NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	246.14
Volume:	259.979
LogP:	-2.079
LogD:	-0.998
LogS:	0.322
# Rotatable Bonds:	4
TPSA:	55.92
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.8
Synthetic Accessibility Score:	3.382
Fsp3:	0.357
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:	-5.505
MDCK Permeability:	1.3752117411058862e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.113
Human Intestinal Absorption (HIA):	0.739
20% Bioavailability (F20%):	0.916
30% Bioavailability (F30%):	0.635

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.317
Plasma Protein Binding (PPB):	11.99693489074707%
Volume Distribution (VD):	0.817
Pgp-substrate:	84.73667907714844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.879
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.815
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.794
CYP3A4-inhibitor:	0.008
CYP3A4-substrate:	0.057

ADMET: Excretion

Clearance (CL):	3.09
Half-life (T1/2):	0.943

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.14
Drug-inuced Liver Injury (DILI):	0.014
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.444
Maximum Recommended Daily Dose:	0.862
Skin Sensitization:	0.028
Carcinogencity:	0.066
Eye Corrosion:	0.008
Eye Irritation:	0.141
Respiratory Toxicity:	0.03

Download Data

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

Natural Product: NPC84827

Natural Product ID:	NPC84827
*Common Name:**	Hypaphorine
IUPAC Name:	(2S)-3-(1H-indol-3-yl)-2-(trimethylazaniumyl)propanoate
Synonyms:
Standard InCHIKey:	AOHCBEAZXHZMOR-ZDUSSCGKSA-N
Standard InCHI:	InChI=1S/C14H18N2O2/c1-16(2,3)13(14(17)18)8-10-9-15-12-7-5-4-6-11(10)12/h4-7,9,13,15H,8H2,1-3H3/t13-/m0/s1
SMILES:	[O-]C(=O)[C@@H]([N+](C)(C)C)Cc1c[nH]c2c1cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2235164
PubChem CID:	442106
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives [CHEMONTID:0002404] Alpha amino acids [CHEMONTID:0004146] L-alpha-amino acids

*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
NPO17784	Botrylloides tyreum	Species	Styelidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15217298]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	root	n.a.	PMID[16564530]
NPO31147	Pisolithus microcarpus	Species	Pisolithaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17370110]
NPO3802	Pisolithus tinctorius	Species	Pisolithaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24997926]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29359942]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[31944695]
NPO8301	Erythrina suberosa	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[5348524]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	Roots; Tubers	n.a.	n.a.	PMID[7714535]
NPO3802	Pisolithus tinctorius	Species	Pisolithaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9951730]
NPO8301	Erythrina suberosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3802	Pisolithus tinctorius	Species	Pisolithaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8301	Erythrina suberosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8301	Erythrina suberosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6792	Hedysarum polybotrys	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17784	Botrylloides tyreum	Species	Styelidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6944	Senegalia senegal	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4371	Rissoella verruculosa	Species	Rissoellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12702	Sarcocapnos baetica	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14858	Human immunodeficiency	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO17941	Aloe peglerae	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17864	Callicarpa furfuracea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6005	Osmundaria fimbriata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8301	Erythrina suberosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5332	Smallanthus fruticosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6792	Hedysarum polybotrys	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3802	Pisolithus tinctorius	Species	Pisolithaceae	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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	20.4	%	PMID[522298]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	27.8	%	PMID[522298]

☑ 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 NPC84827 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	349
0.1-0.2	3181
0.2-0.3	17345
0.3-0.4	14441
0.4-0.5	2809
0.5-0.6	2182
0.6-0.7	1514
0.7-0.8	715
0.8-0.85	118
0.85-0.9	18
0.9-0.95	18
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC145885
1.0	High Similarity	NPC14113
0.9689	High Similarity	NPC248041
0.9689	High Similarity	NPC126709
0.9568	High Similarity	NPC283219
0.9565	High Similarity	NPC267885
0.9503	High Similarity	NPC203468
0.9503	High Similarity	NPC110500
0.9503	High Similarity	NPC149155
0.9255	High Similarity	NPC78020
0.9226	High Similarity	NPC235684
0.908	High Similarity	NPC262898
0.9023	High Similarity	NPC179701
0.9006	High Similarity	NPC321708
0.8929	High Similarity	NPC469896
0.8869	High Similarity	NPC219336
0.8869	High Similarity	NPC55772
0.881	High Similarity	NPC217372
0.881	High Similarity	NPC15573
0.881	High Similarity	NPC111275
0.881	High Similarity	NPC183662
0.8757	High Similarity	NPC213468
0.8663	High Similarity	NPC228835
0.8659	High Similarity	NPC282231
0.8647	High Similarity	NPC11126
0.8626	High Similarity	NPC473376
0.8621	High Similarity	NPC17059
0.8614	High Similarity	NPC160105
0.8614	High Similarity	NPC474561
0.8614	High Similarity	NPC49954
0.8598	High Similarity	NPC279918
0.8571	High Similarity	NPC213629
0.8563	High Similarity	NPC94752
0.8563	High Similarity	NPC315555
0.85	High Similarity	NPC171317
0.8457	Intermediate Similarity	NPC62749
0.8453	Intermediate Similarity	NPC293917
0.8452	Intermediate Similarity	NPC63751
0.8441	Intermediate Similarity	NPC478158
0.8439	Intermediate Similarity	NPC71037
0.8415	Intermediate Similarity	NPC476874
0.8412	Intermediate Similarity	NPC314603
0.8407	Intermediate Similarity	NPC315491
0.8407	Intermediate Similarity	NPC45459
0.8405	Intermediate Similarity	NPC259644
0.8405	Intermediate Similarity	NPC469786
0.8405	Intermediate Similarity	NPC25008
0.8405	Intermediate Similarity	NPC469760
0.8405	Intermediate Similarity	NPC469765
0.8405	Intermediate Similarity	NPC73952
0.8405	Intermediate Similarity	NPC469763
0.8393	Intermediate Similarity	NPC54988
0.8383	Intermediate Similarity	NPC194640
0.8354	Intermediate Similarity	NPC80597
0.8354	Intermediate Similarity	NPC70922
0.8354	Intermediate Similarity	NPC211572
0.8354	Intermediate Similarity	NPC212376
0.8354	Intermediate Similarity	NPC75540
0.8333	Intermediate Similarity	NPC233936
0.8291	Intermediate Similarity	NPC73767
0.8278	Intermediate Similarity	NPC88315
0.8263	Intermediate Similarity	NPC54744
0.8261	Intermediate Similarity	NPC314372
0.8253	Intermediate Similarity	NPC469762
0.825	Intermediate Similarity	NPC190296
0.8242	Intermediate Similarity	NPC272483
0.8239	Intermediate Similarity	NPC165495
0.822	Intermediate Similarity	NPC478157
0.8193	Intermediate Similarity	NPC469785
0.8187	Intermediate Similarity	NPC281049
0.8182	Intermediate Similarity	NPC469358
0.8177	Intermediate Similarity	NPC472210
0.8177	Intermediate Similarity	NPC81802
0.8177	Intermediate Similarity	NPC247735
0.8177	Intermediate Similarity	NPC269886
0.8177	Intermediate Similarity	NPC472295
0.8176	Intermediate Similarity	NPC110126
0.8171	Intermediate Similarity	NPC91179
0.8168	Intermediate Similarity	NPC229348
0.8166	Intermediate Similarity	NPC311276
0.8165	Intermediate Similarity	NPC84911
0.8161	Intermediate Similarity	NPC59269
0.8161	Intermediate Similarity	NPC248454
0.815	Intermediate Similarity	NPC469938
0.8142	Intermediate Similarity	NPC227582
0.8138	Intermediate Similarity	NPC54420
0.8125	Intermediate Similarity	NPC469783
0.8125	Intermediate Similarity	NPC469779
0.8125	Intermediate Similarity	NPC469768
0.8125	Intermediate Similarity	NPC469780
0.8125	Intermediate Similarity	NPC469767
0.8125	Intermediate Similarity	NPC469784
0.8125	Intermediate Similarity	NPC469761
0.8122	Intermediate Similarity	NPC472292
0.8115	Intermediate Similarity	NPC207020
0.8115	Intermediate Similarity	NPC75634
0.8111	Intermediate Similarity	NPC314333
0.8111	Intermediate Similarity	NPC329858
0.8111	Intermediate Similarity	NPC83111
0.8101	Intermediate Similarity	NPC96102
0.8101	Intermediate Similarity	NPC261195
0.8101	Intermediate Similarity	NPC29886
0.8098	Intermediate Similarity	NPC67288
0.8098	Intermediate Similarity	NPC473640
0.8095	Intermediate Similarity	NPC230869
0.8083	Intermediate Similarity	NPC36405
0.8079	Intermediate Similarity	NPC143533
0.8075	Intermediate Similarity	NPC469766
0.8072	Intermediate Similarity	NPC200214
0.8066	Intermediate Similarity	NPC138370
0.8065	Intermediate Similarity	NPC475506
0.8063	Intermediate Similarity	NPC82370
0.8061	Intermediate Similarity	NPC105818
0.8061	Intermediate Similarity	NPC24678
0.8056	Intermediate Similarity	NPC196251
0.8056	Intermediate Similarity	NPC111602
0.8056	Intermediate Similarity	NPC175474
0.8056	Intermediate Similarity	NPC63199
0.8056	Intermediate Similarity	NPC102338
0.8054	Intermediate Similarity	NPC100321
0.8054	Intermediate Similarity	NPC74413
0.8053	Intermediate Similarity	NPC162860
0.805	Intermediate Similarity	NPC105127
0.8045	Intermediate Similarity	NPC474707
0.8037	Intermediate Similarity	NPC159856
0.8034	Intermediate Similarity	NPC477003
0.8031	Intermediate Similarity	NPC313640
0.8021	Intermediate Similarity	NPC155143
0.8021	Intermediate Similarity	NPC118940
0.8011	Intermediate Similarity	NPC213308
0.8011	Intermediate Similarity	NPC252338
0.8	Intermediate Similarity	NPC204565
0.8	Intermediate Similarity	NPC278434
0.8	Intermediate Similarity	NPC317030
0.7989	Intermediate Similarity	NPC472293
0.7989	Intermediate Similarity	NPC11445
0.7978	Intermediate Similarity	NPC163055
0.7976	Intermediate Similarity	NPC285469
0.7967	Intermediate Similarity	NPC117244
0.7967	Intermediate Similarity	NPC473763
0.7956	Intermediate Similarity	NPC173028
0.7956	Intermediate Similarity	NPC65215
0.7955	Intermediate Similarity	NPC284775
0.7953	Intermediate Similarity	NPC40779
0.7946	Intermediate Similarity	NPC156704
0.7941	Intermediate Similarity	NPC131718
0.7939	Intermediate Similarity	NPC471957
0.7935	Intermediate Similarity	NPC195239
0.7935	Intermediate Similarity	NPC294693
0.7935	Intermediate Similarity	NPC19692
0.7935	Intermediate Similarity	NPC157828
0.7935	Intermediate Similarity	NPC220151
0.7926	Intermediate Similarity	NPC193761
0.7926	Intermediate Similarity	NPC260900
0.7923	Intermediate Similarity	NPC55493
0.7919	Intermediate Similarity	NPC201700
0.7914	Intermediate Similarity	NPC470497
0.7912	Intermediate Similarity	NPC154339
0.791	Intermediate Similarity	NPC248462
0.7907	Intermediate Similarity	NPC42372
0.7906	Intermediate Similarity	NPC266249
0.7901	Intermediate Similarity	NPC279081
0.7886	Intermediate Similarity	NPC161861
0.7884	Intermediate Similarity	NPC476098
0.788	Intermediate Similarity	NPC267343
0.7865	Intermediate Similarity	NPC223791
0.7865	Intermediate Similarity	NPC107077
0.7861	Intermediate Similarity	NPC472297
0.7861	Intermediate Similarity	NPC472296
0.7853	Intermediate Similarity	NPC323927
0.7853	Intermediate Similarity	NPC64436
0.7849	Intermediate Similarity	NPC21174
0.7849	Intermediate Similarity	NPC271797
0.7848	Intermediate Similarity	NPC82295
0.7841	Intermediate Similarity	NPC293216
0.7838	Intermediate Similarity	NPC202812
0.7835	Intermediate Similarity	NPC471194
0.7835	Intermediate Similarity	NPC471193
0.7835	Intermediate Similarity	NPC6865
0.7835	Intermediate Similarity	NPC153980
0.7831	Intermediate Similarity	NPC57398
0.7824	Intermediate Similarity	NPC123839
0.7821	Intermediate Similarity	NPC191415
0.7819	Intermediate Similarity	NPC214428
0.7814	Intermediate Similarity	NPC472112
0.7807	Intermediate Similarity	NPC131887
0.7807	Intermediate Similarity	NPC52557
0.7807	Intermediate Similarity	NPC470499
0.78	Intermediate Similarity	NPC64216
0.7796	Intermediate Similarity	NPC245916
0.7791	Intermediate Similarity	NPC230002
0.7791	Intermediate Similarity	NPC16667
0.779	Intermediate Similarity	NPC308931
0.779	Intermediate Similarity	NPC280290
0.779	Intermediate Similarity	NPC15102
0.779	Intermediate Similarity	NPC99939
0.7784	Intermediate Similarity	NPC474177
0.7784	Intermediate Similarity	NPC320968
0.7784	Intermediate Similarity	NPC72956
0.7778	Intermediate Similarity	NPC300183

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 NPC84827 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	205
0.1-0.2	509
0.2-0.3	994
0.3-0.4	1575
0.4-0.5	2493
0.5-0.6	2249
0.6-0.7	907
0.7-0.8	194
0.8-0.85	15
0.85-0.9	1
0.9-0.95	8
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9503	High Similarity	NPD482	Approved
0.9444	High Similarity	NPD749	Clinical (unspecified phase)
0.9321	High Similarity	NPD750	Phase 2
0.9277	High Similarity	NPD2092	Phase 2
0.9277	High Similarity	NPD2095	Phase 2
0.9277	High Similarity	NPD2094	Phase 2
0.9222	High Similarity	NPD2096	Phase 2
0.9222	High Similarity	NPD2091	Phase 2
0.8935	High Similarity	NPD5728	Clinical (unspecified phase)
0.8512	High Similarity	NPD4184	Clinical (unspecified phase)
0.8453	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.8407	Intermediate Similarity	NPD484	Approved
0.8396	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.8351	Intermediate Similarity	NPD7470	Discontinued
0.8291	Intermediate Similarity	NPD786	Approved
0.8254	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.8201	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD6595	Phase 3
0.8161	Intermediate Similarity	NPD2144	Approved
0.8128	Intermediate Similarity	NPD5901	Discontinued
0.8111	Intermediate Similarity	NPD4499	Approved
0.8101	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.8042	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.8034	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD3038	Discontinued
0.8023	Intermediate Similarity	NPD3178	Discontinued
0.8021	Intermediate Similarity	NPD8073	Approved
0.7989	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7979	Intermediate Similarity	NPD8072	Approved
0.7979	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD1722	Approved
0.7955	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD5818	Discontinued
0.7938	Intermediate Similarity	NPD7970	Approved
0.7938	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD8272	Phase 2
0.7935	Intermediate Similarity	NPD7618	Phase 3
0.7935	Intermediate Similarity	NPD7619	Phase 3
0.7919	Intermediate Similarity	NPD2844	Phase 3
0.7901	Intermediate Similarity	NPD8431	Approved
0.7895	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD7957	Phase 1
0.7892	Intermediate Similarity	NPD3100	Discontinued
0.787	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7846	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD5426	Phase 3
0.7841	Intermediate Similarity	NPD5065	Approved
0.7835	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD2510	Approved
0.7812	Intermediate Similarity	NPD2509	Approved
0.7802	Intermediate Similarity	NPD3961	Discontinued
0.7797	Intermediate Similarity	NPD4075	Phase 2
0.7766	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7747	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD7944	Discontinued
0.7738	Intermediate Similarity	NPD2172	Phase 1
0.7733	Intermediate Similarity	NPD1403	Approved
0.7733	Intermediate Similarity	NPD1404	Approved
0.7727	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD4601	Approved
0.7725	Intermediate Similarity	NPD4600	Approved
0.7716	Intermediate Similarity	NPD3394	Approved
0.7716	Intermediate Similarity	NPD3389	Approved
0.7716	Intermediate Similarity	NPD3393	Approved
0.7709	Intermediate Similarity	NPD4076	Approved
0.7709	Intermediate Similarity	NPD4079	Approved
0.7679	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7668	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD6664	Approved
0.7657	Intermediate Similarity	NPD4174	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD3505	Approved
0.7654	Intermediate Similarity	NPD3506	Approved
0.7644	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD6665	Discontinued
0.7632	Intermediate Similarity	NPD4500	Approved
0.7632	Intermediate Similarity	NPD4501	Approved
0.7629	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD1326	Approved
0.7571	Intermediate Similarity	NPD1325	Approved
0.7563	Intermediate Similarity	NPD8093	Discontinued
0.7557	Intermediate Similarity	NPD2639	Approved
0.7557	Intermediate Similarity	NPD2642	Approved
0.7553	Intermediate Similarity	NPD4602	Approved
0.7544	Intermediate Similarity	NPD2837	Discontinued
0.7543	Intermediate Similarity	NPD3323	Discontinued
0.7541	Intermediate Similarity	NPD6178	Phase 3
0.7539	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD2641	Approved
0.7514	Intermediate Similarity	NPD4326	Phase 2
0.7514	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD2640	Approved
0.75	Intermediate Similarity	NPD802	Phase 2
0.75	Intermediate Similarity	NPD1038	Approved
0.7474	Intermediate Similarity	NPD7948	Phase 1
0.7463	Intermediate Similarity	NPD7711	Discontinued
0.7455	Intermediate Similarity	NPD2896	Discontinued
0.7444	Intermediate Similarity	NPD4128	Approved
0.7444	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD3583	Phase 2
0.7427	Intermediate Similarity	NPD7730	Approved
0.7427	Intermediate Similarity	NPD4463	Approved
0.7427	Intermediate Similarity	NPD7731	Approved
0.7427	Intermediate Similarity	NPD4462	Approved
0.7416	Intermediate Similarity	NPD7791	Approved
0.7416	Intermediate Similarity	NPD7950	Approved
0.7416	Intermediate Similarity	NPD7789	Approved
0.7416	Intermediate Similarity	NPD7953	Approved
0.7416	Intermediate Similarity	NPD7790	Approved
0.7416	Intermediate Similarity	NPD7951	Approved
0.7416	Intermediate Similarity	NPD7952	Approved
0.7415	Intermediate Similarity	NPD7271	Approved
0.7407	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD5003	Discontinued
0.738	Intermediate Similarity	NPD1534	Approved
0.7379	Intermediate Similarity	NPD7603	Discontinued
0.7377	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD1630	Approved
0.7366	Intermediate Similarity	NPD6217	Discontinued
0.7365	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD4181	Approved
0.7358	Intermediate Similarity	NPD6479	Discontinued
0.7356	Intermediate Similarity	NPD7824	Approved
0.7351	Intermediate Similarity	NPD7564	Discontinued
0.735	Intermediate Similarity	NPD8094	Discontinued
0.7348	Intermediate Similarity	NPD5322	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD4383	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3609	Approved
0.7333	Intermediate Similarity	NPD3610	Approved
0.7333	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6176	Phase 1
0.7326	Intermediate Similarity	NPD4948	Discontinued
0.7322	Intermediate Similarity	NPD8386	Phase 2
0.731	Intermediate Similarity	NPD4703	Approved
0.731	Intermediate Similarity	NPD4702	Approved
0.7308	Intermediate Similarity	NPD7781	Approved
0.7308	Intermediate Similarity	NPD7780	Approved
0.7306	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD6999	Discontinued
0.7304	Intermediate Similarity	NPD6242	Discontinued
0.7303	Intermediate Similarity	NPD2915	Discontinued
0.7296	Intermediate Similarity	NPD6987	Phase 1
0.7296	Intermediate Similarity	NPD3947	Discontinued
0.7289	Intermediate Similarity	NPD200	Phase 2
0.7289	Intermediate Similarity	NPD201	Phase 2
0.7287	Intermediate Similarity	NPD7233	Approved
0.7287	Intermediate Similarity	NPD7234	Approved
0.7283	Intermediate Similarity	NPD6452	Discontinued
0.7278	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7865	Approved
0.7263	Intermediate Similarity	NPD5611	Phase 2
0.7263	Intermediate Similarity	NPD5505	Discontinued
0.7259	Intermediate Similarity	NPD7001	Phase 3
0.725	Intermediate Similarity	NPD5475	Discontinued
0.7249	Intermediate Similarity	NPD2565	Phase 2
0.7249	Intermediate Similarity	NPD2564	Approved
0.7247	Intermediate Similarity	NPD1631	Approved
0.7243	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD4848	Phase 1
0.7236	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD5254	Discontinued
0.7234	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD5017	Discontinued
0.7222	Intermediate Similarity	NPD4638	Approved
0.7222	Intermediate Similarity	NPD4639	Approved
0.7222	Intermediate Similarity	NPD4640	Approved
0.7222	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD1996	Discontinued
0.7211	Intermediate Similarity	NPD2336	Approved
0.7208	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD3319	Phase 1
0.7204	Intermediate Similarity	NPD5106	Approved
0.7204	Intermediate Similarity	NPD4345	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD3318	Approved
0.7204	Intermediate Similarity	NPD5105	Approved
0.7204	Intermediate Similarity	NPD3320	Approved
0.7202	Intermediate Similarity	NPD4804	Approved
0.72	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD5898	Approved
0.7189	Intermediate Similarity	NPD5897	Approved
0.7189	Intermediate Similarity	NPD5473	Discontinued
0.7189	Intermediate Similarity	NPD5899	Approved
0.7188	Intermediate Similarity	NPD4427	Phase 2
0.7179	Intermediate Similarity	NPD2305	Discontinued
0.7179	Intermediate Similarity	NPD5043	Discontinued
0.7178	Intermediate Similarity	NPD3654	Approved
0.7172	Intermediate Similarity	NPD2008	Discontinued

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