NPASS Compound

Structure

NPC471320 OpenBabel07101718312D 28 28 0 0 0 0 0 0 0 0999 V2000 -12.1244 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9904 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9904 3.5000 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 -12.1244 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -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 -5.1962 -1.0000 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 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 -4.3301 -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 -3.4641 -1.0000 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 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 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 2 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 19 1 0 0 0 0 16 17 2 0 0 0 0 16 18 1 0 0 0 0 17 20 1 0 0 0 0 18 21 2 0 0 0 0 19 22 1 0 0 0 0 20 24 2 0 0 0 0 21 24 1 0 0 0 0 22 26 1 0 0 0 0 23 24 1 0 0 0 0 23 27 1 0 0 0 0 25 26 2 3 0 0 0 25 27 1 0 0 0 0 25 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	386.33
Volume:	450.001
LogP:	7.0
LogD:	4.645
LogS:	-2.646
# Rotatable Bonds:	19
TPSA:	41.13
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.217
Synthetic Accessibility Score:	2.091
Fsp3:	0.64
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.036
MDCK Permeability:	3.298378942417912e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.873
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.662
Plasma Protein Binding (PPB):	98.72818756103516%
Volume Distribution (VD):	2.343
Pgp-substrate:	0.44386377930641174%

ADMET: Metabolism

CYP1A2-inhibitor:	0.202
CYP1A2-substrate:	0.357
CYP2C19-inhibitor:	0.635
CYP2C19-substrate:	0.178
CYP2C9-inhibitor:	0.252
CYP2C9-substrate:	0.976
CYP2D6-inhibitor:	0.716
CYP2D6-substrate:	0.891
CYP3A4-inhibitor:	0.802
CYP3A4-substrate:	0.102

ADMET: Excretion

Clearance (CL):	4.803
Half-life (T1/2):	0.619

ADMET: Toxicity

hERG Blockers:	0.743
Human Hepatotoxicity (H-HT):	0.062
Drug-inuced Liver Injury (DILI):	0.021
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.012
Maximum Recommended Daily Dose:	0.037
Skin Sensitization:	0.937
Carcinogencity:	0.03
Eye Corrosion:	0.003
Eye Irritation:	0.036
Respiratory Toxicity:	0.662

Download Data

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

Natural Product: NPC471320

Natural Product ID:	NPC471320
*Common Name:**	1-Benzyl-3-[(Z)-Heptadec-8-Enyl]Urea
IUPAC Name:	1-benzyl-3-[(Z)-heptadec-8-enyl]urea
Synonyms:
Standard InCHIKey:	FFRBOORQGDEJEA-KTKRTIGZSA-N
Standard InCHI:	InChI=1S/C25H42N2O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-22-26-25(28)27-23-24-20-17-16-18-21-24/h9-10,16-18,20-21H,2-8,11-15,19,22-23H2,1H3,(H2,26,27,28)/b10-9-
SMILES:	CCCCCCCC/C=CCCCCCCCN=C(NCc1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2413178
PubChem CID:	71770550
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives

*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
NPO18988	Lepidium meyenii	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932133]
NPO18988	Lepidium meyenii	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23891163]
NPO18988	Lepidium meyenii	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24972328]
NPO18988	Lepidium meyenii	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33320645]
NPO18988	Lepidium meyenii	Species	Brassicaceae	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
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1418	Individual Protein	Anandamide amidohydrolase	Homo sapiens	Inhibition	=	14.2	%	PMID[571145]
NPT1418	Individual Protein	Anandamide amidohydrolase	Homo sapiens	Inhibition	=	61.3	%	PMID[571145]

☑ 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 NPC471320 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	213
0.1-0.2	3597
0.2-0.3	15953
0.3-0.4	16384
0.4-0.5	5215
0.5-0.6	1123
0.6-0.7	170
0.7-0.8	37
0.8-0.85	1
0.85-0.9	1
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471319
0.9239	High Similarity	NPC108339
0.809	Intermediate Similarity	NPC12857
0.7959	Intermediate Similarity	NPC469330
0.7864	Intermediate Similarity	NPC474430
0.7766	Intermediate Similarity	NPC169016
0.7708	Intermediate Similarity	NPC473031
0.7667	Intermediate Similarity	NPC271642
0.7667	Intermediate Similarity	NPC139658
0.7653	Intermediate Similarity	NPC78041
0.7653	Intermediate Similarity	NPC471307
0.7653	Intermediate Similarity	NPC141139
0.7653	Intermediate Similarity	NPC159178
0.7653	Intermediate Similarity	NPC121872
0.7653	Intermediate Similarity	NPC209764
0.7653	Intermediate Similarity	NPC74936
0.76	Intermediate Similarity	NPC322040
0.76	Intermediate Similarity	NPC7067
0.7556	Intermediate Similarity	NPC98976
0.7551	Intermediate Similarity	NPC470877
0.7426	Intermediate Similarity	NPC471309
0.7423	Intermediate Similarity	NPC258046
0.7391	Intermediate Similarity	NPC98269
0.7391	Intermediate Similarity	NPC325662
0.7355	Intermediate Similarity	NPC471321
0.7355	Intermediate Similarity	NPC471306
0.7303	Intermediate Similarity	NPC219246
0.7184	Intermediate Similarity	NPC329430
0.7115	Intermediate Similarity	NPC317400
0.7113	Intermediate Similarity	NPC104070
0.7113	Intermediate Similarity	NPC119677
0.7111	Intermediate Similarity	NPC229235
0.71	Intermediate Similarity	NPC12429
0.7071	Intermediate Similarity	NPC203076
0.7065	Intermediate Similarity	NPC113000
0.7065	Intermediate Similarity	NPC299134
0.7065	Intermediate Similarity	NPC122327
0.7065	Intermediate Similarity	NPC112609
0.701	Intermediate Similarity	NPC14326
0.7	Intermediate Similarity	NPC471638
0.6989	Remote Similarity	NPC276699
0.6975	Remote Similarity	NPC273830
0.6967	Remote Similarity	NPC477937
0.6957	Remote Similarity	NPC244738
0.6952	Remote Similarity	NPC25565
0.6907	Remote Similarity	NPC231986
0.6905	Remote Similarity	NPC471322
0.6893	Remote Similarity	NPC470926
0.6893	Remote Similarity	NPC245259
0.6887	Remote Similarity	NPC473501
0.6887	Remote Similarity	NPC475439
0.6881	Remote Similarity	NPC471310
0.6881	Remote Similarity	NPC202613
0.6881	Remote Similarity	NPC471317
0.6869	Remote Similarity	NPC133162
0.6857	Remote Similarity	NPC58674
0.6842	Remote Similarity	NPC290638
0.6818	Remote Similarity	NPC469974
0.68	Remote Similarity	NPC3210
0.6768	Remote Similarity	NPC474088
0.6698	Remote Similarity	NPC303045
0.6698	Remote Similarity	NPC161972
0.6636	Remote Similarity	NPC327226
0.6635	Remote Similarity	NPC78154
0.6635	Remote Similarity	NPC172128
0.6612	Remote Similarity	NPC326232
0.661	Remote Similarity	NPC101139
0.6579	Remote Similarity	NPC164802
0.6574	Remote Similarity	NPC311242
0.6571	Remote Similarity	NPC226438
0.6562	Remote Similarity	NPC32858
0.6562	Remote Similarity	NPC194857
0.6549	Remote Similarity	NPC327481
0.6538	Remote Similarity	NPC314835
0.6518	Remote Similarity	NPC304761
0.6518	Remote Similarity	NPC150254
0.6518	Remote Similarity	NPC194390
0.6518	Remote Similarity	NPC88267
0.6518	Remote Similarity	NPC275467
0.6518	Remote Similarity	NPC224610
0.6518	Remote Similarity	NPC147000
0.6518	Remote Similarity	NPC113326
0.6518	Remote Similarity	NPC226778
0.6509	Remote Similarity	NPC473661
0.6496	Remote Similarity	NPC474584
0.6486	Remote Similarity	NPC329375
0.6476	Remote Similarity	NPC316108
0.6471	Remote Similarity	NPC288232
0.646	Remote Similarity	NPC67043
0.646	Remote Similarity	NPC143516
0.646	Remote Similarity	NPC474695
0.6441	Remote Similarity	NPC314141
0.6439	Remote Similarity	NPC132636
0.6429	Remote Similarity	NPC164859
0.6423	Remote Similarity	NPC71684
0.6404	Remote Similarity	NPC130898
0.6404	Remote Similarity	NPC474973
0.6404	Remote Similarity	NPC45033
0.6404	Remote Similarity	NPC474804
0.6396	Remote Similarity	NPC469457
0.6346	Remote Similarity	NPC17497
0.6346	Remote Similarity	NPC305602
0.6346	Remote Similarity	NPC60408
0.6339	Remote Similarity	NPC239854
0.6339	Remote Similarity	NPC291610
0.6325	Remote Similarity	NPC319579
0.632	Remote Similarity	NPC283130
0.632	Remote Similarity	NPC328683
0.6303	Remote Similarity	NPC276949
0.6303	Remote Similarity	NPC35850
0.63	Remote Similarity	NPC192623
0.6293	Remote Similarity	NPC473676
0.6293	Remote Similarity	NPC77294
0.6273	Remote Similarity	NPC472258
0.6271	Remote Similarity	NPC275410
0.6261	Remote Similarity	NPC471447
0.6261	Remote Similarity	NPC473498
0.625	Remote Similarity	NPC214200
0.625	Remote Similarity	NPC471318
0.625	Remote Similarity	NPC33742
0.625	Remote Similarity	NPC228400
0.6239	Remote Similarity	NPC20142
0.6239	Remote Similarity	NPC215351
0.623	Remote Similarity	NPC313449
0.6222	Remote Similarity	NPC210849
0.6216	Remote Similarity	NPC164514
0.6216	Remote Similarity	NPC290515
0.6216	Remote Similarity	NPC303611
0.6216	Remote Similarity	NPC108606
0.6216	Remote Similarity	NPC226096
0.6212	Remote Similarity	NPC267237
0.6207	Remote Similarity	NPC142297
0.6183	Remote Similarity	NPC476687
0.6183	Remote Similarity	NPC476689
0.6183	Remote Similarity	NPC476685
0.6174	Remote Similarity	NPC476198
0.6161	Remote Similarity	NPC12730
0.6159	Remote Similarity	NPC314114
0.6148	Remote Similarity	NPC470544
0.6147	Remote Similarity	NPC291070
0.6147	Remote Similarity	NPC246757
0.6139	Remote Similarity	NPC475289
0.6139	Remote Similarity	NPC309279
0.6139	Remote Similarity	NPC475573
0.6134	Remote Similarity	NPC475013
0.6134	Remote Similarity	NPC329011
0.6132	Remote Similarity	NPC30445
0.6132	Remote Similarity	NPC325441
0.6129	Remote Similarity	NPC283760
0.6126	Remote Similarity	NPC293628
0.6126	Remote Similarity	NPC122493
0.6126	Remote Similarity	NPC33168
0.6126	Remote Similarity	NPC10781
0.6121	Remote Similarity	NPC231705
0.6121	Remote Similarity	NPC274089
0.6121	Remote Similarity	NPC191215
0.6117	Remote Similarity	NPC134825
0.6106	Remote Similarity	NPC29601
0.6106	Remote Similarity	NPC155847
0.6106	Remote Similarity	NPC289381
0.6102	Remote Similarity	NPC258056
0.6098	Remote Similarity	NPC470545
0.6078	Remote Similarity	NPC307456
0.6071	Remote Similarity	NPC322598
0.6067	Remote Similarity	NPC65873
0.6067	Remote Similarity	NPC300345
0.6067	Remote Similarity	NPC212114
0.6067	Remote Similarity	NPC120441
0.6066	Remote Similarity	NPC197470
0.6061	Remote Similarity	NPC325479
0.6058	Remote Similarity	NPC168861
0.605	Remote Similarity	NPC474149
0.6048	Remote Similarity	NPC470546
0.6048	Remote Similarity	NPC314992
0.6048	Remote Similarity	NPC320656
0.6038	Remote Similarity	NPC262295
0.6038	Remote Similarity	NPC198747
0.6034	Remote Similarity	NPC211551
0.6034	Remote Similarity	NPC473418
0.6033	Remote Similarity	NPC476048
0.6033	Remote Similarity	NPC187036
0.6031	Remote Similarity	NPC226662
0.6031	Remote Similarity	NPC89490
0.6029	Remote Similarity	NPC214988
0.6019	Remote Similarity	NPC191444
0.6019	Remote Similarity	NPC258627
0.6018	Remote Similarity	NPC125732
0.6016	Remote Similarity	NPC2265
0.6016	Remote Similarity	NPC239357
0.6016	Remote Similarity	NPC313673
0.6016	Remote Similarity	NPC22746
0.6	Remote Similarity	NPC178902
0.6	Remote Similarity	NPC474974
0.6	Remote Similarity	NPC71140
0.5985	Remote Similarity	NPC329896
0.5985	Remote Similarity	NPC475090
0.5985	Remote Similarity	NPC475105
0.5985	Remote Similarity	NPC126458
0.5982	Remote Similarity	NPC324569
0.5981	Remote Similarity	NPC262393

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 NPC471320 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	152
0.1-0.2	544
0.2-0.3	1319
0.3-0.4	2596
0.4-0.5	3083
0.5-0.6	1115
0.6-0.7	293
0.7-0.8	44
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8696	High Similarity	NPD9	Approved
0.8696	High Similarity	NPD297	Approved
0.8105	Intermediate Similarity	NPD9348	Approved
0.8105	Intermediate Similarity	NPD9350	Approved
0.8105	Intermediate Similarity	NPD9351	Phase 3
0.8105	Intermediate Similarity	NPD9349	Approved
0.7912	Intermediate Similarity	NPD5371	Approved
0.7912	Intermediate Similarity	NPD5372	Approved
0.789	Intermediate Similarity	NPD1813	Discontinued
0.78	Intermediate Similarity	NPD2507	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD304	Approved
0.7789	Intermediate Similarity	NPD305	Approved
0.7632	Intermediate Similarity	NPD6892	Discontinued
0.76	Intermediate Similarity	NPD199	Approved
0.76	Intermediate Similarity	NPD197	Approved
0.76	Intermediate Similarity	NPD243	Approved
0.76	Intermediate Similarity	NPD8	Approved
0.7582	Intermediate Similarity	NPD603	Approved
0.7576	Intermediate Similarity	NPD7160	Approved
0.7524	Intermediate Similarity	NPD1396	Approved
0.75	Intermediate Similarity	NPD9505	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD296	Approved
0.75	Intermediate Similarity	NPD293	Approved
0.75	Intermediate Similarity	NPD6690	Approved
0.75	Intermediate Similarity	NPD295	Approved
0.7434	Intermediate Similarity	NPD6660	Discontinued
0.7419	Intermediate Similarity	NPD590	Approved
0.7419	Intermediate Similarity	NPD589	Approved
0.7396	Intermediate Similarity	NPD2539	Approved
0.7396	Intermediate Similarity	NPD785	Approved
0.7396	Intermediate Similarity	NPD2538	Approved
0.7395	Intermediate Similarity	NPD6900	Discontinued
0.7358	Intermediate Similarity	NPD5655	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5554	Approved
0.7327	Intermediate Similarity	NPD1814	Approved
0.7327	Intermediate Similarity	NPD1812	Approved
0.7292	Intermediate Similarity	NPD830	Approved
0.7292	Intermediate Similarity	NPD831	Approved
0.7282	Intermediate Similarity	NPD2005	Discontinued
0.7234	Intermediate Similarity	NPD507	Approved
0.7234	Intermediate Similarity	NPD508	Approved
0.7222	Intermediate Similarity	NPD414	Discontinued
0.7196	Intermediate Similarity	NPD5103	Approved
0.7179	Intermediate Similarity	NPD7342	Discontinued
0.7168	Intermediate Similarity	NPD2665	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6561	Approved
0.7168	Intermediate Similarity	NPD6562	Approved
0.713	Intermediate Similarity	NPD1028	Approved
0.713	Intermediate Similarity	NPD1026	Approved
0.7117	Intermediate Similarity	NPD1107	Approved
0.7117	Intermediate Similarity	NPD1108	Approved
0.7115	Intermediate Similarity	NPD838	Approved
0.7107	Intermediate Similarity	NPD3606	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD2206	Approved
0.7091	Intermediate Similarity	NPD2243	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD2207	Approved
0.7087	Intermediate Similarity	NPD1080	Approved
0.708	Intermediate Similarity	NPD480	Approved
0.7065	Intermediate Similarity	NPD9593	Approved
0.7065	Intermediate Similarity	NPD9592	Approved
0.7065	Intermediate Similarity	NPD9588	Approved
0.7065	Intermediate Similarity	NPD80	Approved
0.7065	Intermediate Similarity	NPD9594	Approved
0.7065	Intermediate Similarity	NPD9591	Approved
0.7065	Intermediate Similarity	NPD9589	Approved
0.7065	Intermediate Similarity	NPD9590	Approved
0.7059	Intermediate Similarity	NPD3000	Approved
0.7059	Intermediate Similarity	NPD2997	Approved
0.7059	Intermediate Similarity	NPD2998	Approved
0.7048	Intermediate Similarity	NPD528	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD9395	Approved
0.703	Intermediate Similarity	NPD5656	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4144	Approved
0.7021	Intermediate Similarity	NPD4147	Approved
0.7018	Intermediate Similarity	NPD1656	Phase 2
0.7	Intermediate Similarity	NPD187	Approved
0.7	Intermediate Similarity	NPD782	Approved
0.7	Intermediate Similarity	NPD3428	Approved
0.7	Intermediate Similarity	NPD3426	Approved
0.7	Intermediate Similarity	NPD4146	Approved
0.7	Intermediate Similarity	NPD2002	Discontinued
0.7	Intermediate Similarity	NPD781	Approved
0.7	Intermediate Similarity	NPD783	Approved
0.7	Intermediate Similarity	NPD780	Approved
0.7	Intermediate Similarity	NPD4145	Approved
0.6991	Remote Similarity	NPD753	Approved
0.6983	Remote Similarity	NPD2463	Approved
0.6983	Remote Similarity	NPD2467	Approved
0.6983	Remote Similarity	NPD2464	Approved
0.6961	Remote Similarity	NPD5915	Approved
0.6957	Remote Similarity	NPD7062	Discontinued
0.6957	Remote Similarity	NPD9728	Phase 1
0.6923	Remote Similarity	NPD735	Approved
0.6923	Remote Similarity	NPD736	Approved
0.6923	Remote Similarity	NPD837	Approved
0.6917	Remote Similarity	NPD2131	Approved
0.6916	Remote Similarity	NPD787	Suspended
0.6916	Remote Similarity	NPD1946	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD563	Approved
0.6909	Remote Similarity	NPD564	Approved
0.6909	Remote Similarity	NPD1269	Approved
0.6909	Remote Similarity	NPD1268	Approved
0.6893	Remote Similarity	NPD4543	Discontinued
0.6891	Remote Similarity	NPD5961	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD505	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD2244	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1053	Approved
0.6875	Remote Similarity	NPD1051	Approved
0.6875	Remote Similarity	NPD1052	Approved
0.6869	Remote Similarity	NPD3429	Approved
0.6869	Remote Similarity	NPD3427	Approved
0.6864	Remote Similarity	NPD1216	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD483	Approved
0.686	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.686	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD6105	Discontinued
0.6827	Remote Similarity	NPD4405	Approved
0.6827	Remote Similarity	NPD4407	Approved
0.6827	Remote Similarity	NPD4408	Approved
0.6818	Remote Similarity	NPD488	Approved
0.6818	Remote Similarity	NPD489	Approved
0.6818	Remote Similarity	NPD4936	Approved
0.6818	Remote Similarity	NPD4937	Approved
0.6818	Remote Similarity	NPD3407	Phase 3
0.681	Remote Similarity	NPD2543	Discontinued
0.6792	Remote Similarity	NPD157	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD1417	Approved
0.6789	Remote Similarity	NPD1419	Approved
0.6789	Remote Similarity	NPD4119	Approved
0.6783	Remote Similarity	NPD4165	Phase 2
0.6783	Remote Similarity	NPD3066	Phase 2
0.6783	Remote Similarity	NPD7121	Approved
0.6777	Remote Similarity	NPD4323	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD9393	Approved
0.6771	Remote Similarity	NPD9397	Approved
0.6765	Remote Similarity	NPD588	Approved
0.6765	Remote Similarity	NPD587	Approved
0.6762	Remote Similarity	NPD4542	Approved
0.6762	Remote Similarity	NPD6549	Approved
0.6762	Remote Similarity	NPD2878	Approved
0.6762	Remote Similarity	NPD4545	Approved
0.6762	Remote Similarity	NPD6548	Approved
0.6757	Remote Similarity	NPD5717	Approved
0.6757	Remote Similarity	NPD1406	Approved
0.6752	Remote Similarity	NPD7508	Discontinued
0.6748	Remote Similarity	NPD2143	Discontinued
0.6746	Remote Similarity	NPD4857	Phase 1
0.6735	Remote Similarity	NPD4026	Approved
0.6735	Remote Similarity	NPD3035	Approved
0.6735	Remote Similarity	NPD4027	Approved
0.6733	Remote Similarity	NPD5252	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD2678	Approved
0.6726	Remote Similarity	NPD2679	Approved
0.6723	Remote Similarity	NPD18	Approved
0.672	Remote Similarity	NPD7582	Discontinued
0.67	Remote Similarity	NPD5178	Approved
0.6699	Remote Similarity	NPD771	Phase 3
0.6698	Remote Similarity	NPD1081	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD1916	Discontinued
0.6667	Remote Similarity	NPD4170	Approved
0.6667	Remote Similarity	NPD1724	Approved
0.6667	Remote Similarity	NPD9538	Approved
0.6667	Remote Similarity	NPD4169	Approved
0.6667	Remote Similarity	NPD4701	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4117	Approved
0.6667	Remote Similarity	NPD292	Approved
0.6667	Remote Similarity	NPD294	Approved
0.6667	Remote Similarity	NPD7120	Approved
0.6667	Remote Similarity	NPD1539	Approved
0.6667	Remote Similarity	NPD1479	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5716	Approved
0.6636	Remote Similarity	NPD2895	Discontinued
0.6636	Remote Similarity	NPD1540	Approved
0.6634	Remote Similarity	NPD2208	Approved
0.6634	Remote Similarity	NPD2205	Approved
0.6633	Remote Similarity	NPD260	Discontinued
0.6604	Remote Similarity	NPD3982	Approved
0.6604	Remote Similarity	NPD3980	Approved
0.6602	Remote Similarity	NPD3345	Approved
0.6602	Remote Similarity	NPD5675	Discontinued
0.66	Remote Similarity	NPD2001	Discontinued
0.66	Remote Similarity	NPD4635	Approved
0.6598	Remote Similarity	NPD9563	Approved
0.6598	Remote Similarity	NPD9564	Approved
0.6598	Remote Similarity	NPD79	Approved
0.6591	Remote Similarity	NPD3156	Discontinued
0.6583	Remote Similarity	NPD5511	Discontinued
0.6579	Remote Similarity	NPD477	Phase 1
0.6577	Remote Similarity	NPD1542	Approved
0.6574	Remote Similarity	NPD5598	Approved
0.6574	Remote Similarity	NPD5597	Approved
0.6571	Remote Similarity	NPD530	Approved
0.6566	Remote Similarity	NPD472	Approved
0.6562	Remote Similarity	NPD6076	Approved
0.6562	Remote Similarity	NPD6075	Approved
0.6555	Remote Similarity	NPD5162	Approved
0.6552	Remote Similarity	NPD2999	Approved
0.6552	Remote Similarity	NPD3001	Approved
0.6545	Remote Similarity	NPD4760	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5780	Phase 2

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