Structure

Physi-Chem Properties

Molecular Weight:  123.07
Volume:  132.95
LogP:  0.198
LogD:  -0.035
LogS:  0.056
# Rotatable Bonds:  1
TPSA:  46.25
# H-Bond Aceptor:  2
# H-Bond Donor:  3
# Rings:  1
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.581
Synthetic Accessibility Score:  1.596
Fsp3:  0.143
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.534
MDCK Permeability:  2.5817651476245373e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.011
Human Intestinal Absorption (HIA):  0.017
20% Bioavailability (F20%):  0.187
30% Bioavailability (F30%):  0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.083
Plasma Protein Binding (PPB):  17.13528823852539%
Volume Distribution (VD):  1.697
Pgp-substrate:  79.00721740722656%

ADMET: Metabolism

CYP1A2-inhibitor:  0.615
CYP1A2-substrate:  0.318
CYP2C19-inhibitor:  0.143
CYP2C19-substrate:  0.166
CYP2C9-inhibitor:  0.021
CYP2C9-substrate:  0.837
CYP2D6-inhibitor:  0.345
CYP2D6-substrate:  0.893
CYP3A4-inhibitor:  0.042
CYP3A4-substrate:  0.224

ADMET: Excretion

Clearance (CL):  13.426
Half-life (T1/2):  0.887

ADMET: Toxicity

hERG Blockers:  0.069
Human Hepatotoxicity (H-HT):  0.128
Drug-inuced Liver Injury (DILI):  0.031
AMES Toxicity:  0.089
Rat Oral Acute Toxicity:  0.936
Maximum Recommended Daily Dose:  0.039
Skin Sensitization:  0.833
Carcinogencity:  0.13
Eye Corrosion:  0.991
Eye Irritation:  0.157
Respiratory Toxicity:  0.787

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General Info & Identifiers & Properties  
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Similar NPs/Drugs  

  Natural Product: NPC29601

Natural Product ID:  NPC29601
Common Name*:   4-Hydroxybenzylamine
IUPAC Name:   4-(aminomethyl)phenol
Synonyms:   4-(Aminomethyl)Phenol; 4-Hydroxybenzylamine
Standard InCHIKey:  RQJDUEKERVZLLU-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C7H9NO/c8-5-6-1-3-7(9)4-2-6/h1-4,9H,5,8H2
SMILES:  c1cc(ccc1CN)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL202519
PubChem CID:   97472
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0000185] Phenylmethylamines

*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
NPO784 Sinapis alba Species Brassicaceae Eukaryota n.a. seed n.a. DOI[10.1007/s11418-005-0009-z]
NPO26343 Fagopyrum esculentum Species Polygonaceae Eukaryota n.a. seed n.a. PMID[10898633]
NPO22309 Gastrodia elata Species Orchidaceae Eukaryota n.a. tuber n.a. PMID[15180301]
NPO22309 Gastrodia elata Species Orchidaceae Eukaryota n.a. n.a. n.a. PMID[17381154]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[25700090]
NPO22309 Gastrodia elata Species Orchidaceae Eukaryota n.a. n.a. n.a. PMID[25843525]
NPO26343 Fagopyrum esculentum Species Polygonaceae Eukaryota n.a. n.a. Database[FooDB]
NPO26343 Fagopyrum esculentum Species Polygonaceae Eukaryota Flower n.a. n.a. Database[FooDB]
NPO26343 Fagopyrum esculentum Species Polygonaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO26343 Fagopyrum esculentum Species Polygonaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO26343 Fagopyrum esculentum Species Polygonaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO784 Sinapis alba Species Brassicaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO26343 Fagopyrum esculentum Species Polygonaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota n.a. n.a. Database[FooDB]
NPO784 Sinapis alba Species Brassicaceae Eukaryota n.a. n.a. Database[FooDB]
NPO26343 Fagopyrum esculentum Species Polygonaceae Eukaryota n.a. n.a. Database[FooDB]
NPO784 Sinapis alba Species Brassicaceae Eukaryota n.a. n.a. Database[FooDB]
NPO784 Sinapis alba Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22309 Gastrodia elata Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23017 Urtica dioica Species Urticaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26343 Fagopyrum esculentum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23275 Galeola faberi Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22309 Gastrodia elata Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26343 Fagopyrum esculentum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO784 Sinapis alba Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23017 Urtica dioica Species Urticaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23275 Galeola faberi Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO784 Sinapis alba Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23017 Urtica dioica Species Urticaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26343 Fagopyrum esculentum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22309 Gastrodia elata Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22309 Gastrodia elata Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO784 Sinapis alba Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29007 Brassica juncea Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO784 Sinapis alba Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22309 Gastrodia elata Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23275 Galeola faberi Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26343 Fagopyrum esculentum Species Polygonaceae 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
NPT675 Individual Protein Succinate semialdehyde dehydrogenase Homo sapiens IC50 > 1000000.0 nM PMID[492195]
NPT674 Individual Protein Gamma-amino-N-butyrate transaminase Homo sapiens IC50 = 15400.0 nM PMID[492195]
NPT26109 SINGLE PROTEIN Cytokinin dehydrogenase 1 Zea mays Kcat/Km = 0.1583 n.a. PMID[492196]
NPT26109 SINGLE PROTEIN Cytokinin dehydrogenase 1 Zea mays Km = 5500.0 nM PMID[492196]
NPT26109 SINGLE PROTEIN Cytokinin dehydrogenase 1 Zea mays Kcat = 0.871 /s PMID[492196]

☑ 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 NPC29601 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
0.9271 High Similarity NPC125732
0.88 High Similarity NPC68055
0.8654 High Similarity NPC172046
0.86 High Similarity NPC289381
0.86 High Similarity NPC155847
0.8476 Intermediate Similarity NPC290566
0.8476 Intermediate Similarity NPC145638
0.8431 Intermediate Similarity NPC178902
0.8411 Intermediate Similarity NPC146422
0.8298 Intermediate Similarity NPC124436
0.8298 Intermediate Similarity NPC265146
0.8218 Intermediate Similarity NPC107619
0.8211 Intermediate Similarity NPC248817
0.8211 Intermediate Similarity NPC175313
0.819 Intermediate Similarity NPC231705
0.8165 Intermediate Similarity NPC59387
0.8163 Intermediate Similarity NPC151764
0.8125 Intermediate Similarity NPC197783
0.8113 Intermediate Similarity NPC142297
0.8041 Intermediate Similarity NPC23167
0.8041 Intermediate Similarity NPC184169
0.8037 Intermediate Similarity NPC96224
0.8037 Intermediate Similarity NPC153690
0.8037 Intermediate Similarity NPC24101
0.8018 Intermediate Similarity NPC213
0.8018 Intermediate Similarity NPC160179
0.8018 Intermediate Similarity NPC10286
0.7965 Intermediate Similarity NPC85276
0.7963 Intermediate Similarity NPC258056
0.7959 Intermediate Similarity NPC104216
0.7959 Intermediate Similarity NPC25493
0.7959 Intermediate Similarity NPC113460
0.7946 Intermediate Similarity NPC106551
0.7946 Intermediate Similarity NPC188867
0.7946 Intermediate Similarity NPC281686
0.7925 Intermediate Similarity NPC42383
0.789 Intermediate Similarity NPC474149
0.7881 Intermediate Similarity NPC318965
0.7879 Intermediate Similarity NPC242240
0.7879 Intermediate Similarity NPC258219
0.7879 Intermediate Similarity NPC123273
0.7879 Intermediate Similarity NPC98772
0.7879 Intermediate Similarity NPC280347
0.7879 Intermediate Similarity NPC318325
0.7879 Intermediate Similarity NPC177420
0.7835 Intermediate Similarity NPC150837
0.7835 Intermediate Similarity NPC286904
0.7826 Intermediate Similarity NPC118522
0.7826 Intermediate Similarity NPC169207
0.7826 Intermediate Similarity NPC115627
0.78 Intermediate Similarity NPC300478
0.78 Intermediate Similarity NPC300017
0.78 Intermediate Similarity NPC55561
0.7768 Intermediate Similarity NPC142599
0.7768 Intermediate Similarity NPC115803
0.7755 Intermediate Similarity NPC155393
0.7745 Intermediate Similarity NPC20142
0.7745 Intermediate Similarity NPC215351
0.7739 Intermediate Similarity NPC239697
0.7739 Intermediate Similarity NPC283760
0.7723 Intermediate Similarity NPC204210
0.7723 Intermediate Similarity NPC155908
0.7723 Intermediate Similarity NPC45040
0.7723 Intermediate Similarity NPC304541
0.7723 Intermediate Similarity NPC270547
0.7719 Intermediate Similarity NPC137096
0.7706 Intermediate Similarity NPC97811
0.7699 Intermediate Similarity NPC222982
0.7692 Intermediate Similarity NPC315921
0.7677 Intermediate Similarity NPC307235
0.7677 Intermediate Similarity NPC407
0.7647 Intermediate Similarity NPC181709
0.7647 Intermediate Similarity NPC325292
0.7647 Intermediate Similarity NPC138117
0.7611 Intermediate Similarity NPC118202
0.7607 Intermediate Similarity NPC318357
0.76 Intermediate Similarity NPC27974
0.7573 Intermediate Similarity NPC128062
0.7573 Intermediate Similarity NPC27323
0.7573 Intermediate Similarity NPC81010
0.7573 Intermediate Similarity NPC151715
0.7573 Intermediate Similarity NPC316301
0.7573 Intermediate Similarity NPC32977
0.7563 Intermediate Similarity NPC13020
0.7563 Intermediate Similarity NPC140359
0.7544 Intermediate Similarity NPC317254
0.7542 Intermediate Similarity NPC27581
0.7525 Intermediate Similarity NPC70436
0.7524 Intermediate Similarity NPC303611
0.7524 Intermediate Similarity NPC290515
0.7524 Intermediate Similarity NPC164514
0.7524 Intermediate Similarity NPC226096
0.7524 Intermediate Similarity NPC108606
0.75 Intermediate Similarity NPC142638
0.75 Intermediate Similarity NPC8392
0.75 Intermediate Similarity NPC286006
0.75 Intermediate Similarity NPC313650
0.75 Intermediate Similarity NPC274678
0.75 Intermediate Similarity NPC26244
0.75 Intermediate Similarity NPC317784
0.75 Intermediate Similarity NPC107522
0.75 Intermediate Similarity NPC208757
0.7478 Intermediate Similarity NPC82963
0.7455 Intermediate Similarity NPC186469
0.7451 Intermediate Similarity NPC47950
0.7451 Intermediate Similarity NPC312304
0.7451 Intermediate Similarity NPC192
0.7429 Intermediate Similarity NPC82664
0.7429 Intermediate Similarity NPC292730
0.7429 Intermediate Similarity NPC216520
0.7429 Intermediate Similarity NPC202986
0.7429 Intermediate Similarity NPC132271
0.7429 Intermediate Similarity NPC473388
0.7426 Intermediate Similarity NPC19680
0.7417 Intermediate Similarity NPC318777
0.7414 Intermediate Similarity NPC38458
0.7414 Intermediate Similarity NPC283468
0.7414 Intermediate Similarity NPC311737
0.7383 Intermediate Similarity NPC70201
0.7379 Intermediate Similarity NPC306074
0.7379 Intermediate Similarity NPC231150
0.7377 Intermediate Similarity NPC323775
0.7377 Intermediate Similarity NPC236347
0.7368 Intermediate Similarity NPC26524
0.736 Intermediate Similarity NPC33338
0.736 Intermediate Similarity NPC302171
0.736 Intermediate Similarity NPC300020
0.7358 Intermediate Similarity NPC201967
0.7358 Intermediate Similarity NPC77492
0.7358 Intermediate Similarity NPC225464
0.7358 Intermediate Similarity NPC32674
0.7358 Intermediate Similarity NPC260000
0.7358 Intermediate Similarity NPC109955
0.735 Intermediate Similarity NPC122009
0.7345 Intermediate Similarity NPC21890
0.7339 Intermediate Similarity NPC256838
0.7321 Intermediate Similarity NPC71266
0.7317 Intermediate Similarity NPC16031
0.7317 Intermediate Similarity NPC145888
0.7317 Intermediate Similarity NPC161593
0.7315 Intermediate Similarity NPC327226
0.7312 Intermediate Similarity NPC100980
0.7311 Intermediate Similarity NPC326079
0.7308 Intermediate Similarity NPC210497
0.7308 Intermediate Similarity NPC162314
0.7308 Intermediate Similarity NPC55903
0.7308 Intermediate Similarity NPC94139
0.7308 Intermediate Similarity NPC147284
0.7308 Intermediate Similarity NPC306884
0.7308 Intermediate Similarity NPC271440
0.7308 Intermediate Similarity NPC29373
0.7308 Intermediate Similarity NPC3358
0.729 Intermediate Similarity NPC132078
0.729 Intermediate Similarity NPC51333
0.729 Intermediate Similarity NPC92730
0.729 Intermediate Similarity NPC78119
0.729 Intermediate Similarity NPC128723
0.729 Intermediate Similarity NPC245561
0.729 Intermediate Similarity NPC122005
0.729 Intermediate Similarity NPC171843
0.729 Intermediate Similarity NPC275104
0.729 Intermediate Similarity NPC280869
0.729 Intermediate Similarity NPC216468
0.729 Intermediate Similarity NPC130193
0.729 Intermediate Similarity NPC252821
0.729 Intermediate Similarity NPC131587
0.729 Intermediate Similarity NPC80027
0.7288 Intermediate Similarity NPC268572
0.7288 Intermediate Similarity NPC319950
0.7265 Intermediate Similarity NPC120075
0.7248 Intermediate Similarity NPC311660
0.7238 Intermediate Similarity NPC245187
0.7238 Intermediate Similarity NPC152415
0.7238 Intermediate Similarity NPC76938
0.7222 Intermediate Similarity NPC213730
0.7222 Intermediate Similarity NPC223393
0.7222 Intermediate Similarity NPC161571
0.7222 Intermediate Similarity NPC225506
0.7222 Intermediate Similarity NPC253746
0.7222 Intermediate Similarity NPC52472
0.7222 Intermediate Similarity NPC275053
0.7222 Intermediate Similarity NPC248573
0.7209 Intermediate Similarity NPC238412
0.7193 Intermediate Similarity NPC280382
0.7182 Intermediate Similarity NPC150254
0.7182 Intermediate Similarity NPC304761
0.7182 Intermediate Similarity NPC147000
0.7182 Intermediate Similarity NPC226778
0.7172 Intermediate Similarity NPC146703
0.717 Intermediate Similarity NPC257182
0.717 Intermediate Similarity NPC144682
0.717 Intermediate Similarity NPC246679
0.717 Intermediate Similarity NPC32714
0.7168 Intermediate Similarity NPC316052
0.7167 Intermediate Similarity NPC284078
0.7156 Intermediate Similarity NPC40258
0.7156 Intermediate Similarity NPC110764
0.7156 Intermediate Similarity NPC471578
0.7156 Intermediate Similarity NPC91461
0.7156 Intermediate Similarity NPC472585

  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 NPC29601 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
0.89 High Similarity NPD9608 Approved
0.89 High Similarity NPD9610 Approved
0.8476 Intermediate Similarity NPD9380 Clinical (unspecified phase)
0.8411 Intermediate Similarity NPD9377 Approved
0.8411 Intermediate Similarity NPD9379 Approved
0.8298 Intermediate Similarity NPD111 Approved
0.7946 Intermediate Similarity NPD9568 Approved
0.7928 Intermediate Similarity NPD9618 Approved
0.7928 Intermediate Similarity NPD9614 Approved
0.7913 Intermediate Similarity NPD2688 Clinical (unspecified phase)
0.7876 Intermediate Similarity NPD16 Approved
0.7876 Intermediate Similarity NPD317 Approved
0.7876 Intermediate Similarity NPD856 Approved
0.7876 Intermediate Similarity NPD318 Approved
0.7826 Intermediate Similarity NPD9381 Approved
0.7826 Intermediate Similarity NPD9384 Approved
0.7719 Intermediate Similarity NPD9613 Approved
0.7719 Intermediate Similarity NPD9616 Approved
0.7719 Intermediate Similarity NPD9615 Approved
0.7692 Intermediate Similarity NPD9273 Approved
0.7685 Intermediate Similarity NPD1444 Approved
0.7685 Intermediate Similarity NPD1445 Approved
0.7679 Intermediate Similarity NPD2228 Approved
0.7679 Intermediate Similarity NPD2234 Approved
0.7679 Intermediate Similarity NPD2229 Approved
0.7652 Intermediate Similarity NPD316 Approved
0.7573 Intermediate Similarity NPD2933 Approved
0.7573 Intermediate Similarity NPD1432 Clinical (unspecified phase)
0.7573 Intermediate Similarity NPD2934 Approved
0.7563 Intermediate Similarity NPD9622 Approved
0.7544 Intermediate Similarity NPD256 Approved
0.7544 Intermediate Similarity NPD255 Approved
0.7524 Intermediate Similarity NPD9612 Approved
0.7524 Intermediate Similarity NPD9611 Approved
0.7524 Intermediate Similarity NPD9609 Approved
0.75 Intermediate Similarity NPD9634 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD2859 Approved
0.75 Intermediate Similarity NPD5310 Approved
0.75 Intermediate Similarity NPD2860 Approved
0.75 Intermediate Similarity NPD5311 Approved
0.7479 Intermediate Similarity NPD2561 Approved
0.7479 Intermediate Similarity NPD2337 Clinical (unspecified phase)
0.7479 Intermediate Similarity NPD2562 Approved
0.7477 Intermediate Similarity NPD1792 Phase 2
0.7456 Intermediate Similarity NPD1793 Approved
0.7456 Intermediate Similarity NPD1791 Approved
0.7438 Intermediate Similarity NPD3053 Approved
0.7438 Intermediate Similarity NPD3055 Approved
0.7377 Intermediate Similarity NPD9619 Approved
0.7377 Intermediate Similarity NPD2195 Approved
0.7377 Intermediate Similarity NPD9620 Approved
0.7377 Intermediate Similarity NPD9621 Approved
0.7377 Intermediate Similarity NPD2194 Approved
0.735 Intermediate Similarity NPD5304 Approved
0.735 Intermediate Similarity NPD5303 Approved
0.7317 Intermediate Similarity NPD9569 Approved
0.7312 Intermediate Similarity NPD9087 Approved
0.7311 Intermediate Similarity NPD1671 Clinical (unspecified phase)
0.7311 Intermediate Similarity NPD1983 Approved
0.7311 Intermediate Similarity NPD1981 Approved
0.7311 Intermediate Similarity NPD1980 Approved
0.7295 Intermediate Similarity NPD1129 Approved
0.7295 Intermediate Similarity NPD1131 Approved
0.7295 Intermediate Similarity NPD1133 Approved
0.7295 Intermediate Similarity NPD1134 Approved
0.7295 Intermediate Similarity NPD1135 Approved
0.729 Intermediate Similarity NPD3020 Approved
0.7288 Intermediate Similarity NPD4093 Discontinued
0.7236 Intermediate Similarity NPD7451 Discontinued
0.7222 Intermediate Similarity NPD1242 Phase 1
0.7182 Intermediate Similarity NPD309 Approved
0.7182 Intermediate Similarity NPD310 Approved
0.7182 Intermediate Similarity NPD311 Approved
0.7182 Intermediate Similarity NPD10 Approved
0.7182 Intermediate Similarity NPD314 Approved
0.7182 Intermediate Similarity NPD315 Approved
0.717 Intermediate Similarity NPD1809 Phase 2
0.717 Intermediate Similarity NPD844 Approved
0.7156 Intermediate Similarity NPD940 Approved
0.7156 Intermediate Similarity NPD846 Approved
0.7154 Intermediate Similarity NPD1632 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD3144 Approved
0.7143 Intermediate Similarity NPD845 Approved
0.7143 Intermediate Similarity NPD598 Approved
0.7143 Intermediate Similarity NPD597 Approved
0.7143 Intermediate Similarity NPD3145 Approved
0.7143 Intermediate Similarity NPD2028 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD601 Approved
0.7103 Intermediate Similarity NPD288 Approved
0.7099 Intermediate Similarity NPD6809 Clinical (unspecified phase)
0.7087 Intermediate Similarity NPD259 Phase 1
0.7087 Intermediate Similarity NPD1132 Approved
0.7087 Intermediate Similarity NPD1130 Approved
0.7087 Intermediate Similarity NPD2674 Phase 3
0.7087 Intermediate Similarity NPD1136 Approved
0.7083 Intermediate Similarity NPD5238 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD1751 Approved
0.7073 Intermediate Similarity NPD196 Phase 1
0.7063 Intermediate Similarity NPD9537 Phase 1
0.7063 Intermediate Similarity NPD3136 Phase 2
0.7063 Intermediate Similarity NPD9536 Phase 1
0.7059 Intermediate Similarity NPD2226 Clinical (unspecified phase)
0.7043 Intermediate Similarity NPD9508 Approved
0.7031 Intermediate Similarity NPD3059 Approved
0.7031 Intermediate Similarity NPD3061 Approved
0.7031 Intermediate Similarity NPD3062 Approved
0.701 Intermediate Similarity NPD9088 Approved
0.7009 Intermediate Similarity NPD595 Approved
0.7009 Intermediate Similarity NPD593 Approved
0.6992 Remote Similarity NPD4659 Approved
0.6977 Remote Similarity NPD555 Phase 2
0.696 Remote Similarity NPD599 Approved
0.696 Remote Similarity NPD859 Approved
0.696 Remote Similarity NPD258 Approved
0.696 Remote Similarity NPD257 Approved
0.696 Remote Similarity NPD858 Approved
0.696 Remote Similarity NPD602 Approved
0.6957 Remote Similarity NPD9280 Clinical (unspecified phase)
0.6953 Remote Similarity NPD829 Discontinued
0.6953 Remote Similarity NPD6405 Approved
0.6953 Remote Similarity NPD6407 Approved
0.6942 Remote Similarity NPD2667 Approved
0.6942 Remote Similarity NPD2668 Approved
0.694 Remote Similarity NPD7066 Clinical (unspecified phase)
0.6923 Remote Similarity NPD817 Approved
0.6923 Remote Similarity NPD5314 Approved
0.6923 Remote Similarity NPD2568 Approved
0.6923 Remote Similarity NPD823 Approved
0.6917 Remote Similarity NPD1759 Phase 1
0.6911 Remote Similarity NPD2235 Phase 2
0.6911 Remote Similarity NPD2231 Phase 2
0.6909 Remote Similarity NPD289 Clinical (unspecified phase)
0.6907 Remote Similarity NPD9294 Approved
0.6905 Remote Similarity NPD3635 Approved
0.6905 Remote Similarity NPD3636 Approved
0.6905 Remote Similarity NPD3637 Approved
0.6889 Remote Similarity NPD302 Approved
0.688 Remote Similarity NPD4103 Phase 2
0.688 Remote Similarity NPD4104 Clinical (unspecified phase)
0.6855 Remote Similarity NPD4129 Approved
0.685 Remote Similarity NPD3594 Approved
0.685 Remote Similarity NPD600 Approved
0.685 Remote Similarity NPD3595 Approved
0.685 Remote Similarity NPD596 Approved
0.6847 Remote Similarity NPD854 Approved
0.6847 Remote Similarity NPD855 Approved
0.6842 Remote Similarity NPD9507 Approved
0.6838 Remote Similarity NPD2422 Clinical (unspecified phase)
0.6838 Remote Similarity NPD3845 Phase 1
0.6833 Remote Similarity NPD1758 Phase 1
0.6825 Remote Similarity NPD558 Phase 2
0.681 Remote Similarity NPD9376 Approved
0.6797 Remote Similarity NPD9718 Approved
0.6794 Remote Similarity NPD3052 Approved
0.6794 Remote Similarity NPD3054 Approved
0.6791 Remote Similarity NPD7153 Discontinued
0.6767 Remote Similarity NPD9570 Approved
0.6748 Remote Similarity NPD3421 Phase 3
0.6746 Remote Similarity NPD3568 Approved
0.6746 Remote Similarity NPD3567 Approved
0.6742 Remote Similarity NPD3552 Approved
0.6742 Remote Similarity NPD3554 Approved
0.6742 Remote Similarity NPD3555 Approved
0.6742 Remote Similarity NPD3553 Approved
0.6741 Remote Similarity NPD2459 Approved
0.6741 Remote Similarity NPD2460 Phase 3
0.6741 Remote Similarity NPD2458 Approved
0.6733 Remote Similarity NPD9089 Approved
0.6726 Remote Similarity NPD179 Clinical (unspecified phase)
0.6724 Remote Similarity NPD3022 Approved
0.6724 Remote Similarity NPD3021 Approved
0.6721 Remote Similarity NPD2594 Approved
0.6721 Remote Similarity NPD2595 Approved
0.672 Remote Similarity NPD3676 Clinical (unspecified phase)
0.6719 Remote Similarity NPD2614 Approved
0.6719 Remote Similarity NPD2606 Approved
0.6719 Remote Similarity NPD2605 Approved
0.6716 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6696 Remote Similarity NPD4818 Approved
0.6696 Remote Similarity NPD4817 Approved
0.6696 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6695 Remote Similarity NPD821 Approved
0.6694 Remote Similarity NPD313 Approved
0.6694 Remote Similarity NPD5350 Clinical (unspecified phase)
0.6694 Remote Similarity NPD5351 Clinical (unspecified phase)
0.6692 Remote Similarity NPD6866 Clinical (unspecified phase)
0.6692 Remote Similarity NPD839 Approved
0.6692 Remote Similarity NPD840 Approved
0.6692 Remote Similarity NPD6867 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5156 Approved
0.6667 Remote Similarity NPD5155 Approved
0.6642 Remote Similarity NPD1537 Approved
0.6642 Remote Similarity NPD7450 Phase 2
0.6642 Remote Similarity NPD1519 Approved
0.6642 Remote Similarity NPD1538 Phase 1
0.6641 Remote Similarity NPD825 Approved
0.6641 Remote Similarity NPD826 Approved
0.6637 Remote Similarity NPD9500 Approved
0.6637 Remote Similarity NPD4656 Approved
0.6637 Remote Similarity NPD3681 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