NPASS Compound

Structure

CID306669 OpenBabel06191716112D 25 28 0 0 0 0 0 0 0 0999 V2000 8.1010 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5029 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3690 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6369 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5029 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6369 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9049 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9049 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3690 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5029 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7709 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7709 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3690 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6369 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2350 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0388 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0388 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2350 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5029 -2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.1010 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1010 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0878 -0.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0878 -2.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8547 3.0439 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 3 1 0 0 0 0 2 11 2 0 0 0 0 3 16 2 0 0 0 0 4 5 1 0 0 0 0 4 12 1 0 0 0 0 5 20 1 0 0 0 0 6 11 1 0 0 0 0 6 15 2 0 0 0 0 7 12 2 0 0 0 0 7 17 1 0 0 0 0 8 13 2 0 0 0 0 8 18 1 0 0 0 0 9 14 2 0 0 0 0 9 20 1 0 0 0 0 10 23 1 0 0 0 0 10 24 1 0 0 0 0 11 14 1 0 0 0 0 12 13 1 0 0 0 0 13 15 1 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 16 19 1 0 0 0 0 16 22 1 0 0 0 0 17 18 2 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 19 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	321.1
Volume:	319.464
LogP:	3.176
LogD:	2.831
LogS:	-5.561
# Rotatable Bonds:	1
TPSA:	49.69
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.691
Synthetic Accessibility Score:	2.672
Fsp3:	0.211
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.888
MDCK Permeability:	2.3951753973960876e-05
Pgp-inhibitor:	0.23
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.805
Plasma Protein Binding (PPB):	94.63236236572266%
Volume Distribution (VD):	1.165
Pgp-substrate:	2.9903619289398193%

ADMET: Metabolism

CYP1A2-inhibitor:	0.961
CYP1A2-substrate:	0.5
CYP2C19-inhibitor:	0.916
CYP2C19-substrate:	0.077
CYP2C9-inhibitor:	0.827
CYP2C9-substrate:	0.916
CYP2D6-inhibitor:	0.698
CYP2D6-substrate:	0.935
CYP3A4-inhibitor:	0.936
CYP3A4-substrate:	0.278

ADMET: Excretion

Clearance (CL):	6.574
Half-life (T1/2):	0.2

ADMET: Toxicity

hERG Blockers:	0.162
Human Hepatotoxicity (H-HT):	0.194
Drug-inuced Liver Injury (DILI):	0.797
AMES Toxicity:	0.931
Rat Oral Acute Toxicity:	0.103
Maximum Recommended Daily Dose:	0.897
Skin Sensitization:	0.247
Carcinogencity:	0.953
Eye Corrosion:	0.003
Eye Irritation:	0.041
Respiratory Toxicity:	0.765

Download Data

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

Natural Product: NPC306669

Natural Product ID:	NPC306669
*Common Name:**	Berberrubine Chloride
IUPAC Name:	n.a.
Synonyms:	Beberrubine Chloride; Berberrubine; Berberrubine Chloride
Standard InCHIKey:	GYFSYEVKFOOLFZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H15NO4.ClH/c1-22-16-3-2-11-6-15-13-8-18-17(23-10-24-18)7-12(13)4-5-20(15)9-14(11)19(16)21;/h2-3,6-9H,4-5,10H2,1H3;1H
SMILES:	COc1ccc2-c(cn3CCc4cc5c(cc4-c3c2)OCO5)c1=O.Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1223099
PubChem CID:	72703 85469308
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001909] Protoberberine alkaloids and derivatives

*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
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[11000020]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21401114]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26538	Phellodendron chinese	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29008	Coptis teeta	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29008	Coptis teeta	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22242	Phellodendron chinense	Species	Rutaceae	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
EC50	2
GI50	54
IC50	8
Others	19

Activity Type	# Activity
Cell Line	63
Individual Protein	2
Organism	2
Others	16

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	Inhibition	=	99.0	%	PMID[561896]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	CC50	=	169200.0	nM	PMID[561896]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	79799.47	nM	PMID[561897]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	69984.2	nM	PMID[561897]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	52844.53	nM	PMID[561897]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	92896.64	nM	PMID[561897]
NPT573	Cell Line	M19-MEL	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT574	Cell Line	XF498	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	40364.54	nM	PMID[561897]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	96605.09	nM	PMID[561897]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	82985.08	nM	PMID[561897]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT731	Cell Line	LXFL 529	Homo sapiens	GI50	n.a.	10000.0	nM	PMID[561897]
NPT576	Cell Line	DMS-114	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	53951.06	nM	PMID[561897]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT577	Cell Line	RXF 631	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT578	Cell Line	SNB-78	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	80723.5	nM	PMID[561897]
NPT579	Cell Line	DLD-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	96382.9	nM	PMID[561897]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT732	Cell Line	HOP-18	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[561897]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	36930.0	nM	PMID[561899]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	50000.0	nM	PMID[561899]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	50000.0	nM	PMID[561899]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	6920.0	nM	PMID[561900]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	34310.0	nM	PMID[561900]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	=	7660.0	nM	PMID[561900]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	11360.0	nM	PMID[561900]
NPT589	Individual Protein	Serum albumin	Bos taurus	Kb	=	1.51	10'3L/mol	PMID[561901]
NPT35	Others	n.a.		LogP	=	-1.06	n.a.	PMID[561895]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	=	76.95	%	PMID[561896]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	2800.0	nM	PMID[561896]
NPT27	Others	Unspecified		TI	=	60.42	n.a.	PMID[561896]
NPT35	Others	n.a.		Solubility	=	500000.0	nM	PMID[561901]
NPT35	Others	n.a.		Solubility	=	1000000.0	nM	PMID[561901]
NPT35	Others	n.a.		Solubility	=	2000000.0	nM	PMID[561901]
NPT35	Others	n.a.		Solubility	=	4200000.0	nM	PMID[561901]
NPT35	Others	n.a.		LogP	=	1.6	n.a.	PMID[561901]
NPT35	Others	n.a.		LogP	=	1.1	n.a.	PMID[561901]
NPT35	Others	n.a.		LogP	=	0.9	n.a.	PMID[561901]
NPT35	Others	n.a.		LogP	=	-0.02	n.a.	PMID[561901]
NPT35	Others	n.a.		LogD	=	4.6	n.a.	PMID[561901]
NPT35	Others	n.a.		LogD	=	2.5	n.a.	PMID[561901]
NPT35	Others	n.a.		LogD	=	1.4	n.a.	PMID[561901]
NPT35	Others	n.a.		LogD	=	0.01	n.a.	PMID[561901]
NPT35	Others	n.a.		pKa	=	5.0	n.a.	PMID[561901]
NPT35	Others	n.a.		EC50	=	87000.0	nM	PMID[561902]

☑ 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 NPC306669 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	495
0.1-0.2	3272
0.2-0.3	12427
0.3-0.4	4325
0.4-0.5	14607
0.5-0.6	5597
0.6-0.7	1689
0.7-0.8	233
0.8-0.85	44
0.85-0.9	4
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.962	High Similarity	NPC4669
0.9477	High Similarity	NPC57512
0.9281	High Similarity	NPC476580
0.9108	High Similarity	NPC106786
0.8938	High Similarity	NPC59567
0.882	High Similarity	NPC476569
0.8679	High Similarity	NPC93593
0.8662	High Similarity	NPC223125
0.8608	High Similarity	NPC476579
0.8553	High Similarity	NPC223124
0.8421	Intermediate Similarity	NPC7018
0.8324	Intermediate Similarity	NPC116007
0.8302	Intermediate Similarity	NPC475959
0.8218	Intermediate Similarity	NPC83511
0.821	Intermediate Similarity	NPC233029
0.821	Intermediate Similarity	NPC210148
0.8204	Intermediate Similarity	NPC231198
0.8148	Intermediate Similarity	NPC8337
0.8148	Intermediate Similarity	NPC85747
0.811	Intermediate Similarity	NPC41178
0.811	Intermediate Similarity	NPC138487
0.811	Intermediate Similarity	NPC216459
0.8098	Intermediate Similarity	NPC148898
0.8061	Intermediate Similarity	NPC146288
0.8012	Intermediate Similarity	NPC474708
0.8	Intermediate Similarity	NPC78733
0.7964	Intermediate Similarity	NPC111485
0.7953	Intermediate Similarity	NPC86469
0.7953	Intermediate Similarity	NPC475845
0.7952	Intermediate Similarity	NPC234392
0.7952	Intermediate Similarity	NPC31311
0.7931	Intermediate Similarity	NPC5167
0.7908	Intermediate Similarity	NPC160193
0.7895	Intermediate Similarity	NPC471604
0.7895	Intermediate Similarity	NPC57812
0.7895	Intermediate Similarity	NPC474324
0.7875	Intermediate Similarity	NPC128019
0.7875	Intermediate Similarity	NPC136860
0.7875	Intermediate Similarity	NPC476567
0.787	Intermediate Similarity	NPC24954
0.7862	Intermediate Similarity	NPC188163
0.7862	Intermediate Similarity	NPC213206
0.7862	Intermediate Similarity	NPC328750
0.7862	Intermediate Similarity	NPC474915
0.7861	Intermediate Similarity	NPC67978
0.7861	Intermediate Similarity	NPC303581
0.7857	Intermediate Similarity	NPC118804
0.7857	Intermediate Similarity	NPC477080
0.7853	Intermediate Similarity	NPC37144
0.7853	Intermediate Similarity	NPC59907
0.7841	Intermediate Similarity	NPC27887
0.7811	Intermediate Similarity	NPC232924
0.7811	Intermediate Similarity	NPC306902
0.7811	Intermediate Similarity	NPC160298
0.7811	Intermediate Similarity	NPC477559
0.7811	Intermediate Similarity	NPC266753
0.7811	Intermediate Similarity	NPC226428
0.7799	Intermediate Similarity	NPC314682
0.7785	Intermediate Similarity	NPC252107
0.7778	Intermediate Similarity	NPC247972
0.7778	Intermediate Similarity	NPC16805
0.7778	Intermediate Similarity	NPC130926
0.7778	Intermediate Similarity	NPC302527
0.7778	Intermediate Similarity	NPC167546
0.7778	Intermediate Similarity	NPC238530
0.7778	Intermediate Similarity	NPC276944
0.7778	Intermediate Similarity	NPC232514
0.7771	Intermediate Similarity	NPC308267
0.7746	Intermediate Similarity	NPC241055
0.774	Intermediate Similarity	NPC474745
0.774	Intermediate Similarity	NPC149285
0.7733	Intermediate Similarity	NPC24264
0.7733	Intermediate Similarity	NPC476432
0.7727	Intermediate Similarity	NPC85613
0.7722	Intermediate Similarity	NPC169387
0.7722	Intermediate Similarity	NPC99078
0.7722	Intermediate Similarity	NPC416184
0.7722	Intermediate Similarity	NPC477259
0.7711	Intermediate Similarity	NPC119669
0.7711	Intermediate Similarity	NPC476568
0.7706	Intermediate Similarity	NPC97072
0.7706	Intermediate Similarity	NPC215829
0.7697	Intermediate Similarity	NPC470088
0.7692	Intermediate Similarity	NPC63152
0.7688	Intermediate Similarity	NPC100566
0.7688	Intermediate Similarity	NPC247389
0.7688	Intermediate Similarity	NPC210918
0.7684	Intermediate Similarity	NPC474325
0.7683	Intermediate Similarity	NPC16107
0.7683	Intermediate Similarity	NPC210437
0.7683	Intermediate Similarity	NPC476144
0.7683	Intermediate Similarity	NPC106295
0.7683	Intermediate Similarity	NPC51957
0.7679	Intermediate Similarity	NPC76079
0.7674	Intermediate Similarity	NPC255607
0.7674	Intermediate Similarity	NPC168409
0.7674	Intermediate Similarity	NPC225774
0.7674	Intermediate Similarity	NPC3375
0.7673	Intermediate Similarity	NPC470707
0.7673	Intermediate Similarity	NPC220923
0.767	Intermediate Similarity	NPC304675
0.7658	Intermediate Similarity	NPC136330
0.7658	Intermediate Similarity	NPC196609
0.7658	Intermediate Similarity	NPC205178
0.7658	Intermediate Similarity	NPC230698
0.7658	Intermediate Similarity	NPC251454
0.7658	Intermediate Similarity	NPC277042
0.7658	Intermediate Similarity	NPC73883
0.7658	Intermediate Similarity	NPC255817
0.7654	Intermediate Similarity	NPC102760
0.7644	Intermediate Similarity	NPC266176
0.7644	Intermediate Similarity	NPC82533
0.7644	Intermediate Similarity	NPC158148
0.7644	Intermediate Similarity	NPC290759
0.7643	Intermediate Similarity	NPC160692
0.7636	Intermediate Similarity	NPC130941
0.7636	Intermediate Similarity	NPC7467
0.763	Intermediate Similarity	NPC219341
0.7627	Intermediate Similarity	NPC474470
0.7627	Intermediate Similarity	NPC287588
0.7627	Intermediate Similarity	NPC237044
0.7616	Intermediate Similarity	NPC320104
0.7611	Intermediate Similarity	NPC474746
0.7611	Intermediate Similarity	NPC475981
0.761	Intermediate Similarity	NPC131204
0.761	Intermediate Similarity	NPC301050
0.76	Intermediate Similarity	NPC75958
0.7595	Intermediate Similarity	NPC167096
0.759	Intermediate Similarity	NPC219162
0.7586	Intermediate Similarity	NPC190332
0.7586	Intermediate Similarity	NPC298979
0.7586	Intermediate Similarity	NPC181653
0.7584	Intermediate Similarity	NPC121400
0.7581	Intermediate Similarity	NPC71124
0.7572	Intermediate Similarity	NPC39103
0.7572	Intermediate Similarity	NPC2770
0.7564	Intermediate Similarity	NPC200555
0.7564	Intermediate Similarity	NPC196026
0.7562	Intermediate Similarity	NPC253429
0.7561	Intermediate Similarity	NPC185838
0.7561	Intermediate Similarity	NPC469978
0.7557	Intermediate Similarity	NPC225597
0.7557	Intermediate Similarity	NPC470739
0.7557	Intermediate Similarity	NPC19520
0.7557	Intermediate Similarity	NPC477640
0.7557	Intermediate Similarity	NPC149090
0.7554	Intermediate Similarity	NPC254957
0.7547	Intermediate Similarity	NPC11147
0.7545	Intermediate Similarity	NPC192768
0.7545	Intermediate Similarity	NPC274026
0.7545	Intermediate Similarity	NPC151895
0.7545	Intermediate Similarity	NPC97221
0.7545	Intermediate Similarity	NPC220858
0.7545	Intermediate Similarity	NPC88249
0.7543	Intermediate Similarity	NPC475686
0.7543	Intermediate Similarity	NPC470324
0.7543	Intermediate Similarity	NPC58766
0.754	Intermediate Similarity	NPC5374
0.753	Intermediate Similarity	NPC135538
0.753	Intermediate Similarity	NPC428
0.753	Intermediate Similarity	NPC24233
0.753	Intermediate Similarity	NPC147390
0.753	Intermediate Similarity	NPC246587
0.753	Intermediate Similarity	NPC476571
0.7529	Intermediate Similarity	NPC304659
0.7529	Intermediate Similarity	NPC86144
0.7527	Intermediate Similarity	NPC230098
0.7514	Intermediate Similarity	NPC2314
0.7514	Intermediate Similarity	NPC189470
0.75	Intermediate Similarity	NPC475780
0.75	Intermediate Similarity	NPC6152
0.75	Intermediate Similarity	NPC179704
0.75	Intermediate Similarity	NPC474475
0.75	Intermediate Similarity	NPC226708
0.7487	Intermediate Similarity	NPC23080
0.7487	Intermediate Similarity	NPC193906
0.7486	Intermediate Similarity	NPC284842
0.7474	Intermediate Similarity	NPC207971
0.7473	Intermediate Similarity	NPC477258
0.7472	Intermediate Similarity	NPC229166
0.7472	Intermediate Similarity	NPC199465
0.7472	Intermediate Similarity	NPC128560
0.7472	Intermediate Similarity	NPC49353
0.7471	Intermediate Similarity	NPC169742
0.747	Intermediate Similarity	NPC179825
0.747	Intermediate Similarity	NPC95075
0.747	Intermediate Similarity	NPC191376
0.747	Intermediate Similarity	NPC90844
0.747	Intermediate Similarity	NPC253883
0.747	Intermediate Similarity	NPC321505
0.747	Intermediate Similarity	NPC476151
0.7459	Intermediate Similarity	NPC249405
0.7458	Intermediate Similarity	NPC65403
0.7457	Intermediate Similarity	NPC153631
0.7456	Intermediate Similarity	NPC133011
0.7456	Intermediate Similarity	NPC82285
0.7453	Intermediate Similarity	NPC225745
0.7442	Intermediate Similarity	NPC216816
0.7438	Intermediate Similarity	NPC180647
0.7436	Intermediate Similarity	NPC172403

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 NPC306669 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	290
0.1-0.2	715
0.2-0.3	956
0.3-0.4	1475
0.4-0.5	2833
0.5-0.6	2138
0.6-0.7	681
0.7-0.8	57
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7914	Intermediate Similarity	NPD3639	Approved
0.7914	Intermediate Similarity	NPD3640	Phase 3
0.7914	Intermediate Similarity	NPD3641	Approved
0.7872	Intermediate Similarity	NPD4859	Phase 1
0.7862	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6031	Approved
0.7697	Intermediate Similarity	NPD6030	Approved
0.7683	Intermediate Similarity	NPD4584	Approved
0.7658	Intermediate Similarity	NPD2492	Phase 1
0.7588	Intermediate Similarity	NPD5977	Approved
0.7588	Intermediate Similarity	NPD5978	Approved
0.7543	Intermediate Similarity	NPD2898	Approved
0.75	Intermediate Similarity	NPD5457	Discontinued
0.7471	Intermediate Similarity	NPD6107	Approved
0.7455	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD4166	Phase 2
0.7394	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7298	Approved
0.7342	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD4420	Approved
0.7294	Intermediate Similarity	NPD4017	Approved
0.725	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5312	Approved
0.7222	Intermediate Similarity	NPD5313	Approved
0.7209	Intermediate Similarity	NPD4772	Phase 2
0.7209	Intermediate Similarity	NPD4773	Phase 2
0.7204	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5718	Phase 2
0.7182	Intermediate Similarity	NPD3885	Approved
0.7174	Intermediate Similarity	NPD6618	Phase 2
0.7151	Intermediate Similarity	NPD4481	Phase 3
0.7151	Intermediate Similarity	NPD7291	Discontinued
0.7151	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD5006	Approved
0.715	Intermediate Similarity	NPD5005	Approved
0.7143	Intermediate Similarity	NPD6297	Approved
0.712	Intermediate Similarity	NPD7281	Phase 3
0.712	Intermediate Similarity	NPD7280	Phase 3
0.712	Intermediate Similarity	NPD2971	Approved
0.712	Intermediate Similarity	NPD2968	Approved
0.712	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7110	Phase 1
0.7047	Intermediate Similarity	NPD4107	Approved
0.7039	Intermediate Similarity	NPD6071	Discontinued
0.703	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD4585	Approved
0.7022	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1307	Phase 2
0.7006	Intermediate Similarity	NPD1309	Phase 2
0.6989	Remote Similarity	NPD6853	Approved
0.6989	Remote Similarity	NPD2563	Approved
0.6989	Remote Similarity	NPD2560	Approved
0.6989	Remote Similarity	NPD6851	Approved
0.6983	Remote Similarity	NPD7802	Discontinued
0.6977	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4010	Discontinued
0.6923	Remote Similarity	NPD4482	Phase 3
0.6914	Remote Similarity	NPD6386	Approved
0.6914	Remote Similarity	NPD6385	Approved
0.691	Remote Similarity	NPD7833	Phase 2
0.691	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.691	Remote Similarity	NPD7831	Phase 2
0.6901	Remote Similarity	NPD3124	Discontinued
0.6897	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD824	Approved
0.6895	Remote Similarity	NPD2488	Approved
0.6895	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD2490	Approved
0.6885	Remote Similarity	NPD8252	Approved
0.6885	Remote Similarity	NPD8251	Approved
0.6885	Remote Similarity	NPD8099	Discontinued
0.6882	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5241	Discontinued
0.6878	Remote Similarity	NPD3349	Phase 2
0.6869	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6896	Approved
0.6867	Remote Similarity	NPD6895	Approved
0.6859	Remote Similarity	NPD7296	Approved
0.6857	Remote Similarity	NPD6876	Approved
0.6857	Remote Similarity	NPD6875	Approved
0.6854	Remote Similarity	NPD6788	Approved
0.6848	Remote Similarity	NPD8156	Discontinued
0.6839	Remote Similarity	NPD5582	Discontinued
0.6836	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7225	Discontinued
0.6821	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5089	Approved
0.6818	Remote Similarity	NPD5090	Approved
0.6818	Remote Similarity	NPD6873	Phase 2
0.6816	Remote Similarity	NPD5604	Discontinued
0.6813	Remote Similarity	NPD2970	Approved
0.6813	Remote Similarity	NPD2969	Approved
0.6807	Remote Similarity	NPD2653	Approved
0.6804	Remote Similarity	NPD2975	Approved
0.6804	Remote Similarity	NPD2973	Approved
0.6804	Remote Similarity	NPD5564	Approved
0.6804	Remote Similarity	NPD2974	Approved
0.6802	Remote Similarity	NPD3057	Approved
0.6802	Remote Similarity	NPD5297	Approved
0.6788	Remote Similarity	NPD6493	Phase 3
0.6782	Remote Similarity	NPD4727	Phase 1
0.6782	Remote Similarity	NPD683	Approved
0.6776	Remote Similarity	NPD2489	Approved
0.6776	Remote Similarity	NPD27	Approved
0.6774	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD5071	Phase 2
0.6763	Remote Similarity	NPD1424	Approved
0.6758	Remote Similarity	NPD3051	Approved
0.6753	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD3816	Phase 1
0.6749	Remote Similarity	NPD3815	Phase 1
0.6742	Remote Similarity	NPD2977	Approved
0.6742	Remote Similarity	NPD2978	Approved
0.674	Remote Similarity	NPD5677	Discontinued
0.6732	Remote Similarity	NPD8149	Discontinued
0.673	Remote Similarity	NPD3705	Approved
0.6725	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD6687	Approved
0.6721	Remote Similarity	NPD5242	Approved
0.6721	Remote Similarity	NPD6688	Approved
0.672	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD2972	Approved
0.6717	Remote Similarity	NPD3533	Approved
0.6705	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD2358	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD4580	Approved
0.6701	Remote Similarity	NPD6612	Phase 2
0.6687	Remote Similarity	NPD3109	Approved
0.6687	Remote Similarity	NPD3110	Approved
0.6686	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD1670	Discontinued
0.6685	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD5087	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD4917	Discontinued
0.6667	Remote Similarity	NPD3452	Approved
0.6667	Remote Similarity	NPD743	Approved
0.6667	Remote Similarity	NPD2494	Approved
0.6667	Remote Similarity	NPD2493	Approved
0.6667	Remote Similarity	NPD2335	Discontinued
0.6667	Remote Similarity	NPD3450	Approved
0.6649	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD4210	Discontinued
0.6647	Remote Similarity	NPD3656	Approved
0.6633	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD3448	Approved
0.6633	Remote Similarity	NPD2491	Approved
0.6632	Remote Similarity	NPD7668	Phase 2
0.6632	Remote Similarity	NPD8053	Approved
0.6632	Remote Similarity	NPD8054	Approved
0.6631	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD2674	Phase 3
0.6624	Remote Similarity	NPD5536	Phase 2
0.6615	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD3924	Approved
0.6598	Remote Similarity	NPD3921	Approved
0.6598	Remote Similarity	NPD3923	Approved
0.6598	Remote Similarity	NPD3922	Approved
0.6596	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD3140	Approved
0.6587	Remote Similarity	NPD3142	Approved
0.658	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.658	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD7028	Phase 2
0.6571	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.657	Remote Similarity	NPD4237	Approved
0.657	Remote Similarity	NPD4236	Phase 3
0.6569	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD4583	Approved
0.6567	Remote Similarity	NPD4582	Approved
0.6559	Remote Similarity	NPD6720	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD2120	Phase 2
0.6552	Remote Similarity	NPD7124	Phase 2
0.6552	Remote Similarity	NPD5950	Discontinued
0.6548	Remote Similarity	NPD7034	Discontinued
0.6543	Remote Similarity	NPD1421	Approved
0.6543	Remote Similarity	NPD1420	Approved
0.6543	Remote Similarity	NPD3920	Phase 2
0.6541	Remote Similarity	NPD2388	Discontinued
0.6538	Remote Similarity	NPD5980	Discovery
0.6537	Remote Similarity	NPD5676	Approved
0.6533	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD7669	Phase 3
0.6527	Remote Similarity	NPD4474	Approved
0.6527	Remote Similarity	NPD4475	Approved
0.6522	Remote Similarity	NPD2821	Approved
0.652	Remote Similarity	NPD3592	Approved
0.652	Remote Similarity	NPD3591	Approved
0.6519	Remote Similarity	NPD5616	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