity NPC274716
0.8914 High Similarity NPC167116
0.8908 High Similarity NPC286119
0.8864 High Similarity NPC95426
0.8864 High Similarity NPC302245
0.8864 High Similarity NPC16357
0.8857 High Similarity NPC30779
0.8814 High Similarity NPC139783
0.8814 High Similarity NPC116465
0.8814 High Similarity NPC65312
0.8814 High Similarity NPC212237
0.8807 High Similarity NPC302275
0.8764 High Similarity NPC275680
0.8764 High Similarity NPC22115
0.8715 High Similarity NPC48490
0.8715 High Similarity NPC206900
0.8715 High Similarity NPC175890
0.8715 High Similarity NPC274661
0.8715 High Similarity NPC11296
0.8715 High Similarity NPC82457
0.8715 High Similarity NPC281581
0.869 High Similarity NPC216816
0.8683 High Similarity NPC25084
0.8683 High Similarity NPC247639
0.8674 High Similarity NPC471113
0.8667 High Similarity NPC60295
0.8667 High Similarity NPC191132
0.8667 High Similarity NPC475597
0.8667 High Similarity NPC473716
0.8619 High Similarity NPC24260
0.8603 High Similarity NPC14507
0.8603 High Similarity NPC47077
0.8571 High Similarity NPC256124
0.8516 High Similarity NPC478093
0.847 Intermediate Similarity NPC30182
0.847 Intermediate Similarity NPC478091
0.847 Intermediate Similarity NPC473589
0.847 Intermediate Similarity NPC478092
0.8457 Intermediate Similarity NPC10871
0.843 Intermediate Similarity NPC475393
0.8343 Intermediate Similarity NPC66573
0.8343 Intermediate Similarity NPC204908
0.8343 Intermediate Similarity NPC83198
0.8342 Intermediate Similarity NPC475654
0.8333 Intermediate Similarity NPC476568
0.8333 Intermediate Similarity NPC250846
0.8333 Intermediate Similarity NPC268503
0.8333 Intermediate Similarity NPC240841
0.8333 Intermediate Similarity NPC317272
0.8333 Intermediate Similarity NPC13916
0.8333 Intermediate Similarity NPC264850
0.8333 Intermediate Similarity NPC42549
0.8333 Intermediate Similarity NPC256012
0.8315 Intermediate Similarity NPC476565
0.8276 Intermediate Similarity NPC24465
0.8261 Intermediate Similarity NPC259350
0.8261 Intermediate Similarity NPC223236
0.8211 Intermediate Similarity NPC254581
0.8204 Intermediate Similarity NPC476144
0.8204 Intermediate Similarity NPC51957
0.8204 Intermediate Similarity NPC106295
0.8204 Intermediate Similarity NPC16107
0.8204 Intermediate Similarity NPC210437
0.8202 Intermediate Similarity NPC152680
0.8202 Intermediate Similarity NPC232386
0.8202 Intermediate Similarity NPC190783
0.8187 Intermediate Similarity NPC123323
0.8155 Intermediate Similarity NPC7467
0.8045 Intermediate Similarity NPC475215
0.8045 Intermediate Similarity NPC108434
0.8023 Intermediate Similarity NPC68328
0.7989 Intermediate Similarity NPC476572
0.7978 Intermediate Similarity NPC204947
0.7977 Intermediate Similarity NPC99659
0.7977 Intermediate Similarity NPC325871
0.7964 Intermediate Similarity NPC476567
0.7964 Intermediate Similarity NPC136860
0.7964 Intermediate Similarity NPC128019
0.7961 Intermediate Similarity NPC201508
0.7953 Intermediate Similarity NPC276665
0.7953 Intermediate Similarity NPC265473
0.7952 Intermediate Similarity NPC188163
0.7952 Intermediate Similarity NPC213206
0.7952 Intermediate Similarity NPC328750
0.7952 Intermediate Similarity NPC474915
0.7944 Intermediate Similarity NPC149090
0.7944 Intermediate Similarity NPC19520
0.7944 Intermediate Similarity NPC239775
0.7898 Intermediate Similarity NPC119649
0.7898 Intermediate Similarity NPC205255
0.7898 Intermediate Similarity NPC271388
0.7898 Intermediate Similarity NPC230956
0.7898 Intermediate Similarity NPC235143
0.7892 Intermediate Similarity NPC314682
0.7889 Intermediate Similarity NPC168753
0.7889 Intermediate Similarity NPC118274
0.7885 Intermediate Similarity NPC96584
0.7885 Intermediate Similarity NPC255800
0.7874 Intermediate Similarity NPC41178
0.7874 Intermediate Similarity NPC107602
0.7874 Intermediate Similarity NPC189266
0.7874 Intermediate Similarity NPC110416
0.7874 Intermediate Similarity NPC2413
0.7874 Intermediate Similarity NPC184026
0.7874 Intermediate Similarity NPC39701
0.7874 Intermediate Similarity NPC207757
0.7874 Intermediate Similarity NPC54379
0.7874 Intermediate Similarity NPC204828
0.7874 Intermediate Similarity NPC244112
0.7874 Intermediate Similarity NPC193949
0.7874 Intermediate Similarity NPC249797
0.7874 Intermediate Similarity NPC276588
0.7874 Intermediate Similarity NPC127674
0.7874 Intermediate Similarity NPC5238
0.7874 Intermediate Similarity NPC216459
0.7874 Intermediate Similarity NPC278799
0.7874 Intermediate Similarity NPC295691
0.7874 Intermediate Similarity NPC469817
0.7874 Intermediate Similarity NPC172765
0.7874 Intermediate Similarity NPC138487
0.7853 Intermediate Similarity NPC79402
0.7853 Intermediate Similarity NPC50380
0.7853 Intermediate Similarity NPC80759
0.7853 Intermediate Similarity NPC179250
0.7845 Intermediate Similarity NPC231371
0.7841 Intermediate Similarity NPC7393
0.7841 Intermediate Similarity NPC329837
0.7841 Intermediate Similarity NPC221864
0.7829 Intermediate Similarity NPC146288
0.7803 Intermediate Similarity NPC81733
0.7803 Intermediate Similarity NPC326316
0.7791 Intermediate Similarity NPC92541
0.779 Intermediate Similarity NPC75958
0.7784 Intermediate Similarity NPC230276
0.7784 Intermediate Similarity NPC257269
0.7778 Intermediate Similarity NPC476151
0.7771 Intermediate Similarity NPC80129
0.7771 Intermediate Similarity NPC187022
0.7761 Intermediate Similarity NPC38964
0.7753 Intermediate Similarity NPC60186
0.773 Intermediate Similarity NPC474507
0.773 Intermediate Similarity NPC40496
0.773 Intermediate Similarity NPC119068
0.7727 Intermediate Similarity NPC323443
0.7727 Intermediate Similarity NPC180756
0.7727 Intermediate Similarity NPC31311
0.7727 Intermediate Similarity NPC234392
0.7722 Intermediate Similarity NPC476432
0.7722 Intermediate Similarity NPC24264

  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 NPC249996 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
0.9341 High Similarity NPD8252 Approved
0.9341 High Similarity NPD8099 Discontinued
0.9341 High Similarity NPD8251 Approved
0.9286 High Similarity NPD8156 Discontinued
0.8966 High Similarity NPD8054 Approved
0.8966 High Similarity NPD8053 Approved
0.8387 Intermediate Similarity NPD8095 Phase 1
0.8256 Intermediate Similarity NPD6788 Approved
0.8204 Intermediate Similarity NPD4584 Approved
0.7952 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.7912 Intermediate Similarity NPD6996 Clinical (unspecified phase)
0.791 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7907 Intermediate Similarity NPD4005 Discontinued
0.7857 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7803 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.779 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD7298 Approved
0.773 Intermediate Similarity NPD8453 Clinical (unspecified phase)
0.7713 Intermediate Similarity NPD7291 Discontinued
0.7697 Intermediate Similarity NPD4055 Discovery
0.7657 Intermediate Similarity NPD4678 Approved
0.7657 Intermediate Similarity NPD4675 Approved
0.7656 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7614 Intermediate Similarity NPD4772 Phase 2
0.7614 Intermediate Similarity NPD4773 Phase 2
0.7572 Intermediate Similarity NPD1424 Approved
0.756 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.756 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7528 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7527 Intermediate Similarity NPD6071 Discontinued
0.75 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7486 Intermediate Similarity NPD6031 Approved
0.7486 Intermediate Similarity NPD6030 Approved
0.7457 Intermediate Similarity NPD7124 Phase 2
0.7435 Intermediate Similarity NPD7906 Approved
0.7432 Intermediate Similarity NPD3051 Approved
0.7418 Intermediate Similarity NPD5677 Discontinued
0.7403 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD7833 Phase 2
0.7403 Intermediate Similarity NPD7831 Phase 2
0.7401 Intermediate Similarity NPD4017 Approved
0.7377 Intermediate Similarity NPD7802 Discontinued
0.7371 Intermediate Similarity NPD7447 Phase 1
0.7371 Intermediate Similarity NPD4123 Phase 3
0.7354 Intermediate Similarity NPD7549 Discontinued
0.7354 Intermediate Similarity NPD7132 Clinical (unspecified phase)
0.7351 Intermediate Similarity NPD4481 Phase 3
0.7347 Intermediate Similarity NPD7034 Discontinued
0.7333 Intermediate Similarity NPD5772 Approved
0.7333 Intermediate Similarity NPD5773 Approved
0.7297 Intermediate Similarity NPD2969 Approved
0.7297 Intermediate Similarity NPD2970 Approved
0.7293 Intermediate Similarity NPD2560 Approved
0.7293 Intermediate Similarity NPD2563 Approved
0.7288 Intermediate Similarity NPD3640 Phase 3
0.7288 Intermediate Similarity NPD3641 Approved
0.7288 Intermediate Similarity NPD3639 Approved
0.7288 Intermediate Similarity NPD2122 Discontinued
0.7283 Intermediate Similarity NPD6107 Approved
0.7278 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7262 Intermediate Similarity NPD4474 Approved
0.7262 Intermediate Similarity NPD4475 Approved
0.7241 Intermediate Similarity NPD6748 Discontinued
0.7225 Intermediate Similarity NPD7313 Approved
0.7225 Intermediate Similarity NPD7312 Approved
0.7225 Intermediate Similarity NPD7311 Approved
0.7225 Intermediate Similarity NPD7310 Approved
0.7216 Intermediate Similarity NPD7212 Phase 2
0.7216 Intermediate Similarity NPD7213 Phase 3
0.7207 Intermediate Similarity NPD8158 Clinical (unspecified phase)
0.7202 Intermediate Similarity NPD5718 Phase 2
0.72 Intermediate Similarity NPD3692 Discontinued
0.7193 Intermediate Similarity NPD2200 Suspended
0.7188 Intermediate Similarity NPD7309 Approved
0.7186 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7166 Intermediate Similarity NPD2489 Approved
0.7166 Intermediate Similarity NPD27 Approved
0.7164 Intermediate Similarity NPD5006 Approved
0.7164 Intermediate Similarity NPD5005 Approved
0.7143 Intermediate Similarity NPD7466 Approved
0.7135 Intermediate Similarity NPD5917 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD4578 Approved
0.7135 Intermediate Similarity NPD4577 Approved
0.7128 Intermediate Similarity NPD3489 Phase 3
0.7127 Intermediate Similarity NPD5090 Approved
0.7127 Intermediate Similarity NPD5089 Approved
0.7119 Intermediate Similarity NPD7598 Phase 2
0.7113 Intermediate Similarity NPD4663 Approved
0.7111 Intermediate Similarity NPD6523 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD3920 Phase 2
0.709 Intermediate Similarity NPD7493 Clinical (unspecified phase)
0.7085 Intermediate Similarity NPD6621 Clinical (unspecified phase)
0.7079 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7056 Intermediate Similarity NPD3923 Approved
0.7056 Intermediate Similarity NPD3922 Approved
0.7056 Intermediate Similarity NPD3921 Approved
0.7056 Intermediate Similarity NPD3924 Approved
0.7053 Intermediate Similarity NPD5313 Approved
0.7053 Intermediate Similarity NPD5312 Approved
0.7047 Intermediate Similarity NPD2968 Approved
0.7047 Intermediate Similarity NPD2971 Approved
0.7045 Intermediate Similarity NPD6331 Phase 2
0.7033 Intermediate Similarity NPD6072 Discontinued
0.7029 Intermediate Similarity NPD7045 Clinical (unspecified phase)
0.7022 Intermediate Similarity NPD3124 Discontinued
0.7006 Intermediate Similarity NPD5241 Discontinued
0.6994 Remote Similarity NPD6111 Discontinued
0.6994 Remote Similarity NPD6896 Approved
0.6994 Remote Similarity NPD6895 Approved
0.6973 Remote Similarity NPD4581 Clinical (unspecified phase)
0.6968 Remote Similarity NPD4010 Discontinued
0.6966 Remote Similarity NPD6783 Clinical (unspecified phase)
0.6965 Remote Similarity NPD4420 Approved
0.6959 Remote Similarity NPD7477 Discontinued
0.6957 Remote Similarity NPD4585 Approved
0.6957 Remote Similarity NPD7046 Clinical (unspecified phase)
0.6944 Remote Similarity NPD5261 Clinical (unspecified phase)
0.6944 Remote Similarity NPD7526 Approved
0.6944 Remote Similarity NPD7527 Clinical (unspecified phase)
0.6944 Remote Similarity NPD52 Approved
0.6941 Remote Similarity NPD2669 Clinical (unspecified phase)
0.6938 Remote Similarity NPD3816 Phase 1
0.6938 Remote Similarity NPD3815 Phase 1
0.6935 Remote Similarity NPD8070 Approved
0.6935 Remote Similarity NPD5604 Discontinued
0.6932 Remote Similarity NPD7153 Discontinued
0.6919 Remote Similarity NPD5525 Clinical (unspecified phase)
0.6915 Remote Similarity NPD2973 Approved
0.6915 Remote Similarity NPD2974 Approved
0.6915 Remote Similarity NPD2975 Approved
0.691 Remote Similarity NPD5084 Clinical (unspecified phase)
0.6902 Remote Similarity NPD5720 Discontinued
0.6901 Remote Similarity NPD5110 Phase 2
0.6901 Remote Similarity NPD5111 Phase 2
0.6901 Remote Similarity NPD5109 Approved
0.6895 Remote Similarity NPD2898 Approved
0.6878 Remote Similarity NPD4166 Phase 2
0.6875 Remote Similarity NPD3656 Approved
0.6857 Remote Similarity NPD7827 Phase 1
0.6857 Remote Similarity NPD6380 Phase 1
0.6856 Remote Similarity NPD3386 Phase 2
0.6851 Remote Similarity NPD3647 Clinical (unspecified phase)
0.6848 Remote Similarity NPD7438 Suspended
0.6847 Remote Similarity NPD3837 Clinical (unspecified phase)
0.684 Remote Similarity NPD8149 Discontinued
0.6839 Remote Similarity NPD1772 Clinical (unspecified phase)
0.6837 Remote Similarity NPD6851 Approved
0.6837 Remote Similarity NPD6853 Approved
0.6833 Remote Similarity NPD2421 Approved
0.6833 Remote Similarity NPD2420 Approved
0.6822 Remote Similarity NPD8318 Clinical (unspecified phase)
0.6818 Remote Similarity NPD6841 Approved
0.6818 Remote Similarity NPD7243 Clinical (unspecified phase)
0.6818 Remote Similarity NPD6843 Phase 3
0.6818 Remote Similarity NPD6842 Approved
0.6814 Remote Similarity NPD4580 Approved
0.6813 Remote Similarity NPD5976 Discontinued
0.6811 Remote Similarity NPD5722 Discontinued
0.6804 Remote Similarity NPD6297 Approved
0.6802 Remote Similarity NPD6812 Clinical (unspecified phase)
0.6798 Remote Similarity NPD5177 Phase 3
0.6793 Remote Similarity NPD3296 Phase 1
0.6791 Remote Similarity NPD7773 Phase 2
0.6784 Remote Similarity NPD2845 Phase 2
0.6784 Remote Similarity NPD2843 Phase 2
0.678 Remote Similarity NPD2493 Approved
0.678 Remote Similarity NPD2494 Approved
0.678 Remote Similarity NPD3450 Approved
0.678 Remote Similarity NPD3452 Approved
0.6779 Remote Similarity NPD7263 Phase 2
0.6771 Remote Similarity NPD5966 Clinical (unspecified phase)
0.6766 Remote Similarity NPD7125 Discontinued
0.6766 Remote Similarity NPD6046 Clinical (unspecified phase)
0.6763 Remote Similarity NPD2674 Phase 3
0.6758 Remote Similarity NPD1350 Approved
0.6758 Remote Similarity NPD1351 Approved
0.6758 Remote Similarity NPD1349 Approved
0.6757 Remote Similarity NPD6494 Phase 2
0.6757 Remote Similarity NPD7109 Clinical (unspecified phase)
0.6757 Remote Similarity NPD7110 Phase 1
0.6754 Remote Similarity NPD5242 Approved
0.6754 Remote Similarity NPD4083 Discontinued
0.6752 Remote Similarity NPD7955 Approved
0.6752 Remote Similarity NPD7956 Approved
0.675 Remote Similarity NPD2488 Approved
0.675 Remote Similarity NPD2490 Approved
0.6748 Remote Similarity NPD7590 Clinical (unspecified phase)
0.6746 Remote Similarity NPD2922 Phase 1
0.6746 Remote Similarity NPD7258 Clinical (unspecified phase)
0.674 Remote Similarity NPD7837 Clinical (unspecified phase)
0.6738 Remote Similarity NPD6063 Approved
0.6732 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6732 Remote Similarity NPD6612 Phase 2
0.6728 Remote Similarity NPD6997 Phase 2
0.6724 Remote Similarity NPD3109 Approved
0.6724 Remote Similarity NPD3110 Approved
0.6723 Remote Similarity NPD2161 Phase 2
0.6722 Remote Similarity NPD2219 Phase 1
0.672 Remote Similarity NPD3382 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