NPASS Compound

Structure

CID311753 OpenBabel06191716122D 22 22 0 0 1 0 0 0 0 0999 V2000 -0.0000 -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 0.8660 -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 -0.8660 -0.5000 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 -4.3301 1.5000 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 0.0000 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 -3.4641 1.0000 0.0000 C 0 0 1 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 -7.7942 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 -7.7942 2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 N 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 -4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 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 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 5 1 0 0 0 0 3 6 2 0 0 0 0 4 7 1 0 0 0 0 4 8 1 0 0 0 0 5 10 2 0 0 0 0 6 10 1 0 0 0 0 8 17 1 0 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 11 7 1 6 0 0 0 11 12 1 0 0 0 0 11 18 1 0 0 0 0 12 19 2 0 0 0 0 12 20 1 0 0 0 0 13 15 2 0 0 0 0 13 16 1 0 0 0 0 13 17 1 0 0 0 0 14 18 2 3 0 0 0 14 21 1 0 0 0 0 14 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.15
Volume:	305.473
LogP:	-0.068
LogD:	-0.002
LogS:	-2.07
# Rotatable Bonds:	11
TPSA:	137.53
# H-Bond Aceptor:	8
# H-Bond Donor:	6
# Rings:	1
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.271
Synthetic Accessibility Score:	2.455
Fsp3:	0.357
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.392
MDCK Permeability:	0.00043184918467886746
Pgp-inhibitor:	0.0
Pgp-substrate:	0.281
Human Intestinal Absorption (HIA):	0.499
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.806
Plasma Protein Binding (PPB):	17.910358428955078%
Volume Distribution (VD):	0.327
Pgp-substrate:	67.24537658691406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.05
CYP2C19-inhibitor:	0.042
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.073
CYP2D6-inhibitor:	0.162
CYP2D6-substrate:	0.285
CYP3A4-inhibitor:	0.004
CYP3A4-substrate:	0.026

ADMET: Excretion

Clearance (CL):	4.782
Half-life (T1/2):	0.877

ADMET: Toxicity

hERG Blockers:	0.136
Human Hepatotoxicity (H-HT):	0.052
Drug-inuced Liver Injury (DILI):	0.442
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.085
Maximum Recommended Daily Dose:	0.012
Skin Sensitization:	0.143
Carcinogencity:	0.055
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.101

Download Data

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

Natural Product: NPC311753

Natural Product ID:	NPC311753
*Common Name:**	(2S)-5-(Diaminomethylideneazaniumyl)-2-(Phenylmethoxycarbonylamino)Pentanoate
IUPAC Name:	(2S)-5-(diaminomethylideneazaniumyl)-2-(phenylmethoxycarbonylamino)pentanoate
Synonyms:
Standard InCHIKey:	SJSSFUMSAFMFNM-NSHDSACASA-N
Standard InCHI:	InChI=1S/C14H20N4O4/c15-13(16)17-8-4-7-11(12(19)20)18-14(21)22-9-10-5-2-1-3-6-10/h1-3,5-6,11H,4,7-9H2,(H,18,21)(H,19,20)(H4,15,16,17)/t11-/m0/s1
SMILES:	c1ccc(cc1)COC(=N[C@@H](CCCNC(=N)N)C(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1423296
PubChem CID:	1549129 71055
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0001097] Benzyloxycarbonyls

*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
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17432574]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[18787781]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21302967]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27228227]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9544564]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	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
Potency	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT483	Individual Protein	Prelamin-A/C	Homo sapiens	Potency	=	5011.9	nM	PMID[521698]

☑ 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 NPC311753 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	132
0.1-0.2	1228
0.2-0.3	6018
0.3-0.4	13074
0.4-0.5	18024
0.5-0.6	3664
0.6-0.7	520
0.7-0.8	34
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8175	Intermediate Similarity	NPC48202
0.7826	Intermediate Similarity	NPC314835
0.7708	Intermediate Similarity	NPC311658
0.7386	Intermediate Similarity	NPC114806
0.7383	Intermediate Similarity	NPC300443
0.732	Intermediate Similarity	NPC24617
0.7279	Intermediate Similarity	NPC476278
0.7279	Intermediate Similarity	NPC314114
0.7246	Intermediate Similarity	NPC477937
0.7185	Intermediate Similarity	NPC476183
0.7172	Intermediate Similarity	NPC214988
0.7165	Intermediate Similarity	NPC327481
0.7133	Intermediate Similarity	NPC267237
0.7132	Intermediate Similarity	NPC476184
0.7132	Intermediate Similarity	NPC476281
0.7101	Intermediate Similarity	NPC476260
0.7101	Intermediate Similarity	NPC476241
0.7099	Intermediate Similarity	NPC474584
0.7087	Intermediate Similarity	NPC67043
0.7068	Intermediate Similarity	NPC197470
0.7063	Intermediate Similarity	NPC164859
0.705	Intermediate Similarity	NPC476179
0.705	Intermediate Similarity	NPC476125
0.7023	Intermediate Similarity	NPC329011
0.6987	Remote Similarity	NPC62104
0.6987	Remote Similarity	NPC1390
0.697	Remote Similarity	NPC273814
0.6957	Remote Similarity	NPC198254
0.6957	Remote Similarity	NPC274198
0.6957	Remote Similarity	NPC142577
0.6957	Remote Similarity	NPC27581
0.6957	Remote Similarity	NPC276506
0.6947	Remote Similarity	NPC319579
0.6935	Remote Similarity	NPC324569
0.6935	Remote Similarity	NPC293628
0.6935	Remote Similarity	NPC122493
0.6935	Remote Similarity	NPC10781
0.6929	Remote Similarity	NPC4974
0.6928	Remote Similarity	NPC473404
0.6923	Remote Similarity	NPC324850
0.6912	Remote Similarity	NPC314992
0.6889	Remote Similarity	NPC2265
0.6875	Remote Similarity	NPC150254
0.6875	Remote Similarity	NPC326966
0.6875	Remote Similarity	NPC226778
0.6875	Remote Similarity	NPC147000
0.6875	Remote Similarity	NPC304761
0.6853	Remote Similarity	NPC325651
0.6846	Remote Similarity	NPC168861
0.6835	Remote Similarity	NPC160493
0.6831	Remote Similarity	NPC199738
0.6831	Remote Similarity	NPC210950
0.6828	Remote Similarity	NPC470392
0.6813	Remote Similarity	NPC5719
0.6813	Remote Similarity	NPC217804
0.6813	Remote Similarity	NPC22883
0.6813	Remote Similarity	NPC210377
0.6805	Remote Similarity	NPC235194
0.68	Remote Similarity	NPC326241
0.6795	Remote Similarity	NPC473580
0.679	Remote Similarity	NPC280022
0.679	Remote Similarity	NPC66490
0.6788	Remote Similarity	NPC196243
0.677	Remote Similarity	NPC15068
0.6765	Remote Similarity	NPC188867
0.6765	Remote Similarity	NPC106551
0.6765	Remote Similarity	NPC281686
0.6763	Remote Similarity	NPC273830
0.6757	Remote Similarity	NPC132636
0.6742	Remote Similarity	NPC24777
0.6728	Remote Similarity	NPC63040
0.672	Remote Similarity	NPC3371
0.6719	Remote Similarity	NPC327226
0.6715	Remote Similarity	NPC169328
0.6713	Remote Similarity	NPC476353
0.6693	Remote Similarity	NPC12730
0.6691	Remote Similarity	NPC190663
0.6687	Remote Similarity	NPC129486
0.6686	Remote Similarity	NPC102959
0.6667	Remote Similarity	NPC237420
0.6667	Remote Similarity	NPC35996
0.6667	Remote Similarity	NPC153554
0.6667	Remote Similarity	NPC469666
0.6667	Remote Similarity	NPC310467
0.6647	Remote Similarity	NPC61332
0.6647	Remote Similarity	NPC60516
0.6647	Remote Similarity	NPC240130
0.6643	Remote Similarity	NPC326079
0.6628	Remote Similarity	NPC94862
0.6627	Remote Similarity	NPC17698
0.6625	Remote Similarity	NPC475544
0.6625	Remote Similarity	NPC469243
0.6623	Remote Similarity	NPC91953
0.6619	Remote Similarity	NPC239697
0.6619	Remote Similarity	NPC319950
0.6614	Remote Similarity	NPC164514
0.6614	Remote Similarity	NPC226096
0.6614	Remote Similarity	NPC108606
0.6614	Remote Similarity	NPC290515
0.6614	Remote Similarity	NPC303611
0.6596	Remote Similarity	NPC474862
0.6596	Remote Similarity	NPC26285
0.6579	Remote Similarity	NPC204546
0.6577	Remote Similarity	NPC6570
0.6573	Remote Similarity	NPC477552
0.6573	Remote Similarity	NPC477550
0.6571	Remote Similarity	NPC80150
0.6571	Remote Similarity	NPC326232
0.6566	Remote Similarity	NPC475532
0.6561	Remote Similarity	NPC473341
0.6556	Remote Similarity	NPC197921
0.6552	Remote Similarity	NPC296712
0.6547	Remote Similarity	NPC317784
0.6547	Remote Similarity	NPC142638
0.6536	Remote Similarity	NPC315266
0.6534	Remote Similarity	NPC302715
0.6533	Remote Similarity	NPC287358
0.6531	Remote Similarity	NPC246079
0.6527	Remote Similarity	NPC165285
0.6519	Remote Similarity	NPC269340
0.6513	Remote Similarity	NPC469360
0.6512	Remote Similarity	NPC228400
0.6512	Remote Similarity	NPC214200
0.6509	Remote Similarity	NPC97526
0.6509	Remote Similarity	NPC119652
0.6508	Remote Similarity	NPC215351
0.6508	Remote Similarity	NPC20142
0.6504	Remote Similarity	NPC220893
0.6503	Remote Similarity	NPC223207
0.65	Remote Similarity	NPC477551
0.649	Remote Similarity	NPC319645
0.6486	Remote Similarity	NPC88667
0.6484	Remote Similarity	NPC322598
0.6475	Remote Similarity	NPC89377
0.6471	Remote Similarity	NPC314388
0.6471	Remote Similarity	NPC66518
0.6471	Remote Similarity	NPC315283
0.6467	Remote Similarity	NPC237227
0.6463	Remote Similarity	NPC290755
0.6463	Remote Similarity	NPC304074
0.6463	Remote Similarity	NPC471771
0.6462	Remote Similarity	NPC318154
0.6458	Remote Similarity	NPC47667
0.6458	Remote Similarity	NPC474479
0.6452	Remote Similarity	NPC258627
0.6446	Remote Similarity	NPC46009
0.6439	Remote Similarity	NPC211551
0.6438	Remote Similarity	NPC161593
0.6438	Remote Similarity	NPC16031
0.6438	Remote Similarity	NPC145888
0.6434	Remote Similarity	NPC6975
0.6433	Remote Similarity	NPC7817
0.6433	Remote Similarity	NPC475168
0.6429	Remote Similarity	NPC313867
0.6429	Remote Similarity	NPC316008
0.6424	Remote Similarity	NPC281104
0.6419	Remote Similarity	NPC45191
0.6419	Remote Similarity	NPC246913
0.6414	Remote Similarity	NPC65310
0.6414	Remote Similarity	NPC124776
0.6409	Remote Similarity	NPC473450
0.6408	Remote Similarity	NPC71684
0.64	Remote Similarity	NPC470441
0.6395	Remote Similarity	NPC471321
0.6395	Remote Similarity	NPC471306
0.6387	Remote Similarity	NPC314358
0.6383	Remote Similarity	NPC283760
0.6382	Remote Similarity	NPC239762
0.6382	Remote Similarity	NPC163392
0.6378	Remote Similarity	NPC194699
0.6378	Remote Similarity	NPC219350
0.6358	Remote Similarity	NPC471264
0.6358	Remote Similarity	NPC127741
0.6358	Remote Similarity	NPC471265
0.6357	Remote Similarity	NPC137096
0.6349	Remote Similarity	NPC265521
0.634	Remote Similarity	NPC241086
0.634	Remote Similarity	NPC318984
0.634	Remote Similarity	NPC317741
0.634	Remote Similarity	NPC282087
0.634	Remote Similarity	NPC318028
0.634	Remote Similarity	NPC259800
0.634	Remote Similarity	NPC328137
0.6338	Remote Similarity	NPC478016
0.6338	Remote Similarity	NPC477061
0.6338	Remote Similarity	NPC478015
0.6338	Remote Similarity	NPC45777
0.6338	Remote Similarity	NPC478014
0.6333	Remote Similarity	NPC474473
0.6319	Remote Similarity	NPC469443
0.6316	Remote Similarity	NPC476198
0.6313	Remote Similarity	NPC477638
0.6313	Remote Similarity	NPC477632
0.6312	Remote Similarity	NPC470902
0.6311	Remote Similarity	NPC58616
0.6303	Remote Similarity	NPC63931
0.6303	Remote Similarity	NPC472923
0.6299	Remote Similarity	NPC57976
0.6296	Remote Similarity	NPC93343
0.6294	Remote Similarity	NPC202521

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 NPC311753 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	84
0.1-0.2	338
0.2-0.3	929
0.3-0.4	2051
0.4-0.5	3624
0.5-0.6	1774
0.6-0.7	329
0.7-0.8	21
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7671	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6681	Discovery
0.745	Intermediate Similarity	NPD7523	Phase 3
0.7434	Intermediate Similarity	NPD7495	Discontinued
0.7434	Intermediate Similarity	NPD8019	Approved
0.7407	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD6078	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD8076	Discontinued
0.7285	Intermediate Similarity	NPD6670	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD1329	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD1330	Phase 2
0.7234	Intermediate Similarity	NPD3632	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD2198	Approved
0.7174	Intermediate Similarity	NPD2199	Approved
0.7143	Intermediate Similarity	NPD5292	Approved
0.7143	Intermediate Similarity	NPD5291	Approved
0.7103	Intermediate Similarity	NPD6901	Phase 3
0.7089	Intermediate Similarity	NPD8303	Discontinued
0.7087	Intermediate Similarity	NPD1040	Phase 2
0.7068	Intermediate Similarity	NPD1348	Approved
0.705	Intermediate Similarity	NPD3125	Approved
0.7042	Intermediate Similarity	NPD3136	Phase 2
0.7034	Intermediate Similarity	NPD3528	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4175	Approved
0.7021	Intermediate Similarity	NPD4177	Approved
0.7	Intermediate Similarity	NPD3606	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD770	Discontinued
0.698	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4762	Approved
0.6957	Remote Similarity	NPD4761	Approved
0.6935	Remote Similarity	NPD9566	Approved
0.6929	Remote Similarity	NPD196	Phase 1
0.6928	Remote Similarity	NPD2186	Approved
0.6928	Remote Similarity	NPD7613	Discontinued
0.6928	Remote Similarity	NPD6689	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD2218	Phase 2
0.6912	Remote Similarity	NPD2217	Approved
0.6906	Remote Similarity	NPD3073	Approved
0.6906	Remote Similarity	NPD3072	Approved
0.6906	Remote Similarity	NPD3071	Approved
0.6897	Remote Similarity	NPD4791	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD3123	Discovery
0.6875	Remote Similarity	NPD315	Approved
0.6875	Remote Similarity	NPD314	Approved
0.6875	Remote Similarity	NPD311	Approved
0.6875	Remote Similarity	NPD10	Approved
0.6875	Remote Similarity	NPD309	Approved
0.6875	Remote Similarity	NPD310	Approved
0.6866	Remote Similarity	NPD747	Discontinued
0.6863	Remote Similarity	NPD1664	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD4757	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD7508	Discontinued
0.6788	Remote Similarity	NPD4479	Discontinued
0.6781	Remote Similarity	NPD5296	Approved
0.6781	Remote Similarity	NPD3373	Approved
0.6781	Remote Similarity	NPD4153	Approved
0.6765	Remote Similarity	NPD9568	Approved
0.6757	Remote Similarity	NPD6852	Discontinued
0.6742	Remote Similarity	NPD550	Approved
0.6742	Remote Similarity	NPD551	Approved
0.6735	Remote Similarity	NPD3908	Approved
0.6733	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD4151	Approved
0.6709	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD794	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD6073	Approved
0.6689	Remote Similarity	NPD5725	Approved
0.6667	Remote Similarity	NPD3040	Approved
0.6667	Remote Similarity	NPD2240	Approved
0.6667	Remote Similarity	NPD1370	Approved
0.6667	Remote Similarity	NPD2203	Discontinued
0.6667	Remote Similarity	NPD1373	Approved
0.6667	Remote Similarity	NPD6967	Phase 2
0.6667	Remote Similarity	NPD2239	Approved
0.6667	Remote Similarity	NPD4006	Discontinued
0.6667	Remote Similarity	NPD1371	Approved
0.6667	Remote Similarity	NPD5323	Approved
0.6667	Remote Similarity	NPD1374	Approved
0.6645	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD5299	Approved
0.6623	Remote Similarity	NPD7978	Discontinued
0.6621	Remote Similarity	NPD4676	Approved
0.6621	Remote Similarity	NPD5263	Approved
0.6614	Remote Similarity	NPD9609	Approved
0.6614	Remote Similarity	NPD9611	Approved
0.6614	Remote Similarity	NPD9612	Approved
0.6601	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5618	Discontinued
0.6596	Remote Similarity	NPD4706	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD1801	Approved
0.6581	Remote Similarity	NPD1802	Approved
0.6573	Remote Similarity	NPD5367	Discontinued
0.6571	Remote Similarity	NPD7342	Discontinued
0.6562	Remote Similarity	NPD5356	Approved
0.6562	Remote Similarity	NPD5355	Approved
0.6562	Remote Similarity	NPD9712	Approved
0.6556	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD6624	Discontinued
0.6549	Remote Similarity	NPD2584	Suspended
0.6533	Remote Similarity	NPD8154	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4621	Approved
0.6531	Remote Similarity	NPD4619	Approved
0.6528	Remote Similarity	NPD6302	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD5200	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD2956	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD6237	Clinical (unspecified phase)
0.651	Remote Similarity	NPD555	Phase 2
0.6503	Remote Similarity	NPD4677	Discontinued
0.6494	Remote Similarity	NPD1662	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD5239	Approved
0.6493	Remote Similarity	NPD9713	Approved
0.6493	Remote Similarity	NPD5236	Approved
0.6493	Remote Similarity	NPD5240	Approved
0.6493	Remote Similarity	NPD5235	Approved
0.6493	Remote Similarity	NPD5237	Approved
0.649	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.649	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.649	Remote Similarity	NPD1110	Approved
0.649	Remote Similarity	NPD1109	Approved
0.649	Remote Similarity	NPD2661	Clinical (unspecified phase)
0.649	Remote Similarity	NPD3170	Approved
0.6486	Remote Similarity	NPD5745	Approved
0.6486	Remote Similarity	NPD259	Phase 1
0.6486	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD5747	Discontinued
0.6484	Remote Similarity	NPD9710	Approved
0.6484	Remote Similarity	NPD9711	Approved
0.6479	Remote Similarity	NPD4480	Approved
0.6471	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD4794	Discontinued
0.6463	Remote Similarity	NPD5163	Phase 2
0.6463	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD854	Approved
0.6462	Remote Similarity	NPD855	Approved
0.6452	Remote Similarity	NPD2887	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD2201	Approved
0.6442	Remote Similarity	NPD4564	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD4565	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD999	Phase 2
0.6438	Remote Similarity	NPD9569	Approved
0.6433	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD7528	Approved
0.6429	Remote Similarity	NPD5264	Approved
0.6429	Remote Similarity	NPD8162	Phase 2
0.6429	Remote Similarity	NPD5265	Approved
0.6429	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD2567	Approved
0.6424	Remote Similarity	NPD4214	Discontinued
0.6424	Remote Similarity	NPD1536	Approved
0.6424	Remote Similarity	NPD2569	Approved
0.6414	Remote Similarity	NPD2627	Approved
0.6414	Remote Similarity	NPD2159	Approved
0.6414	Remote Similarity	NPD2628	Approved
0.6414	Remote Similarity	NPD2625	Approved
0.6414	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD2626	Approved
0.6414	Remote Similarity	NPD2160	Approved
0.6403	Remote Similarity	NPD5162	Approved
0.6397	Remote Similarity	NPD9508	Approved
0.6395	Remote Similarity	NPD2614	Approved
0.6395	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD4731	Phase 3
0.6391	Remote Similarity	NPD810	Approved
0.6391	Remote Similarity	NPD812	Approved
0.6391	Remote Similarity	NPD811	Approved
0.6391	Remote Similarity	NPD2559	Approved
0.6391	Remote Similarity	NPD2551	Approved
0.6389	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD7484	Phase 3
0.6386	Remote Similarity	NPD7485	Phase 3
0.6382	Remote Similarity	NPD6865	Phase 2
0.6382	Remote Similarity	NPD6864	Phase 2
0.638	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD593	Approved
0.6377	Remote Similarity	NPD595	Approved
0.6364	Remote Similarity	NPD6119	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD253	Approved
0.6357	Remote Similarity	NPD1758	Phase 1
0.6357	Remote Similarity	NPD9613	Approved
0.6357	Remote Similarity	NPD9616	Approved
0.6357	Remote Similarity	NPD317	Approved
0.6357	Remote Similarity	NPD9615	Approved
0.6357	Remote Similarity	NPD318	Approved
0.6351	Remote Similarity	NPD5746	Approved
0.6349	Remote Similarity	NPD1814	Approved
0.6349	Remote Similarity	NPD1812	Approved
0.6345	Remote Similarity	NPD3098	Discontinued
0.634	Remote Similarity	NPD1538	Phase 1
0.634	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.634	Remote Similarity	NPD1537	Approved
0.634	Remote Similarity	NPD4173	Approved
0.634	Remote Similarity	NPD4172	Approved
0.634	Remote Similarity	NPD1519	Approved
0.6333	Remote Similarity	NPD6623	Phase 3

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