NPASS Compound

Structure

NPC470471 OpenBabel07101718192D 24 24 0 0 0 0 0 0 0 0999 V2000 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -11.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -6.0000 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 0.0000 -2.0000 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 0.8660 -4.5000 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 -0.0000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -12.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -8.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -5.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 3 1 0 0 0 0 2 7 1 0 0 0 0 3 8 1 0 0 0 0 4 9 1 0 0 0 0 4 10 1 0 0 0 0 5 6 2 0 0 0 0 5 13 1 0 0 0 0 6 16 1 0 0 0 0 7 20 1 0 0 0 0 8 21 1 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 13 2 0 0 0 0 11 14 1 0 0 0 0 12 13 1 0 0 0 0 12 15 2 0 0 0 0 14 17 2 0 0 0 0 14 18 1 0 0 0 0 15 17 1 0 0 0 0 15 19 1 0 0 0 0 16 22 2 3 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	461.03
Volume:	369.987
LogP:	2.014
LogD:	1.536
LogS:	-3.115
# Rotatable Bonds:	12
TPSA:	76.38
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	1
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.349
Synthetic Accessibility Score:	2.436
Fsp3:	0.471
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.744
MDCK Permeability:	2.7346279239282012e-05
Pgp-inhibitor:	0.139
Pgp-substrate:	0.214
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.196
Plasma Protein Binding (PPB):	74.5567398071289%
Volume Distribution (VD):	1.103
Pgp-substrate:	42.499568939208984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.938
CYP1A2-substrate:	0.599
CYP2C19-inhibitor:	0.118
CYP2C19-substrate:	0.302
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.65
CYP2D6-inhibitor:	0.732
CYP2D6-substrate:	0.865
CYP3A4-inhibitor:	0.152
CYP3A4-substrate:	0.194

ADMET: Excretion

Clearance (CL):	1.22
Half-life (T1/2):	0.397

ADMET: Toxicity

hERG Blockers:	0.837
Human Hepatotoxicity (H-HT):	0.175
Drug-inuced Liver Injury (DILI):	0.128
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.926
Maximum Recommended Daily Dose:	0.745
Skin Sensitization:	0.752
Carcinogencity:	0.037
Eye Corrosion:	0.004
Eye Irritation:	0.013
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC470471

Natural Product ID:	NPC470471
*Common Name:**	Ianthelliformisamine B
IUPAC Name:	(E)-N-[3-(4-aminobutylamino)propyl]-3-(3,5-dibromo-4-methoxyphenyl)prop-2-enamide
Synonyms:	Ianthelliformisamine B
Standard InCHIKey:	RQACVBWPNQWEEU-AATRIKPKSA-N
Standard InCHI:	InChI=1S/C17H25Br2N3O2/c1-24-17-14(18)11-13(12-15(17)19)5-6-16(23)22-10-4-9-21-8-3-2-7-20/h5-6,11-12,21H,2-4,7-10,20H2,1H3,(H,22,23)/b6-5+
SMILES:	COC1=C(C=C(C=C1Br)C=CC(=O)NCCCNCCCCN)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2047173
PubChem CID:	59051761
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0002810] Cinnamic acid amides

*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
NPO32712	suberea ianthelliformis	Species	Aplysinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22515429]

☑ 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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1548	Organism	Pseudomonas aeruginosa PAO1	Pseudomonas aeruginosa PAO1	Inhibition	=	80.0	%	PMID[520922]

☑ 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 NPC470471 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	210
0.1-0.2	3078
0.2-0.3	13502
0.3-0.4	6123
0.4-0.5	14363
0.5-0.6	4861
0.6-0.7	488
0.7-0.8	59
0.8-0.85	6
0.85-0.9	4
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9845	High Similarity	NPC470470
0.9478	High Similarity	NPC470472
0.8865	High Similarity	NPC76412
0.8777	High Similarity	NPC78530
0.8511	High Similarity	NPC135349
0.8356	Intermediate Similarity	NPC47672
0.8311	Intermediate Similarity	NPC233926
0.8311	Intermediate Similarity	NPC156311
0.8156	Intermediate Similarity	NPC213471
0.8074	Intermediate Similarity	NPC272463
0.8015	Intermediate Similarity	NPC110131
0.7986	Intermediate Similarity	NPC474128
0.7972	Intermediate Similarity	NPC128877
0.7943	Intermediate Similarity	NPC303993
0.7931	Intermediate Similarity	NPC308571
0.7919	Intermediate Similarity	NPC258222
0.7902	Intermediate Similarity	NPC474673
0.7762	Intermediate Similarity	NPC235633
0.7748	Intermediate Similarity	NPC469711
0.7692	Intermediate Similarity	NPC166837
0.7682	Intermediate Similarity	NPC109968
0.766	Intermediate Similarity	NPC99280
0.7652	Intermediate Similarity	NPC115803
0.7535	Intermediate Similarity	NPC135173
0.7534	Intermediate Similarity	NPC197045
0.7483	Intermediate Similarity	NPC296085
0.7483	Intermediate Similarity	NPC71629
0.7463	Intermediate Similarity	NPC303370
0.7453	Intermediate Similarity	NPC477255
0.7444	Intermediate Similarity	NPC59387
0.7413	Intermediate Similarity	NPC474087
0.7361	Intermediate Similarity	NPC475735
0.7347	Intermediate Similarity	NPC470249
0.7319	Intermediate Similarity	NPC263835
0.7292	Intermediate Similarity	NPC474091
0.7278	Intermediate Similarity	NPC259071
0.7278	Intermediate Similarity	NPC77435
0.7273	Intermediate Similarity	NPC143450
0.7262	Intermediate Similarity	NPC477254
0.7246	Intermediate Similarity	NPC256369
0.7246	Intermediate Similarity	NPC43275
0.7241	Intermediate Similarity	NPC473724
0.723	Intermediate Similarity	NPC470248
0.7192	Intermediate Similarity	NPC97870
0.7192	Intermediate Similarity	NPC247018
0.7192	Intermediate Similarity	NPC307123
0.7176	Intermediate Similarity	NPC121571
0.7176	Intermediate Similarity	NPC8093
0.7163	Intermediate Similarity	NPC116562
0.7153	Intermediate Similarity	NPC258992
0.7143	Intermediate Similarity	NPC163810
0.7126	Intermediate Similarity	NPC227953
0.7123	Intermediate Similarity	NPC11449
0.7114	Intermediate Similarity	NPC309667
0.7113	Intermediate Similarity	NPC211218
0.7105	Intermediate Similarity	NPC470247
0.7099	Intermediate Similarity	NPC42383
0.7075	Intermediate Similarity	NPC474753
0.7068	Intermediate Similarity	NPC146530
0.7063	Intermediate Similarity	NPC95733
0.7063	Intermediate Similarity	NPC62101
0.7034	Intermediate Similarity	NPC186898
0.7029	Intermediate Similarity	NPC471338
0.7029	Intermediate Similarity	NPC474678
0.7021	Intermediate Similarity	NPC83279
0.702	Intermediate Similarity	NPC40321
0.7014	Intermediate Similarity	NPC320242
0.6989	Remote Similarity	NPC202866
0.6989	Remote Similarity	NPC475843
0.6987	Remote Similarity	NPC20755
0.6986	Remote Similarity	NPC471306
0.6986	Remote Similarity	NPC471321
0.698	Remote Similarity	NPC120114
0.698	Remote Similarity	NPC71888
0.6966	Remote Similarity	NPC301713
0.6966	Remote Similarity	NPC251466
0.6959	Remote Similarity	NPC158078
0.694	Remote Similarity	NPC309982
0.694	Remote Similarity	NPC97811
0.6923	Remote Similarity	NPC298486
0.6918	Remote Similarity	NPC202776
0.6918	Remote Similarity	NPC159987
0.6918	Remote Similarity	NPC78061
0.6918	Remote Similarity	NPC122359
0.6918	Remote Similarity	NPC251571
0.6918	Remote Similarity	NPC153990
0.6908	Remote Similarity	NPC470250
0.6897	Remote Similarity	NPC71105
0.6897	Remote Similarity	NPC182147
0.6897	Remote Similarity	NPC246133
0.6897	Remote Similarity	NPC29477
0.6897	Remote Similarity	NPC207541
0.6897	Remote Similarity	NPC170583
0.6897	Remote Similarity	NPC152186
0.6889	Remote Similarity	NPC471337
0.6875	Remote Similarity	NPC328267
0.6871	Remote Similarity	NPC155838
0.6866	Remote Similarity	NPC142297
0.6863	Remote Similarity	NPC470709
0.6857	Remote Similarity	NPC323948
0.6849	Remote Similarity	NPC156944
0.6846	Remote Similarity	NPC166624
0.6846	Remote Similarity	NPC274732
0.6846	Remote Similarity	NPC471953
0.6839	Remote Similarity	NPC79076
0.6839	Remote Similarity	NPC174607
0.6838	Remote Similarity	NPC473358
0.6831	Remote Similarity	NPC160120
0.6831	Remote Similarity	NPC17388
0.6831	Remote Similarity	NPC321133
0.6831	Remote Similarity	NPC41801
0.6831	Remote Similarity	NPC289330
0.6831	Remote Similarity	NPC53596
0.6831	Remote Similarity	NPC471308
0.6828	Remote Similarity	NPC300955
0.6824	Remote Similarity	NPC52029
0.6824	Remote Similarity	NPC195749
0.6824	Remote Similarity	NPC35961
0.6821	Remote Similarity	NPC237227
0.6818	Remote Similarity	NPC248822
0.6812	Remote Similarity	NPC26524
0.6803	Remote Similarity	NPC99798
0.6803	Remote Similarity	NPC41331
0.6803	Remote Similarity	NPC291449
0.6803	Remote Similarity	NPC157740
0.68	Remote Similarity	NPC184465
0.68	Remote Similarity	NPC147847
0.6796	Remote Similarity	NPC123140
0.6791	Remote Similarity	NPC231705
0.6781	Remote Similarity	NPC141739
0.6781	Remote Similarity	NPC136112
0.6776	Remote Similarity	NPC474587
0.6776	Remote Similarity	NPC475132
0.6765	Remote Similarity	NPC469979
0.6765	Remote Similarity	NPC54543
0.6761	Remote Similarity	NPC283760
0.6759	Remote Similarity	NPC217277
0.6757	Remote Similarity	NPC246974
0.6757	Remote Similarity	NPC147247
0.6757	Remote Similarity	NPC271808
0.6744	Remote Similarity	NPC475396
0.6741	Remote Similarity	NPC186469
0.6735	Remote Similarity	NPC218323
0.6733	Remote Similarity	NPC214869
0.6732	Remote Similarity	NPC475293
0.6725	Remote Similarity	NPC473462
0.6725	Remote Similarity	NPC298981
0.6725	Remote Similarity	NPC126128
0.6725	Remote Similarity	NPC207819
0.6725	Remote Similarity	NPC110454
0.6712	Remote Similarity	NPC213414
0.6711	Remote Similarity	NPC470706
0.6692	Remote Similarity	NPC192596
0.6692	Remote Similarity	NPC178902
0.6691	Remote Similarity	NPC96224
0.6691	Remote Similarity	NPC471495
0.6691	Remote Similarity	NPC24101
0.669	Remote Similarity	NPC471314
0.669	Remote Similarity	NPC471315
0.6667	Remote Similarity	NPC114102
0.6667	Remote Similarity	NPC255550
0.6667	Remote Similarity	NPC226001
0.6667	Remote Similarity	NPC308885
0.6648	Remote Similarity	NPC473892
0.6648	Remote Similarity	NPC475658
0.6645	Remote Similarity	NPC473463
0.6644	Remote Similarity	NPC469977
0.6644	Remote Similarity	NPC13020
0.6644	Remote Similarity	NPC140359
0.6644	Remote Similarity	NPC105999
0.6642	Remote Similarity	NPC258056
0.6631	Remote Similarity	NPC470746
0.6631	Remote Similarity	NPC471336
0.6623	Remote Similarity	NPC130595
0.6623	Remote Similarity	NPC93882
0.662	Remote Similarity	NPC120075
0.6617	Remote Similarity	NPC51633
0.6612	Remote Similarity	NPC473450
0.6609	Remote Similarity	NPC74618
0.6609	Remote Similarity	NPC301941
0.6609	Remote Similarity	NPC214188
0.6608	Remote Similarity	NPC225130
0.6599	Remote Similarity	NPC236265
0.6597	Remote Similarity	NPC180207
0.6596	Remote Similarity	NPC37302
0.6596	Remote Similarity	NPC10286
0.6596	Remote Similarity	NPC213
0.6594	Remote Similarity	NPC474149
0.6579	Remote Similarity	NPC313737
0.6579	Remote Similarity	NPC285078
0.6579	Remote Similarity	NPC6854
0.6577	Remote Similarity	NPC191302
0.6575	Remote Similarity	NPC296202
0.6552	Remote Similarity	NPC318357
0.6552	Remote Similarity	NPC183262
0.6547	Remote Similarity	NPC21890
0.6544	Remote Similarity	NPC113457
0.6541	Remote Similarity	NPC9373
0.6538	Remote Similarity	NPC471581
0.6538	Remote Similarity	NPC189724

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 NPC470471 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	137
0.1-0.2	730
0.2-0.3	1270
0.3-0.4	2474
0.4-0.5	3054
0.5-0.6	1209
0.6-0.7	271
0.7-0.8	5
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
0.75	Intermediate Similarity	NPD2184	Approved
0.75	Intermediate Similarity	NPD2183	Approved
0.7192	Intermediate Similarity	NPD1423	Approved
0.7133	Intermediate Similarity	NPD1770	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD3175	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD1820	Approved
0.7014	Intermediate Similarity	NPD1817	Approved
0.7014	Intermediate Similarity	NPD1819	Approved
0.7014	Intermediate Similarity	NPD1818	Approved
0.7007	Intermediate Similarity	NPD593	Approved
0.7007	Intermediate Similarity	NPD595	Approved
0.6993	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD2458	Approved
0.6993	Remote Similarity	NPD2459	Approved
0.6993	Remote Similarity	NPD2460	Phase 3
0.6939	Remote Similarity	NPD3164	Approved
0.6939	Remote Similarity	NPD3180	Approved
0.6939	Remote Similarity	NPD3165	Approved
0.6939	Remote Similarity	NPD3167	Approved
0.6939	Remote Similarity	NPD5163	Phase 2
0.6939	Remote Similarity	NPD9718	Approved
0.6939	Remote Similarity	NPD3179	Approved
0.6939	Remote Similarity	NPD3166	Approved
0.6933	Remote Similarity	NPD3054	Approved
0.6933	Remote Similarity	NPD3052	Approved
0.6918	Remote Similarity	NPD4993	Discontinued
0.6892	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD3049	Approved
0.6875	Remote Similarity	NPD2428	Approved
0.6875	Remote Similarity	NPD2429	Approved
0.6831	Remote Similarity	NPD2556	Approved
0.6831	Remote Similarity	NPD2554	Approved
0.6831	Remote Similarity	NPD2668	Approved
0.6831	Remote Similarity	NPD2667	Approved
0.6797	Remote Similarity	NPD3156	Discontinued
0.6781	Remote Similarity	NPD1794	Approved
0.6772	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD3985	Discontinued
0.677	Remote Similarity	NPD1009	Approved
0.6759	Remote Similarity	NPD1669	Approved
0.6747	Remote Similarity	NPD1411	Approved
0.6739	Remote Similarity	NPD821	Approved
0.6738	Remote Similarity	NPD856	Approved
0.6738	Remote Similarity	NPD16	Approved
0.6733	Remote Similarity	NPD840	Approved
0.6733	Remote Similarity	NPD839	Approved
0.6711	Remote Similarity	NPD6179	Discontinued
0.671	Remote Similarity	NPD7153	Discontinued
0.6709	Remote Similarity	NPD6087	Phase 1
0.6689	Remote Similarity	NPD2250	Discontinued
0.6667	Remote Similarity	NPD2504	Approved
0.6667	Remote Similarity	NPD2505	Approved
0.6667	Remote Similarity	NPD3060	Approved
0.6667	Remote Similarity	NPD1039	Discontinued
0.6667	Remote Similarity	NPD3145	Approved
0.6667	Remote Similarity	NPD3144	Approved
0.6667	Remote Similarity	NPD2874	Phase 2
0.6626	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD5481	Discontinued
0.6624	Remote Similarity	NPD1662	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD2245	Discovery
0.6623	Remote Similarity	NPD3163	Approved
0.6623	Remote Similarity	NPD3162	Approved
0.6623	Remote Similarity	NPD2674	Phase 3
0.6603	Remote Similarity	NPD4149	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD2240	Approved
0.6581	Remote Similarity	NPD2239	Approved
0.6579	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD5266	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD2040	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD2561	Approved
0.6575	Remote Similarity	NPD2233	Approved
0.6575	Remote Similarity	NPD2232	Approved
0.6575	Remote Similarity	NPD2235	Phase 2
0.6575	Remote Similarity	NPD2230	Approved
0.6575	Remote Similarity	NPD2562	Approved
0.6575	Remote Similarity	NPD2231	Phase 2
0.6562	Remote Similarity	NPD6419	Discontinued
0.6561	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD4162	Approved
0.6549	Remote Similarity	NPD3596	Phase 2
0.6543	Remote Similarity	NPD5267	Discontinued
0.6531	Remote Similarity	NPD6582	Phase 2
0.6531	Remote Similarity	NPD3685	Discontinued
0.6531	Remote Similarity	NPD6583	Phase 3
0.6516	Remote Similarity	NPD2661	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD6380	Phase 1
0.6513	Remote Similarity	NPD3530	Approved
0.6513	Remote Similarity	NPD3531	Approved
0.6513	Remote Similarity	NPD3532	Approved
0.6513	Remote Similarity	NPD5745	Approved
0.6503	Remote Similarity	NPD317	Approved
0.6503	Remote Similarity	NPD318	Approved
0.65	Remote Similarity	NPD5165	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD1044	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD3336	Discovery
0.6486	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD1725	Approved
0.646	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.646	Remote Similarity	NPD3536	Discontinued
0.6456	Remote Similarity	NPD6364	Approved
0.6456	Remote Similarity	NPD44	Approved
0.6454	Remote Similarity	NPD592	Approved
0.6454	Remote Similarity	NPD594	Approved
0.6452	Remote Similarity	NPD3554	Approved
0.6452	Remote Similarity	NPD3555	Approved
0.6452	Remote Similarity	NPD3553	Approved
0.6452	Remote Similarity	NPD3552	Approved
0.6438	Remote Similarity	NPD3281	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD4083	Discontinued
0.6433	Remote Similarity	NPD3656	Approved
0.642	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.642	Remote Similarity	NPD7526	Approved
0.642	Remote Similarity	NPD52	Approved
0.642	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD4129	Approved
0.6414	Remote Similarity	NPD2595	Approved
0.6414	Remote Similarity	NPD6382	Discontinued
0.6414	Remote Similarity	NPD2594	Approved
0.641	Remote Similarity	NPD3693	Clinical (unspecified phase)
0.641	Remote Similarity	NPD2155	Approved
0.641	Remote Similarity	NPD2154	Approved
0.641	Remote Similarity	NPD7425	Clinical (unspecified phase)
0.641	Remote Similarity	NPD2156	Approved
0.641	Remote Similarity	NPD1169	Approved
0.6407	Remote Similarity	NPD3556	Approved
0.6407	Remote Similarity	NPD3557	Approved
0.6407	Remote Similarity	NPD3558	Approved
0.6407	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD3560	Approved
0.6405	Remote Similarity	NPD554	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7451	Discontinued
0.64	Remote Similarity	NPD6584	Phase 3
0.6397	Remote Similarity	NPD9610	Approved
0.6397	Remote Similarity	NPD9608	Approved
0.6387	Remote Similarity	NPD2653	Approved
0.6387	Remote Similarity	NPD2157	Approved
0.6382	Remote Similarity	NPD5746	Approved
0.6382	Remote Similarity	NPD3136	Phase 2
0.638	Remote Similarity	NPD7131	Phase 3
0.6376	Remote Similarity	NPD5310	Approved
0.6376	Remote Similarity	NPD2922	Phase 1
0.6376	Remote Similarity	NPD196	Phase 1
0.6376	Remote Similarity	NPD5311	Approved
0.6375	Remote Similarity	NPD3692	Discontinued
0.6364	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD2407	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD1712	Approved
0.6352	Remote Similarity	NPD5289	Phase 2
0.6345	Remote Similarity	NPD6581	Approved
0.6345	Remote Similarity	NPD2486	Discontinued
0.6345	Remote Similarity	NPD6580	Approved
0.6345	Remote Similarity	NPD316	Approved
0.634	Remote Similarity	NPD5718	Phase 2
0.6333	Remote Similarity	NPD3053	Approved
0.6333	Remote Similarity	NPD1133	Approved
0.6333	Remote Similarity	NPD1131	Approved
0.6333	Remote Similarity	NPD1232	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD1135	Approved
0.6333	Remote Similarity	NPD1134	Approved
0.6333	Remote Similarity	NPD1318	Phase 2
0.6333	Remote Similarity	NPD3055	Approved
0.6333	Remote Similarity	NPD3567	Approved
0.6333	Remote Similarity	NPD1129	Approved
0.6333	Remote Similarity	NPD3568	Approved
0.6331	Remote Similarity	NPD8031	Discontinued
0.6331	Remote Similarity	NPD2684	Approved
0.6329	Remote Similarity	NPD1035	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD3421	Phase 3
0.6327	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD600	Approved
0.6316	Remote Similarity	NPD2614	Approved
0.6316	Remote Similarity	NPD596	Approved
0.6306	Remote Similarity	NPD4108	Discontinued
0.6303	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD1798	Approved
0.6301	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD1797	Approved
0.6299	Remote Similarity	NPD7477	Discontinued
0.6299	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD1785	Approved
0.6296	Remote Similarity	NPD1786	Approved
0.6296	Remote Similarity	NPD1787	Approved
0.6291	Remote Similarity	NPD3690	Phase 2
0.6291	Remote Similarity	NPD7018	Phase 2
0.6291	Remote Similarity	NPD3691	Phase 2
0.6291	Remote Similarity	NPD7905	Discontinued
0.6289	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD1391	Approved
0.6287	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD4227	Discontinued
0.6286	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD2989	Phase 2
0.6282	Remote Similarity	NPD2986	Phase 2
0.6282	Remote Similarity	NPD4579	Clinical (unspecified phase)

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