NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	165.12
Volume:	184.837
LogP:	0.442
LogD:	0.927
LogS:	-0.147
# Rotatable Bonds:	3
TPSA:	32.26
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.708
Synthetic Accessibility Score:	2.567
Fsp3:	0.4
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:	-4.719
MDCK Permeability:	1.694751153991092e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.841
Plasma Protein Binding (PPB):	16.202104568481445%
Volume Distribution (VD):	3.431
Pgp-substrate:	75.13471221923828%

ADMET: Metabolism

CYP1A2-inhibitor:	0.215
CYP1A2-substrate:	0.126
CYP2C19-inhibitor:	0.051
CYP2C19-substrate:	0.876
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.188
CYP2D6-inhibitor:	0.345
CYP2D6-substrate:	0.795
CYP3A4-inhibitor:	0.014
CYP3A4-substrate:	0.37

ADMET: Excretion

Clearance (CL):	7.875
Half-life (T1/2):	0.503

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.189
Drug-inuced Liver Injury (DILI):	0.017
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.604
Maximum Recommended Daily Dose:	0.871
Skin Sensitization:	0.086
Carcinogencity:	0.017
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.732

Download Data

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

Natural Product: NPC304761

Natural Product ID:	NPC304761
*Common Name:**	(1R,2R)-2-(Methylamino)-1-Phenylpropan-1-Ol
IUPAC Name:	(1R,2R)-2-(methylamino)-1-phenylpropan-1-ol
Synonyms:
Standard InCHIKey:	KWGRBVOPPLSCSI-SCZZXKLOSA-N
Standard InCHI:	InChI=1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10+/m1/s1
SMILES:	CN[C@@H]([C@@H](c1ccccc1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2110905
PubChem CID:	62946
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]
NPO12238	Ephedra lepidosperma	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25122	Conium maculatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12705	Ephedra monosperma	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]
NPO22155	Ephedra saxatilis	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18715.1	Ephedra minuta var. dioeca	Varieties	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21507.1	Ephedra intermedia var. tibetica	Varieties	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23538	Ephedra distachya	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15961	Sida cordifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31194	Ephedra procera	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7976	Ephedra gerardiana	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]
NPO27206	Ephedra tweediana	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20178	Ephedra regeliana	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9315	Ephedra likiangensis	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20722	Ephedra przewalskii	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20178	Ephedra regeliana	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7976	Ephedra gerardiana	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15961	Sida cordifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18715.1	Ephedra minuta var. dioeca	Varieties	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28125	Ephedra equisetina	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18085.1	Ephedra major subsp. procera	Subspecies	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21507.1	Ephedra intermedia var. tibetica	Varieties	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12705	Ephedra monosperma	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]
NPO25122	Conium maculatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23538	Ephedra distachya	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27206	Ephedra tweediana	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22155	Ephedra saxatilis	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12238	Ephedra lepidosperma	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20722	Ephedra przewalskii	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]
NPO9315	Ephedra likiangensis	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7976	Ephedra gerardiana	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23538	Ephedra distachya	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25122	Conium maculatum	Species	Apiaceae	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[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]
NPO12705	Ephedra monosperma	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23538	Ephedra distachya	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15961	Sida cordifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7976	Ephedra gerardiana	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]
NPO25122	Conium maculatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9315	Ephedra likiangensis	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

Activity Type	# Activity
Others	3
Potency	2

Activity Type	# Activity
Individual Protein	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1817	Individual Protein	Aryl sulfotransferase	Rattus norvegicus	Km	=	11000000.0	nM	PMID[465848]
NPT1817	Individual Protein	Aryl sulfotransferase	Rattus norvegicus	Vmax	=	40.4	nM min-1	PMID[465848]
NPT1817	Individual Protein	Aryl sulfotransferase	Rattus norvegicus	Ratio	=	0.1	n.a.	PMID[465848]
NPT2	Others	Unspecified		Potency	n.a.	15848.9	nM	PMID[465849]
NPT2	Others	Unspecified		Potency	n.a.	22387.2	nM	PMID[465849]

☑ 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 NPC304761 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	102
0.1-0.2	1141
0.2-0.3	7190
0.3-0.4	13798
0.4-0.5	14642
0.5-0.6	4749
0.6-0.7	940
0.7-0.8	109
0.8-0.85	8
0.85-0.9	2
0.9-0.95	11
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC147000
1.0	High Similarity	NPC150254
1.0	High Similarity	NPC226778
0.9792	High Similarity	NPC327226
0.9479	High Similarity	NPC108606
0.9479	High Similarity	NPC303611
0.9479	High Similarity	NPC226096
0.9479	High Similarity	NPC290515
0.9479	High Similarity	NPC164514
0.9286	High Similarity	NPC228400
0.9286	High Similarity	NPC214200
0.9167	High Similarity	NPC20142
0.9167	High Similarity	NPC215351
0.8624	High Similarity	NPC10286
0.8624	High Similarity	NPC213
0.8585	High Similarity	NPC24777
0.8468	Intermediate Similarity	NPC137096
0.8073	Intermediate Similarity	NPC292758
0.8073	Intermediate Similarity	NPC290566
0.8073	Intermediate Similarity	NPC145638
0.8073	Intermediate Similarity	NPC65855
0.7965	Intermediate Similarity	NPC101139
0.7917	Intermediate Similarity	NPC103326
0.7917	Intermediate Similarity	NPC329319
0.7917	Intermediate Similarity	NPC87299
0.7917	Intermediate Similarity	NPC99394
0.787	Intermediate Similarity	NPC211551
0.7812	Intermediate Similarity	NPC117180
0.7769	Intermediate Similarity	NPC323775
0.7769	Intermediate Similarity	NPC236347
0.7769	Intermediate Similarity	NPC322366
0.7755	Intermediate Similarity	NPC304538
0.7736	Intermediate Similarity	NPC125732
0.7706	Intermediate Similarity	NPC67043
0.77	Intermediate Similarity	NPC211237
0.7685	Intermediate Similarity	NPC68055
0.767	Intermediate Similarity	NPC265521
0.7664	Intermediate Similarity	NPC155847
0.7664	Intermediate Similarity	NPC289381
0.7627	Intermediate Similarity	NPC326232
0.7611	Intermediate Similarity	NPC269340
0.76	Intermediate Similarity	NPC208757
0.7521	Intermediate Similarity	NPC307020
0.7475	Intermediate Similarity	NPC172984
0.7459	Intermediate Similarity	NPC474479
0.7458	Intermediate Similarity	NPC85276
0.7398	Intermediate Similarity	NPC320242
0.7398	Intermediate Similarity	NPC136112
0.7398	Intermediate Similarity	NPC141739
0.7396	Intermediate Similarity	NPC66655
0.7395	Intermediate Similarity	NPC283760
0.7358	Intermediate Similarity	NPC58674
0.7353	Intermediate Similarity	NPC198747
0.7345	Intermediate Similarity	NPC97811
0.7339	Intermediate Similarity	NPC316797
0.7333	Intermediate Similarity	NPC118522
0.7333	Intermediate Similarity	NPC115627
0.7333	Intermediate Similarity	NPC169207
0.7328	Intermediate Similarity	NPC1986
0.7328	Intermediate Similarity	NPC474544
0.7297	Intermediate Similarity	NPC88267
0.7297	Intermediate Similarity	NPC224610
0.7297	Intermediate Similarity	NPC194390
0.7297	Intermediate Similarity	NPC113326
0.7292	Intermediate Similarity	NPC139658
0.7288	Intermediate Similarity	NPC281686
0.7288	Intermediate Similarity	NPC188867
0.7288	Intermediate Similarity	NPC106551
0.728	Intermediate Similarity	NPC469666
0.7273	Intermediate Similarity	NPC133050
0.7255	Intermediate Similarity	NPC93843
0.7222	Intermediate Similarity	NPC122493
0.7222	Intermediate Similarity	NPC10781
0.7222	Intermediate Similarity	NPC293628
0.7212	Intermediate Similarity	NPC1793
0.7207	Intermediate Similarity	NPC178902
0.7197	Intermediate Similarity	NPC168861
0.7188	Intermediate Similarity	NPC247018
0.7188	Intermediate Similarity	NPC97870
0.7188	Intermediate Similarity	NPC307123
0.7182	Intermediate Similarity	NPC29601
0.7179	Intermediate Similarity	NPC26524
0.7155	Intermediate Similarity	NPC21890
0.7143	Intermediate Similarity	NPC2265
0.7143	Intermediate Similarity	NPC204546
0.7143	Intermediate Similarity	NPC40488
0.7129	Intermediate Similarity	NPC146703
0.7119	Intermediate Similarity	NPC118202
0.7107	Intermediate Similarity	NPC239697
0.7105	Intermediate Similarity	NPC186469
0.7103	Intermediate Similarity	NPC325292
0.7103	Intermediate Similarity	NPC138117
0.7097	Intermediate Similarity	NPC285394
0.7094	Intermediate Similarity	NPC146422
0.7083	Intermediate Similarity	NPC122327
0.7083	Intermediate Similarity	NPC113000
0.7083	Intermediate Similarity	NPC112609
0.7083	Intermediate Similarity	NPC108218
0.708	Intermediate Similarity	NPC42383
0.7075	Intermediate Similarity	NPC226438
0.7073	Intermediate Similarity	NPC474862
0.7064	Intermediate Similarity	NPC324569
0.7059	Intermediate Similarity	NPC317254
0.7059	Intermediate Similarity	NPC168855
0.7045	Intermediate Similarity	NPC214988
0.7037	Intermediate Similarity	NPC161972
0.7037	Intermediate Similarity	NPC303045
0.703	Intermediate Similarity	NPC475199
0.703	Intermediate Similarity	NPC283012
0.7025	Intermediate Similarity	NPC317784
0.7025	Intermediate Similarity	NPC314992
0.7025	Intermediate Similarity	NPC142638
0.7018	Intermediate Similarity	NPC231705
0.7018	Intermediate Similarity	NPC327481
0.7	Intermediate Similarity	NPC192623
0.6992	Remote Similarity	NPC273830
0.6992	Remote Similarity	NPC56634
0.699	Remote Similarity	NPC474354
0.6984	Remote Similarity	NPC65310
0.6983	Remote Similarity	NPC258056
0.6981	Remote Similarity	NPC316108
0.6972	Remote Similarity	NPC25565
0.6972	Remote Similarity	NPC3371
0.6972	Remote Similarity	NPC313650
0.697	Remote Similarity	NPC224544
0.6964	Remote Similarity	NPC318154
0.6957	Remote Similarity	NPC142297
0.6947	Remote Similarity	NPC293377
0.6947	Remote Similarity	NPC260045
0.6947	Remote Similarity	NPC76785
0.6947	Remote Similarity	NPC9687
0.6947	Remote Similarity	NPC273907
0.6947	Remote Similarity	NPC474787
0.6947	Remote Similarity	NPC118099
0.6947	Remote Similarity	NPC475598
0.6947	Remote Similarity	NPC151706
0.6947	Remote Similarity	NPC474811
0.6947	Remote Similarity	NPC90194
0.6947	Remote Similarity	NPC474855
0.6947	Remote Similarity	NPC475318
0.6947	Remote Similarity	NPC49577
0.6947	Remote Similarity	NPC79465
0.6947	Remote Similarity	NPC476102
0.6935	Remote Similarity	NPC27581
0.6923	Remote Similarity	NPC474149
0.6923	Remote Similarity	NPC474211
0.6916	Remote Similarity	NPC79917
0.6916	Remote Similarity	NPC300017
0.6911	Remote Similarity	NPC190663
0.6909	Remote Similarity	NPC473501
0.6909	Remote Similarity	NPC33168
0.6909	Remote Similarity	NPC475439
0.6903	Remote Similarity	NPC164859
0.6897	Remote Similarity	NPC153690
0.6891	Remote Similarity	NPC59387
0.6887	Remote Similarity	NPC199567
0.6887	Remote Similarity	NPC470877
0.6875	Remote Similarity	NPC311753
0.6875	Remote Similarity	NPC208302
0.687	Remote Similarity	NPC267237
0.6869	Remote Similarity	NPC98269
0.6869	Remote Similarity	NPC325662
0.6869	Remote Similarity	NPC290638
0.686	Remote Similarity	NPC82963
0.6855	Remote Similarity	NPC326079
0.6847	Remote Similarity	NPC107619
0.6847	Remote Similarity	NPC474073
0.6847	Remote Similarity	NPC322598
0.6846	Remote Similarity	NPC326599
0.6846	Remote Similarity	NPC329595
0.6837	Remote Similarity	NPC189371
0.6832	Remote Similarity	NPC328178
0.6829	Remote Similarity	NPC319950
0.6827	Remote Similarity	NPC99482
0.6825	Remote Similarity	NPC328267
0.6822	Remote Similarity	NPC209764
0.6822	Remote Similarity	NPC159178
0.6822	Remote Similarity	NPC78041
0.6822	Remote Similarity	NPC471307
0.6822	Remote Similarity	NPC141139
0.6822	Remote Similarity	NPC121872
0.6822	Remote Similarity	NPC74936
0.6818	Remote Similarity	NPC21959
0.6803	Remote Similarity	NPC311737
0.6803	Remote Similarity	NPC38458
0.68	Remote Similarity	NPC160493
0.68	Remote Similarity	NPC12857
0.6794	Remote Similarity	NPC300020
0.6794	Remote Similarity	NPC33338
0.6794	Remote Similarity	NPC149379
0.6794	Remote Similarity	NPC302171
0.6792	Remote Similarity	NPC407
0.6792	Remote Similarity	NPC23167
0.6792	Remote Similarity	NPC307235
0.6791	Remote Similarity	NPC231163
0.6791	Remote Similarity	NPC318591
0.6786	Remote Similarity	NPC12730
0.6783	Remote Similarity	NPC476198
0.6772	Remote Similarity	NPC477248
0.6772	Remote Similarity	NPC171372

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 NPC304761 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	101
0.1-0.2	446
0.2-0.3	1089
0.3-0.4	2278
0.4-0.5	2883
0.5-0.6	1580
0.6-0.7	609
0.7-0.8	135
0.8-0.85	12
0.85-0.9	7
0.9-0.95	6
0.95-1	4

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD314	Approved
1.0	High Similarity	NPD311	Approved
1.0	High Similarity	NPD315	Approved
1.0	High Similarity	NPD309	Approved
1.0	High Similarity	NPD10	Approved
1.0	High Similarity	NPD310	Approved
0.9479	High Similarity	NPD9609	Approved
0.9479	High Similarity	NPD9611	Approved
0.9479	High Similarity	NPD9612	Approved
0.9192	High Similarity	NPD854	Approved
0.9192	High Similarity	NPD855	Approved
0.8807	High Similarity	NPD317	Approved
0.8807	High Similarity	NPD318	Approved
0.8727	High Similarity	NPD2227	Clinical (unspecified phase)
0.8649	High Similarity	NPD1710	Approved
0.8636	High Similarity	NPD828	Approved
0.8585	High Similarity	NPD550	Approved
0.8585	High Similarity	NPD551	Approved
0.8468	Intermediate Similarity	NPD9613	Approved
0.8468	Intermediate Similarity	NPD16	Approved
0.8468	Intermediate Similarity	NPD9616	Approved
0.8468	Intermediate Similarity	NPD9615	Approved
0.8468	Intermediate Similarity	NPD856	Approved
0.8393	Intermediate Similarity	NPD316	Approved
0.8348	Intermediate Similarity	NPD2562	Approved
0.8348	Intermediate Similarity	NPD2561	Approved
0.8348	Intermediate Similarity	NPD4273	Approved
0.8198	Intermediate Similarity	NPD9614	Approved
0.8198	Intermediate Similarity	NPD9618	Approved
0.8158	Intermediate Similarity	NPD770	Discontinued
0.8113	Intermediate Similarity	NPD9608	Approved
0.8113	Intermediate Similarity	NPD9610	Approved
0.8073	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.8053	Intermediate Similarity	NPD6775	Clinical (unspecified phase)
0.7983	Intermediate Similarity	NPD1131	Approved
0.7983	Intermediate Similarity	NPD1135	Approved
0.7983	Intermediate Similarity	NPD1133	Approved
0.7983	Intermediate Similarity	NPD1134	Approved
0.7983	Intermediate Similarity	NPD1129	Approved
0.7963	Intermediate Similarity	NPD812	Approved
0.7963	Intermediate Similarity	NPD811	Approved
0.7963	Intermediate Similarity	NPD810	Approved
0.7917	Intermediate Similarity	NPD602	Approved
0.7917	Intermediate Similarity	NPD599	Approved
0.789	Intermediate Similarity	NPD4095	Clinical (unspecified phase)
0.7807	Intermediate Similarity	NPD7508	Discontinued
0.7805	Intermediate Similarity	NPD601	Approved
0.7805	Intermediate Similarity	NPD864	Approved
0.7805	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD598	Approved
0.7805	Intermediate Similarity	NPD597	Approved
0.7805	Intermediate Similarity	NPD865	Approved
0.7798	Intermediate Similarity	NPD2559	Approved
0.7798	Intermediate Similarity	NPD2551	Approved
0.7769	Intermediate Similarity	NPD859	Approved
0.7769	Intermediate Similarity	NPD9620	Approved
0.7769	Intermediate Similarity	NPD9619	Approved
0.7769	Intermediate Similarity	NPD858	Approved
0.7769	Intermediate Similarity	NPD9621	Approved
0.7757	Intermediate Similarity	NPD4719	Phase 2
0.7742	Intermediate Similarity	NPD1132	Approved
0.7742	Intermediate Similarity	NPD1130	Approved
0.7742	Intermediate Similarity	NPD1136	Approved
0.7679	Intermediate Similarity	NPD4025	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD1814	Approved
0.767	Intermediate Similarity	NPD1812	Approved
0.76	Intermediate Similarity	NPD829	Discontinued
0.7593	Intermediate Similarity	NPD4817	Approved
0.7593	Intermediate Similarity	NPD4818	Approved
0.7586	Intermediate Similarity	NPD5500	Discontinued
0.7565	Intermediate Similarity	NPD593	Approved
0.7565	Intermediate Similarity	NPD595	Approved
0.7559	Intermediate Similarity	NPD3054	Approved
0.7559	Intermediate Similarity	NPD3052	Approved
0.7559	Intermediate Similarity	NPD3528	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD2568	Approved
0.7522	Intermediate Similarity	NPD4254	Approved
0.7522	Intermediate Similarity	NPD4253	Approved
0.7521	Intermediate Similarity	NPD4659	Approved
0.7521	Intermediate Similarity	NPD9622	Approved
0.75	Intermediate Similarity	NPD3552	Approved
0.75	Intermediate Similarity	NPD3555	Approved
0.75	Intermediate Similarity	NPD3553	Approved
0.75	Intermediate Similarity	NPD296	Approved
0.75	Intermediate Similarity	NPD293	Approved
0.75	Intermediate Similarity	NPD3554	Approved
0.75	Intermediate Similarity	NPD295	Approved
0.7422	Intermediate Similarity	NPD823	Approved
0.7422	Intermediate Similarity	NPD817	Approved
0.7398	Intermediate Similarity	NPD1817	Approved
0.7398	Intermediate Similarity	NPD1794	Approved
0.7398	Intermediate Similarity	NPD1820	Approved
0.7398	Intermediate Similarity	NPD1818	Approved
0.7398	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD4103	Phase 2
0.7398	Intermediate Similarity	NPD1819	Approved
0.7396	Intermediate Similarity	NPD9294	Approved
0.7364	Intermediate Similarity	NPD3683	Approved
0.7364	Intermediate Similarity	NPD4658	Approved
0.7364	Intermediate Similarity	NPD4656	Approved
0.7364	Intermediate Similarity	NPD4231	Approved
0.7364	Intermediate Similarity	NPD3682	Approved
0.7364	Intermediate Similarity	NPD3680	Approved
0.7364	Intermediate Similarity	NPD3681	Approved
0.7364	Intermediate Similarity	NPD4229	Approved
0.7339	Intermediate Similarity	NPD2553	Approved
0.7339	Intermediate Similarity	NPD2550	Approved
0.7339	Intermediate Similarity	NPD2555	Approved
0.7339	Intermediate Similarity	NPD2558	Approved
0.7339	Intermediate Similarity	NPD2552	Approved
0.7339	Intermediate Similarity	NPD2549	Approved
0.7333	Intermediate Similarity	NPD7342	Discontinued
0.7333	Intermediate Similarity	NPD9384	Approved
0.7333	Intermediate Similarity	NPD5723	Approved
0.7333	Intermediate Similarity	NPD9381	Approved
0.7323	Intermediate Similarity	NPD6407	Approved
0.7323	Intermediate Similarity	NPD6405	Approved
0.7321	Intermediate Similarity	NPD1444	Approved
0.7321	Intermediate Similarity	NPD1445	Approved
0.7317	Intermediate Similarity	NPD9587	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD3123	Discovery
0.7288	Intermediate Similarity	NPD9568	Approved
0.7273	Intermediate Similarity	NPD4188	Approved
0.7273	Intermediate Similarity	NPD4189	Approved
0.7266	Intermediate Similarity	NPD3059	Approved
0.7266	Intermediate Similarity	NPD3061	Approved
0.7266	Intermediate Similarity	NPD3062	Approved
0.7264	Intermediate Similarity	NPD3719	Approved
0.7264	Intermediate Similarity	NPD3718	Approved
0.7258	Intermediate Similarity	NPD3055	Approved
0.7258	Intermediate Similarity	NPD3053	Approved
0.7258	Intermediate Similarity	NPD3826	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD827	Approved
0.7222	Intermediate Similarity	NPD600	Approved
0.7222	Intermediate Similarity	NPD596	Approved
0.7222	Intermediate Similarity	NPD528	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD9566	Approved
0.7213	Intermediate Similarity	NPD3381	Discontinued
0.7213	Intermediate Similarity	NPD3974	Phase 2
0.7188	Intermediate Similarity	NPD1423	Approved
0.7177	Intermediate Similarity	NPD2198	Approved
0.7177	Intermediate Similarity	NPD2199	Approved
0.7168	Intermediate Similarity	NPD3526	Approved
0.7168	Intermediate Similarity	NPD3524	Approved
0.7165	Intermediate Similarity	NPD3167	Approved
0.7165	Intermediate Similarity	NPD3166	Approved
0.7165	Intermediate Similarity	NPD3165	Approved
0.7165	Intermediate Similarity	NPD3164	Approved
0.7165	Intermediate Similarity	NPD4274	Approved
0.7165	Intermediate Similarity	NPD3720	Discontinued
0.7165	Intermediate Similarity	NPD3136	Phase 2
0.7165	Intermediate Similarity	NPD4275	Approved
0.7155	Intermediate Similarity	NPD4573	Approved
0.7155	Intermediate Similarity	NPD4571	Approved
0.7155	Intermediate Similarity	NPD4572	Approved
0.7154	Intermediate Similarity	NPD5314	Approved
0.7154	Intermediate Similarity	NPD6817	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3047	Approved
0.7143	Intermediate Similarity	NPD179	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3046	Approved
0.7143	Intermediate Similarity	NPD3048	Approved
0.7131	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD1792	Phase 2
0.7129	Intermediate Similarity	NPD830	Approved
0.7129	Intermediate Similarity	NPD831	Approved
0.7097	Intermediate Similarity	NPD5158	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5157	Phase 1
0.7097	Intermediate Similarity	NPD5159	Phase 2
0.7094	Intermediate Similarity	NPD9379	Approved
0.7094	Intermediate Similarity	NPD9377	Approved
0.709	Intermediate Similarity	NPD3638	Discontinued
0.7083	Intermediate Similarity	NPD9592	Approved
0.7083	Intermediate Similarity	NPD9588	Approved
0.7083	Intermediate Similarity	NPD80	Approved
0.7083	Intermediate Similarity	NPD9594	Approved
0.7083	Intermediate Similarity	NPD9589	Approved
0.7083	Intermediate Similarity	NPD9590	Approved
0.7083	Intermediate Similarity	NPD9591	Approved
0.7083	Intermediate Similarity	NPD9593	Approved
0.708	Intermediate Similarity	NPD5717	Approved
0.7071	Intermediate Similarity	NPD590	Approved
0.7071	Intermediate Similarity	NPD589	Approved
0.7059	Intermediate Similarity	NPD785	Approved
0.7049	Intermediate Similarity	NPD2556	Approved
0.7049	Intermediate Similarity	NPD2554	Approved
0.7049	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD7725	Approved
0.7043	Intermediate Similarity	NPD4720	Approved
0.7043	Intermediate Similarity	NPD4717	Approved
0.7043	Intermediate Similarity	NPD4718	Approved
0.704	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD2228	Approved
0.7034	Intermediate Similarity	NPD2234	Approved
0.7034	Intermediate Similarity	NPD2229	Approved
0.7031	Intermediate Similarity	NPD3179	Approved
0.7031	Intermediate Similarity	NPD4497	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD3180	Approved
0.7025	Intermediate Similarity	NPD2106	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2217	Approved
0.7025	Intermediate Similarity	NPD2226	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data