Structure

Physi-Chem Properties

Molecular Weight:  315.18
Volume:  341.616
LogP:  2.92
LogD:  3.044
LogS:  -3.123
# Rotatable Bonds:  8
TPSA:  30.93
# H-Bond Aceptor:  4
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.747
Synthetic Accessibility Score:  1.717
Fsp3:  0.368
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:  -4.532
MDCK Permeability:  2.329735980310943e-05
Pgp-inhibitor:  0.997
Pgp-substrate:  0.568
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.497
30% Bioavailability (F30%):  0.67

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.988
Plasma Protein Binding (PPB):  81.5875244140625%
Volume Distribution (VD):  2.155
Pgp-substrate:  4.645596981048584%

ADMET: Metabolism

CYP1A2-inhibitor:  0.385
CYP1A2-substrate:  0.975
CYP2C19-inhibitor:  0.494
CYP2C19-substrate:  0.968
CYP2C9-inhibitor:  0.044
CYP2C9-substrate:  0.731
CYP2D6-inhibitor:  0.966
CYP2D6-substrate:  0.952
CYP3A4-inhibitor:  0.306
CYP3A4-substrate:  0.919

ADMET: Excretion

Clearance (CL):  11.872
Half-life (T1/2):  0.727

ADMET: Toxicity

hERG Blockers:  0.993
Human Hepatotoxicity (H-HT):  0.283
Drug-inuced Liver Injury (DILI):  0.815
AMES Toxicity:  0.018
Rat Oral Acute Toxicity:  0.442
Maximum Recommended Daily Dose:  0.243
Skin Sensitization:  0.901
Carcinogencity:  0.051
Eye Corrosion:  0.112
Eye Irritation:  0.023
Respiratory Toxicity:  0.901

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

  Natural Product: NPC172403

Natural Product ID:  NPC172403
Common Name*:   (3,4-Dimethoxy-Benzyl)-[2-(4-Methoxy-Phenyl)-Ethyl]-Methyl-Amine
IUPAC Name:   N-[(3,4-dimethoxyphenyl)methyl]-2-(4-methoxyphenyl)-N-methylethanamine
Synonyms:  
Standard InCHIKey:  LTXRLUQBZWBCGH-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C19H25NO3/c1-20(12-11-15-5-8-17(21-2)9-6-15)14-16-7-10-18(22-3)19(13-16)23-4/h5-10,13H,11-12,14H2,1-4H3
SMILES:  COc1ccc(cc1)CCN(Cc1ccc(c(c1)OC)OC)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL105087
PubChem CID:   441586
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0001775] Amaryllidaceae alkaloids
        • [CHEMONTID:0004121] Norbelladine-type amaryllidaceae alkaloids

*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
NPO4207 Chlidanthus fragrans Species Amaryllidaceae Eukaryota n.a. n.a. n.a. PMID[21615016]
NPO1346 Nerine bowdenii Species Amaryllidaceae Eukaryota n.a. n.a. n.a. PMID[22312717]
NPO1346 Nerine bowdenii Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4207 Chlidanthus fragrans Species Amaryllidaceae 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
NPT2 Others Unspecified IC50 = 87000.0 nM PMID[530473]
NPT597 Organism Spinacia oleracea Spinacia oleracea Fresh weight = 22.3 ng g-1 PMID[530473]
NPT597 Organism Spinacia oleracea Spinacia oleracea Fresh weight = 174.4 ng g-1 PMID[530473]
NPT597 Organism Spinacia oleracea Spinacia oleracea Fresh weight = 123.5 ng g-1 PMID[530473]

☑ 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 NPC172403 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
0.9206 High Similarity NPC160193
0.916 High Similarity NPC314682
0.9091 High Similarity NPC474915
0.9091 High Similarity NPC188163
0.9091 High Similarity NPC213206
0.9091 High Similarity NPC328750
0.8855 High Similarity NPC11147
0.8824 High Similarity NPC185838
0.8815 High Similarity NPC128019
0.8815 High Similarity NPC476567
0.8815 High Similarity NPC136860
0.8769 High Similarity NPC118419
0.8702 High Similarity NPC160692
0.8696 High Similarity NPC476151
0.8696 High Similarity NPC179825
0.8696 High Similarity NPC210437
0.8696 High Similarity NPC51957
0.8696 High Similarity NPC191376
0.8696 High Similarity NPC106295
0.8696 High Similarity NPC321505
0.8696 High Similarity NPC476144
0.8696 High Similarity NPC16107
0.8651 High Similarity NPC298486
0.8647 High Similarity NPC7018
0.8647 High Similarity NPC167944
0.8647 High Similarity NPC42793
0.8647 High Similarity NPC131204
0.8647 High Similarity NPC301050
0.8647 High Similarity NPC231884
0.8633 High Similarity NPC135538
0.8633 High Similarity NPC475959
0.8633 High Similarity NPC428
0.8633 High Similarity NPC24233
0.8633 High Similarity NPC7467
0.8633 High Similarity NPC147390
0.8633 High Similarity NPC476571
0.8633 High Similarity NPC246587
0.8582 High Similarity NPC253429
0.8571 High Similarity NPC103379
0.8571 High Similarity NPC477565
0.8551 High Similarity NPC130926
0.8527 High Similarity NPC301713
0.8507 High Similarity NPC416184
0.8451 Intermediate Similarity NPC81733
0.8451 Intermediate Similarity NPC326316
0.8444 Intermediate Similarity NPC193528
0.844 Intermediate Similarity NPC207824
0.844 Intermediate Similarity NPC60538
0.844 Intermediate Similarity NPC92541
0.844 Intermediate Similarity NPC219162
0.838 Intermediate Similarity NPC97221
0.838 Intermediate Similarity NPC220858
0.838 Intermediate Similarity NPC88249
0.838 Intermediate Similarity NPC192768
0.838 Intermediate Similarity NPC151895
0.8346 Intermediate Similarity NPC93882
0.8346 Intermediate Similarity NPC130595
0.8322 Intermediate Similarity NPC76213
0.8322 Intermediate Similarity NPC277669
0.8322 Intermediate Similarity NPC476568
0.832 Intermediate Similarity NPC120075
0.8298 Intermediate Similarity NPC95075
0.8298 Intermediate Similarity NPC253883
0.8298 Intermediate Similarity NPC90844
0.8298 Intermediate Similarity NPC144863
0.8284 Intermediate Similarity NPC6854
0.8284 Intermediate Similarity NPC313737
0.8284 Intermediate Similarity NPC285078
0.8276 Intermediate Similarity NPC39701
0.8276 Intermediate Similarity NPC172765
0.8276 Intermediate Similarity NPC54379
0.8276 Intermediate Similarity NPC216459
0.8276 Intermediate Similarity NPC189266
0.8276 Intermediate Similarity NPC193949
0.8276 Intermediate Similarity NPC2413
0.8276 Intermediate Similarity NPC138487
0.8276 Intermediate Similarity NPC207757
0.8276 Intermediate Similarity NPC249797
0.8276 Intermediate Similarity NPC184026
0.8276 Intermediate Similarity NPC204828
0.8276 Intermediate Similarity NPC469817
0.8276 Intermediate Similarity NPC276588
0.8276 Intermediate Similarity NPC110416
0.8276 Intermediate Similarity NPC295691
0.8276 Intermediate Similarity NPC41178
0.8276 Intermediate Similarity NPC93593
0.8276 Intermediate Similarity NPC5238
0.8276 Intermediate Similarity NPC278799
0.8276 Intermediate Similarity NPC127674
0.8271 Intermediate Similarity NPC308885
0.8271 Intermediate Similarity NPC255550
0.8264 Intermediate Similarity NPC210148
0.8264 Intermediate Similarity NPC233029
0.8261 Intermediate Similarity NPC323204
0.8258 Intermediate Similarity NPC155838
0.8252 Intermediate Similarity NPC13397
0.8252 Intermediate Similarity NPC274026
0.8239 Intermediate Similarity NPC130941
0.8222 Intermediate Similarity NPC218530
0.8219 Intermediate Similarity NPC25084
0.8219 Intermediate Similarity NPC146288
0.8219 Intermediate Similarity NPC247639
0.8209 Intermediate Similarity NPC214869
0.8207 Intermediate Similarity NPC477564
0.8207 Intermediate Similarity NPC2295
0.8195 Intermediate Similarity NPC35961
0.8195 Intermediate Similarity NPC52029
0.8195 Intermediate Similarity NPC195749
0.8194 Intermediate Similarity NPC476579
0.8163 Intermediate Similarity NPC476572
0.8156 Intermediate Similarity NPC110337
0.8154 Intermediate Similarity NPC217277
0.8151 Intermediate Similarity NPC187022
0.8151 Intermediate Similarity NPC325871
0.8151 Intermediate Similarity NPC99659
0.8151 Intermediate Similarity NPC80129
0.8138 Intermediate Similarity NPC82285
0.8138 Intermediate Similarity NPC133011
0.8138 Intermediate Similarity NPC148898
0.8134 Intermediate Similarity NPC114102
0.8134 Intermediate Similarity NPC476570
0.8095 Intermediate Similarity NPC126519
0.8095 Intermediate Similarity NPC234392
0.8095 Intermediate Similarity NPC203784
0.8095 Intermediate Similarity NPC31311
0.8095 Intermediate Similarity NPC170503
0.8085 Intermediate Similarity NPC294249
0.8077 Intermediate Similarity NPC471315
0.8077 Intermediate Similarity NPC471314
0.806 Intermediate Similarity NPC262641
0.8054 Intermediate Similarity NPC266753
0.8054 Intermediate Similarity NPC477559
0.8054 Intermediate Similarity NPC306902
0.8054 Intermediate Similarity NPC232924
0.8054 Intermediate Similarity NPC27410
0.8054 Intermediate Similarity NPC166014
0.8054 Intermediate Similarity NPC160298
0.8045 Intermediate Similarity NPC251571
0.8045 Intermediate Similarity NPC153990
0.8041 Intermediate Similarity NPC129603
0.803 Intermediate Similarity NPC318965
0.8029 Intermediate Similarity NPC475828
0.8028 Intermediate Similarity NPC145304
0.8027 Intermediate Similarity NPC244112
0.8027 Intermediate Similarity NPC78733
0.8014 Intermediate Similarity NPC26601
0.8014 Intermediate Similarity NPC476580
0.8 Intermediate Similarity NPC165106
0.8 Intermediate Similarity NPC211992
0.8 Intermediate Similarity NPC60186
0.8 Intermediate Similarity NPC470925
0.8 Intermediate Similarity NPC153631
0.7987 Intermediate Similarity NPC216816
0.7987 Intermediate Similarity NPC477080
0.7987 Intermediate Similarity NPC111485
0.7986 Intermediate Similarity NPC37144
0.7986 Intermediate Similarity NPC231572
0.7986 Intermediate Similarity NPC59907
0.7984 Intermediate Similarity NPC321133
0.7973 Intermediate Similarity NPC147091
0.7972 Intermediate Similarity NPC473934
0.7971 Intermediate Similarity NPC99078
0.7947 Intermediate Similarity NPC233650
0.7947 Intermediate Similarity NPC475393
0.7919 Intermediate Similarity NPC40389
0.7919 Intermediate Similarity NPC148014
0.7919 Intermediate Similarity NPC78359
0.7919 Intermediate Similarity NPC65490
0.7919 Intermediate Similarity NPC315707
0.7914 Intermediate Similarity NPC252107
0.7914 Intermediate Similarity NPC220923
0.7914 Intermediate Similarity NPC470707
0.791 Intermediate Similarity NPC186898
0.7905 Intermediate Similarity NPC76079
0.7899 Intermediate Similarity NPC205178
0.7899 Intermediate Similarity NPC73883
0.7899 Intermediate Similarity NPC277042
0.7899 Intermediate Similarity NPC136330
0.7899 Intermediate Similarity NPC196609
0.7899 Intermediate Similarity NPC255817
0.7899 Intermediate Similarity NPC251454
0.7899 Intermediate Similarity NPC230698
0.7895 Intermediate Similarity NPC238530
0.7895 Intermediate Similarity NPC232514
0.7895 Intermediate Similarity NPC276944
0.7895 Intermediate Similarity NPC134858
0.7895 Intermediate Similarity NPC225774
0.7891 Intermediate Similarity NPC470924
0.7883 Intermediate Similarity NPC266425
0.7879 Intermediate Similarity NPC13020
0.7879 Intermediate Similarity NPC140359
0.7877 Intermediate Similarity NPC223125
0.7874 Intermediate Similarity NPC475815
0.7874 Intermediate Similarity NPC473264
0.7874 Intermediate Similarity NPC47194
0.7867 Intermediate Similarity NPC92191
0.7867 Intermediate Similarity NPC59028
0.7867 Intermediate Similarity NPC118804
0.7857 Intermediate Similarity NPC210086
0.7852 Intermediate Similarity NPC186063

  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 NPC172403 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
0.9127 High Similarity NPD5752 Clinical (unspecified phase)
0.9091 High Similarity NPD4664 Clinical (unspecified phase)
0.8984 High Similarity NPD5718 Phase 2
0.8696 High Similarity NPD4584 Approved
0.8647 High Similarity NPD6895 Approved
0.8647 High Similarity NPD6896 Approved
0.8473 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.8451 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.8451 Intermediate Similarity NPD4017 Approved
0.8444 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.8444 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.844 Intermediate Similarity NPD6030 Approved
0.844 Intermediate Similarity NPD6031 Approved
0.8346 Intermediate Similarity NPD2674 Phase 3
0.8271 Intermediate Similarity NPD3145 Approved
0.8271 Intermediate Similarity NPD3144 Approved
0.8214 Intermediate Similarity NPD5241 Discontinued
0.8214 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.8201 Intermediate Similarity NPD4162 Approved
0.8201 Intermediate Similarity NPD3060 Approved
0.8189 Intermediate Similarity NPD2595 Approved
0.8189 Intermediate Similarity NPD2594 Approved
0.8182 Intermediate Similarity NPD3641 Approved
0.8182 Intermediate Similarity NPD3640 Phase 3
0.8182 Intermediate Similarity NPD3639 Approved
0.8169 Intermediate Similarity NPD1424 Approved
0.8156 Intermediate Similarity NPD7124 Phase 2
0.8156 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.8151 Intermediate Similarity NPD7298 Approved
0.8108 Intermediate Similarity NPD6788 Approved
0.8106 Intermediate Similarity NPD7905 Discontinued
0.8095 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.8085 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.8054 Intermediate Similarity NPD7831 Phase 2
0.8054 Intermediate Similarity NPD7833 Phase 2
0.8054 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.8027 Intermediate Similarity NPD5720 Discontinued
0.8 Intermediate Similarity NPD5283 Phase 1
0.7984 Intermediate Similarity NPD2667 Approved
0.7984 Intermediate Similarity NPD2668 Approved
0.7959 Intermediate Similarity NPD4773 Phase 2
0.7959 Intermediate Similarity NPD4772 Phase 2
0.7947 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7943 Intermediate Similarity NPD5177 Phase 3
0.7941 Intermediate Similarity NPD554 Clinical (unspecified phase)
0.7931 Intermediate Similarity NPD6662 Clinical (unspecified phase)
0.7919 Intermediate Similarity NPD2563 Approved
0.7919 Intermediate Similarity NPD2560 Approved
0.7917 Intermediate Similarity NPD4123 Phase 3
0.7899 Intermediate Similarity NPD2653 Approved
0.7899 Intermediate Similarity NPD2492 Phase 1
0.7895 Intermediate Similarity NPD7802 Discontinued
0.7879 Intermediate Similarity NPD1420 Approved
0.7879 Intermediate Similarity NPD1421 Approved
0.7872 Intermediate Similarity NPD7153 Discontinued
0.7829 Intermediate Similarity NPD5677 Discontinued
0.7829 Intermediate Similarity NPD2486 Discontinued
0.7823 Intermediate Similarity NPD824 Approved
0.782 Intermediate Similarity NPD7258 Clinical (unspecified phase)
0.7817 Intermediate Similarity NPD4237 Approved
0.7817 Intermediate Similarity NPD4236 Phase 3
0.781 Intermediate Similarity NPD4474 Approved
0.781 Intermediate Similarity NPD4475 Approved
0.7808 Intermediate Similarity NPD5976 Discontinued
0.78 Intermediate Similarity NPD5977 Approved
0.78 Intermediate Similarity NPD5978 Approved
0.7786 Intermediate Similarity NPD3294 Phase 2
0.777 Intermediate Similarity NPD1337 Clinical (unspecified phase)
0.777 Intermediate Similarity NPD2986 Phase 2
0.777 Intermediate Similarity NPD2989 Phase 2
0.7727 Intermediate Similarity NPD4010 Discontinued
0.7718 Intermediate Similarity NPD7110 Phase 1
0.7718 Intermediate Similarity NPD7109 Clinical (unspecified phase)
0.7714 Intermediate Similarity NPD6111 Discontinued
0.7704 Intermediate Similarity NPD2990 Approved
0.7704 Intermediate Similarity NPD2987 Approved
0.7687 Intermediate Similarity NPD2922 Phase 1
0.7681 Intermediate Similarity NPD3530 Approved
0.7681 Intermediate Similarity NPD3531 Approved
0.7681 Intermediate Similarity NPD3532 Approved
0.7676 Intermediate Similarity NPD3656 Approved
0.7674 Intermediate Similarity NPD3596 Phase 2
0.7669 Intermediate Similarity NPD2233 Approved
0.7669 Intermediate Similarity NPD2232 Approved
0.7669 Intermediate Similarity NPD2230 Approved
0.7651 Intermediate Similarity NPD6876 Approved
0.7651 Intermediate Similarity NPD6875 Approved
0.7651 Intermediate Similarity NPD4678 Approved
0.7651 Intermediate Similarity NPD4675 Approved
0.7643 Intermediate Similarity NPD8252 Approved
0.7643 Intermediate Similarity NPD8251 Approved
0.7643 Intermediate Similarity NPD8099 Discontinued
0.7639 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7639 Intermediate Similarity NPD6331 Phase 2
0.763 Intermediate Similarity NPD3053 Approved
0.763 Intermediate Similarity NPD4098 Discontinued
0.763 Intermediate Similarity NPD3055 Approved
0.7615 Intermediate Similarity NPD5536 Phase 2
0.7613 Intermediate Similarity NPD6071 Discontinued
0.7612 Intermediate Similarity NPD1669 Approved
0.7606 Intermediate Similarity NPD2161 Phase 2
0.7603 Intermediate Similarity NPD3124 Discontinued
0.76 Intermediate Similarity NPD6385 Approved
0.76 Intermediate Similarity NPD6386 Approved
0.7595 Intermediate Similarity NPD8156 Discontinued
0.758 Intermediate Similarity NPD5966 Clinical (unspecified phase)
0.7564 Intermediate Similarity NPD4083 Discontinued
0.7564 Intermediate Similarity NPD6687 Approved
0.7564 Intermediate Similarity NPD6688 Approved
0.7556 Intermediate Similarity NPD5310 Approved
0.7556 Intermediate Similarity NPD5311 Approved
0.7551 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7548 Intermediate Similarity NPD6107 Approved
0.7532 Intermediate Similarity NPD5708 Clinical (unspecified phase)
0.7518 Intermediate Similarity NPD4579 Clinical (unspecified phase)
0.7517 Intermediate Similarity NPD4210 Discontinued
0.7517 Intermediate Similarity NPD3977 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD2898 Approved
0.75 Intermediate Similarity NPD6382 Discontinued
0.75 Intermediate Similarity NPD1044 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD4166 Phase 2
0.75 Intermediate Similarity NPD3110 Approved
0.75 Intermediate Similarity NPD2238 Phase 2
0.75 Intermediate Similarity NPD2977 Approved
0.75 Intermediate Similarity NPD3109 Approved
0.75 Intermediate Similarity NPD2978 Approved
0.75 Intermediate Similarity NPD6297 Approved
0.75 Intermediate Similarity NPD3647 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD6873 Phase 2
0.7483 Intermediate Similarity NPD3156 Discontinued
0.7482 Intermediate Similarity NPD6812 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD5604 Discontinued
0.7448 Intermediate Similarity NPD44 Approved
0.7448 Intermediate Similarity NPD2459 Approved
0.7448 Intermediate Similarity NPD2458 Approved
0.7448 Intermediate Similarity NPD6364 Approved
0.7448 Intermediate Similarity NPD2460 Phase 3
0.7445 Intermediate Similarity NPD6584 Phase 3
0.7444 Intermediate Similarity NPD2423 Clinical (unspecified phase)
0.7429 Intermediate Similarity NPD2245 Discovery
0.7424 Intermediate Similarity NPD6581 Approved
0.7424 Intermediate Similarity NPD6580 Approved
0.7422 Intermediate Similarity NPD228 Approved
0.7413 Intermediate Similarity NPD6380 Phase 1
0.7413 Intermediate Similarity NPD3693 Clinical (unspecified phase)
0.7385 Intermediate Similarity NPD593 Approved
0.7385 Intermediate Similarity NPD595 Approved
0.7368 Intermediate Similarity NPD3444 Approved
0.7368 Intermediate Similarity NPD3049 Approved
0.7368 Intermediate Similarity NPD3443 Approved
0.7368 Intermediate Similarity NPD3445 Approved
0.7368 Intermediate Similarity NPD6830 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD5297 Approved
0.7362 Intermediate Similarity NPD7280 Phase 3
0.7362 Intermediate Similarity NPD7281 Phase 3
0.7357 Intermediate Similarity NPD5111 Phase 2
0.7357 Intermediate Similarity NPD5110 Phase 2
0.7357 Intermediate Similarity NPD3374 Clinical (unspecified phase)
0.7357 Intermediate Similarity NPD5109 Approved
0.7355 Intermediate Similarity NPD4055 Discovery
0.7353 Intermediate Similarity NPD2429 Approved
0.7353 Intermediate Similarity NPD2428 Approved
0.7333 Intermediate Similarity NPD1914 Approved
0.7329 Intermediate Similarity NPD3885 Approved
0.7328 Intermediate Similarity NPD2557 Approved
0.732 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7319 Intermediate Similarity NPD7018 Phase 2
0.7317 Intermediate Similarity NPD6853 Approved
0.7317 Intermediate Similarity NPD6618 Phase 2
0.7317 Intermediate Similarity NPD8054 Approved
0.7317 Intermediate Similarity NPD8053 Approved
0.7317 Intermediate Similarity NPD6851 Approved
0.7315 Intermediate Similarity NPD1771 Clinical (unspecified phase)
0.7313 Intermediate Similarity NPD2556 Approved
0.7313 Intermediate Similarity NPD2554 Approved
0.731 Intermediate Similarity NPD1375 Discontinued
0.7301 Intermediate Similarity NPD7132 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD2120 Phase 2
0.729 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7285 Intermediate Similarity NPD3687 Approved
0.7285 Intermediate Similarity NPD3686 Approved
0.7279 Intermediate Similarity NPD2981 Phase 2
0.7278 Intermediate Similarity NPD3051 Approved
0.7273 Intermediate Similarity NPD5772 Approved
0.7273 Intermediate Similarity NPD5773 Approved
0.7267 Intermediate Similarity NPD6090 Discontinued
0.7267 Intermediate Similarity NPD5312 Approved
0.7267 Intermediate Similarity NPD5313 Approved
0.7267 Intermediate Similarity NPD6890 Discontinued
0.726 Intermediate Similarity NPD1372 Clinical (unspecified phase)
0.726 Intermediate Similarity NPD4597 Approved
0.726 Intermediate Similarity NPD4598 Approved
0.7256 Intermediate Similarity NPD5917 Clinical (unspecified phase)
0.7254 Intermediate Similarity NPD3061 Approved
0.7254 Intermediate Similarity NPD3059 Approved
0.7254 Intermediate Similarity NPD3062 Approved
0.7248 Intermediate Similarity NPD7598 Phase 2
0.7248 Intermediate Similarity NPD2420 Approved
0.7248 Intermediate Similarity NPD2421 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