NPASS Compound

Structure

CID19114 OpenBabel06191715342D 25 28 0 0 1 0 0 0 0 0999 V2000 2.5207 -0.4485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6812 -2.9093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8409 -2.4245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6789 -0.9700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6792 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2002 -1.4534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3605 -0.9686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3610 -2.9089 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6804 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0806 1.7540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5213 -2.4240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2005 -2.4235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8406 -1.4544 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0003 -0.9695 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8403 0.4848 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6807 -0.9691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8409 1.4540 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8401 0.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5210 -1.4539 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2816 2.7021 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0714 -2.9259 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5615 2.1020 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8398 1.4853 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 4 2 0 0 0 0 3 12 1 0 0 0 0 5 6 1 0 0 0 0 5 15 1 0 0 0 0 6 16 1 0 0 0 0 7 8 1 0 0 0 0 7 13 1 0 0 0 0 8 20 1 0 0 0 0 9 12 2 0 0 0 0 9 13 1 0 0 0 0 10 17 1 0 0 0 0 10 19 1 0 0 0 0 11 18 1 0 0 0 0 11 22 1 0 0 0 0 12 20 1 0 0 0 0 13 23 2 0 0 0 0 14 4 1 1 0 0 0 14 15 1 0 0 0 0 14 17 1 0 0 0 0 15 21 1 6 0 0 0 16 18 1 0 0 0 0 16 21 1 6 0 0 0 17 20 1 6 0 0 0 18 24 1 6 0 0 0 19 21 1 0 0 0 0 19 25 2 0 0 0 0 20 1 1 6 0 0 0 21 2 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.2
Volume:	362.161
LogP:	1.41
LogD:	1.013
LogS:	-2.316
# Rotatable Bonds:	2
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.807
Synthetic Accessibility Score:	4.745
Fsp3:	0.714
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:	-4.818
MDCK Permeability:	2.642002255015541e-05
Pgp-inhibitor:	0.963
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.48
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.575
Plasma Protein Binding (PPB):	53.81653594970703%
Volume Distribution (VD):	0.498
Pgp-substrate:	43.472373962402344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.365
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.778
CYP2C9-inhibitor:	0.018
CYP2C9-substrate:	0.053
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.094
CYP3A4-inhibitor:	0.026
CYP3A4-substrate:	0.699

ADMET: Excretion

Clearance (CL):	9.361
Half-life (T1/2):	0.894

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.075
Drug-inuced Liver Injury (DILI):	0.201
AMES Toxicity:	0.212
Rat Oral Acute Toxicity:	0.967
Maximum Recommended Daily Dose:	0.916
Skin Sensitization:	0.921
Carcinogencity:	0.869
Eye Corrosion:	0.605
Eye Irritation:	0.214
Respiratory Toxicity:	0.991

Download Data

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

Natural Product: NPC19114

Natural Product ID:	NPC19114
*Common Name:**	Neridienone B
IUPAC Name:	(8R,9S,10R,13S,14S,17S)-17-[(1S)-1,2-dihydroxyethyl]-10,13-dimethyl-2,8,9,11,14,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-3,12-dione
Synonyms:	neridienone B
Standard InCHIKey:	NCBLKWGLSQARQJ-BJSXQCTJSA-N
Standard InCHI:	InChI=1S/C21H28O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(24)11-22)21(15,2)19(25)10-17(14)20/h3-4,9,14-18,22,24H,5-8,10-11H2,1-2H3/t14-,15-,16+,17-,18+,20-,21-/m0/s1
SMILES:	OC[C@H]([C@H]1CC[C@@H]2[C@]1(C)C(=O)C[C@H]1[C@H]2C=CC2=CC(=O)CC[C@]12C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL219812
PubChem CID:	44418781
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001295] Hydroxysteroids [CHEMONTID:0003095] 21-hydroxysteroids

*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
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1039/C39730000707]
NPO1071	Parerythropodium fulvum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[11277760]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	leaves	Niigata City, Niigata Province, Japan	2000-Nov	PMID[15730243]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16933868]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17253842]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	stems and twigs	n.a.	n.a.	PMID[17595134]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	stems and twigs	Niigata City, Niigata Province, Japan	2001-NOV	PMID[17595134]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18491868]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19731587]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29693393]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	Leaves; Stems	n.a.	n.a.	PMID[9214727]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6520	Myrica multiflora	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3664	Mesembryanthemum anatomicum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2342	Cytisus scoparius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14048	Cryptotaenia japonica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2747	Hypericum triquetrifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13325	Plantago lanceolata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13325	Plantago lanceolata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6520	Myrica multiflora	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14048	Cryptotaenia japonica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3664	Mesembryanthemum anatomicum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2342	Cytisus scoparius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2518	Crinum kirkii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2747	Hypericum triquetrifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2342	Cytisus scoparius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14048	Cryptotaenia japonica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO351	Cirsium dipsacolepis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2518	Crinum kirkii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5197	Streptomyces eurythermus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO4253	Viguiera annua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6776	Trifolium apertum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1308	Veronica pectinata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3664	Mesembryanthemum anatomicum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2361	Aconitum brevicalcaratum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8585	Verpa digitaliformis	Species	Morchellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14048	Cryptotaenia japonica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6377	Cocculus diversifolius	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4082	Ophiarthrum elegans	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7097	Rhynchosporium orthosporum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12987	Rhododendron farrerae	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2342	Cytisus scoparius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6974	Solanum racemigerum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8840	Ptilidium ciliare	Species	Ptilidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18054	Curvularia coicis	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13325	Plantago lanceolata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5591	Fucus spiralis	Species	Fucaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1607	Croton rhamnifolius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6520	Myrica multiflora	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20132	Scutellaria seleriana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2747	Hypericum triquetrifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO715	Teucrium pestalozzae	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15583	Tripodanthus acutifolius	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5980	Eria subsessilis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1071	Parerythropodium fulvum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO3146	Ammodendron conollyi	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8472	Knightia deplanchei	Species	Proteaceae	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	3
Others	6

Activity Type	# Activity
Cell Line	2
Others	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1475	Cell Line	WI-38 VA13	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[477615]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[477615]
NPT2	Others	Unspecified		Activity	=	110.0	%	PMID[477615]
NPT2	Others	Unspecified		Activity	=	154.0	%	PMID[477615]
NPT2	Others	Unspecified		Activity	=	148.0	%	PMID[477615]
NPT2	Others	Unspecified		Activity	=	113.0	%	PMID[477615]
NPT2	Others	Unspecified		Activity	=	141.0	%	PMID[477615]
NPT2	Others	Unspecified		Activity	=	100.0	%	PMID[477615]
NPT27	Others	Unspecified		IC50	=	73.5	ug.mL-1	PMID[477615]

☑ 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 NPC19114 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	171
0.1-0.2	861
0.2-0.3	4353
0.3-0.4	12420
0.4-0.5	10485
0.5-0.6	7557
0.6-0.7	5101
0.7-0.8	1483
0.8-0.85	224
0.85-0.9	39
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9529	High Similarity	NPC136548
0.9205	High Similarity	NPC129913
0.8977	High Similarity	NPC44181
0.8966	High Similarity	NPC89077
0.8953	High Similarity	NPC473246
0.8901	High Similarity	NPC473172
0.8876	High Similarity	NPC477943
0.8791	High Similarity	NPC134826
0.875	High Similarity	NPC222613
0.875	High Similarity	NPC475022
0.875	High Similarity	NPC118648
0.875	High Similarity	NPC473168
0.8736	High Similarity	NPC85774
0.8736	High Similarity	NPC214043
0.871	High Similarity	NPC473164
0.8696	High Similarity	NPC473162
0.8667	High Similarity	NPC86319
0.8667	High Similarity	NPC275740
0.8652	High Similarity	NPC58063
0.8652	High Similarity	NPC90652
0.8652	High Similarity	NPC99909
0.8636	High Similarity	NPC469948
0.8602	High Similarity	NPC127063
0.8587	High Similarity	NPC250575
0.8587	High Similarity	NPC66429
0.8587	High Similarity	NPC152897
0.8587	High Similarity	NPC474807
0.8587	High Similarity	NPC474736
0.8587	High Similarity	NPC472930
0.8556	High Similarity	NPC470417
0.8556	High Similarity	NPC471722
0.8556	High Similarity	NPC328539
0.8556	High Similarity	NPC143767
0.8556	High Similarity	NPC131470
0.8539	High Similarity	NPC72133
0.8539	High Similarity	NPC31564
0.8539	High Similarity	NPC145879
0.8539	High Similarity	NPC474732
0.8539	High Similarity	NPC474778
0.8539	High Similarity	NPC474733
0.8539	High Similarity	NPC327115
0.8523	High Similarity	NPC227064
0.8523	High Similarity	NPC58841
0.8523	High Similarity	NPC237712
0.8523	High Similarity	NPC321187
0.8523	High Similarity	NPC329043
0.8523	High Similarity	NPC161423
0.8511	High Similarity	NPC117133
0.8511	High Similarity	NPC249954
0.8478	Intermediate Similarity	NPC185936
0.8478	Intermediate Similarity	NPC168027
0.8462	Intermediate Similarity	NPC1015
0.8462	Intermediate Similarity	NPC31985
0.8462	Intermediate Similarity	NPC32830
0.8462	Intermediate Similarity	NPC186688
0.8444	Intermediate Similarity	NPC141292
0.8444	Intermediate Similarity	NPC475740
0.8444	Intermediate Similarity	NPC287079
0.8444	Intermediate Similarity	NPC93778
0.8438	Intermediate Similarity	NPC316964
0.8427	Intermediate Similarity	NPC474083
0.8427	Intermediate Similarity	NPC474218
0.8421	Intermediate Similarity	NPC473161
0.8404	Intermediate Similarity	NPC472932
0.8404	Intermediate Similarity	NPC263347
0.8404	Intermediate Similarity	NPC259286
0.8391	Intermediate Similarity	NPC121984
0.8387	Intermediate Similarity	NPC69454
0.8387	Intermediate Similarity	NPC472942
0.8372	Intermediate Similarity	NPC472490
0.8372	Intermediate Similarity	NPC474113
0.837	Intermediate Similarity	NPC191684
0.837	Intermediate Similarity	NPC69622
0.837	Intermediate Similarity	NPC46281
0.837	Intermediate Similarity	NPC183283
0.8352	Intermediate Similarity	NPC292491
0.8352	Intermediate Similarity	NPC310752
0.8333	Intermediate Similarity	NPC235464
0.8333	Intermediate Similarity	NPC471717
0.8333	Intermediate Similarity	NPC166745
0.8333	Intermediate Similarity	NPC103051
0.8316	Intermediate Similarity	NPC192428
0.8316	Intermediate Similarity	NPC155676
0.8315	Intermediate Similarity	NPC221758
0.8315	Intermediate Similarity	NPC82902
0.8315	Intermediate Similarity	NPC59453
0.8298	Intermediate Similarity	NPC8993
0.8298	Intermediate Similarity	NPC56525
0.8298	Intermediate Similarity	NPC166906
0.8295	Intermediate Similarity	NPC151519
0.8295	Intermediate Similarity	NPC212083
0.8283	Intermediate Similarity	NPC255309
0.828	Intermediate Similarity	NPC473998
0.828	Intermediate Similarity	NPC272746
0.828	Intermediate Similarity	NPC204341
0.828	Intermediate Similarity	NPC475806
0.828	Intermediate Similarity	NPC63748
0.8276	Intermediate Similarity	NPC472478
0.8265	Intermediate Similarity	NPC477915
0.8265	Intermediate Similarity	NPC473163
0.8265	Intermediate Similarity	NPC473424
0.8261	Intermediate Similarity	NPC309603
0.8261	Intermediate Similarity	NPC77168
0.8261	Intermediate Similarity	NPC119416
0.8261	Intermediate Similarity	NPC473999
0.8261	Intermediate Similarity	NPC123912
0.8261	Intermediate Similarity	NPC326627
0.8261	Intermediate Similarity	NPC268406
0.8261	Intermediate Similarity	NPC84271
0.8261	Intermediate Similarity	NPC102414
0.8261	Intermediate Similarity	NPC54689
0.8261	Intermediate Similarity	NPC310010
0.8261	Intermediate Similarity	NPC26959
0.8247	Intermediate Similarity	NPC287833
0.8247	Intermediate Similarity	NPC474720
0.8247	Intermediate Similarity	NPC51370
0.8242	Intermediate Similarity	NPC317590
0.8242	Intermediate Similarity	NPC138756
0.8229	Intermediate Similarity	NPC161147
0.8229	Intermediate Similarity	NPC474785
0.8229	Intermediate Similarity	NPC474938
0.8222	Intermediate Similarity	NPC471224
0.8222	Intermediate Similarity	NPC470574
0.8211	Intermediate Similarity	NPC222845
0.8211	Intermediate Similarity	NPC200702
0.8211	Intermediate Similarity	NPC45324
0.8211	Intermediate Similarity	NPC173875
0.8211	Intermediate Similarity	NPC317586
0.8211	Intermediate Similarity	NPC318282
0.8211	Intermediate Similarity	NPC473170
0.8211	Intermediate Similarity	NPC470016
0.8211	Intermediate Similarity	NPC280725
0.8211	Intermediate Similarity	NPC174948
0.8211	Intermediate Similarity	NPC469995
0.8211	Intermediate Similarity	NPC162001
0.8202	Intermediate Similarity	NPC69279
0.8202	Intermediate Similarity	NPC278648
0.8202	Intermediate Similarity	NPC83569
0.8202	Intermediate Similarity	NPC476082
0.82	Intermediate Similarity	NPC96377
0.8191	Intermediate Similarity	NPC25750
0.8191	Intermediate Similarity	NPC475255
0.8191	Intermediate Similarity	NPC109305
0.8191	Intermediate Similarity	NPC233118
0.8182	Intermediate Similarity	NPC111323
0.8182	Intermediate Similarity	NPC116797
0.8172	Intermediate Similarity	NPC136801
0.8172	Intermediate Similarity	NPC320026
0.8172	Intermediate Similarity	NPC48010
0.8172	Intermediate Similarity	NPC289213
0.8152	Intermediate Similarity	NPC471724
0.8152	Intermediate Similarity	NPC247406
0.8152	Intermediate Similarity	NPC48866
0.8152	Intermediate Similarity	NPC158778
0.8144	Intermediate Similarity	NPC114274
0.8144	Intermediate Similarity	NPC147954
0.8144	Intermediate Similarity	NPC197386
0.8132	Intermediate Similarity	NPC20688
0.8132	Intermediate Similarity	NPC94666
0.8132	Intermediate Similarity	NPC469994
0.8132	Intermediate Similarity	NPC94755
0.8132	Intermediate Similarity	NPC51014
0.8125	Intermediate Similarity	NPC472941
0.8125	Intermediate Similarity	NPC456
0.8125	Intermediate Similarity	NPC328371
0.8125	Intermediate Similarity	NPC471463
0.8125	Intermediate Similarity	NPC328162
0.8125	Intermediate Similarity	NPC305483
0.8125	Intermediate Similarity	NPC96859
0.8119	Intermediate Similarity	NPC43285
0.8119	Intermediate Similarity	NPC58370
0.8118	Intermediate Similarity	NPC114236
0.8111	Intermediate Similarity	NPC33913
0.8111	Intermediate Similarity	NPC472265
0.8105	Intermediate Similarity	NPC49670
0.8105	Intermediate Similarity	NPC209662
0.8105	Intermediate Similarity	NPC111015
0.8105	Intermediate Similarity	NPC245972
0.8105	Intermediate Similarity	NPC474690
0.8105	Intermediate Similarity	NPC318332
0.8105	Intermediate Similarity	NPC469406
0.8105	Intermediate Similarity	NPC299100
0.8105	Intermediate Similarity	NPC196485
0.8105	Intermediate Similarity	NPC67831
0.8105	Intermediate Similarity	NPC174051
0.81	Intermediate Similarity	NPC209502
0.81	Intermediate Similarity	NPC204833
0.81	Intermediate Similarity	NPC477812
0.809	Intermediate Similarity	NPC193347
0.809	Intermediate Similarity	NPC103486
0.8085	Intermediate Similarity	NPC297265
0.8085	Intermediate Similarity	NPC154101
0.8085	Intermediate Similarity	NPC262870
0.8085	Intermediate Similarity	NPC155304
0.8085	Intermediate Similarity	NPC189520
0.8085	Intermediate Similarity	NPC233116
0.8081	Intermediate Similarity	NPC87351
0.8081	Intermediate Similarity	NPC204450
0.8081	Intermediate Similarity	NPC195290
0.8068	Intermediate Similarity	NPC2482

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 NPC19114 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	150
0.1-0.2	1144
0.2-0.3	3856
0.3-0.4	2760
0.4-0.5	721
0.5-0.6	215
0.6-0.7	145
0.7-0.8	137
0.8-0.85	21
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8966	High Similarity	NPD5279	Phase 3
0.8539	High Similarity	NPD3618	Phase 1
0.8523	High Similarity	NPD3666	Approved
0.8523	High Similarity	NPD3133	Approved
0.8523	High Similarity	NPD3665	Phase 1
0.8478	Intermediate Similarity	NPD5284	Approved
0.8478	Intermediate Similarity	NPD6079	Approved
0.8478	Intermediate Similarity	NPD5281	Approved
0.8462	Intermediate Similarity	NPD5328	Approved
0.8333	Intermediate Similarity	NPD5280	Approved
0.8333	Intermediate Similarity	NPD4694	Approved
0.8316	Intermediate Similarity	NPD5221	Approved
0.8316	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8316	Intermediate Similarity	NPD5222	Approved
0.8316	Intermediate Similarity	NPD4697	Phase 3
0.8315	Intermediate Similarity	NPD4786	Approved
0.8295	Intermediate Similarity	NPD3667	Approved
0.8261	Intermediate Similarity	NPD4753	Phase 2
0.8229	Intermediate Similarity	NPD5173	Approved
0.8211	Intermediate Similarity	NPD4629	Approved
0.8211	Intermediate Similarity	NPD5210	Approved
0.8132	Intermediate Similarity	NPD5690	Phase 2
0.809	Intermediate Similarity	NPD4223	Phase 3
0.809	Intermediate Similarity	NPD4221	Approved
0.8061	Intermediate Similarity	NPD4696	Approved
0.8061	Intermediate Similarity	NPD5285	Approved
0.8061	Intermediate Similarity	NPD5286	Approved
0.8041	Intermediate Similarity	NPD4755	Approved
0.8	Intermediate Similarity	NPD4687	Approved
0.8	Intermediate Similarity	NPD4202	Approved
0.798	Intermediate Similarity	NPD5223	Approved
0.7912	Intermediate Similarity	NPD4197	Approved
0.79	Intermediate Similarity	NPD5225	Approved
0.79	Intermediate Similarity	NPD5211	Phase 2
0.79	Intermediate Similarity	NPD4633	Approved
0.79	Intermediate Similarity	NPD5226	Approved
0.79	Intermediate Similarity	NPD5224	Approved
0.7879	Intermediate Similarity	NPD4700	Approved
0.7835	Intermediate Similarity	NPD5695	Phase 3
0.7826	Intermediate Similarity	NPD5329	Approved
0.7822	Intermediate Similarity	NPD5174	Approved
0.7822	Intermediate Similarity	NPD5175	Approved
0.7812	Intermediate Similarity	NPD6399	Phase 3
0.7791	Intermediate Similarity	NPD5733	Approved
0.7789	Intermediate Similarity	NPD4096	Approved
0.7789	Intermediate Similarity	NPD5207	Approved
0.7766	Intermediate Similarity	NPD4518	Approved
0.7765	Intermediate Similarity	NPD5276	Approved
0.7745	Intermediate Similarity	NPD5141	Approved
0.7742	Intermediate Similarity	NPD4689	Approved
0.7742	Intermediate Similarity	NPD5205	Approved
0.7742	Intermediate Similarity	NPD4693	Phase 3
0.7742	Intermediate Similarity	NPD4138	Approved
0.7742	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD4688	Approved
0.7742	Intermediate Similarity	NPD4690	Approved
0.7717	Intermediate Similarity	NPD3668	Phase 3
0.7714	Intermediate Similarity	NPD4634	Approved
0.7708	Intermediate Similarity	NPD5694	Approved
0.7677	Intermediate Similarity	NPD6084	Phase 2
0.7677	Intermediate Similarity	NPD6083	Phase 2
0.7647	Intermediate Similarity	NPD4754	Approved
0.764	Intermediate Similarity	NPD3617	Approved
0.7629	Intermediate Similarity	NPD5133	Approved
0.7604	Intermediate Similarity	NPD5692	Phase 3
0.76	Intermediate Similarity	NPD5696	Approved
0.7596	Intermediate Similarity	NPD5697	Approved
0.7586	Intermediate Similarity	NPD4058	Approved
0.7579	Intermediate Similarity	NPD5737	Approved
0.7579	Intermediate Similarity	NPD6672	Approved
0.7556	Intermediate Similarity	NPD4195	Approved
0.7553	Intermediate Similarity	NPD6409	Approved
0.7553	Intermediate Similarity	NPD6684	Approved
0.7553	Intermediate Similarity	NPD7146	Approved
0.7553	Intermediate Similarity	NPD7521	Approved
0.7553	Intermediate Similarity	NPD7334	Approved
0.7553	Intermediate Similarity	NPD5330	Approved
0.7526	Intermediate Similarity	NPD6050	Approved
0.7526	Intermediate Similarity	NPD7515	Phase 2
0.7524	Intermediate Similarity	NPD4730	Approved
0.7524	Intermediate Similarity	NPD6011	Approved
0.7524	Intermediate Similarity	NPD5168	Approved
0.7524	Intermediate Similarity	NPD4729	Approved
0.7524	Intermediate Similarity	NPD6899	Approved
0.7524	Intermediate Similarity	NPD6881	Approved
0.75	Intermediate Similarity	NPD5739	Approved
0.75	Intermediate Similarity	NPD7128	Approved
0.75	Intermediate Similarity	NPD4632	Approved
0.75	Intermediate Similarity	NPD6675	Approved
0.75	Intermediate Similarity	NPD4768	Approved
0.75	Intermediate Similarity	NPD6402	Approved
0.75	Intermediate Similarity	NPD4767	Approved
0.7477	Intermediate Similarity	NPD6650	Approved
0.7477	Intermediate Similarity	NPD6649	Approved
0.7473	Intermediate Similarity	NPD4695	Discontinued
0.7453	Intermediate Similarity	NPD6373	Approved
0.7453	Intermediate Similarity	NPD6372	Approved
0.7453	Intermediate Similarity	NPD6012	Approved
0.7453	Intermediate Similarity	NPD6013	Approved
0.7453	Intermediate Similarity	NPD6014	Approved
0.7442	Intermediate Similarity	NPD4747	Approved
0.7429	Intermediate Similarity	NPD5701	Approved
0.7429	Intermediate Similarity	NPD6412	Phase 2
0.7419	Intermediate Similarity	NPD4788	Approved
0.7416	Intermediate Similarity	NPD6933	Approved
0.7407	Intermediate Similarity	NPD8297	Approved
0.7396	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6903	Approved
0.7391	Intermediate Similarity	NPD4692	Approved
0.7391	Intermediate Similarity	NPD4139	Approved
0.7383	Intermediate Similarity	NPD5249	Phase 3
0.7383	Intermediate Similarity	NPD7290	Approved
0.7383	Intermediate Similarity	NPD6883	Approved
0.7383	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD5248	Approved
0.7383	Intermediate Similarity	NPD5247	Approved
0.7383	Intermediate Similarity	NPD5250	Approved
0.7383	Intermediate Similarity	NPD5135	Approved
0.7383	Intermediate Similarity	NPD5251	Approved
0.7383	Intermediate Similarity	NPD7102	Approved
0.7383	Intermediate Similarity	NPD5169	Approved
0.7368	Intermediate Similarity	NPD4623	Approved
0.7368	Intermediate Similarity	NPD4519	Discontinued
0.7358	Intermediate Similarity	NPD5128	Approved
0.7358	Intermediate Similarity	NPD7320	Approved
0.7347	Intermediate Similarity	NPD6411	Approved
0.7326	Intermediate Similarity	NPD4137	Phase 3
0.732	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD5215	Approved
0.7315	Intermediate Similarity	NPD5127	Approved
0.7315	Intermediate Similarity	NPD6869	Approved
0.7315	Intermediate Similarity	NPD8130	Phase 1
0.7315	Intermediate Similarity	NPD6847	Approved
0.7315	Intermediate Similarity	NPD6617	Approved
0.7315	Intermediate Similarity	NPD5217	Approved
0.7315	Intermediate Similarity	NPD5216	Approved
0.7303	Intermediate Similarity	NPD7339	Approved
0.7303	Intermediate Similarity	NPD6942	Approved
0.7297	Intermediate Similarity	NPD7115	Discovery
0.7283	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6882	Approved
0.7241	Intermediate Similarity	NPD4691	Approved
0.7222	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD5091	Approved
0.72	Intermediate Similarity	NPD7748	Approved
0.7191	Intermediate Similarity	NPD6924	Approved
0.7191	Intermediate Similarity	NPD6926	Approved
0.7157	Intermediate Similarity	NPD7902	Approved
0.7156	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6101	Approved
0.7143	Intermediate Similarity	NPD6009	Approved
0.7143	Intermediate Similarity	NPD6673	Approved
0.7143	Intermediate Similarity	NPD6904	Approved
0.7143	Intermediate Similarity	NPD6080	Approved
0.7143	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD5654	Approved
0.7117	Intermediate Similarity	NPD5167	Approved
0.7105	Intermediate Similarity	NPD6319	Approved
0.7097	Intermediate Similarity	NPD7525	Registered
0.7083	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD6868	Approved
0.7053	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7144	Approved
0.7045	Intermediate Similarity	NPD7143	Approved
0.7041	Intermediate Similarity	NPD5208	Approved
0.7019	Intermediate Similarity	NPD6404	Discontinued
0.7018	Intermediate Similarity	NPD4522	Approved
0.7009	Intermediate Similarity	NPD6008	Approved
0.7	Intermediate Similarity	NPD5693	Phase 1
0.6991	Remote Similarity	NPD6317	Approved
0.699	Remote Similarity	NPD5959	Approved
0.6966	Remote Similarity	NPD7152	Approved
0.6966	Remote Similarity	NPD7151	Approved
0.6966	Remote Similarity	NPD7150	Approved
0.6957	Remote Similarity	NPD6054	Approved
0.6932	Remote Similarity	NPD6922	Approved
0.6932	Remote Similarity	NPD6923	Approved
0.693	Remote Similarity	NPD6314	Approved
0.693	Remote Similarity	NPD6335	Approved
0.693	Remote Similarity	NPD6313	Approved
0.6923	Remote Similarity	NPD7638	Approved
0.6903	Remote Similarity	NPD6274	Approved
0.6897	Remote Similarity	NPD5983	Phase 2
0.6897	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6015	Approved
0.6897	Remote Similarity	NPD6016	Approved
0.687	Remote Similarity	NPD7101	Approved
0.687	Remote Similarity	NPD7100	Approved
0.6863	Remote Similarity	NPD7900	Approved
0.6863	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6001	Approved
0.686	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7640	Approved
0.6857	Remote Similarity	NPD7639	Approved
0.6838	Remote Similarity	NPD5988	Approved
0.6838	Remote Similarity	NPD6370	Approved
0.6837	Remote Similarity	NPD6098	Approved
0.6832	Remote Similarity	NPD8035	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data