NPASS Compound

Structure

NPC159178 OpenBabel07101719252D 33 33 0 0 0 0 0 0 0 0999 V2000 -3.4641 18.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 18.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 18.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 17.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 16.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 15.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 15.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 14.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 13.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 12.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 12.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 11.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 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 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 -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 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 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 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 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 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 21 25 1 0 0 0 0 22 23 2 0 0 0 0 22 24 1 0 0 0 0 23 26 1 0 0 0 0 24 27 2 0 0 0 0 25 28 1 0 0 0 0 26 30 2 0 0 0 0 27 30 1 0 0 0 0 28 31 1 0 0 0 0 29 30 1 0 0 0 0 29 32 1 0 0 0 0 31 32 2 3 0 0 0 31 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	455.41
Volume:	542.78
LogP:	9.689
LogD:	5.078
LogS:	-2.814
# Rotatable Bonds:	24
TPSA:	29.1
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.129
Synthetic Accessibility Score:	2.187
Fsp3:	0.71
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.088
MDCK Permeability:	1.219901332660811e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.911
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027
Plasma Protein Binding (PPB):	100.5512466430664%
Volume Distribution (VD):	3.24
Pgp-substrate:	0.34599030017852783%

ADMET: Metabolism

CYP1A2-inhibitor:	0.06
CYP1A2-substrate:	0.184
CYP2C19-inhibitor:	0.258
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.082
CYP2C9-substrate:	0.947
CYP2D6-inhibitor:	0.63
CYP2D6-substrate:	0.272
CYP3A4-inhibitor:	0.455
CYP3A4-substrate:	0.073

ADMET: Excretion

Clearance (CL):	4.319
Half-life (T1/2):	0.383

ADMET: Toxicity

hERG Blockers:	0.984
Human Hepatotoxicity (H-HT):	0.065
Drug-inuced Liver Injury (DILI):	0.033
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.019
Maximum Recommended Daily Dose:	0.024
Skin Sensitization:	0.972
Carcinogencity:	0.02
Eye Corrosion:	0.006
Eye Irritation:	0.089
Respiratory Toxicity:	0.799

Download Data

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

Natural Product: NPC159178

Natural Product ID:	NPC159178
*Common Name:**	(Z)-N-Benzyltetracos-15-Enamide
IUPAC Name:	(Z)-N-benzyltetracos-15-enamide
Synonyms:
Standard InCHIKey:	LQJKLTWHJMDOQD-KTKRTIGZSA-N
Standard InCHI:	InChI=1S/C31H53NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25-28-31(33)32-29-30-26-23-22-24-27-30/h9-10,22-24,26-27H,2-8,11-21,25,28-29H2,1H3,(H,32,33)/b10-9-
SMILES:	CCCCCCCC/C=CCCCCCCCCCCCCCC(=NCc1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2413163
PubChem CID:	73347575
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000331] Fatty amides [CHEMONTID:0001096] N-acyl amines

*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
IC50	1
Others	2

Activity Type	# Activity
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1418	Individual Protein	Anandamide amidohydrolase	Homo sapiens	IC50	>	500000.0	nM	PMID[457242]
NPT1418	Individual Protein	Anandamide amidohydrolase	Homo sapiens	Inhibition	<	10.0	%	PMID[457242]
NPT1418	Individual Protein	Anandamide amidohydrolase	Homo sapiens	Inhibition	=	49.2	%	PMID[457242]

☑ 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 NPC159178 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	104
0.1-0.2	1479
0.2-0.3	8567
0.3-0.4	18663
0.4-0.5	10491
0.5-0.6	2714
0.6-0.7	520
0.7-0.8	120
0.8-0.85	13
0.85-0.9	13
0.9-0.95	0
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC121872
1.0	High Similarity	NPC74936
1.0	High Similarity	NPC471307
1.0	High Similarity	NPC78041
1.0	High Similarity	NPC209764
1.0	High Similarity	NPC141139
0.9881	High Similarity	NPC470877
0.9655	High Similarity	NPC471309
0.8901	High Similarity	NPC58674
0.8842	High Similarity	NPC471310
0.8842	High Similarity	NPC471317
0.8804	High Similarity	NPC25565
0.875	High Similarity	NPC473031
0.871	High Similarity	NPC475439
0.871	High Similarity	NPC473501
0.8652	High Similarity	NPC12429
0.8646	High Similarity	NPC202613
0.8539	High Similarity	NPC471638
0.8495	Intermediate Similarity	NPC303045
0.8495	Intermediate Similarity	NPC161972
0.8462	Intermediate Similarity	NPC316108
0.8462	Intermediate Similarity	NPC172128
0.837	Intermediate Similarity	NPC226438
0.8316	Intermediate Similarity	NPC311242
0.8182	Intermediate Similarity	NPC113326
0.8182	Intermediate Similarity	NPC194390
0.8182	Intermediate Similarity	NPC88267
0.8182	Intermediate Similarity	NPC224610
0.8172	Intermediate Similarity	NPC245259
0.8043	Intermediate Similarity	NPC325441
0.8022	Intermediate Similarity	NPC203076
0.7978	Intermediate Similarity	NPC14326
0.7955	Intermediate Similarity	NPC192623
0.7925	Intermediate Similarity	NPC471318
0.7872	Intermediate Similarity	NPC258627
0.7788	Intermediate Similarity	NPC258056
0.7778	Intermediate Similarity	NPC12730
0.7755	Intermediate Similarity	NPC33168
0.7742	Intermediate Similarity	NPC198747
0.7717	Intermediate Similarity	NPC3210
0.7714	Intermediate Similarity	NPC474149
0.77	Intermediate Similarity	NPC469457
0.767	Intermediate Similarity	NPC231705
0.767	Intermediate Similarity	NPC327481
0.7653	Intermediate Similarity	NPC471319
0.7653	Intermediate Similarity	NPC471320
0.7596	Intermediate Similarity	NPC142297
0.7573	Intermediate Similarity	NPC211551
0.757	Intermediate Similarity	NPC474584
0.7549	Intermediate Similarity	NPC178681
0.75	Intermediate Similarity	NPC35850
0.75	Intermediate Similarity	NPC160120
0.75	Intermediate Similarity	NPC276949
0.75	Intermediate Similarity	NPC53596
0.75	Intermediate Similarity	NPC289330
0.75	Intermediate Similarity	NPC471308
0.75	Intermediate Similarity	NPC78154
0.75	Intermediate Similarity	NPC271642
0.75	Intermediate Similarity	NPC17388
0.7471	Intermediate Similarity	NPC299134
0.7449	Intermediate Similarity	NPC476483
0.7431	Intermediate Similarity	NPC33742
0.7386	Intermediate Similarity	NPC98976
0.7383	Intermediate Similarity	NPC319579
0.7379	Intermediate Similarity	NPC178902
0.7379	Intermediate Similarity	NPC164859
0.7364	Intermediate Similarity	NPC317254
0.7356	Intermediate Similarity	NPC244738
0.7347	Intermediate Similarity	NPC265521
0.7333	Intermediate Similarity	NPC191215
0.7333	Intermediate Similarity	NPC274089
0.7297	Intermediate Similarity	NPC470544
0.7241	Intermediate Similarity	NPC208302
0.7232	Intermediate Similarity	NPC169328
0.7232	Intermediate Similarity	NPC254088
0.7232	Intermediate Similarity	NPC470545
0.7222	Intermediate Similarity	NPC325662
0.7222	Intermediate Similarity	NPC98269
0.7196	Intermediate Similarity	NPC24101
0.7196	Intermediate Similarity	NPC96224
0.7191	Intermediate Similarity	NPC189371
0.7184	Intermediate Similarity	NPC214200
0.7184	Intermediate Similarity	NPC228400
0.7168	Intermediate Similarity	NPC237420
0.7168	Intermediate Similarity	NPC310467
0.7168	Intermediate Similarity	NPC470546
0.7156	Intermediate Similarity	NPC329011
0.7155	Intermediate Similarity	NPC471314
0.7155	Intermediate Similarity	NPC471315
0.7143	Intermediate Similarity	NPC12857
0.7129	Intermediate Similarity	NPC3371
0.7128	Intermediate Similarity	NPC477770
0.7128	Intermediate Similarity	NPC15839
0.7126	Intermediate Similarity	NPC219246
0.7117	Intermediate Similarity	NPC118202
0.7115	Intermediate Similarity	NPC318154
0.7105	Intermediate Similarity	NPC283760
0.7079	Intermediate Similarity	NPC108218
0.7054	Intermediate Similarity	NPC188010
0.7054	Intermediate Similarity	NPC197470
0.7043	Intermediate Similarity	NPC478015
0.7043	Intermediate Similarity	NPC476990
0.7043	Intermediate Similarity	NPC45777
0.7043	Intermediate Similarity	NPC477061
0.7043	Intermediate Similarity	NPC478014
0.7043	Intermediate Similarity	NPC478016
0.7037	Intermediate Similarity	NPC153690
0.703	Intermediate Similarity	NPC108339
0.703	Intermediate Similarity	NPC20142
0.703	Intermediate Similarity	NPC215351
0.7018	Intermediate Similarity	NPC314992
0.7009	Intermediate Similarity	NPC130898
0.7009	Intermediate Similarity	NPC474804
0.7009	Intermediate Similarity	NPC474973
0.7	Intermediate Similarity	NPC323164
0.6991	Remote Similarity	NPC82963
0.6991	Remote Similarity	NPC2265
0.699	Remote Similarity	NPC108606
0.699	Remote Similarity	NPC226096
0.699	Remote Similarity	NPC303611
0.699	Remote Similarity	NPC164514
0.699	Remote Similarity	NPC290515
0.6989	Remote Similarity	NPC184030
0.6989	Remote Similarity	NPC309279
0.6989	Remote Similarity	NPC164449
0.6983	Remote Similarity	NPC202521
0.6983	Remote Similarity	NPC71684
0.6964	Remote Similarity	NPC470550
0.6964	Remote Similarity	NPC205652
0.6957	Remote Similarity	NPC224544
0.6952	Remote Similarity	NPC327226
0.6947	Remote Similarity	NPC104070
0.6947	Remote Similarity	NPC146703
0.6932	Remote Similarity	NPC229235
0.693	Remote Similarity	NPC38458
0.693	Remote Similarity	NPC311737
0.6923	Remote Similarity	NPC139658
0.6923	Remote Similarity	NPC252878
0.6916	Remote Similarity	NPC143516
0.6915	Remote Similarity	NPC231986
0.6915	Remote Similarity	NPC307456
0.6897	Remote Similarity	NPC190663
0.6893	Remote Similarity	NPC10781
0.6893	Remote Similarity	NPC293628
0.6893	Remote Similarity	NPC122493
0.6889	Remote Similarity	NPC122327
0.6889	Remote Similarity	NPC112609
0.6889	Remote Similarity	NPC113000
0.6875	Remote Similarity	NPC169016
0.6875	Remote Similarity	NPC1986
0.6875	Remote Similarity	NPC474544
0.6864	Remote Similarity	NPC6975
0.6864	Remote Similarity	NPC46427
0.6857	Remote Similarity	NPC155847
0.6857	Remote Similarity	NPC289381
0.6842	Remote Similarity	NPC147957
0.6842	Remote Similarity	NPC121478
0.6842	Remote Similarity	NPC73637
0.6842	Remote Similarity	NPC475199
0.6842	Remote Similarity	NPC239357
0.6842	Remote Similarity	NPC283012
0.6827	Remote Similarity	NPC322598
0.6822	Remote Similarity	NPC304761
0.6822	Remote Similarity	NPC226778
0.6822	Remote Similarity	NPC150254
0.6822	Remote Similarity	NPC147000
0.6814	Remote Similarity	NPC142599
0.6813	Remote Similarity	NPC276699
0.681	Remote Similarity	NPC43275
0.681	Remote Similarity	NPC268572
0.6807	Remote Similarity	NPC22746
0.6786	Remote Similarity	NPC273814
0.678	Remote Similarity	NPC160493
0.6771	Remote Similarity	NPC474088
0.6771	Remote Similarity	NPC119677
0.6771	Remote Similarity	NPC44830
0.6759	Remote Similarity	NPC476198
0.6759	Remote Similarity	NPC67043
0.6754	Remote Similarity	NPC235421
0.6752	Remote Similarity	NPC80150
0.6752	Remote Similarity	NPC200964
0.675	Remote Similarity	NPC101719
0.675	Remote Similarity	NPC47667
0.6737	Remote Similarity	NPC133050
0.6733	Remote Similarity	NPC470926
0.6731	Remote Similarity	NPC324569
0.6723	Remote Similarity	NPC35996
0.6723	Remote Similarity	NPC472415
0.6721	Remote Similarity	NPC471313
0.6721	Remote Similarity	NPC471311
0.672	Remote Similarity	NPC285078
0.672	Remote Similarity	NPC6854
0.672	Remote Similarity	NPC313737
0.6701	Remote Similarity	NPC304538
0.6698	Remote Similarity	NPC29601
0.6697	Remote Similarity	NPC45033
0.6694	Remote Similarity	NPC477937
0.6667	Remote Similarity	NPC290638
0.6667	Remote Similarity	NPC99394
0.6667	Remote Similarity	NPC275467

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 NPC159178 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	98
0.1-0.2	608
0.2-0.3	1004
0.3-0.4	2403
0.4-0.5	3082
0.5-0.6	1502
0.6-0.7	377
0.7-0.8	70
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9767	High Similarity	NPD6690	Approved
0.8478	Intermediate Similarity	NPD1812	Approved
0.8478	Intermediate Similarity	NPD1814	Approved
0.8333	Intermediate Similarity	NPD187	Approved
0.8298	Intermediate Similarity	NPD4814	Discontinued
0.8247	Intermediate Similarity	NPD4760	Clinical (unspecified phase)
0.8191	Intermediate Similarity	NPD1080	Approved
0.8021	Intermediate Similarity	NPD2507	Clinical (unspecified phase)
0.7938	Intermediate Similarity	NPD2487	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD4165	Phase 2
0.7905	Intermediate Similarity	NPD3066	Phase 2
0.7767	Intermediate Similarity	NPD6038	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD5371	Approved
0.7753	Intermediate Similarity	NPD5372	Approved
0.7742	Intermediate Similarity	NPD9538	Approved
0.766	Intermediate Similarity	NPD1101	Approved
0.7624	Intermediate Similarity	NPD4119	Approved
0.7604	Intermediate Similarity	NPD530	Approved
0.7573	Intermediate Similarity	NPD5717	Approved
0.7551	Intermediate Similarity	NPD1081	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD1542	Approved
0.7547	Intermediate Similarity	NPD3644	Approved
0.7547	Intermediate Similarity	NPD3643	Approved
0.7547	Intermediate Similarity	NPD3642	Approved
0.7526	Intermediate Similarity	NPD752	Approved
0.7524	Intermediate Similarity	NPD2679	Approved
0.7524	Intermediate Similarity	NPD2678	Approved
0.75	Intermediate Similarity	NPD3147	Approved
0.75	Intermediate Similarity	NPD2658	Approved
0.75	Intermediate Similarity	NPD3148	Approved
0.75	Intermediate Similarity	NPD3150	Approved
0.75	Intermediate Similarity	NPD3149	Approved
0.75	Intermediate Similarity	NPD2659	Approved
0.7476	Intermediate Similarity	NPD179	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD2895	Discontinued
0.7451	Intermediate Similarity	NPD1540	Approved
0.7449	Intermediate Similarity	NPD1394	Approved
0.7429	Intermediate Similarity	NPD6406	Approved
0.7426	Intermediate Similarity	NPD1067	Discontinued
0.7416	Intermediate Similarity	NPD603	Approved
0.7411	Intermediate Similarity	NPD2210	Approved
0.7411	Intermediate Similarity	NPD2212	Approved
0.7407	Intermediate Similarity	NPD1764	Approved
0.7407	Intermediate Similarity	NPD1762	Approved
0.7404	Intermediate Similarity	NPD563	Approved
0.7404	Intermediate Similarity	NPD564	Approved
0.7379	Intermediate Similarity	NPD5103	Approved
0.7379	Intermediate Similarity	NPD2244	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD2622	Approved
0.7356	Intermediate Similarity	NPD9728	Phase 1
0.7327	Intermediate Similarity	NPD4117	Approved
0.7308	Intermediate Similarity	NPD3407	Phase 3
0.7282	Intermediate Similarity	NPD4818	Approved
0.7282	Intermediate Similarity	NPD5716	Approved
0.7282	Intermediate Similarity	NPD1419	Approved
0.7282	Intermediate Similarity	NPD1417	Approved
0.7282	Intermediate Similarity	NPD4817	Approved
0.7273	Intermediate Similarity	NPD1066	Discontinued
0.7273	Intermediate Similarity	NPD720	Approved
0.7273	Intermediate Similarity	NPD3719	Approved
0.7273	Intermediate Similarity	NPD3718	Approved
0.7273	Intermediate Similarity	NPD719	Approved
0.7273	Intermediate Similarity	NPD1409	Phase 3
0.7238	Intermediate Similarity	NPD1018	Approved
0.7238	Intermediate Similarity	NPD999	Phase 2
0.7234	Intermediate Similarity	NPD2538	Approved
0.7234	Intermediate Similarity	NPD2539	Approved
0.7232	Intermediate Similarity	NPD6360	Discontinued
0.713	Intermediate Similarity	NPD1107	Approved
0.713	Intermediate Similarity	NPD1108	Approved
0.7115	Intermediate Similarity	NPD854	Approved
0.7115	Intermediate Similarity	NPD855	Approved
0.7115	Intermediate Similarity	NPD4719	Phase 2
0.7103	Intermediate Similarity	NPD2243	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD472	Approved
0.7091	Intermediate Similarity	NPD181	Approved
0.708	Intermediate Similarity	NPD7522	Discontinued
0.7075	Intermediate Similarity	NPD1040	Phase 2
0.7065	Intermediate Similarity	NPD508	Approved
0.7065	Intermediate Similarity	NPD507	Approved
0.7059	Intermediate Similarity	NPD1875	Phase 1
0.7054	Intermediate Similarity	NPD1348	Approved
0.7043	Intermediate Similarity	NPD7342	Discontinued
0.7037	Intermediate Similarity	NPD7156	Discontinued
0.7034	Intermediate Similarity	NPD6325	Discontinued
0.7033	Intermediate Similarity	NPD4147	Approved
0.7033	Intermediate Similarity	NPD4144	Approved
0.7027	Intermediate Similarity	NPD1682	Approved
0.7027	Intermediate Similarity	NPD1680	Approved
0.7027	Intermediate Similarity	NPD1681	Approved
0.7018	Intermediate Similarity	NPD2218	Phase 2
0.7018	Intermediate Similarity	NPD2217	Approved
0.7	Intermediate Similarity	NPD3651	Discontinued
0.699	Remote Similarity	NPD9611	Approved
0.699	Remote Similarity	NPD9609	Approved
0.699	Remote Similarity	NPD9612	Approved
0.6957	Remote Similarity	NPD5981	Approved
0.6942	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD9712	Approved
0.6909	Remote Similarity	NPD4253	Approved
0.6909	Remote Similarity	NPD4254	Approved
0.6903	Remote Similarity	NPD7508	Discontinued
0.6893	Remote Similarity	NPD9566	Approved
0.6891	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD5578	Approved
0.6889	Remote Similarity	NPD9590	Approved
0.6889	Remote Similarity	NPD9594	Approved
0.6889	Remote Similarity	NPD80	Approved
0.6889	Remote Similarity	NPD9591	Approved
0.6889	Remote Similarity	NPD9592	Approved
0.6889	Remote Similarity	NPD9593	Approved
0.6889	Remote Similarity	NPD9588	Approved
0.6889	Remote Similarity	NPD9589	Approved
0.6887	Remote Similarity	NPD4656	Approved
0.6887	Remote Similarity	NPD3683	Approved
0.6887	Remote Similarity	NPD1415	Approved
0.6887	Remote Similarity	NPD3680	Approved
0.6887	Remote Similarity	NPD4231	Approved
0.6887	Remote Similarity	NPD4229	Approved
0.6887	Remote Similarity	NPD4658	Approved
0.6887	Remote Similarity	NPD3682	Approved
0.6887	Remote Similarity	NPD3681	Approved
0.6882	Remote Similarity	NPD1053	Approved
0.6882	Remote Similarity	NPD1051	Approved
0.6882	Remote Similarity	NPD1052	Approved
0.6875	Remote Similarity	NPD23	Approved
0.687	Remote Similarity	NPD6093	Discontinued
0.6869	Remote Similarity	NPD5656	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD3772	Phase 3
0.6863	Remote Similarity	NPD7344	Phase 1
0.6863	Remote Similarity	NPD7343	Discovery
0.686	Remote Similarity	NPD4895	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6302	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD253	Approved
0.6827	Remote Similarity	NPD9711	Approved
0.6827	Remote Similarity	NPD9710	Approved
0.6822	Remote Similarity	NPD309	Approved
0.6822	Remote Similarity	NPD311	Approved
0.6822	Remote Similarity	NPD315	Approved
0.6822	Remote Similarity	NPD10	Approved
0.6822	Remote Similarity	NPD310	Approved
0.6822	Remote Similarity	NPD314	Approved
0.6814	Remote Similarity	NPD5631	Phase 3
0.681	Remote Similarity	NPD1922	Discontinued
0.681	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD9722	Approved
0.6792	Remote Similarity	NPD9721	Approved
0.6789	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7121	Approved
0.6774	Remote Similarity	NPD296	Approved
0.6774	Remote Similarity	NPD293	Approved
0.6774	Remote Similarity	NPD295	Approved
0.6774	Remote Similarity	NPD7477	Discontinued
0.6774	Remote Similarity	NPD8118	Discontinued
0.6757	Remote Similarity	NPD2583	Phase 2
0.6754	Remote Similarity	NPD4031	Approved
0.6754	Remote Similarity	NPD4032	Approved
0.675	Remote Similarity	NPD5367	Discontinued
0.6748	Remote Similarity	NPD4738	Phase 2
0.6737	Remote Similarity	NPD4027	Approved
0.6737	Remote Similarity	NPD4026	Approved
0.6737	Remote Similarity	NPD3035	Approved
0.6733	Remote Similarity	NPD3000	Approved
0.6733	Remote Similarity	NPD517	Discontinued
0.6733	Remote Similarity	NPD2997	Approved
0.6733	Remote Similarity	NPD2998	Approved
0.6731	Remote Similarity	NPD528	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD5702	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD505	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD589	Approved
0.6702	Remote Similarity	NPD590	Approved
0.6701	Remote Similarity	NPD5178	Approved
0.6701	Remote Similarity	NPD9395	Approved
0.67	Remote Similarity	NPD9	Approved
0.67	Remote Similarity	NPD5347	Phase 2
0.67	Remote Similarity	NPD297	Approved
0.67	Remote Similarity	NPD5346	Phase 2
0.6697	Remote Similarity	NPD1444	Approved
0.6697	Remote Similarity	NPD1445	Approved
0.6696	Remote Similarity	NPD1841	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5162	Approved
0.6696	Remote Similarity	NPD3123	Discovery
0.6695	Remote Similarity	NPD5770	Phase 3
0.6695	Remote Similarity	NPD2956	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD8011	Discontinued
0.6667	Remote Similarity	NPD9608	Approved
0.6667	Remote Similarity	NPD4170	Approved
0.6667	Remote Similarity	NPD4405	Approved
0.6667	Remote Similarity	NPD4793	Discontinued
0.6667	Remote Similarity	NPD4408	Approved
0.6667	Remote Similarity	NPD1724	Approved
0.6667	Remote Similarity	NPD4407	Approved
0.6667	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4169	Approved
0.6667	Remote Similarity	NPD4701	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD292	Approved
0.6667	Remote Similarity	NPD294	Approved
0.6667	Remote Similarity	NPD9610	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