Structure

Physi-Chem Properties

Molecular Weight:  179.13
Volume:  202.133
LogP:  1.458
LogD:  1.214
LogS:  -0.947
# Rotatable Bonds:  3
TPSA:  23.47
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.763
Synthetic Accessibility Score:  2.622
Fsp3:  0.455
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:  -5.017
MDCK Permeability:  1.3144119293428957e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.035
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.008
30% Bioavailability (F30%):  0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.975
Plasma Protein Binding (PPB):  24.916736602783203%
Volume Distribution (VD):  3.783
Pgp-substrate:  71.1818618774414%

ADMET: Metabolism

CYP1A2-inhibitor:  0.145
CYP1A2-substrate:  0.376
CYP2C19-inhibitor:  0.027
CYP2C19-substrate:  0.968
CYP2C9-inhibitor:  0.005
CYP2C9-substrate:  0.203
CYP2D6-inhibitor:  0.847
CYP2D6-substrate:  0.9
CYP3A4-inhibitor:  0.004
CYP3A4-substrate:  0.68

ADMET: Excretion

Clearance (CL):  10.469
Half-life (T1/2):  0.562

ADMET: Toxicity

hERG Blockers:  0.073
Human Hepatotoxicity (H-HT):  0.125
Drug-inuced Liver Injury (DILI):  0.026
AMES Toxicity:  0.007
Rat Oral Acute Toxicity:  0.876
Maximum Recommended Daily Dose:  0.104
Skin Sensitization:  0.086
Carcinogencity:  0.063
Eye Corrosion:  0.007
Eye Irritation:  0.083
Respiratory Toxicity:  0.936

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General Info & Identifiers & Properties  
Structure MOL file  
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  Natural Product: NPC228400

Natural Product ID:  NPC228400
Common Name*:   Methylephedrine
IUPAC Name:   (1R)-2-(dimethylamino)-1-phenylpropan-1-ol
Synonyms:   DL-Methylephedrine HCl; DL-Methylephedrine Saccharinate; L-Methylephedrine HCl; Methylephedrine
Standard InCHIKey:  FMCGSUUBYTWNDP-UMJHXOGRSA-N
Standard InCHI:  InChI=1S/C11H17NO/c1-9(12(2)3)11(13)10-7-5-4-6-8-10/h4-9,11,13H,1-3H3/t9?,11-/m0/s1
SMILES:  CC([C@@H](c1ccccc1)O)N(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1589978
PubChem CID:   9851505
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0002811] Phenylpropanes

*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
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. root n.a. PMID[18975262]
NPO28125 Ephedra equisetina Species Ephedraceae Eukaryota n.a. n.a. n.a. PMID[21465337]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. PMID[24333010]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28125 Ephedra equisetina Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21507 Ephedra intermedia Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28125 Ephedra equisetina Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21507 Ephedra intermedia Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21507 Ephedra intermedia Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28125 Ephedra equisetina Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21507 Ephedra intermedia Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28125 Ephedra equisetina Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28125 Ephedra equisetina Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21507 Ephedra intermedia Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18176 Ephedra sinica Species Ephedraceae 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
NPT48 Individual Protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 35481.3 nM PMID[558258]
NPT5 Individual Protein Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Homo sapiens Potency n.a. 2511.9 nM PMID[558258]
NPT35 Others n.a. pKa = 9.0 n.a. PMID[558257]
NPT35 Others n.a. LogP = 1.55 n.a. PMID[558257]
NPT35 Others n.a. log K = -0.14 n.a. PMID[558257]
NPT35 Others n.a. log K = 0.64 n.a. PMID[558257]
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 19952.6 nM PMID[558258]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 10691.0 nM PMID[558258]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 8492.1 nM PMID[558258]

☑ 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 NPC228400 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 NPC214200
0.9286 High Similarity NPC147000
0.9286 High Similarity NPC150254
0.9286 High Similarity NPC304761
0.9286 High Similarity NPC226778
0.9082 High Similarity NPC327226
0.8969 High Similarity NPC303611
0.8969 High Similarity NPC290515
0.8969 High Similarity NPC108606
0.8969 High Similarity NPC164514
0.8969 High Similarity NPC226096
0.866 High Similarity NPC215351
0.866 High Similarity NPC20142
0.8654 High Similarity NPC292758
0.8654 High Similarity NPC65855
0.8269 Intermediate Similarity NPC211551
0.8191 Intermediate Similarity NPC304538
0.8172 Intermediate Similarity NPC87299
0.8172 Intermediate Similarity NPC99394
0.8172 Intermediate Similarity NPC103326
0.8172 Intermediate Similarity NPC329319
0.8065 Intermediate Similarity NPC117180
0.8058 Intermediate Similarity NPC289381
0.8058 Intermediate Similarity NPC155847
0.8018 Intermediate Similarity NPC213
0.8018 Intermediate Similarity NPC10286
0.8017 Intermediate Similarity NPC307020
0.7982 Intermediate Similarity NPC269340
0.7963 Intermediate Similarity NPC24777
0.7938 Intermediate Similarity NPC211237
0.79 Intermediate Similarity NPC265521
0.7885 Intermediate Similarity NPC316797
0.7876 Intermediate Similarity NPC137096
0.775 Intermediate Similarity NPC469666
0.7745 Intermediate Similarity NPC58674
0.7708 Intermediate Similarity NPC172984
0.7679 Intermediate Similarity NPC1986
0.7679 Intermediate Similarity NPC474544
0.7672 Intermediate Similarity NPC326232
0.7664 Intermediate Similarity NPC88267
0.7664 Intermediate Similarity NPC113326
0.7664 Intermediate Similarity NPC194390
0.7664 Intermediate Similarity NPC224610
0.7636 Intermediate Similarity NPC145638
0.7636 Intermediate Similarity NPC290566
0.7634 Intermediate Similarity NPC66655
0.76 Intermediate Similarity NPC1793
0.7576 Intermediate Similarity NPC198747
0.7563 Intermediate Similarity NPC285394
0.7544 Intermediate Similarity NPC101139
0.75 Intermediate Similarity NPC133050
0.7475 Intermediate Similarity NPC93843
0.7456 Intermediate Similarity NPC118202
0.7438 Intermediate Similarity NPC65310
0.7423 Intermediate Similarity NPC283012
0.7423 Intermediate Similarity NPC475199
0.7407 Intermediate Similarity NPC178902
0.7404 Intermediate Similarity NPC161972
0.7404 Intermediate Similarity NPC303045
0.7395 Intermediate Similarity NPC474862
0.7391 Intermediate Similarity NPC317254
0.7381 Intermediate Similarity NPC474811
0.7381 Intermediate Similarity NPC79465
0.7381 Intermediate Similarity NPC260045
0.7381 Intermediate Similarity NPC151706
0.7381 Intermediate Similarity NPC476102
0.7381 Intermediate Similarity NPC9687
0.7381 Intermediate Similarity NPC474855
0.7381 Intermediate Similarity NPC293377
0.7381 Intermediate Similarity NPC118099
0.7381 Intermediate Similarity NPC76785
0.7381 Intermediate Similarity NPC90194
0.7381 Intermediate Similarity NPC474787
0.7381 Intermediate Similarity NPC475318
0.7381 Intermediate Similarity NPC49577
0.7381 Intermediate Similarity NPC273907
0.7381 Intermediate Similarity NPC475598
0.7377 Intermediate Similarity NPC322366
0.7374 Intermediate Similarity NPC474354
0.7364 Intermediate Similarity NPC231705
0.7358 Intermediate Similarity NPC322598
0.7333 Intermediate Similarity NPC25565
0.7321 Intermediate Similarity NPC258056
0.7312 Intermediate Similarity NPC108218
0.7311 Intermediate Similarity NPC56634
0.7308 Intermediate Similarity NPC325292
0.7308 Intermediate Similarity NPC138117
0.73 Intermediate Similarity NPC474211
0.7297 Intermediate Similarity NPC142297
0.729 Intermediate Similarity NPC125732
0.7282 Intermediate Similarity NPC79917
0.7282 Intermediate Similarity NPC226438
0.7273 Intermediate Similarity NPC168855
0.7264 Intermediate Similarity NPC33168
0.7264 Intermediate Similarity NPC473501
0.7264 Intermediate Similarity NPC475439
0.7257 Intermediate Similarity NPC474149
0.7255 Intermediate Similarity NPC470877
0.7248 Intermediate Similarity NPC68055
0.7236 Intermediate Similarity NPC236347
0.7236 Intermediate Similarity NPC323775
0.7227 Intermediate Similarity NPC190663
0.7213 Intermediate Similarity NPC477248
0.7213 Intermediate Similarity NPC474479
0.7213 Intermediate Similarity NPC477249
0.72 Intermediate Similarity NPC99482
0.7196 Intermediate Similarity NPC474073
0.7188 Intermediate Similarity NPC224544
0.7184 Intermediate Similarity NPC121872
0.7184 Intermediate Similarity NPC141139
0.7184 Intermediate Similarity NPC74936
0.7184 Intermediate Similarity NPC316108
0.7184 Intermediate Similarity NPC471307
0.7184 Intermediate Similarity NPC78041
0.7184 Intermediate Similarity NPC209764
0.7184 Intermediate Similarity NPC159178
0.7179 Intermediate Similarity NPC82963
0.717 Intermediate Similarity NPC313650
0.717 Intermediate Similarity NPC3371
0.7165 Intermediate Similarity NPC132847
0.7156 Intermediate Similarity NPC318154
0.7143 Intermediate Similarity NPC283760
0.7119 Intermediate Similarity NPC311737
0.7119 Intermediate Similarity NPC38458
0.7117 Intermediate Similarity NPC476198
0.7117 Intermediate Similarity NPC67043
0.7115 Intermediate Similarity NPC300017
0.7113 Intermediate Similarity NPC469894
0.7107 Intermediate Similarity NPC252878
0.7107 Intermediate Similarity NPC160493
0.7103 Intermediate Similarity NPC311242
0.7099 Intermediate Similarity NPC251439
0.7097 Intermediate Similarity NPC208302
0.7087 Intermediate Similarity NPC25493
0.7087 Intermediate Similarity NPC199567
0.7087 Intermediate Similarity NPC113460
0.7087 Intermediate Similarity NPC208757
0.7083 Intermediate Similarity NPC321133
0.708 Intermediate Similarity NPC24101
0.708 Intermediate Similarity NPC96224
0.708 Intermediate Similarity NPC153690
0.7073 Intermediate Similarity NPC474847
0.7073 Intermediate Similarity NPC95733
0.7073 Intermediate Similarity NPC171372
0.7073 Intermediate Similarity NPC62101
0.7064 Intermediate Similarity NPC469481
0.7064 Intermediate Similarity NPC469457
0.7059 Intermediate Similarity NPC473031
0.7053 Intermediate Similarity NPC189371
0.7049 Intermediate Similarity NPC46427
0.7041 Intermediate Similarity NPC164449
0.7041 Intermediate Similarity NPC184030
0.7041 Intermediate Similarity NPC328178
0.704 Intermediate Similarity NPC17374
0.703 Intermediate Similarity NPC3210
0.7019 Intermediate Similarity NPC280347
0.7019 Intermediate Similarity NPC318325
0.7019 Intermediate Similarity NPC123273
0.7019 Intermediate Similarity NPC242240
0.7019 Intermediate Similarity NPC177420
0.7019 Intermediate Similarity NPC172128
0.7016 Intermediate Similarity NPC141739
0.7016 Intermediate Similarity NPC320242
0.7016 Intermediate Similarity NPC29477
0.7016 Intermediate Similarity NPC136112
0.7009 Intermediate Similarity NPC21959
0.7 Intermediate Similarity NPC146703
0.7 Intermediate Similarity NPC319950
0.699 Remote Similarity NPC407
0.699 Remote Similarity NPC23167
0.699 Remote Similarity NPC307235
0.6981 Remote Similarity NPC471309
0.6972 Remote Similarity NPC216468
0.6972 Remote Similarity NPC51333
0.6972 Remote Similarity NPC132078
0.6972 Remote Similarity NPC12730
0.6972 Remote Similarity NPC78119
0.6972 Remote Similarity NPC128723
0.6967 Remote Similarity NPC84281
0.6967 Remote Similarity NPC169485
0.6967 Remote Similarity NPC317474
0.6967 Remote Similarity NPC213126
0.6967 Remote Similarity NPC142577
0.6967 Remote Similarity NPC291027
0.6967 Remote Similarity NPC109151
0.6961 Remote Similarity NPC203076
0.6952 Remote Similarity NPC245259
0.6952 Remote Similarity NPC55561
0.6942 Remote Similarity NPC115627
0.6942 Remote Similarity NPC476990
0.6942 Remote Similarity NPC118522
0.6942 Remote Similarity NPC169207
0.6942 Remote Similarity NPC80150
0.6935 Remote Similarity NPC4974
0.693 Remote Similarity NPC97811
0.6923 Remote Similarity NPC276949
0.6923 Remote Similarity NPC27974
0.6923 Remote Similarity NPC26524
0.6923 Remote Similarity NPC104216
0.6923 Remote Similarity NPC35850

  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 NPC228400 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
0.9894 High Similarity NPD854 Approved
0.9894 High Similarity NPD855 Approved
0.9286 High Similarity NPD315 Approved
0.9286 High Similarity NPD310 Approved
0.9286 High Similarity NPD311 Approved
0.9286 High Similarity NPD314 Approved
0.9286 High Similarity NPD309 Approved
0.9286 High Similarity NPD10 Approved
0.8969 High Similarity NPD9612 Approved
0.8969 High Similarity NPD9611 Approved
0.8969 High Similarity NPD9609 Approved
0.8611 High Similarity NPD6775 Clinical (unspecified phase)
0.8544 High Similarity NPD810 Approved
0.8544 High Similarity NPD811 Approved
0.8544 High Similarity NPD812 Approved
0.8462 Intermediate Similarity NPD4095 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD4719 Phase 2
0.8288 Intermediate Similarity NPD2227 Clinical (unspecified phase)
0.8224 Intermediate Similarity NPD4025 Clinical (unspecified phase)
0.8214 Intermediate Similarity NPD1710 Approved
0.8198 Intermediate Similarity NPD828 Approved
0.8198 Intermediate Similarity NPD317 Approved
0.8198 Intermediate Similarity NPD318 Approved
0.8155 Intermediate Similarity NPD4818 Approved
0.8155 Intermediate Similarity NPD4817 Approved
0.8056 Intermediate Similarity NPD4253 Approved
0.8056 Intermediate Similarity NPD4254 Approved
0.8036 Intermediate Similarity NPD856 Approved
0.8036 Intermediate Similarity NPD16 Approved
0.8017 Intermediate Similarity NPD4659 Approved
0.7963 Intermediate Similarity NPD551 Approved
0.7963 Intermediate Similarity NPD550 Approved
0.7931 Intermediate Similarity NPD4273 Approved
0.7931 Intermediate Similarity NPD2562 Approved
0.7931 Intermediate Similarity NPD2561 Approved
0.7905 Intermediate Similarity NPD4656 Approved
0.7905 Intermediate Similarity NPD3682 Approved
0.7905 Intermediate Similarity NPD4658 Approved
0.7905 Intermediate Similarity NPD3681 Approved
0.7905 Intermediate Similarity NPD4229 Approved
0.7905 Intermediate Similarity NPD4231 Approved
0.7905 Intermediate Similarity NPD3680 Approved
0.7905 Intermediate Similarity NPD3683 Approved
0.7885 Intermediate Similarity NPD2553 Approved
0.7885 Intermediate Similarity NPD2555 Approved
0.7885 Intermediate Similarity NPD2550 Approved
0.7885 Intermediate Similarity NPD2552 Approved
0.7885 Intermediate Similarity NPD2558 Approved
0.7885 Intermediate Similarity NPD2549 Approved
0.7881 Intermediate Similarity NPD4104 Clinical (unspecified phase)
0.7881 Intermediate Similarity NPD4103 Phase 2
0.7876 Intermediate Similarity NPD9613 Approved
0.7876 Intermediate Similarity NPD9616 Approved
0.7876 Intermediate Similarity NPD9615 Approved
0.785 Intermediate Similarity NPD1445 Approved
0.785 Intermediate Similarity NPD1444 Approved
0.7826 Intermediate Similarity NPD5723 Approved
0.781 Intermediate Similarity NPD4188 Approved
0.781 Intermediate Similarity NPD4189 Approved
0.7807 Intermediate Similarity NPD316 Approved
0.7788 Intermediate Similarity NPD3123 Discovery
0.7768 Intermediate Similarity NPD9618 Approved
0.7768 Intermediate Similarity NPD9614 Approved
0.7692 Intermediate Similarity NPD3974 Phase 2
0.7685 Intermediate Similarity NPD3524 Approved
0.7685 Intermediate Similarity NPD3526 Approved
0.7664 Intermediate Similarity NPD9610 Approved
0.7664 Intermediate Similarity NPD3048 Approved
0.7664 Intermediate Similarity NPD3046 Approved
0.7664 Intermediate Similarity NPD3047 Approved
0.7664 Intermediate Similarity NPD9608 Approved
0.7658 Intermediate Similarity NPD4572 Approved
0.7658 Intermediate Similarity NPD4573 Approved
0.7658 Intermediate Similarity NPD4571 Approved
0.7636 Intermediate Similarity NPD1792 Phase 2
0.7636 Intermediate Similarity NPD9380 Clinical (unspecified phase)
0.7634 Intermediate Similarity NPD9294 Approved
0.7586 Intermediate Similarity NPD770 Discontinued
0.7583 Intermediate Similarity NPD1134 Approved
0.7583 Intermediate Similarity NPD1129 Approved
0.7583 Intermediate Similarity NPD1135 Approved
0.7583 Intermediate Similarity NPD1131 Approved
0.7583 Intermediate Similarity NPD1133 Approved
0.7563 Intermediate Similarity NPD5157 Phase 1
0.7563 Intermediate Similarity NPD5158 Clinical (unspecified phase)
0.7563 Intermediate Similarity NPD5159 Phase 2
0.7545 Intermediate Similarity NPD4717 Approved
0.7545 Intermediate Similarity NPD4718 Approved
0.7545 Intermediate Similarity NPD4720 Approved
0.7523 Intermediate Similarity NPD2559 Approved
0.7523 Intermediate Similarity NPD2551 Approved
0.7522 Intermediate Similarity NPD2229 Approved
0.7522 Intermediate Similarity NPD2228 Approved
0.7522 Intermediate Similarity NPD2234 Approved
0.7521 Intermediate Similarity NPD602 Approved
0.7521 Intermediate Similarity NPD7725 Approved
0.7521 Intermediate Similarity NPD599 Approved
0.7521 Intermediate Similarity NPD5238 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD2500 Approved
0.75 Intermediate Similarity NPD2226 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD2499 Approved
0.7456 Intermediate Similarity NPD1793 Approved
0.7456 Intermediate Similarity NPD1791 Approved
0.7438 Intermediate Similarity NPD2160 Approved
0.7438 Intermediate Similarity NPD2628 Approved
0.7438 Intermediate Similarity NPD2625 Approved
0.7438 Intermediate Similarity NPD2626 Approved
0.7438 Intermediate Similarity NPD2627 Approved
0.7438 Intermediate Similarity NPD2159 Approved
0.7419 Intermediate Similarity NPD598 Approved
0.7419 Intermediate Similarity NPD865 Approved
0.7419 Intermediate Similarity NPD601 Approved
0.7419 Intermediate Similarity NPD864 Approved
0.7419 Intermediate Similarity NPD3056 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD597 Approved
0.7414 Intermediate Similarity NPD2485 Approved
0.7414 Intermediate Similarity NPD2484 Approved
0.7395 Intermediate Similarity NPD5338 Clinical (unspecified phase)
0.7395 Intermediate Similarity NPD5351 Clinical (unspecified phase)
0.7395 Intermediate Similarity NPD5350 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD7508 Discontinued
0.7379 Intermediate Similarity NPD1812 Approved
0.7379 Intermediate Similarity NPD1814 Approved
0.7379 Intermediate Similarity NPD6690 Approved
0.7377 Intermediate Similarity NPD859 Approved
0.7377 Intermediate Similarity NPD858 Approved
0.7364 Intermediate Similarity NPD5704 Approved
0.7364 Intermediate Similarity NPD5705 Approved
0.7364 Intermediate Similarity NPD5706 Approved
0.736 Intermediate Similarity NPD1130 Approved
0.736 Intermediate Similarity NPD1132 Approved
0.736 Intermediate Similarity NPD1136 Approved
0.735 Intermediate Similarity NPD5303 Approved
0.735 Intermediate Similarity NPD5304 Approved
0.7339 Intermediate Similarity NPD179 Clinical (unspecified phase)
0.7323 Intermediate Similarity NPD6817 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD6025 Phase 1
0.7273 Intermediate Similarity NPD5717 Approved
0.7265 Intermediate Similarity NPD7522 Discontinued
0.7258 Intermediate Similarity NPD5202 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD801 Discontinued
0.7248 Intermediate Similarity NPD1415 Approved
0.7236 Intermediate Similarity NPD9619 Approved
0.7236 Intermediate Similarity NPD9620 Approved
0.7236 Intermediate Similarity NPD9621 Approved
0.7227 Intermediate Similarity NPD7342 Discontinued
0.7222 Intermediate Similarity NPD829 Discontinued
0.72 Intermediate Similarity NPD4275 Approved
0.72 Intermediate Similarity NPD4274 Approved
0.72 Intermediate Similarity NPD3720 Discontinued
0.719 Intermediate Similarity NPD7250 Approved
0.719 Intermediate Similarity NPD7249 Approved
0.7188 Intermediate Similarity NPD3052 Approved
0.7188 Intermediate Similarity NPD2568 Approved
0.7188 Intermediate Similarity NPD3528 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD3054 Approved
0.7179 Intermediate Similarity NPD5500 Discontinued
0.7156 Intermediate Similarity NPD4119 Approved
0.7155 Intermediate Similarity NPD593 Approved
0.7155 Intermediate Similarity NPD595 Approved
0.7143 Intermediate Similarity NPD6038 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6406 Approved
0.7143 Intermediate Similarity NPD4621 Approved
0.7143 Intermediate Similarity NPD4093 Discontinued
0.7143 Intermediate Similarity NPD4619 Approved
0.7143 Intermediate Similarity NPD3719 Approved
0.7143 Intermediate Similarity NPD3718 Approved
0.7132 Intermediate Similarity NPD3552 Approved
0.7132 Intermediate Similarity NPD3554 Approved
0.7132 Intermediate Similarity NPD3555 Approved
0.7132 Intermediate Similarity NPD3553 Approved
0.7131 Intermediate Similarity NPD9622 Approved
0.713 Intermediate Similarity NPD2496 Approved
0.713 Intermediate Similarity NPD2497 Approved
0.712 Intermediate Similarity NPD5203 Approved
0.712 Intermediate Similarity NPD4617 Approved
0.712 Intermediate Similarity NPD5201 Approved
0.712 Intermediate Similarity NPD4620 Approved
0.7113 Intermediate Similarity NPD1051 Approved
0.7113 Intermediate Similarity NPD1053 Approved
0.7113 Intermediate Similarity NPD1052 Approved
0.7109 Intermediate Similarity NPD7430 Approved
0.7109 Intermediate Similarity NPD7431 Approved
0.7107 Intermediate Similarity NPD2173 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD2667 Approved
0.7083 Intermediate Similarity NPD2668 Approved
0.7077 Intermediate Similarity NPD1753 Discontinued
0.7075 Intermediate Similarity NPD4814 Discontinued
0.7064 Intermediate Similarity NPD4760 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD4016 Approved
0.7059 Intermediate Similarity NPD7042 Phase 3
0.7054 Intermediate Similarity NPD817 Approved
0.7054 Intermediate Similarity NPD823 Approved
0.704 Intermediate Similarity NPD767 Phase 1
0.704 Intermediate Similarity NPD3661 Approved
0.704 Intermediate Similarity NPD3664 Approved
0.704 Intermediate Similarity NPD3662 Phase 3
0.704 Intermediate Similarity NPD3663 Approved
0.704 Intermediate Similarity NPD5204 Approved
0.7034 Intermediate Similarity NPD5291 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