NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	249.17
Volume:	277.471
LogP:	2.791
LogD:	2.655
LogS:	-2.843
# Rotatable Bonds:	8
TPSA:	41.49
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.694
Synthetic Accessibility Score:	2.604
Fsp3:	0.467
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:	-4.548
MDCK Permeability:	2.2953398001845926e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.362
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.383

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.255
Plasma Protein Binding (PPB):	79.23778533935547%
Volume Distribution (VD):	3.067
Pgp-substrate:	36.85040283203125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.85
CYP1A2-substrate:	0.105
CYP2C19-inhibitor:	0.051
CYP2C19-substrate:	0.893
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.099
CYP2D6-inhibitor:	0.877
CYP2D6-substrate:	0.899
CYP3A4-inhibitor:	0.033
CYP3A4-substrate:	0.633

ADMET: Excretion

Clearance (CL):	13.028
Half-life (T1/2):	0.366

ADMET: Toxicity

hERG Blockers:	0.171
Human Hepatotoxicity (H-HT):	0.098
Drug-inuced Liver Injury (DILI):	0.013
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.524
Maximum Recommended Daily Dose:	0.892
Skin Sensitization:	0.451
Carcinogencity:	0.062
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.868

Download Data

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

Natural Product: NPC136112

Natural Product ID:	NPC136112
*Common Name:**	(2R)-1-(Propan-2-Ylamino)-3-(2-Prop-2-Enylphenoxy)Propan-2-Ol
IUPAC Name:	(2R)-1-(propan-2-ylamino)-3-(2-prop-2-enylphenoxy)propan-2-ol
Synonyms:
Standard InCHIKey:	PAZJSJFMUHDSTF-CQSZACIVSA-N
Standard InCHI:	InChI=1S/C15H23NO2/c1-4-7-13-8-5-6-9-15(13)18-11-14(17)10-16-12(2)3/h4-6,8-9,12,14,16-17H,1,7,10-11H2,2-3H3/t14-/m1/s1
SMILES:	C=CCc1ccccc1OC[C@@H](CNC(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1395661
PubChem CID:	203685
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002341] Phenol ethers

*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
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1016/S0040-4039(01)00209-X]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10575373]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15467205]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16808005]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23102654]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31103896]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28928	Piper nigrum	Species	Piperaceae	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
AC50	4
IC50	3
Ki	2
Others	2
Potency	11

Activity Type	# Activity
Individual Protein	17
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	Potency	=	3162.3	nM	PMID[540359]
NPT210	Individual Protein	Thyroid stimulating hormone receptor	Homo sapiens	Potency	=	5011.9	nM	PMID[540359]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	Potency	=	6309.6	nM	PMID[540360]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	Potency	=	10000.0	nM	PMID[540359]
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	251.2	nM	PMID[540360]
NPT1139	Individual Protein	Arachidonate 15-lipoxygenase, type II	Homo sapiens	Potency	n.a.	15848.9	nM	PMID[540360]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	AC50	=	6309.57	nM	PMID[540360]
NPT208	Individual Protein	Cytochrome P450 1A2	Homo sapiens	AC50	=	7943.28	nM	PMID[540359]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	AC50	=	10000.0	nM	PMID[540359]
NPT208	Individual Protein	Cytochrome P450 1A2	Homo sapiens	AC50	=	3162.28	nM	PMID[540360]
NPT226	Individual Protein	Beta-2 adrenergic receptor	Homo sapiens	IC50	=	2.344	nM	PMID[540362]
NPT225	Individual Protein	Beta-1 adrenergic receptor	Homo sapiens	Ki	=	64.57	nM	PMID[540362]
NPT225	Individual Protein	Beta-1 adrenergic receptor	Homo sapiens	IC50	=	436.52	nM	PMID[540362]
NPT226	Individual Protein	Beta-2 adrenergic receptor	Homo sapiens	IC50	=	75.86	nM	PMID[540362]
NPT226	Individual Protein	Beta-2 adrenergic receptor	Homo sapiens	Ki	=	18.2	nM	PMID[540362]
NPT95	Individual Protein	Muscarinic acetylcholine receptor M1	Rattus norvegicus	Potency	=	3981.1	nM	PMID[540359]
NPT2	Others	Unspecified		Potency	n.a.	25929.0	nM	PMID[540361]
NPT2	Others	Unspecified		Potency	n.a.	25929.0	nM	PMID[540359]
NPT2	Others	Unspecified		Potency	n.a.	7943.3	nM	PMID[540360]
NPT2	Others	Unspecified		Ratio IC50	=	5.8	n.a.	PMID[540362]
NPT2	Others	Unspecified		Ratio Ki	=	3.55	n.a.	PMID[540362]

☑ 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 NPC136112 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	135
0.1-0.2	1111
0.2-0.3	7536
0.3-0.4	11238
0.4-0.5	6730
0.5-0.6	12294
0.6-0.7	3493
0.7-0.8	147
0.8-0.85	4
0.85-0.9	0
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC141739
0.9667	High Similarity	NPC320242
0.9206	High Similarity	NPC97870
0.9206	High Similarity	NPC307123
0.9206	High Similarity	NPC247018
0.9147	High Similarity	NPC318591
0.9147	High Similarity	NPC231163
0.8382	Intermediate Similarity	NPC204546
0.813	Intermediate Similarity	NPC26524
0.8083	Intermediate Similarity	NPC194034
0.8	Intermediate Similarity	NPC328267
0.7787	Intermediate Similarity	NPC186469
0.7724	Intermediate Similarity	NPC97811
0.771	Intermediate Similarity	NPC211992
0.7686	Intermediate Similarity	NPC108875
0.7686	Intermediate Similarity	NPC38079
0.7652	Intermediate Similarity	NPC298486
0.7623	Intermediate Similarity	NPC470393
0.76	Intermediate Similarity	NPC46844
0.7578	Intermediate Similarity	NPC10286
0.7578	Intermediate Similarity	NPC213
0.754	Intermediate Similarity	NPC21890
0.7521	Intermediate Similarity	NPC51633
0.752	Intermediate Similarity	NPC24777
0.7483	Intermediate Similarity	NPC160931
0.7483	Intermediate Similarity	NPC37205
0.748	Intermediate Similarity	NPC115379
0.748	Intermediate Similarity	NPC42383
0.7464	Intermediate Similarity	NPC329595
0.7464	Intermediate Similarity	NPC326599
0.7462	Intermediate Similarity	NPC137096
0.7459	Intermediate Similarity	NPC192596
0.7417	Intermediate Similarity	NPC313918
0.7417	Intermediate Similarity	NPC95755
0.741	Intermediate Similarity	NPC274732
0.7405	Intermediate Similarity	NPC329980
0.7398	Intermediate Similarity	NPC304761
0.7398	Intermediate Similarity	NPC150254
0.7398	Intermediate Similarity	NPC226778
0.7398	Intermediate Similarity	NPC147000
0.7385	Intermediate Similarity	NPC290470
0.7385	Intermediate Similarity	NPC154256
0.7368	Intermediate Similarity	NPC473875
0.736	Intermediate Similarity	NPC251306
0.7355	Intermediate Similarity	NPC100870
0.7333	Intermediate Similarity	NPC140359
0.7333	Intermediate Similarity	NPC255253
0.7333	Intermediate Similarity	NPC13020
0.7328	Intermediate Similarity	NPC120075
0.7323	Intermediate Similarity	NPC95977
0.7302	Intermediate Similarity	NPC146530
0.7293	Intermediate Similarity	NPC263835
0.7293	Intermediate Similarity	NPC321133
0.7292	Intermediate Similarity	NPC83289
0.7292	Intermediate Similarity	NPC189724
0.7292	Intermediate Similarity	NPC212850
0.729	Intermediate Similarity	NPC469479
0.7287	Intermediate Similarity	NPC301735
0.7286	Intermediate Similarity	NPC208757
0.7285	Intermediate Similarity	NPC203424
0.7285	Intermediate Similarity	NPC206372
0.7273	Intermediate Similarity	NPC283616
0.7266	Intermediate Similarity	NPC55300
0.7266	Intermediate Similarity	NPC166837
0.7239	Intermediate Similarity	NPC475529
0.7237	Intermediate Similarity	NPC477564
0.7237	Intermediate Similarity	NPC2295
0.7237	Intermediate Similarity	NPC233926
0.7236	Intermediate Similarity	NPC327226
0.7226	Intermediate Similarity	NPC158900
0.7218	Intermediate Similarity	NPC256369
0.7209	Intermediate Similarity	NPC165646
0.7206	Intermediate Similarity	NPC474130
0.7203	Intermediate Similarity	NPC318429
0.72	Intermediate Similarity	NPC473855
0.72	Intermediate Similarity	NPC8302
0.7188	Intermediate Similarity	NPC137685
0.7185	Intermediate Similarity	NPC226712
0.7174	Intermediate Similarity	NPC236347
0.7174	Intermediate Similarity	NPC322366
0.7174	Intermediate Similarity	NPC323775
0.7163	Intermediate Similarity	NPC470392
0.7153	Intermediate Similarity	NPC253429
0.7153	Intermediate Similarity	NPC62101
0.7153	Intermediate Similarity	NPC95733
0.7152	Intermediate Similarity	NPC47672
0.7143	Intermediate Similarity	NPC326801
0.7143	Intermediate Similarity	NPC262641
0.7143	Intermediate Similarity	NPC101503
0.7143	Intermediate Similarity	NPC5932
0.7134	Intermediate Similarity	NPC124433
0.7134	Intermediate Similarity	NPC293871
0.7133	Intermediate Similarity	NPC264956
0.7132	Intermediate Similarity	NPC204535
0.7132	Intermediate Similarity	NPC195873
0.7132	Intermediate Similarity	NPC46586
0.7132	Intermediate Similarity	NPC71090
0.7122	Intermediate Similarity	NPC198798
0.7114	Intermediate Similarity	NPC245974
0.7111	Intermediate Similarity	NPC318357
0.7109	Intermediate Similarity	NPC290566
0.7109	Intermediate Similarity	NPC474272
0.7109	Intermediate Similarity	NPC145638
0.7101	Intermediate Similarity	NPC29477
0.7099	Intermediate Similarity	NPC235250
0.7099	Intermediate Similarity	NPC161696
0.7095	Intermediate Similarity	NPC247298
0.7095	Intermediate Similarity	NPC294249
0.709	Intermediate Similarity	NPC163036
0.7089	Intermediate Similarity	NPC469505
0.7087	Intermediate Similarity	NPC233320
0.7087	Intermediate Similarity	NPC258171
0.708	Intermediate Similarity	NPC217277
0.708	Intermediate Similarity	NPC211218
0.7073	Intermediate Similarity	NPC471576
0.7071	Intermediate Similarity	NPC283079
0.7071	Intermediate Similarity	NPC471306
0.7071	Intermediate Similarity	NPC471321
0.7068	Intermediate Similarity	NPC164386
0.7059	Intermediate Similarity	NPC290451
0.7059	Intermediate Similarity	NPC127389
0.7055	Intermediate Similarity	NPC477838
0.7055	Intermediate Similarity	NPC477837
0.7042	Intermediate Similarity	NPC471953
0.704	Intermediate Similarity	NPC305205
0.7037	Intermediate Similarity	NPC60589
0.7037	Intermediate Similarity	NPC469708
0.7037	Intermediate Similarity	NPC232295
0.7034	Intermediate Similarity	NPC474673
0.7031	Intermediate Similarity	NPC241549
0.7029	Intermediate Similarity	NPC109822
0.7029	Intermediate Similarity	NPC48990
0.7029	Intermediate Similarity	NPC94276
0.7029	Intermediate Similarity	NPC114901
0.7029	Intermediate Similarity	NPC293701
0.7021	Intermediate Similarity	NPC97326
0.7016	Intermediate Similarity	NPC214200
0.7016	Intermediate Similarity	NPC228400
0.7008	Intermediate Similarity	NPC41594
0.7	Intermediate Similarity	NPC321956
0.7	Intermediate Similarity	NPC291847
0.7	Intermediate Similarity	NPC473993
0.7	Intermediate Similarity	NPC469386
0.6993	Remote Similarity	NPC160692
0.6993	Remote Similarity	NPC76213
0.6993	Remote Similarity	NPC277669
0.6992	Remote Similarity	NPC303611
0.6992	Remote Similarity	NPC290515
0.6992	Remote Similarity	NPC226096
0.6992	Remote Similarity	NPC108606
0.6992	Remote Similarity	NPC164514
0.6985	Remote Similarity	NPC198734
0.6985	Remote Similarity	NPC83279
0.6985	Remote Similarity	NPC269242
0.6985	Remote Similarity	NPC469412
0.6978	Remote Similarity	NPC194519
0.6978	Remote Similarity	NPC207179
0.6978	Remote Similarity	NPC167571
0.6978	Remote Similarity	NPC470510
0.6978	Remote Similarity	NPC278552
0.6974	Remote Similarity	NPC207824
0.6974	Remote Similarity	NPC60538
0.697	Remote Similarity	NPC470837
0.6966	Remote Similarity	NPC470249
0.6963	Remote Similarity	NPC43275
0.6963	Remote Similarity	NPC135961
0.6963	Remote Similarity	NPC311595
0.6963	Remote Similarity	NPC32152
0.6963	Remote Similarity	NPC24474
0.696	Remote Similarity	NPC84325
0.6957	Remote Similarity	NPC307020
0.6953	Remote Similarity	NPC227894
0.695	Remote Similarity	NPC222572
0.695	Remote Similarity	NPC87224
0.6947	Remote Similarity	NPC474920
0.6947	Remote Similarity	NPC266116
0.694	Remote Similarity	NPC323948
0.6934	Remote Similarity	NPC470804
0.6929	Remote Similarity	NPC58607
0.6929	Remote Similarity	NPC227255
0.6929	Remote Similarity	NPC178284
0.6929	Remote Similarity	NPC191037
0.6928	Remote Similarity	NPC469711
0.6923	Remote Similarity	NPC88868
0.6923	Remote Similarity	NPC103799
0.6923	Remote Similarity	NPC231251
0.6923	Remote Similarity	NPC25067
0.6923	Remote Similarity	NPC118419
0.6918	Remote Similarity	NPC14600
0.6918	Remote Similarity	NPC312770
0.6918	Remote Similarity	NPC204848
0.6918	Remote Similarity	NPC193528
0.6918	Remote Similarity	NPC160607
0.6918	Remote Similarity	NPC41473
0.6917	Remote Similarity	NPC101139
0.6917	Remote Similarity	NPC303370
0.6917	Remote Similarity	NPC71853
0.6917	Remote Similarity	NPC301321
0.6912	Remote Similarity	NPC471308
0.6912	Remote Similarity	NPC193193

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 NPC136112 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	112
0.1-0.2	542
0.2-0.3	1361
0.3-0.4	2194
0.4-0.5	2437
0.5-0.6	1553
0.6-0.7	681
0.7-0.8	211
0.8-0.85	32
0.85-0.9	14
0.9-0.95	11
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD1794	Approved
0.9667	High Similarity	NPD1818	Approved
0.9667	High Similarity	NPD1819	Approved
0.9667	High Similarity	NPD1820	Approved
0.9667	High Similarity	NPD1817	Approved
0.936	High Similarity	NPD3162	Approved
0.936	High Similarity	NPD3163	Approved
0.9355	High Similarity	NPD3165	Approved
0.9355	High Similarity	NPD3166	Approved
0.9355	High Similarity	NPD3164	Approved
0.9355	High Similarity	NPD3167	Approved
0.9286	High Similarity	NPD3597	Clinical (unspecified phase)
0.9206	High Similarity	NPD1423	Approved
0.92	High Similarity	NPD3179	Approved
0.92	High Similarity	NPD3180	Approved
0.9147	High Similarity	NPD2155	Approved
0.9147	High Similarity	NPD2154	Approved
0.9147	High Similarity	NPD2156	Approved
0.8788	High Similarity	NPD2239	Approved
0.8788	High Similarity	NPD2240	Approved
0.877	High Similarity	NPD1797	Approved
0.877	High Similarity	NPD1798	Approved
0.873	High Similarity	NPD1770	Clinical (unspecified phase)
0.8682	High Similarity	NPD3056	Clinical (unspecified phase)
0.8647	High Similarity	NPD3175	Clinical (unspecified phase)
0.8613	High Similarity	NPD1774	Approved
0.8603	High Similarity	NPD2677	Approved
0.8603	High Similarity	NPD5160	Discontinued
0.8548	High Similarity	NPD2554	Approved
0.8548	High Similarity	NPD2556	Approved
0.8538	High Similarity	NPD1336	Approved
0.8456	Intermediate Similarity	NPD5062	Approved
0.8456	Intermediate Similarity	NPD5061	Approved
0.8421	Intermediate Similarity	NPD3052	Approved
0.8421	Intermediate Similarity	NPD3054	Approved
0.8361	Intermediate Similarity	NPD593	Approved
0.8361	Intermediate Similarity	NPD595	Approved
0.8357	Intermediate Similarity	NPD2675	Approved
0.8357	Intermediate Similarity	NPD2676	Approved
0.8333	Intermediate Similarity	NPD3531	Approved
0.8333	Intermediate Similarity	NPD3532	Approved
0.8333	Intermediate Similarity	NPD3530	Approved
0.8321	Intermediate Similarity	NPD4162	Approved
0.832	Intermediate Similarity	NPD3049	Approved
0.8286	Intermediate Similarity	NPD4661	Approved
0.8286	Intermediate Similarity	NPD4662	Approved
0.8279	Intermediate Similarity	NPD594	Approved
0.8279	Intermediate Similarity	NPD592	Approved
0.8209	Intermediate Similarity	NPD1341	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD1416	Approved
0.8182	Intermediate Similarity	NPD2651	Approved
0.8182	Intermediate Similarity	NPD2649	Approved
0.8168	Intermediate Similarity	NPD2250	Discontinued
0.8156	Intermediate Similarity	NPD3536	Discontinued
0.8156	Intermediate Similarity	NPD3985	Discontinued
0.8116	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD2236	Approved
0.8083	Intermediate Similarity	NPD290	Approved
0.8045	Intermediate Similarity	NPD6179	Discontinued
0.8045	Intermediate Similarity	NPD5163	Phase 2
0.8016	Intermediate Similarity	NPD1103	Approved
0.8016	Intermediate Similarity	NPD1102	Approved
0.8014	Intermediate Similarity	NPD3122	Phase 3
0.8	Intermediate Similarity	NPD2428	Approved
0.8	Intermediate Similarity	NPD2429	Approved
0.8	Intermediate Similarity	NPD2557	Approved
0.7945	Intermediate Similarity	NPD6677	Suspended
0.7923	Intermediate Similarity	NPD2235	Phase 2
0.7923	Intermediate Similarity	NPD2231	Phase 2
0.7902	Intermediate Similarity	NPD6419	Discontinued
0.7895	Intermediate Similarity	NPD5266	Clinical (unspecified phase)
0.7869	Intermediate Similarity	NPD2684	Approved
0.7836	Intermediate Similarity	NPD596	Approved
0.7836	Intermediate Similarity	NPD600	Approved
0.7795	Intermediate Similarity	NPD3596	Phase 2
0.7734	Intermediate Similarity	NPD317	Approved
0.7734	Intermediate Similarity	NPD16	Approved
0.7734	Intermediate Similarity	NPD318	Approved
0.7734	Intermediate Similarity	NPD856	Approved
0.7718	Intermediate Similarity	NPD3465	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD6032	Approved
0.7697	Intermediate Similarity	NPD4666	Phase 3
0.7687	Intermediate Similarity	NPD558	Phase 2
0.7687	Intermediate Similarity	NPD3691	Phase 2
0.7687	Intermediate Similarity	NPD3690	Phase 2
0.7676	Intermediate Similarity	NPD2460	Phase 3
0.7676	Intermediate Similarity	NPD2459	Approved
0.7676	Intermediate Similarity	NPD2458	Approved
0.7676	Intermediate Similarity	NPD3060	Approved
0.7676	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD5745	Approved
0.7652	Intermediate Similarity	NPD2562	Approved
0.7652	Intermediate Similarity	NPD2561	Approved
0.7651	Intermediate Similarity	NPD5722	Discontinued
0.7651	Intermediate Similarity	NPD4018	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD2661	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD3152	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD5709	Phase 3
0.7619	Intermediate Similarity	NPD7843	Approved
0.7615	Intermediate Similarity	NPD3443	Approved
0.7615	Intermediate Similarity	NPD3444	Approved
0.7615	Intermediate Similarity	NPD3445	Approved
0.7612	Intermediate Similarity	NPD1134	Approved
0.7612	Intermediate Similarity	NPD1135	Approved
0.7612	Intermediate Similarity	NPD1133	Approved
0.7612	Intermediate Similarity	NPD1131	Approved
0.7612	Intermediate Similarity	NPD1129	Approved
0.7594	Intermediate Similarity	NPD6582	Phase 2
0.7594	Intermediate Similarity	NPD3685	Discontinued
0.7594	Intermediate Similarity	NPD6583	Phase 3
0.7589	Intermediate Similarity	NPD1422	Approved
0.7586	Intermediate Similarity	NPD6087	Phase 1
0.7552	Intermediate Similarity	NPD4236	Phase 3
0.7552	Intermediate Similarity	NPD4237	Approved
0.7548	Intermediate Similarity	NPD2216	Approved
0.7548	Intermediate Similarity	NPD2215	Approved
0.7538	Intermediate Similarity	NPD6581	Approved
0.7538	Intermediate Similarity	NPD2486	Discontinued
0.7538	Intermediate Similarity	NPD316	Approved
0.7538	Intermediate Similarity	NPD6580	Approved
0.7536	Intermediate Similarity	NPD2245	Discovery
0.7534	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD550	Approved
0.752	Intermediate Similarity	NPD551	Approved
0.7518	Intermediate Similarity	NPD5746	Approved
0.7516	Intermediate Similarity	NPD2163	Approved
0.7516	Intermediate Similarity	NPD6315	Phase 2
0.75	Intermediate Similarity	NPD3687	Approved
0.75	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD155	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5373	Approved
0.75	Intermediate Similarity	NPD5374	Approved
0.75	Intermediate Similarity	NPD3686	Approved
0.7483	Intermediate Similarity	NPD52	Approved
0.7483	Intermediate Similarity	NPD7526	Approved
0.7483	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD2595	Approved
0.7481	Intermediate Similarity	NPD2594	Approved
0.748	Intermediate Similarity	NPD821	Approved
0.7464	Intermediate Similarity	NPD601	Approved
0.7464	Intermediate Similarity	NPD597	Approved
0.7464	Intermediate Similarity	NPD598	Approved
0.7464	Intermediate Similarity	NPD3374	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD1048	Approved
0.7462	Intermediate Similarity	NPD9613	Approved
0.7462	Intermediate Similarity	NPD9616	Approved
0.7462	Intermediate Similarity	NPD9615	Approved
0.7452	Intermediate Similarity	NPD5880	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD2200	Suspended
0.7444	Intermediate Similarity	NPD776	Approved
0.7442	Intermediate Similarity	NPD7157	Approved
0.7432	Intermediate Similarity	NPD5976	Discontinued
0.7426	Intermediate Similarity	NPD6584	Phase 3
0.7415	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD2874	Phase 2
0.741	Intermediate Similarity	NPD1130	Approved
0.741	Intermediate Similarity	NPD1132	Approved
0.741	Intermediate Similarity	NPD839	Approved
0.741	Intermediate Similarity	NPD840	Approved
0.741	Intermediate Similarity	NPD1136	Approved
0.7405	Intermediate Similarity	NPD6620	Discovery
0.7398	Intermediate Similarity	NPD315	Approved
0.7398	Intermediate Similarity	NPD314	Approved
0.7398	Intermediate Similarity	NPD311	Approved
0.7398	Intermediate Similarity	NPD309	Approved
0.7398	Intermediate Similarity	NPD310	Approved
0.7398	Intermediate Similarity	NPD10	Approved
0.7389	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD2224	Approved
0.7376	Intermediate Similarity	NPD2223	Approved
0.7372	Intermediate Similarity	NPD455	Discontinued
0.7368	Intermediate Similarity	NPD3294	Phase 2
0.7368	Intermediate Similarity	NPD2978	Approved
0.7368	Intermediate Similarity	NPD2977	Approved
0.7361	Intermediate Similarity	NPD1391	Approved
0.7353	Intermediate Similarity	NPD4098	Discontinued
0.7351	Intermediate Similarity	NPD6072	Discontinued
0.7348	Intermediate Similarity	NPD6382	Discontinued
0.7343	Intermediate Similarity	NPD3156	Discontinued
0.7333	Intermediate Similarity	NPD6543	Approved
0.7333	Intermediate Similarity	NPD6542	Approved
0.7333	Intermediate Similarity	NPD6540	Phase 3
0.7333	Intermediate Similarity	NPD6539	Approved
0.7329	Intermediate Similarity	NPD3692	Discontinued
0.7324	Intermediate Similarity	NPD5688	Approved
0.7324	Intermediate Similarity	NPD5689	Approved
0.7323	Intermediate Similarity	NPD2673	Approved
0.7323	Intermediate Similarity	NPD2671	Approved
0.7319	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD3537	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1769	Discontinued
0.7299	Intermediate Similarity	NPD599	Approved
0.7299	Intermediate Similarity	NPD602	Approved
0.7299	Intermediate Similarity	NPD2987	Approved
0.7299	Intermediate Similarity	NPD7018	Phase 2
0.7299	Intermediate Similarity	NPD2990	Approved
0.7297	Intermediate Similarity	NPD2504	Approved
0.7297	Intermediate Similarity	NPD2505	Approved
0.7293	Intermediate Similarity	NPD2667	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