NPASS Compound

Structure

CID172403 OpenBabel06191715542D 23 24 0 0 0 0 0 0 0 0999 V2000 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 23 1 0 0 0 0 5 8 1 0 0 0 0 5 15 2 0 0 0 0 6 9 2 0 0 0 0 6 15 1 0 0 0 0 7 10 2 0 0 0 0 7 16 1 0 0 0 0 8 17 2 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 11 15 1 0 0 0 0 12 20 1 0 0 0 0 13 16 2 0 0 0 0 13 19 1 0 0 0 0 14 16 1 0 0 0 0 14 20 1 0 0 0 0 17 21 1 0 0 0 0 18 19 2 0 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	315.18
Volume:	341.616
LogP:	2.92
LogD:	3.044
LogS:	-3.123
# Rotatable Bonds:	8
TPSA:	30.93
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.747
Synthetic Accessibility Score:	1.717
Fsp3:	0.368
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:	-4.532
MDCK Permeability:	2.329735980310943e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.568
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.497
30% Bioavailability (F30%):	0.67

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.988
Plasma Protein Binding (PPB):	81.5875244140625%
Volume Distribution (VD):	2.155
Pgp-substrate:	4.645596981048584%

ADMET: Metabolism

CYP1A2-inhibitor:	0.385
CYP1A2-substrate:	0.975
CYP2C19-inhibitor:	0.494
CYP2C19-substrate:	0.968
CYP2C9-inhibitor:	0.044
CYP2C9-substrate:	0.731
CYP2D6-inhibitor:	0.966
CYP2D6-substrate:	0.952
CYP3A4-inhibitor:	0.306
CYP3A4-substrate:	0.919

ADMET: Excretion

Clearance (CL):	11.872
Half-life (T1/2):	0.727

ADMET: Toxicity

hERG Blockers:	0.993
Human Hepatotoxicity (H-HT):	0.283
Drug-inuced Liver Injury (DILI):	0.815
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.442
Maximum Recommended Daily Dose:	0.243
Skin Sensitization:	0.901
Carcinogencity:	0.051
Eye Corrosion:	0.112
Eye Irritation:	0.023
Respiratory Toxicity:	0.901

Download Data

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

Natural Product: NPC172403

Natural Product ID:	NPC172403
*Common Name:**	(3,4-Dimethoxy-Benzyl)-[2-(4-Methoxy-Phenyl)-Ethyl]-Methyl-Amine
IUPAC Name:	N-[(3,4-dimethoxyphenyl)methyl]-2-(4-methoxyphenyl)-N-methylethanamine
Synonyms:
Standard InCHIKey:	LTXRLUQBZWBCGH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H25NO3/c1-20(12-11-15-5-8-17(21-2)9-6-15)14-16-7-10-18(22-3)19(13-16)23-4/h5-10,13H,11-12,14H2,1-4H3
SMILES:	COc1ccc(cc1)CCN(Cc1ccc(c(c1)OC)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL105087
PubChem CID:	441586
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001775] Amaryllidaceae alkaloids [CHEMONTID:0004121] Norbelladine-type amaryllidaceae alkaloids

*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
NPO4207	Chlidanthus fragrans	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21615016]
NPO1346	Nerine bowdenii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22312717]
NPO1346	Nerine bowdenii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4207	Chlidanthus fragrans	Species	Amaryllidaceae	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
IC50	1
Others	3

Activity Type	# Activity
Organism	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	87000.0	nM	PMID[530473]
NPT597	Organism	Spinacia oleracea	Spinacia oleracea	Fresh weight	=	22.3	ng g-1	PMID[530473]
NPT597	Organism	Spinacia oleracea	Spinacia oleracea	Fresh weight	=	174.4	ng g-1	PMID[530473]
NPT597	Organism	Spinacia oleracea	Spinacia oleracea	Fresh weight	=	123.5	ng g-1	PMID[530473]

☑ 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 NPC172403 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	250
0.1-0.2	2656
0.2-0.3	12493
0.3-0.4	4744
0.4-0.5	8298
0.5-0.6	10274
0.6-0.7	2922
0.7-0.8	878
0.8-0.85	131
0.85-0.9	44
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9206	High Similarity	NPC160193
0.916	High Similarity	NPC314682
0.9091	High Similarity	NPC474915
0.9091	High Similarity	NPC188163
0.9091	High Similarity	NPC213206
0.9091	High Similarity	NPC328750
0.8855	High Similarity	NPC11147
0.8824	High Similarity	NPC185838
0.8815	High Similarity	NPC128019
0.8815	High Similarity	NPC476567
0.8815	High Similarity	NPC136860
0.8769	High Similarity	NPC118419
0.8702	High Similarity	NPC160692
0.8696	High Similarity	NPC476151
0.8696	High Similarity	NPC179825
0.8696	High Similarity	NPC210437
0.8696	High Similarity	NPC51957
0.8696	High Similarity	NPC191376
0.8696	High Similarity	NPC106295
0.8696	High Similarity	NPC321505
0.8696	High Similarity	NPC476144
0.8696	High Similarity	NPC16107
0.8651	High Similarity	NPC298486
0.8647	High Similarity	NPC7018
0.8647	High Similarity	NPC167944
0.8647	High Similarity	NPC42793
0.8647	High Similarity	NPC131204
0.8647	High Similarity	NPC301050
0.8647	High Similarity	NPC231884
0.8633	High Similarity	NPC135538
0.8633	High Similarity	NPC475959
0.8633	High Similarity	NPC428
0.8633	High Similarity	NPC24233
0.8633	High Similarity	NPC7467
0.8633	High Similarity	NPC147390
0.8633	High Similarity	NPC476571
0.8633	High Similarity	NPC246587
0.8582	High Similarity	NPC253429
0.8571	High Similarity	NPC103379
0.8571	High Similarity	NPC477565
0.8551	High Similarity	NPC130926
0.8527	High Similarity	NPC301713
0.8507	High Similarity	NPC416184
0.8451	Intermediate Similarity	NPC81733
0.8451	Intermediate Similarity	NPC326316
0.8444	Intermediate Similarity	NPC193528
0.844	Intermediate Similarity	NPC207824
0.844	Intermediate Similarity	NPC60538
0.844	Intermediate Similarity	NPC92541
0.844	Intermediate Similarity	NPC219162
0.838	Intermediate Similarity	NPC97221
0.838	Intermediate Similarity	NPC220858
0.838	Intermediate Similarity	NPC88249
0.838	Intermediate Similarity	NPC192768
0.838	Intermediate Similarity	NPC151895
0.8346	Intermediate Similarity	NPC93882
0.8346	Intermediate Similarity	NPC130595
0.8322	Intermediate Similarity	NPC76213
0.8322	Intermediate Similarity	NPC277669
0.8322	Intermediate Similarity	NPC476568
0.832	Intermediate Similarity	NPC120075
0.8298	Intermediate Similarity	NPC95075
0.8298	Intermediate Similarity	NPC253883
0.8298	Intermediate Similarity	NPC90844
0.8298	Intermediate Similarity	NPC144863
0.8284	Intermediate Similarity	NPC6854
0.8284	Intermediate Similarity	NPC313737
0.8284	Intermediate Similarity	NPC285078
0.8276	Intermediate Similarity	NPC39701
0.8276	Intermediate Similarity	NPC172765
0.8276	Intermediate Similarity	NPC54379
0.8276	Intermediate Similarity	NPC216459
0.8276	Intermediate Similarity	NPC189266
0.8276	Intermediate Similarity	NPC193949
0.8276	Intermediate Similarity	NPC2413
0.8276	Intermediate Similarity	NPC138487
0.8276	Intermediate Similarity	NPC207757
0.8276	Intermediate Similarity	NPC249797
0.8276	Intermediate Similarity	NPC184026
0.8276	Intermediate Similarity	NPC204828
0.8276	Intermediate Similarity	NPC469817
0.8276	Intermediate Similarity	NPC276588
0.8276	Intermediate Similarity	NPC110416
0.8276	Intermediate Similarity	NPC295691
0.8276	Intermediate Similarity	NPC41178
0.8276	Intermediate Similarity	NPC93593
0.8276	Intermediate Similarity	NPC5238
0.8276	Intermediate Similarity	NPC278799
0.8276	Intermediate Similarity	NPC127674
0.8271	Intermediate Similarity	NPC308885
0.8271	Intermediate Similarity	NPC255550
0.8264	Intermediate Similarity	NPC210148
0.8264	Intermediate Similarity	NPC233029
0.8261	Intermediate Similarity	NPC323204
0.8258	Intermediate Similarity	NPC155838
0.8252	Intermediate Similarity	NPC13397
0.8252	Intermediate Similarity	NPC274026
0.8239	Intermediate Similarity	NPC130941
0.8222	Intermediate Similarity	NPC218530
0.8219	Intermediate Similarity	NPC25084
0.8219	Intermediate Similarity	NPC146288
0.8219	Intermediate Similarity	NPC247639
0.8209	Intermediate Similarity	NPC214869
0.8207	Intermediate Similarity	NPC477564
0.8207	Intermediate Similarity	NPC2295
0.8195	Intermediate Similarity	NPC35961
0.8195	Intermediate Similarity	NPC52029
0.8195	Intermediate Similarity	NPC195749
0.8194	Intermediate Similarity	NPC476579
0.8163	Intermediate Similarity	NPC476572
0.8156	Intermediate Similarity	NPC110337
0.8154	Intermediate Similarity	NPC217277
0.8151	Intermediate Similarity	NPC187022
0.8151	Intermediate Similarity	NPC325871
0.8151	Intermediate Similarity	NPC99659
0.8151	Intermediate Similarity	NPC80129
0.8138	Intermediate Similarity	NPC82285
0.8138	Intermediate Similarity	NPC133011
0.8138	Intermediate Similarity	NPC148898
0.8134	Intermediate Similarity	NPC114102
0.8134	Intermediate Similarity	NPC476570
0.8095	Intermediate Similarity	NPC126519
0.8095	Intermediate Similarity	NPC234392
0.8095	Intermediate Similarity	NPC203784
0.8095	Intermediate Similarity	NPC31311
0.8095	Intermediate Similarity	NPC170503
0.8085	Intermediate Similarity	NPC294249
0.8077	Intermediate Similarity	NPC471315
0.8077	Intermediate Similarity	NPC471314
0.806	Intermediate Similarity	NPC262641
0.8054	Intermediate Similarity	NPC266753
0.8054	Intermediate Similarity	NPC477559
0.8054	Intermediate Similarity	NPC306902
0.8054	Intermediate Similarity	NPC232924
0.8054	Intermediate Similarity	NPC27410
0.8054	Intermediate Similarity	NPC166014
0.8054	Intermediate Similarity	NPC160298
0.8045	Intermediate Similarity	NPC251571
0.8045	Intermediate Similarity	NPC153990
0.8041	Intermediate Similarity	NPC129603
0.803	Intermediate Similarity	NPC318965
0.8029	Intermediate Similarity	NPC475828
0.8028	Intermediate Similarity	NPC145304
0.8027	Intermediate Similarity	NPC244112
0.8027	Intermediate Similarity	NPC78733
0.8014	Intermediate Similarity	NPC26601
0.8014	Intermediate Similarity	NPC476580
0.8	Intermediate Similarity	NPC165106
0.8	Intermediate Similarity	NPC211992
0.8	Intermediate Similarity	NPC60186
0.8	Intermediate Similarity	NPC470925
0.8	Intermediate Similarity	NPC153631
0.7987	Intermediate Similarity	NPC216816
0.7987	Intermediate Similarity	NPC477080
0.7987	Intermediate Similarity	NPC111485
0.7986	Intermediate Similarity	NPC37144
0.7986	Intermediate Similarity	NPC231572
0.7986	Intermediate Similarity	NPC59907
0.7984	Intermediate Similarity	NPC321133
0.7973	Intermediate Similarity	NPC147091
0.7972	Intermediate Similarity	NPC473934
0.7971	Intermediate Similarity	NPC99078
0.7947	Intermediate Similarity	NPC233650
0.7947	Intermediate Similarity	NPC475393
0.7919	Intermediate Similarity	NPC40389
0.7919	Intermediate Similarity	NPC148014
0.7919	Intermediate Similarity	NPC78359
0.7919	Intermediate Similarity	NPC65490
0.7919	Intermediate Similarity	NPC315707
0.7914	Intermediate Similarity	NPC252107
0.7914	Intermediate Similarity	NPC220923
0.7914	Intermediate Similarity	NPC470707
0.791	Intermediate Similarity	NPC186898
0.7905	Intermediate Similarity	NPC76079
0.7899	Intermediate Similarity	NPC205178
0.7899	Intermediate Similarity	NPC73883
0.7899	Intermediate Similarity	NPC277042
0.7899	Intermediate Similarity	NPC136330
0.7899	Intermediate Similarity	NPC196609
0.7899	Intermediate Similarity	NPC255817
0.7899	Intermediate Similarity	NPC251454
0.7899	Intermediate Similarity	NPC230698
0.7895	Intermediate Similarity	NPC238530
0.7895	Intermediate Similarity	NPC232514
0.7895	Intermediate Similarity	NPC276944
0.7895	Intermediate Similarity	NPC134858
0.7895	Intermediate Similarity	NPC225774
0.7891	Intermediate Similarity	NPC470924
0.7883	Intermediate Similarity	NPC266425
0.7879	Intermediate Similarity	NPC13020
0.7879	Intermediate Similarity	NPC140359
0.7877	Intermediate Similarity	NPC223125
0.7874	Intermediate Similarity	NPC475815
0.7874	Intermediate Similarity	NPC473264
0.7874	Intermediate Similarity	NPC47194
0.7867	Intermediate Similarity	NPC92191
0.7867	Intermediate Similarity	NPC59028
0.7867	Intermediate Similarity	NPC118804
0.7857	Intermediate Similarity	NPC210086
0.7852	Intermediate Similarity	NPC186063

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 NPC172403 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	867
0.2-0.3	1046
0.3-0.4	1719
0.4-0.5	2771
0.5-0.6	1627
0.6-0.7	711
0.7-0.8	200
0.8-0.85	26
0.85-0.9	4
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9127	High Similarity	NPD5752	Clinical (unspecified phase)
0.9091	High Similarity	NPD4664	Clinical (unspecified phase)
0.8984	High Similarity	NPD5718	Phase 2
0.8696	High Similarity	NPD4584	Approved
0.8647	High Similarity	NPD6895	Approved
0.8647	High Similarity	NPD6896	Approved
0.8473	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.8451	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.8451	Intermediate Similarity	NPD4017	Approved
0.8444	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.8444	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.844	Intermediate Similarity	NPD6030	Approved
0.844	Intermediate Similarity	NPD6031	Approved
0.8346	Intermediate Similarity	NPD2674	Phase 3
0.8271	Intermediate Similarity	NPD3145	Approved
0.8271	Intermediate Similarity	NPD3144	Approved
0.8214	Intermediate Similarity	NPD5241	Discontinued
0.8214	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.8201	Intermediate Similarity	NPD4162	Approved
0.8201	Intermediate Similarity	NPD3060	Approved
0.8189	Intermediate Similarity	NPD2595	Approved
0.8189	Intermediate Similarity	NPD2594	Approved
0.8182	Intermediate Similarity	NPD3641	Approved
0.8182	Intermediate Similarity	NPD3640	Phase 3
0.8182	Intermediate Similarity	NPD3639	Approved
0.8169	Intermediate Similarity	NPD1424	Approved
0.8156	Intermediate Similarity	NPD7124	Phase 2
0.8156	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD7298	Approved
0.8108	Intermediate Similarity	NPD6788	Approved
0.8106	Intermediate Similarity	NPD7905	Discontinued
0.8095	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD7831	Phase 2
0.8054	Intermediate Similarity	NPD7833	Phase 2
0.8054	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.8027	Intermediate Similarity	NPD5720	Discontinued
0.8	Intermediate Similarity	NPD5283	Phase 1
0.7984	Intermediate Similarity	NPD2667	Approved
0.7984	Intermediate Similarity	NPD2668	Approved
0.7959	Intermediate Similarity	NPD4773	Phase 2
0.7959	Intermediate Similarity	NPD4772	Phase 2
0.7947	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD5177	Phase 3
0.7941	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD2563	Approved
0.7919	Intermediate Similarity	NPD2560	Approved
0.7917	Intermediate Similarity	NPD4123	Phase 3
0.7899	Intermediate Similarity	NPD2653	Approved
0.7899	Intermediate Similarity	NPD2492	Phase 1
0.7895	Intermediate Similarity	NPD7802	Discontinued
0.7879	Intermediate Similarity	NPD1420	Approved
0.7879	Intermediate Similarity	NPD1421	Approved
0.7872	Intermediate Similarity	NPD7153	Discontinued
0.7829	Intermediate Similarity	NPD5677	Discontinued
0.7829	Intermediate Similarity	NPD2486	Discontinued
0.7823	Intermediate Similarity	NPD824	Approved
0.782	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD4237	Approved
0.7817	Intermediate Similarity	NPD4236	Phase 3
0.781	Intermediate Similarity	NPD4474	Approved
0.781	Intermediate Similarity	NPD4475	Approved
0.7808	Intermediate Similarity	NPD5976	Discontinued
0.78	Intermediate Similarity	NPD5977	Approved
0.78	Intermediate Similarity	NPD5978	Approved
0.7786	Intermediate Similarity	NPD3294	Phase 2
0.777	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD2986	Phase 2
0.777	Intermediate Similarity	NPD2989	Phase 2
0.7727	Intermediate Similarity	NPD4010	Discontinued
0.7718	Intermediate Similarity	NPD7110	Phase 1
0.7718	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD6111	Discontinued
0.7704	Intermediate Similarity	NPD2990	Approved
0.7704	Intermediate Similarity	NPD2987	Approved
0.7687	Intermediate Similarity	NPD2922	Phase 1
0.7681	Intermediate Similarity	NPD3530	Approved
0.7681	Intermediate Similarity	NPD3531	Approved
0.7681	Intermediate Similarity	NPD3532	Approved
0.7676	Intermediate Similarity	NPD3656	Approved
0.7674	Intermediate Similarity	NPD3596	Phase 2
0.7669	Intermediate Similarity	NPD2233	Approved
0.7669	Intermediate Similarity	NPD2232	Approved
0.7669	Intermediate Similarity	NPD2230	Approved
0.7651	Intermediate Similarity	NPD6876	Approved
0.7651	Intermediate Similarity	NPD6875	Approved
0.7651	Intermediate Similarity	NPD4678	Approved
0.7651	Intermediate Similarity	NPD4675	Approved
0.7643	Intermediate Similarity	NPD8252	Approved
0.7643	Intermediate Similarity	NPD8251	Approved
0.7643	Intermediate Similarity	NPD8099	Discontinued
0.7639	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD6331	Phase 2
0.763	Intermediate Similarity	NPD3053	Approved
0.763	Intermediate Similarity	NPD4098	Discontinued
0.763	Intermediate Similarity	NPD3055	Approved
0.7615	Intermediate Similarity	NPD5536	Phase 2
0.7613	Intermediate Similarity	NPD6071	Discontinued
0.7612	Intermediate Similarity	NPD1669	Approved
0.7606	Intermediate Similarity	NPD2161	Phase 2
0.7603	Intermediate Similarity	NPD3124	Discontinued
0.76	Intermediate Similarity	NPD6385	Approved
0.76	Intermediate Similarity	NPD6386	Approved
0.7595	Intermediate Similarity	NPD8156	Discontinued
0.758	Intermediate Similarity	NPD5966	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD4083	Discontinued
0.7564	Intermediate Similarity	NPD6687	Approved
0.7564	Intermediate Similarity	NPD6688	Approved
0.7556	Intermediate Similarity	NPD5310	Approved
0.7556	Intermediate Similarity	NPD5311	Approved
0.7551	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD6107	Approved
0.7532	Intermediate Similarity	NPD5708	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD4210	Discontinued
0.7517	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2898	Approved
0.75	Intermediate Similarity	NPD6382	Discontinued
0.75	Intermediate Similarity	NPD1044	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4166	Phase 2
0.75	Intermediate Similarity	NPD3110	Approved
0.75	Intermediate Similarity	NPD2238	Phase 2
0.75	Intermediate Similarity	NPD2977	Approved
0.75	Intermediate Similarity	NPD3109	Approved
0.75	Intermediate Similarity	NPD2978	Approved
0.75	Intermediate Similarity	NPD6297	Approved
0.75	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6873	Phase 2
0.7483	Intermediate Similarity	NPD3156	Discontinued
0.7482	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD5604	Discontinued
0.7448	Intermediate Similarity	NPD44	Approved
0.7448	Intermediate Similarity	NPD2459	Approved
0.7448	Intermediate Similarity	NPD2458	Approved
0.7448	Intermediate Similarity	NPD6364	Approved
0.7448	Intermediate Similarity	NPD2460	Phase 3
0.7445	Intermediate Similarity	NPD6584	Phase 3
0.7444	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD2245	Discovery
0.7424	Intermediate Similarity	NPD6581	Approved
0.7424	Intermediate Similarity	NPD6580	Approved
0.7422	Intermediate Similarity	NPD228	Approved
0.7413	Intermediate Similarity	NPD6380	Phase 1
0.7413	Intermediate Similarity	NPD3693	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD593	Approved
0.7385	Intermediate Similarity	NPD595	Approved
0.7368	Intermediate Similarity	NPD3444	Approved
0.7368	Intermediate Similarity	NPD3049	Approved
0.7368	Intermediate Similarity	NPD3443	Approved
0.7368	Intermediate Similarity	NPD3445	Approved
0.7368	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD5297	Approved
0.7362	Intermediate Similarity	NPD7280	Phase 3
0.7362	Intermediate Similarity	NPD7281	Phase 3
0.7357	Intermediate Similarity	NPD5111	Phase 2
0.7357	Intermediate Similarity	NPD5110	Phase 2
0.7357	Intermediate Similarity	NPD3374	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD5109	Approved
0.7355	Intermediate Similarity	NPD4055	Discovery
0.7353	Intermediate Similarity	NPD2429	Approved
0.7353	Intermediate Similarity	NPD2428	Approved
0.7333	Intermediate Similarity	NPD1914	Approved
0.7329	Intermediate Similarity	NPD3885	Approved
0.7328	Intermediate Similarity	NPD2557	Approved
0.732	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD7018	Phase 2
0.7317	Intermediate Similarity	NPD6853	Approved
0.7317	Intermediate Similarity	NPD6618	Phase 2
0.7317	Intermediate Similarity	NPD8054	Approved
0.7317	Intermediate Similarity	NPD8053	Approved
0.7317	Intermediate Similarity	NPD6851	Approved
0.7315	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD2556	Approved
0.7313	Intermediate Similarity	NPD2554	Approved
0.731	Intermediate Similarity	NPD1375	Discontinued
0.7301	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD2120	Phase 2
0.729	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD3687	Approved
0.7285	Intermediate Similarity	NPD3686	Approved
0.7279	Intermediate Similarity	NPD2981	Phase 2
0.7278	Intermediate Similarity	NPD3051	Approved
0.7273	Intermediate Similarity	NPD5772	Approved
0.7273	Intermediate Similarity	NPD5773	Approved
0.7267	Intermediate Similarity	NPD6090	Discontinued
0.7267	Intermediate Similarity	NPD5312	Approved
0.7267	Intermediate Similarity	NPD5313	Approved
0.7267	Intermediate Similarity	NPD6890	Discontinued
0.726	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD4597	Approved
0.726	Intermediate Similarity	NPD4598	Approved
0.7256	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD3061	Approved
0.7254	Intermediate Similarity	NPD3059	Approved
0.7254	Intermediate Similarity	NPD3062	Approved
0.7248	Intermediate Similarity	NPD7598	Phase 2
0.7248	Intermediate Similarity	NPD2420	Approved
0.7248	Intermediate Similarity	NPD2421	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