NPASS Compound

Structure

CID191302 OpenBabel06191715572D 24 25 0 0 0 0 0 0 0 0999 V2000 13.0754 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2094 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7453 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6113 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3434 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2094 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4773 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4773 -1.1910 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 11.3434 0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 10 1 0 0 0 0 9 17 1 0 0 0 0 10 20 1 0 0 0 0 11 12 2 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 13 17 2 0 0 0 0 13 19 1 0 0 0 0 14 16 1 0 0 0 0 14 21 1 0 0 0 0 15 23 1 0 0 0 0 15 24 1 0 0 0 0 18 19 2 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 20 21 2 3 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	331.21
Volume:	361.548
LogP:	4.298
LogD:	4.065
LogS:	-4.214
# Rotatable Bonds:	11
TPSA:	47.56
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.64
Synthetic Accessibility Score:	2.234
Fsp3:	0.55
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:	-4.82
MDCK Permeability:	2.900876097555738e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.427
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.494
Plasma Protein Binding (PPB):	97.68409729003906%
Volume Distribution (VD):	0.921
Pgp-substrate:	1.9874686002731323%

ADMET: Metabolism

CYP1A2-inhibitor:	0.911
CYP1A2-substrate:	0.262
CYP2C19-inhibitor:	0.949
CYP2C19-substrate:	0.397
CYP2C9-inhibitor:	0.774
CYP2C9-substrate:	0.94
CYP2D6-inhibitor:	0.932
CYP2D6-substrate:	0.754
CYP3A4-inhibitor:	0.949
CYP3A4-substrate:	0.165

ADMET: Excretion

Clearance (CL):	13.52
Half-life (T1/2):	0.445

ADMET: Toxicity

hERG Blockers:	0.578
Human Hepatotoxicity (H-HT):	0.182
Drug-inuced Liver Injury (DILI):	0.6
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.922
Carcinogencity:	0.727
Eye Corrosion:	0.004
Eye Irritation:	0.107
Respiratory Toxicity:	0.183

Download Data

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

Natural Product: NPC191302

Natural Product ID:	NPC191302
*Common Name:**	9-(Benzo[D][1,3]Dioxol-5-Yl)-N-Isobutylnon-8-Enamide
IUPAC Name:	(E)-9-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)non-8-enamide
Synonyms:
Standard InCHIKey:	RIIYLNBWAREERF-VQHVLOKHSA-N
Standard InCHI:	InChI=1S/C20H29NO3/c1-16(2)14-21-20(22)10-8-6-4-3-5-7-9-17-11-12-18-19(13-17)24-15-23-18/h7,9,11-13,16H,3-6,8,10,14-15H2,1-2H3,(H,21,22)/b9-7+
SMILES:	CC(CN=C(CCCCCC/C=C/c1ccc2c(c1)OCO2)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3338738
PubChem CID:	16122394
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000296] Benzodioxoles

*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
NPO30128	Piper boehmeriaefolium	Species	Piperaceae	Eukaryota	whole plant	Luxi County, Yunnan Province, China	2008-OCT	PMID[21158422]
NPO30128	Piper boehmeriaefolium	Species	Piperaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21158422]
NPO30128	Piper boehmeriaefolium	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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	8

Activity Type	# Activity
Cell Line	7
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[575296]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[575296]
NPT133	Cell Line	ZR-75-1	Homo sapiens	IC50	>	40000.0	nM	PMID[575296]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	>	40000.0	nM	PMID[575296]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	40000.0	nM	PMID[575296]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	>	40000.0	nM	PMID[575296]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	40000.0	nM	PMID[575296]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	40000.0	nM	PMID[575296]

☑ 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 NPC191302 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	157
0.1-0.2	1267
0.2-0.3	5766
0.3-0.4	13151
0.4-0.5	5367
0.5-0.6	11088
0.6-0.7	4734
0.7-0.8	1087
0.8-0.85	50
0.85-0.9	14
0.9-0.95	11
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9672	High Similarity	NPC157740
0.9672	High Similarity	NPC99798
0.9593	High Similarity	NPC246974
0.9593	High Similarity	NPC147247
0.959	High Similarity	NPC156944
0.9512	High Similarity	NPC291449
0.9512	High Similarity	NPC41331
0.9508	High Similarity	NPC170583
0.9508	High Similarity	NPC152186
0.9508	High Similarity	NPC246133
0.9508	High Similarity	NPC207541
0.9508	High Similarity	NPC71105
0.9508	High Similarity	NPC182147
0.9431	High Similarity	NPC251466
0.9426	High Similarity	NPC300955
0.9091	High Similarity	NPC275150
0.8906	High Similarity	NPC470706
0.8828	High Similarity	NPC469977
0.8824	High Similarity	NPC327623
0.8779	High Similarity	NPC284855
0.8779	High Similarity	NPC282477
0.8779	High Similarity	NPC473463
0.8722	High Similarity	NPC254610
0.8605	High Similarity	NPC153990
0.8583	High Similarity	NPC249788
0.855	High Similarity	NPC114102
0.8527	High Similarity	NPC301713
0.85	High Similarity	NPC31279
0.8496	Intermediate Similarity	NPC218530
0.8485	Intermediate Similarity	NPC130595
0.8485	Intermediate Similarity	NPC93882
0.8421	Intermediate Similarity	NPC6854
0.8421	Intermediate Similarity	NPC285078
0.8421	Intermediate Similarity	NPC313737
0.8417	Intermediate Similarity	NPC127326
0.8413	Intermediate Similarity	NPC344161
0.8409	Intermediate Similarity	NPC308885
0.8409	Intermediate Similarity	NPC255550
0.8397	Intermediate Similarity	NPC155838
0.8385	Intermediate Similarity	NPC274356
0.8346	Intermediate Similarity	NPC214869
0.8333	Intermediate Similarity	NPC195749
0.8333	Intermediate Similarity	NPC52029
0.8333	Intermediate Similarity	NPC35961
0.8321	Intermediate Similarity	NPC77572
0.8321	Intermediate Similarity	NPC186898
0.8281	Intermediate Similarity	NPC80241
0.8281	Intermediate Similarity	NPC301641
0.8279	Intermediate Similarity	NPC166837
0.8244	Intermediate Similarity	NPC40352
0.8244	Intermediate Similarity	NPC213711
0.8197	Intermediate Similarity	NPC137685
0.8194	Intermediate Similarity	NPC474560
0.8182	Intermediate Similarity	NPC251571
0.8134	Intermediate Similarity	NPC275950
0.8125	Intermediate Similarity	NPC471308
0.8125	Intermediate Similarity	NPC53596
0.8125	Intermediate Similarity	NPC160120
0.8125	Intermediate Similarity	NPC289330
0.8125	Intermediate Similarity	NPC17388
0.8074	Intermediate Similarity	NPC476345
0.8062	Intermediate Similarity	NPC183262
0.8047	Intermediate Similarity	NPC69670
0.8047	Intermediate Similarity	NPC119949
0.8043	Intermediate Similarity	NPC312770
0.8043	Intermediate Similarity	NPC160607
0.8043	Intermediate Similarity	NPC14600
0.8043	Intermediate Similarity	NPC204848
0.8043	Intermediate Similarity	NPC41473
0.803	Intermediate Similarity	NPC17348
0.8015	Intermediate Similarity	NPC471505
0.8015	Intermediate Similarity	NPC104077
0.8015	Intermediate Similarity	NPC219671
0.8015	Intermediate Similarity	NPC106739
0.8015	Intermediate Similarity	NPC147616
0.8015	Intermediate Similarity	NPC227002
0.8015	Intermediate Similarity	NPC259742
0.8	Intermediate Similarity	NPC173308
0.8	Intermediate Similarity	NPC292792
0.8	Intermediate Similarity	NPC171550
0.8	Intermediate Similarity	NPC114845
0.8	Intermediate Similarity	NPC63574
0.8	Intermediate Similarity	NPC134764
0.8	Intermediate Similarity	NPC181079
0.7986	Intermediate Similarity	NPC299583
0.7984	Intermediate Similarity	NPC173746
0.7984	Intermediate Similarity	NPC257124
0.7984	Intermediate Similarity	NPC156840
0.7984	Intermediate Similarity	NPC8547
0.7971	Intermediate Similarity	NPC145446
0.7971	Intermediate Similarity	NPC137172
0.7969	Intermediate Similarity	NPC474040
0.7956	Intermediate Similarity	NPC196937
0.7956	Intermediate Similarity	NPC169973
0.7941	Intermediate Similarity	NPC318862
0.7939	Intermediate Similarity	NPC471314
0.7939	Intermediate Similarity	NPC471315
0.7914	Intermediate Similarity	NPC95366
0.7914	Intermediate Similarity	NPC252107
0.7914	Intermediate Similarity	NPC470707
0.7914	Intermediate Similarity	NPC248505
0.791	Intermediate Similarity	NPC64948
0.791	Intermediate Similarity	NPC177167
0.791	Intermediate Similarity	NPC158737
0.7907	Intermediate Similarity	NPC57501
0.7907	Intermediate Similarity	NPC43275
0.7907	Intermediate Similarity	NPC310338
0.7907	Intermediate Similarity	NPC281298
0.7899	Intermediate Similarity	NPC96406
0.7891	Intermediate Similarity	NPC212643
0.7891	Intermediate Similarity	NPC164386
0.7891	Intermediate Similarity	NPC120075
0.7891	Intermediate Similarity	NPC33271
0.7891	Intermediate Similarity	NPC199209
0.7883	Intermediate Similarity	NPC97316
0.7879	Intermediate Similarity	NPC13020
0.7879	Intermediate Similarity	NPC140359
0.7879	Intermediate Similarity	NPC31344
0.7879	Intermediate Similarity	NPC317769
0.7868	Intermediate Similarity	NPC477705
0.7868	Intermediate Similarity	NPC477694
0.7868	Intermediate Similarity	NPC184814
0.7857	Intermediate Similarity	NPC296898
0.7857	Intermediate Similarity	NPC165106
0.7852	Intermediate Similarity	NPC158471
0.7852	Intermediate Similarity	NPC165128
0.7852	Intermediate Similarity	NPC226862
0.7852	Intermediate Similarity	NPC57119
0.7846	Intermediate Similarity	NPC242885
0.7846	Intermediate Similarity	NPC117780
0.7846	Intermediate Similarity	NPC227217
0.7846	Intermediate Similarity	NPC95614
0.7846	Intermediate Similarity	NPC56214
0.7846	Intermediate Similarity	NPC165133
0.7846	Intermediate Similarity	NPC232316
0.7842	Intermediate Similarity	NPC99078
0.7842	Intermediate Similarity	NPC184938
0.7842	Intermediate Similarity	NPC101624
0.7842	Intermediate Similarity	NPC174191
0.7842	Intermediate Similarity	NPC142547
0.7842	Intermediate Similarity	NPC135777
0.7836	Intermediate Similarity	NPC473960
0.7833	Intermediate Similarity	NPC310905
0.7833	Intermediate Similarity	NPC12714
0.7829	Intermediate Similarity	NPC470626
0.7829	Intermediate Similarity	NPC474214
0.7826	Intermediate Similarity	NPC193673
0.7826	Intermediate Similarity	NPC103947
0.7826	Intermediate Similarity	NPC94280
0.7826	Intermediate Similarity	NPC471391
0.7826	Intermediate Similarity	NPC159150
0.7826	Intermediate Similarity	NPC471390
0.7826	Intermediate Similarity	NPC328419
0.7826	Intermediate Similarity	NPC45783
0.7823	Intermediate Similarity	NPC36108
0.7823	Intermediate Similarity	NPC7097
0.7823	Intermediate Similarity	NPC246358
0.7823	Intermediate Similarity	NPC233731
0.7812	Intermediate Similarity	NPC111225
0.781	Intermediate Similarity	NPC477706
0.7805	Intermediate Similarity	NPC227894
0.7803	Intermediate Similarity	NPC298486
0.7803	Intermediate Similarity	NPC256167
0.7794	Intermediate Similarity	NPC470633
0.7794	Intermediate Similarity	NPC476748
0.7794	Intermediate Similarity	NPC228769
0.7794	Intermediate Similarity	NPC270849
0.7794	Intermediate Similarity	NPC26653
0.7786	Intermediate Similarity	NPC194359
0.7786	Intermediate Similarity	NPC28641
0.7786	Intermediate Similarity	NPC193528
0.7786	Intermediate Similarity	NPC225745
0.7786	Intermediate Similarity	NPC220923
0.7778	Intermediate Similarity	NPC5462
0.7778	Intermediate Similarity	NPC100129
0.7778	Intermediate Similarity	NPC165646
0.777	Intermediate Similarity	NPC47181
0.777	Intermediate Similarity	NPC180647
0.777	Intermediate Similarity	NPC251454
0.777	Intermediate Similarity	NPC230698
0.777	Intermediate Similarity	NPC255817
0.777	Intermediate Similarity	NPC205178
0.777	Intermediate Similarity	NPC470881
0.777	Intermediate Similarity	NPC264956
0.777	Intermediate Similarity	NPC136330
0.777	Intermediate Similarity	NPC196609
0.777	Intermediate Similarity	NPC73883
0.777	Intermediate Similarity	NPC277042
0.7769	Intermediate Similarity	NPC24474
0.7769	Intermediate Similarity	NPC311595
0.7769	Intermediate Similarity	NPC474320
0.7761	Intermediate Similarity	NPC85830
0.7752	Intermediate Similarity	NPC293619
0.7737	Intermediate Similarity	NPC472024
0.7737	Intermediate Similarity	NPC80600
0.7737	Intermediate Similarity	NPC233224
0.7737	Intermediate Similarity	NPC271208
0.7734	Intermediate Similarity	NPC47194
0.7734	Intermediate Similarity	NPC303370
0.7734	Intermediate Similarity	NPC473264

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 NPC191302 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	132
0.1-0.2	728
0.2-0.3	1300
0.3-0.4	2538
0.4-0.5	2361
0.5-0.6	1372
0.6-0.7	618
0.7-0.8	91
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8485	Intermediate Similarity	NPD2674	Phase 3
0.8409	Intermediate Similarity	NPD3145	Approved
0.8409	Intermediate Similarity	NPD3144	Approved
0.8382	Intermediate Similarity	NPD2161	Phase 2
0.8333	Intermediate Similarity	NPD1357	Approved
0.8219	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.8169	Intermediate Similarity	NPD4739	Approved
0.8143	Intermediate Similarity	NPD6331	Phase 2
0.8074	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3705	Approved
0.8	Intermediate Similarity	NPD7153	Discontinued
0.7984	Intermediate Similarity	NPD228	Approved
0.7955	Intermediate Similarity	NPD2922	Phase 1
0.7941	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD1375	Discontinued
0.7914	Intermediate Similarity	NPD4108	Discontinued
0.791	Intermediate Similarity	NPD1712	Approved
0.7899	Intermediate Similarity	NPD2157	Approved
0.7879	Intermediate Similarity	NPD3685	Discontinued
0.7857	Intermediate Similarity	NPD5283	Phase 1
0.7778	Intermediate Similarity	NPD821	Approved
0.777	Intermediate Similarity	NPD2492	Phase 1
0.7744	Intermediate Similarity	NPD1669	Approved
0.774	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD52	Approved
0.774	Intermediate Similarity	NPD7526	Approved
0.7737	Intermediate Similarity	NPD5110	Phase 2
0.7737	Intermediate Similarity	NPD5111	Phase 2
0.7737	Intermediate Similarity	NPD5109	Approved
0.7708	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD5604	Discontinued
0.7619	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD709	Approved
0.7594	Intermediate Similarity	NPD776	Approved
0.7591	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD2667	Approved
0.7576	Intermediate Similarity	NPD2668	Approved
0.7569	Intermediate Similarity	NPD4236	Phase 3
0.7569	Intermediate Similarity	NPD4237	Approved
0.755	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5773	Approved
0.75	Intermediate Similarity	NPD2977	Approved
0.75	Intermediate Similarity	NPD2978	Approved
0.75	Intermediate Similarity	NPD5772	Approved
0.7482	Intermediate Similarity	NPD5718	Phase 2
0.7466	Intermediate Similarity	NPD2219	Phase 1
0.7432	Intermediate Similarity	NPD4123	Phase 3
0.7407	Intermediate Similarity	NPD2233	Approved
0.7407	Intermediate Similarity	NPD2232	Approved
0.7407	Intermediate Similarity	NPD2230	Approved
0.7394	Intermediate Similarity	NPD2653	Approved
0.7376	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD1558	Phase 1
0.7343	Intermediate Similarity	NPD6896	Approved
0.7343	Intermediate Similarity	NPD6895	Approved
0.7333	Intermediate Similarity	NPD2122	Discontinued
0.7329	Intermediate Similarity	NPD3060	Approved
0.7323	Intermediate Similarity	NPD2684	Approved
0.7319	Intermediate Similarity	NPD6584	Phase 3
0.7305	Intermediate Similarity	NPD1423	Approved
0.7292	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD4110	Phase 3
0.7273	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD2040	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1044	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD4357	Discontinued
0.7237	Intermediate Similarity	NPD4005	Discontinued
0.723	Intermediate Similarity	NPD5241	Discontinued
0.7226	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6111	Discontinued
0.7218	Intermediate Similarity	NPD5536	Phase 2
0.7211	Intermediate Similarity	NPD5177	Phase 3
0.7211	Intermediate Similarity	NPD4162	Approved
0.72	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4678	Approved
0.719	Intermediate Similarity	NPD4675	Approved
0.7183	Intermediate Similarity	NPD839	Approved
0.7183	Intermediate Similarity	NPD840	Approved
0.7183	Intermediate Similarity	NPD3058	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD3027	Phase 3
0.7163	Intermediate Similarity	NPD1024	Discontinued
0.7153	Intermediate Similarity	NPD2231	Phase 2
0.7153	Intermediate Similarity	NPD4097	Suspended
0.7153	Intermediate Similarity	NPD2235	Phase 2
0.7143	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2808	Discontinued
0.7133	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD3620	Phase 2
0.7115	Intermediate Similarity	NPD2358	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD1048	Approved
0.7101	Intermediate Similarity	NPD6582	Phase 2
0.7101	Intermediate Similarity	NPD6583	Phase 3
0.7099	Intermediate Similarity	NPD7843	Approved
0.7097	Intermediate Similarity	NPD5722	Discontinued
0.7083	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1642	Discontinued
0.7078	Intermediate Similarity	NPD7028	Phase 2
0.7068	Intermediate Similarity	NPD7157	Approved
0.7063	Intermediate Similarity	NPD7477	Discontinued
0.7059	Intermediate Similarity	NPD3686	Approved
0.7059	Intermediate Similarity	NPD4210	Discontinued
0.7059	Intermediate Similarity	NPD3687	Approved
0.7044	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD3165	Approved
0.7042	Intermediate Similarity	NPD3164	Approved
0.7042	Intermediate Similarity	NPD3167	Approved
0.7042	Intermediate Similarity	NPD3166	Approved
0.7034	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD5089	Approved
0.7032	Intermediate Similarity	NPD5090	Approved
0.7027	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD3655	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD3596	Phase 2
0.7014	Intermediate Similarity	NPD2238	Phase 2
0.7013	Intermediate Similarity	NPD3111	Phase 1
0.7007	Intermediate Similarity	NPD3847	Discontinued
0.7	Intermediate Similarity	NPD1819	Approved
0.7	Intermediate Similarity	NPD3021	Approved
0.7	Intermediate Similarity	NPD1818	Approved
0.7	Intermediate Similarity	NPD3022	Approved
0.7	Intermediate Similarity	NPD1820	Approved
0.7	Intermediate Similarity	NPD1817	Approved
0.6993	Remote Similarity	NPD1039	Discontinued
0.6978	Remote Similarity	NPD2983	Phase 2
0.6978	Remote Similarity	NPD2982	Phase 2
0.697	Remote Similarity	NPD9379	Approved
0.697	Remote Similarity	NPD9377	Approved
0.6959	Remote Similarity	NPD3656	Approved
0.6954	Remote Similarity	NPD7124	Phase 2
0.695	Remote Similarity	NPD558	Phase 2
0.6934	Remote Similarity	NPD4626	Approved
0.6928	Remote Similarity	NPD6390	Discontinued
0.6923	Remote Similarity	NPD5163	Phase 2
0.6918	Remote Similarity	NPD4055	Discovery
0.6914	Remote Similarity	NPD4083	Discontinued
0.6913	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD7037	Approved
0.6912	Remote Similarity	NPD6580	Approved
0.6912	Remote Similarity	NPD1182	Approved
0.6912	Remote Similarity	NPD6581	Approved
0.6906	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD2981	Phase 2
0.6901	Remote Similarity	NPD3018	Phase 2
0.6901	Remote Similarity	NPD4993	Discontinued
0.6899	Remote Similarity	NPD2563	Approved
0.6899	Remote Similarity	NPD1445	Approved
0.6899	Remote Similarity	NPD1444	Approved
0.6899	Remote Similarity	NPD3134	Approved
0.6899	Remote Similarity	NPD2560	Approved
0.6892	Remote Similarity	NPD6032	Approved
0.6879	Remote Similarity	NPD37	Approved
0.6871	Remote Similarity	NPD7119	Phase 2
0.687	Remote Similarity	NPD556	Approved
0.6867	Remote Similarity	NPD6674	Discontinued
0.6863	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD3146	Approved
0.6861	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD2614	Approved
0.6849	Remote Similarity	NPD3657	Discovery
0.6846	Remote Similarity	NPD290	Approved
0.6846	Remote Similarity	NPD1358	Approved
0.6845	Remote Similarity	NPD7281	Phase 3
0.6845	Remote Similarity	NPD7280	Phase 3
0.6842	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1138	Approved
0.6832	Remote Similarity	NPD2644	Approved
0.6831	Remote Similarity	NPD4624	Approved
0.6829	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD3532	Approved
0.6828	Remote Similarity	NPD3162	Approved
0.6828	Remote Similarity	NPD3531	Approved
0.6828	Remote Similarity	NPD3530	Approved
0.6828	Remote Similarity	NPD3163	Approved
0.6824	Remote Similarity	NPD3846	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1349	Approved
0.6818	Remote Similarity	NPD1351	Approved
0.6818	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1350	Approved
0.6818	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD4773	Phase 2
0.6815	Remote Similarity	NPD4772	Phase 2
0.6815	Remote Similarity	NPD2557	Approved
0.6815	Remote Similarity	NPD6387	Discontinued
0.6815	Remote Similarity	NPD6671	Approved
0.6813	Remote Similarity	NPD7831	Phase 2
0.6813	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD7833	Phase 2
0.6812	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD3179	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