NPASS Compound

Structure

NPC474149 OpenBabel07101718242D 24 24 0 0 1 0 0 0 0 0999 V2000 12.9904 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9904 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 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 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 C 0 0 3 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 18 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 18 1 0 0 0 0 11 13 1 0 0 0 0 11 19 2 0 0 0 0 12 14 2 0 0 0 0 12 19 1 0 0 0 0 13 20 2 0 0 0 0 14 20 1 0 0 0 0 15 16 1 0 0 0 0 15 19 1 0 0 0 0 16 22 1 0 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 20 23 1 0 0 0 0 21 22 2 3 0 0 0 21 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	333.27
Volume:	381.247
LogP:	5.735
LogD:	4.517
LogS:	-3.57
# Rotatable Bonds:	14
TPSA:	49.33
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.486
Synthetic Accessibility Score:	2.431
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.685
MDCK Permeability:	1.7226177078555338e-05
Pgp-inhibitor:	0.039
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.965
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.307
Plasma Protein Binding (PPB):	97.44282531738281%
Volume Distribution (VD):	0.651
Pgp-substrate:	0.906602680683136%

ADMET: Metabolism

CYP1A2-inhibitor:	0.614
CYP1A2-substrate:	0.558
CYP2C19-inhibitor:	0.897
CYP2C19-substrate:	0.14
CYP2C9-inhibitor:	0.737
CYP2C9-substrate:	0.96
CYP2D6-inhibitor:	0.917
CYP2D6-substrate:	0.343
CYP3A4-inhibitor:	0.821
CYP3A4-substrate:	0.208

ADMET: Excretion

Clearance (CL):	8.944
Half-life (T1/2):	0.561

ADMET: Toxicity

hERG Blockers:	0.252
Human Hepatotoxicity (H-HT):	0.304
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.189
Skin Sensitization:	0.948
Carcinogencity:	0.069
Eye Corrosion:	0.004
Eye Irritation:	0.167
Respiratory Toxicity:	0.12

Download Data

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

Natural Product: NPC474149

Natural Product ID:	NPC474149
*Common Name:**	N-[2-(4-Hydroxyphenyl)Ethyl]-3-Methyldodecanamide
IUPAC Name:	N-[2-(4-hydroxyphenyl)ethyl]-3-methyldodecanamide
Synonyms:
Standard InCHIKey:	QMMWRYRRTSIBHU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H35NO2/c1-3-4-5-6-7-8-9-10-18(2)17-21(24)22-16-15-19-11-13-20(23)14-12-19/h11-14,18,23H,3-10,15-17H2,1-2H3,(H,22,24)
SMILES:	CCCCCCCCCC(CC(=NCCc1ccc(cc1)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463001
PubChem CID:	16091484
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0004646] 1-hydroxy-2-unsubstituted benzenoids

*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
NPO28209	Muricea austera	Species	Plexauridae	Eukaryota	n.a.	Pacific coast of Panama	n.a.	PMID[17067146]
NPO28209	Muricea austera	Species	Plexauridae	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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	45000.0	nM	PMID[450112]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	>	50000.0	nM	PMID[450112]

☑ 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 NPC474149 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	143
0.1-0.2	1402
0.2-0.3	7292
0.3-0.4	10625
0.4-0.5	10402
0.5-0.6	9455
0.6-0.7	2648
0.7-0.8	668
0.8-0.85	42
0.85-0.9	10
0.9-0.95	7
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9709	High Similarity	NPC258056
0.9608	High Similarity	NPC231705
0.9515	High Similarity	NPC142297
0.9352	High Similarity	NPC317254
0.9314	High Similarity	NPC178902
0.9083	High Similarity	NPC118202
0.9057	High Similarity	NPC24101
0.9057	High Similarity	NPC96224
0.9018	High Similarity	NPC283760
0.8879	High Similarity	NPC153690
0.875	High Similarity	NPC82963
0.8673	High Similarity	NPC311737
0.8673	High Similarity	NPC38458
0.8571	High Similarity	NPC289381
0.8571	High Similarity	NPC155847
0.8571	High Similarity	NPC142599
0.8558	High Similarity	NPC107619
0.8522	High Similarity	NPC268572
0.8462	Intermediate Similarity	NPC474862
0.8362	Intermediate Similarity	NPC43275
0.8348	Intermediate Similarity	NPC283468
0.8347	Intermediate Similarity	NPC296712
0.8333	Intermediate Similarity	NPC55561
0.8304	Intermediate Similarity	NPC166837
0.8302	Intermediate Similarity	NPC125732
0.8286	Intermediate Similarity	NPC473388
0.8276	Intermediate Similarity	NPC122009
0.8235	Intermediate Similarity	NPC123273
0.8235	Intermediate Similarity	NPC258219
0.8235	Intermediate Similarity	NPC242240
0.8235	Intermediate Similarity	NPC318325
0.8235	Intermediate Similarity	NPC280347
0.8235	Intermediate Similarity	NPC177420
0.8205	Intermediate Similarity	NPC319950
0.819	Intermediate Similarity	NPC26244
0.8145	Intermediate Similarity	NPC326966
0.8137	Intermediate Similarity	NPC113460
0.8137	Intermediate Similarity	NPC25493
0.8136	Intermediate Similarity	NPC53596
0.8136	Intermediate Similarity	NPC160120
0.8136	Intermediate Similarity	NPC289330
0.8136	Intermediate Similarity	NPC17388
0.8136	Intermediate Similarity	NPC471308
0.813	Intermediate Similarity	NPC478147
0.8095	Intermediate Similarity	NPC151715
0.8077	Intermediate Similarity	NPC304541
0.8039	Intermediate Similarity	NPC23167
0.8	Intermediate Similarity	NPC147284
0.8	Intermediate Similarity	NPC306884
0.8	Intermediate Similarity	NPC162314
0.8	Intermediate Similarity	NPC210497
0.8	Intermediate Similarity	NPC3358
0.8	Intermediate Similarity	NPC94139
0.7983	Intermediate Similarity	NPC263835
0.7965	Intermediate Similarity	NPC145638
0.7965	Intermediate Similarity	NPC290566
0.7953	Intermediate Similarity	NPC218530
0.7951	Intermediate Similarity	NPC62101
0.7951	Intermediate Similarity	NPC95733
0.7944	Intermediate Similarity	NPC292730
0.7944	Intermediate Similarity	NPC216520
0.7944	Intermediate Similarity	NPC132271
0.7944	Intermediate Similarity	NPC82664
0.7941	Intermediate Similarity	NPC197783
0.7937	Intermediate Similarity	NPC328070
0.7937	Intermediate Similarity	NPC244866
0.7934	Intermediate Similarity	NPC471314
0.7934	Intermediate Similarity	NPC471315
0.7925	Intermediate Similarity	NPC316301
0.7925	Intermediate Similarity	NPC27323
0.7925	Intermediate Similarity	NPC58674
0.7917	Intermediate Similarity	NPC284078
0.7909	Intermediate Similarity	NPC68055
0.7905	Intermediate Similarity	NPC45040
0.7905	Intermediate Similarity	NPC270547
0.7903	Intermediate Similarity	NPC153990
0.7891	Intermediate Similarity	NPC6570
0.789	Intermediate Similarity	NPC29601
0.7886	Intermediate Similarity	NPC29477
0.7885	Intermediate Similarity	NPC98772
0.7874	Intermediate Similarity	NPC313737
0.7874	Intermediate Similarity	NPC6854
0.7874	Intermediate Similarity	NPC285078
0.787	Intermediate Similarity	NPC77492
0.7869	Intermediate Similarity	NPC307020
0.7869	Intermediate Similarity	NPC211218
0.7864	Intermediate Similarity	NPC184169
0.7863	Intermediate Similarity	NPC213
0.7863	Intermediate Similarity	NPC37302
0.7863	Intermediate Similarity	NPC10286
0.7857	Intermediate Similarity	NPC114102
0.7851	Intermediate Similarity	NPC27581
0.7851	Intermediate Similarity	NPC142577
0.785	Intermediate Similarity	NPC8392
0.7846	Intermediate Similarity	NPC197921
0.7843	Intermediate Similarity	NPC248817
0.7843	Intermediate Similarity	NPC175313
0.784	Intermediate Similarity	NPC325651
0.7833	Intermediate Similarity	NPC321133
0.783	Intermediate Similarity	NPC138117
0.783	Intermediate Similarity	NPC325292
0.7823	Intermediate Similarity	NPC476353
0.781	Intermediate Similarity	NPC192
0.781	Intermediate Similarity	NPC300017
0.7798	Intermediate Similarity	NPC216468
0.7798	Intermediate Similarity	NPC78119
0.7798	Intermediate Similarity	NPC51333
0.7798	Intermediate Similarity	NPC92730
0.7798	Intermediate Similarity	NPC128723
0.7798	Intermediate Similarity	NPC132078
0.7795	Intermediate Similarity	NPC93882
0.7795	Intermediate Similarity	NPC130595
0.7786	Intermediate Similarity	NPC91953
0.7778	Intermediate Similarity	NPC33168
0.7778	Intermediate Similarity	NPC474091
0.7769	Intermediate Similarity	NPC471201
0.7769	Intermediate Similarity	NPC322526
0.776	Intermediate Similarity	NPC251571
0.7759	Intermediate Similarity	NPC146422
0.7757	Intermediate Similarity	NPC128062
0.7752	Intermediate Similarity	NPC64205
0.7748	Intermediate Similarity	NPC196479
0.7745	Intermediate Similarity	NPC265146
0.7745	Intermediate Similarity	NPC124436
0.7736	Intermediate Similarity	NPC204210
0.7736	Intermediate Similarity	NPC155908
0.7734	Intermediate Similarity	NPC267237
0.7727	Intermediate Similarity	NPC225506
0.7727	Intermediate Similarity	NPC213730
0.7727	Intermediate Similarity	NPC248396
0.7727	Intermediate Similarity	NPC48730
0.7727	Intermediate Similarity	NPC129373
0.7717	Intermediate Similarity	NPC473724
0.7717	Intermediate Similarity	NPC308885
0.7717	Intermediate Similarity	NPC255550
0.7714	Intermediate Similarity	NPC141139
0.7714	Intermediate Similarity	NPC121872
0.7714	Intermediate Similarity	NPC74936
0.7714	Intermediate Similarity	NPC209764
0.7714	Intermediate Similarity	NPC78041
0.7714	Intermediate Similarity	NPC471307
0.7714	Intermediate Similarity	NPC159178
0.7712	Intermediate Similarity	NPC303370
0.771	Intermediate Similarity	NPC476989
0.7706	Intermediate Similarity	NPC225464
0.7698	Intermediate Similarity	NPC271808
0.7698	Intermediate Similarity	NPC155838
0.7692	Intermediate Similarity	NPC407
0.7692	Intermediate Similarity	NPC307235
0.7692	Intermediate Similarity	NPC473055
0.7692	Intermediate Similarity	NPC473052
0.7685	Intermediate Similarity	NPC313650
0.7685	Intermediate Similarity	NPC274678
0.7685	Intermediate Similarity	NPC25565
0.7685	Intermediate Similarity	NPC32714
0.768	Intermediate Similarity	NPC301713
0.7672	Intermediate Similarity	NPC163674
0.7672	Intermediate Similarity	NPC227553
0.7667	Intermediate Similarity	NPC85276
0.7658	Intermediate Similarity	NPC7686
0.7658	Intermediate Similarity	NPC40258
0.7658	Intermediate Similarity	NPC91461
0.7656	Intermediate Similarity	NPC214869
0.7652	Intermediate Similarity	NPC168861
0.7652	Intermediate Similarity	NPC469360
0.7638	Intermediate Similarity	NPC52029
0.7638	Intermediate Similarity	NPC35961
0.7638	Intermediate Similarity	NPC195749
0.7636	Intermediate Similarity	NPC260775
0.7636	Intermediate Similarity	NPC252821
0.7636	Intermediate Similarity	NPC122005
0.7623	Intermediate Similarity	NPC473050
0.7623	Intermediate Similarity	NPC473051
0.7619	Intermediate Similarity	NPC470877
0.7619	Intermediate Similarity	NPC27974
0.7619	Intermediate Similarity	NPC104216
0.7615	Intermediate Similarity	NPC475439
0.7615	Intermediate Similarity	NPC473501
0.7611	Intermediate Similarity	NPC154899
0.7611	Intermediate Similarity	NPC233396
0.7611	Intermediate Similarity	NPC138942
0.7611	Intermediate Similarity	NPC211551
0.7596	Intermediate Similarity	NPC198747
0.7596	Intermediate Similarity	NPC155393
0.7593	Intermediate Similarity	NPC76938
0.7593	Intermediate Similarity	NPC152415
0.7589	Intermediate Similarity	NPC302219
0.7589	Intermediate Similarity	NPC222522
0.7589	Intermediate Similarity	NPC24404
0.7589	Intermediate Similarity	NPC85479
0.7589	Intermediate Similarity	NPC106396
0.7589	Intermediate Similarity	NPC242342
0.7589	Intermediate Similarity	NPC53051
0.7589	Intermediate Similarity	NPC71002
0.7589	Intermediate Similarity	NPC168303
0.7589	Intermediate Similarity	NPC249828
0.7589	Intermediate Similarity	NPC313030
0.7589	Intermediate Similarity	NPC94351
0.7589	Intermediate Similarity	NPC146798
0.7589	Intermediate Similarity	NPC168829

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 NPC474149 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	693
0.2-0.3	980
0.3-0.4	1956
0.4-0.5	2770
0.5-0.6	1867
0.6-0.7	625
0.7-0.8	131
0.8-0.85	15
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8649	High Similarity	NPD2234	Approved
0.8649	High Similarity	NPD2229	Approved
0.8649	High Similarity	NPD2228	Approved
0.8349	Intermediate Similarity	NPD1445	Approved
0.8349	Intermediate Similarity	NPD1444	Approved
0.8333	Intermediate Similarity	NPD9608	Approved
0.8333	Intermediate Similarity	NPD9610	Approved
0.8264	Intermediate Similarity	NPD7451	Discontinued
0.819	Intermediate Similarity	NPD2859	Approved
0.819	Intermediate Similarity	NPD2860	Approved
0.8167	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.8131	Intermediate Similarity	NPD3020	Approved
0.8125	Intermediate Similarity	NPD1792	Phase 2
0.8095	Intermediate Similarity	NPD2934	Approved
0.8095	Intermediate Similarity	NPD2933	Approved
0.808	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD3136	Phase 2
0.8051	Intermediate Similarity	NPD4093	Discontinued
0.7983	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD5304	Approved
0.7966	Intermediate Similarity	NPD5303	Approved
0.7965	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD856	Approved
0.7881	Intermediate Similarity	NPD16	Approved
0.7869	Intermediate Similarity	NPD4659	Approved
0.7833	Intermediate Similarity	NPD2668	Approved
0.7833	Intermediate Similarity	NPD2667	Approved
0.7815	Intermediate Similarity	NPD1759	Phase 1
0.7795	Intermediate Similarity	NPD2674	Phase 3
0.7778	Intermediate Similarity	NPD1793	Approved
0.7778	Intermediate Similarity	NPD1791	Approved
0.7769	Intermediate Similarity	NPD3143	Discontinued
0.7769	Intermediate Similarity	NPD3421	Phase 3
0.7759	Intermediate Similarity	NPD9377	Approved
0.7759	Intermediate Similarity	NPD9379	Approved
0.7745	Intermediate Similarity	NPD111	Approved
0.7734	Intermediate Similarity	NPD6346	Approved
0.7731	Intermediate Similarity	NPD317	Approved
0.7731	Intermediate Similarity	NPD1758	Phase 1
0.7731	Intermediate Similarity	NPD318	Approved
0.7724	Intermediate Similarity	NPD1669	Approved
0.7717	Intermediate Similarity	NPD3144	Approved
0.7717	Intermediate Similarity	NPD3145	Approved
0.7705	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7686	Intermediate Similarity	NPD1751	Approved
0.7664	Intermediate Similarity	NPD845	Approved
0.7658	Intermediate Similarity	NPD940	Approved
0.7658	Intermediate Similarity	NPD4818	Approved
0.7658	Intermediate Similarity	NPD846	Approved
0.7658	Intermediate Similarity	NPD4817	Approved
0.7642	Intermediate Similarity	NPD2561	Approved
0.7642	Intermediate Similarity	NPD2562	Approved
0.7642	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD475	Phase 2
0.7612	Intermediate Similarity	NPD7066	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD821	Approved
0.76	Intermediate Similarity	NPD4103	Phase 2
0.76	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7450	Phase 2
0.757	Intermediate Similarity	NPD6690	Approved
0.7563	Intermediate Similarity	NPD255	Approved
0.7563	Intermediate Similarity	NPD256	Approved
0.7545	Intermediate Similarity	NPD9273	Approved
0.7523	Intermediate Similarity	NPD844	Approved
0.7523	Intermediate Similarity	NPD1809	Phase 2
0.7522	Intermediate Similarity	NPD179	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD5310	Approved
0.752	Intermediate Similarity	NPD5311	Approved
0.7519	Intermediate Similarity	NPD6809	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD7978	Discontinued
0.7519	Intermediate Similarity	NPD7477	Discontinued
0.75	Intermediate Similarity	NPD3021	Approved
0.75	Intermediate Similarity	NPD3022	Approved
0.75	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9568	Approved
0.7481	Intermediate Similarity	NPD2157	Approved
0.748	Intermediate Similarity	NPD1712	Approved
0.748	Intermediate Similarity	NPD3636	Approved
0.748	Intermediate Similarity	NPD3635	Approved
0.748	Intermediate Similarity	NPD3637	Approved
0.748	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7479	Intermediate Similarity	NPD9618	Approved
0.7479	Intermediate Similarity	NPD9614	Approved
0.746	Intermediate Similarity	NPD1129	Approved
0.746	Intermediate Similarity	NPD1133	Approved
0.746	Intermediate Similarity	NPD1131	Approved
0.746	Intermediate Similarity	NPD3053	Approved
0.746	Intermediate Similarity	NPD3055	Approved
0.746	Intermediate Similarity	NPD1135	Approved
0.746	Intermediate Similarity	NPD1134	Approved
0.7455	Intermediate Similarity	NPD288	Approved
0.7444	Intermediate Similarity	NPD2161	Phase 2
0.744	Intermediate Similarity	NPD3685	Discontinued
0.7438	Intermediate Similarity	NPD9616	Approved
0.7438	Intermediate Similarity	NPD9615	Approved
0.7438	Intermediate Similarity	NPD9613	Approved
0.7431	Intermediate Similarity	NPD4814	Discontinued
0.7424	Intermediate Similarity	NPD3554	Approved
0.7424	Intermediate Similarity	NPD3553	Approved
0.7424	Intermediate Similarity	NPD3552	Approved
0.7424	Intermediate Similarity	NPD3555	Approved
0.7422	Intermediate Similarity	NPD2606	Approved
0.7422	Intermediate Similarity	NPD2605	Approved
0.7411	Intermediate Similarity	NPD4760	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD2195	Approved
0.7402	Intermediate Similarity	NPD2194	Approved
0.7377	Intermediate Similarity	NPD316	Approved
0.7364	Intermediate Similarity	NPD2372	Approved
0.7364	Intermediate Similarity	NPD5155	Approved
0.7364	Intermediate Similarity	NPD5156	Approved
0.736	Intermediate Similarity	NPD2233	Approved
0.736	Intermediate Similarity	NPD2232	Approved
0.736	Intermediate Similarity	NPD2230	Approved
0.7328	Intermediate Similarity	NPD6406	Approved
0.7317	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD6583	Phase 3
0.7302	Intermediate Similarity	NPD6582	Phase 2
0.7288	Intermediate Similarity	NPD4253	Approved
0.7288	Intermediate Similarity	NPD4254	Approved
0.7287	Intermediate Similarity	NPD3595	Approved
0.7287	Intermediate Similarity	NPD3594	Approved
0.7281	Intermediate Similarity	NPD4229	Approved
0.7281	Intermediate Similarity	NPD3680	Approved
0.7281	Intermediate Similarity	NPD3681	Approved
0.7281	Intermediate Similarity	NPD3683	Approved
0.7281	Intermediate Similarity	NPD4231	Approved
0.7281	Intermediate Similarity	NPD3682	Approved
0.7258	Intermediate Similarity	NPD9384	Approved
0.7258	Intermediate Similarity	NPD9381	Approved
0.7257	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD6407	Approved
0.7252	Intermediate Similarity	NPD6405	Approved
0.7244	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6331	Phase 2
0.7222	Intermediate Similarity	NPD3070	Discontinued
0.7206	Intermediate Similarity	NPD7153	Discontinued
0.7206	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD1101	Approved
0.7194	Intermediate Similarity	NPD6682	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD854	Approved
0.7193	Intermediate Similarity	NPD855	Approved
0.7179	Intermediate Similarity	NPD4095	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6038	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD1755	Approved
0.7165	Intermediate Similarity	NPD9622	Approved
0.7163	Intermediate Similarity	NPD7523	Phase 3
0.7156	Intermediate Similarity	NPD530	Approved
0.7143	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD6584	Phase 3
0.7132	Intermediate Similarity	NPD9620	Approved
0.7132	Intermediate Similarity	NPD9621	Approved
0.7132	Intermediate Similarity	NPD9619	Approved
0.713	Intermediate Similarity	NPD4656	Approved
0.713	Intermediate Similarity	NPD4658	Approved
0.7121	Intermediate Similarity	NPD839	Approved
0.7121	Intermediate Similarity	NPD840	Approved
0.7109	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD3028	Approved
0.7092	Intermediate Similarity	NPD7303	Discontinued
0.7091	Intermediate Similarity	NPD1814	Approved
0.7091	Intermediate Similarity	NPD159	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD1812	Approved
0.709	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD9612	Approved
0.708	Intermediate Similarity	NPD9611	Approved
0.708	Intermediate Similarity	NPD9609	Approved
0.7063	Intermediate Similarity	NPD1981	Approved
0.7063	Intermediate Similarity	NPD1980	Approved
0.7063	Intermediate Similarity	NPD1983	Approved
0.7059	Intermediate Similarity	NPD4750	Phase 3
0.7045	Intermediate Similarity	NPD597	Approved
0.7045	Intermediate Similarity	NPD601	Approved
0.7045	Intermediate Similarity	NPD598	Approved
0.7034	Intermediate Similarity	NPD9507	Approved
0.7029	Intermediate Similarity	NPD2211	Approved
0.7029	Intermediate Similarity	NPD2209	Approved
0.7025	Intermediate Similarity	NPD7635	Approved
0.7018	Intermediate Similarity	NPD9712	Approved
0.7	Intermediate Similarity	NPD4025	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD829	Discontinued
0.6992	Remote Similarity	NPD1130	Approved
0.6992	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD1132	Approved
0.6992	Remote Similarity	NPD1136	Approved
0.6991	Remote Similarity	NPD2487	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD4108	Discontinued
0.6975	Remote Similarity	NPD4718	Approved
0.6975	Remote Similarity	NPD4720	Approved
0.6975	Remote Similarity	NPD2684	Approved
0.6975	Remote Similarity	NPD4717	Approved
0.6972	Remote Similarity	NPD7526	Approved
0.6972	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD52	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