NPASS Compound

Structure

CID80370 OpenBabel06191715422D 21 23 0 0 0 0 0 0 0 0999 V2000 3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 21 1 0 0 0 0 3 4 2 0 0 0 0 3 8 1 0 0 0 0 4 10 1 0 0 0 0 5 8 2 0 0 0 0 5 9 1 0 0 0 0 6 9 2 0 0 0 0 6 12 1 0 0 0 0 7 11 1 0 0 0 0 7 13 2 0 0 0 0 8 14 1 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 10 15 2 0 0 0 0 11 17 2 0 0 0 0 12 14 2 0 0 0 0 12 18 1 0 0 0 0 13 16 1 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 19 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	284.07
Volume:	282.482
LogP:	2.917
LogD:	2.56
LogS:	-4.644
# Rotatable Bonds:	2
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.917
Synthetic Accessibility Score:	2.528
Fsp3:	0.125
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.946
MDCK Permeability:	3.197147452738136e-05
Pgp-inhibitor:	0.037
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.916

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.056
Plasma Protein Binding (PPB):	95.06877899169922%
Volume Distribution (VD):	0.511
Pgp-substrate:	3.548901081085205%

ADMET: Metabolism

CYP1A2-inhibitor:	0.985
CYP1A2-substrate:	0.873
CYP2C19-inhibitor:	0.869
CYP2C19-substrate:	0.1
CYP2C9-inhibitor:	0.753
CYP2C9-substrate:	0.88
CYP2D6-inhibitor:	0.77
CYP2D6-substrate:	0.583
CYP3A4-inhibitor:	0.823
CYP3A4-substrate:	0.151

ADMET: Excretion

Clearance (CL):	7.495
Half-life (T1/2):	0.424

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.808
Drug-inuced Liver Injury (DILI):	0.831
AMES Toxicity:	0.834
Rat Oral Acute Toxicity:	0.888
Maximum Recommended Daily Dose:	0.932
Skin Sensitization:	0.896
Carcinogencity:	0.896
Eye Corrosion:	0.029
Eye Irritation:	0.948
Respiratory Toxicity:	0.722

Download Data

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

Natural Product: NPC80370

Natural Product ID:	NPC80370
*Common Name:**	Denbinobin
IUPAC Name:	5-hydroxy-3,7-dimethoxyphenanthrene-1,4-dione
Synonyms:	Denbinobin
Standard InCHIKey:	KYOONHCJRPIMJE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H12O5/c1-20-9-5-8-3-4-10-11(17)7-13(21-2)16(19)15(10)14(8)12(18)6-9/h3-7,18H,1-2H3
SMILES:	COc1cc2ccc3C(=O)C=C(C(=O)c3c2c(c1)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL400925
PubChem CID:	10423984
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0003007] Phenanthrols

*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
NPO2022	Ephemerantha lonchophylla	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10514302]
NPO12523	Dendrobium moniliforme	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520233]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575955]
NPO12523	Dendrobium moniliforme	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932145]
NPO8966	Callophycus serratus	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16268553]
NPO8966	Callophycus serratus	Species	Solieriaceae	Eukaryota	n.a.	Fijian red alga	n.a.	PMID[16724831]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	stems	Yunnan Province, China	2004	PMID[17253844]
NPO8966	Callophycus serratus	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17715978]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	Stems	purchased from Kyoungdong Oriental Herbal Market, Seoul, Korea	2006-APR	PMID[18052323]
NPO2188	Dendrobium candidum	Species	Orchidaceae	Eukaryota	n.a.	stem	n.a.	PMID[19182417]
NPO8966	Callophycus serratus	Species	Solieriaceae	Eukaryota	n.a.	Fijian red alga	n.a.	PMID[20141173]
NPO23332	Dendrobium fimbriatum	Species	Orchidaceae	Eukaryota	stems	n.a.	n.a.	PMID[25316316]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	Stems	n.a.	n.a.	PMID[27310249]
NPO8966	Callophycus serratus	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30407005]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31291099]
NPO2022	Ephemerantha lonchophylla	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9461658]
NPO5019	Mespilus germanica	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO20900	Dendrobium chrysotoxum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12523	Dendrobium moniliforme	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5019	Mespilus germanica	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO12523	Dendrobium moniliforme	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20900	Dendrobium chrysotoxum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11889	Dendrobium chrysanthum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18039	Herba dendrobii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11242	Gynochthodes parvifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2188	Dendrobium candidum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20900	Dendrobium chrysotoxum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11889	Dendrobium chrysanthum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23332	Dendrobium fimbriatum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20900	Dendrobium chrysotoxum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5019	Mespilus germanica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1575	Mikania luetzelburgii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11889	Dendrobium chrysanthum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8966	Callophycus serratus	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2022	Ephemerantha lonchophylla	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO13053	Corydalis conspersa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO326	Pittosporum brevicalyx	Species	Pittosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6178	Solanum euacanthum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15662	Ligustrum ovalifolium	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11242	Gynochthodes parvifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2188	Dendrobium candidum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12523	Dendrobium moniliforme	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4581	Ungernia victoris	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23332	Dendrobium fimbriatum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15280	Sideritis grandiflora	Species	Lamiaceae	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	1
IC50	1
Others	10

Activity Type	# Activity
Cell Line	10
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	40.4	%	PMID[537061]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	62.0	%	PMID[537061]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	43.0	%	PMID[537061]
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	70.0	%	PMID[537061]
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	44.0	%	PMID[537061]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	>	10.0	%	PMID[537061]
NPT848	Cell Line	N9	Homo sapiens	Activity	>	10.0	%	PMID[537061]
NPT1136	Cell Line	mast cells	Mus musculus	Inhibition	=	29.1	%	PMID[537061]
NPT1136	Cell Line	mast cells	Mus musculus	Inhibition	=	17.6	%	PMID[537061]
NPT91	Cell Line	KB	Homo sapiens	EC50	=	1.3	ug.mL-1	PMID[537063]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	15200.0	nM	PMID[537060]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.4	%	PMID[537062]

☑ 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 NPC80370 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	410
0.1-0.2	1781
0.2-0.3	4067
0.3-0.4	10587
0.4-0.5	7580
0.5-0.6	3627
0.6-0.7	5736
0.7-0.8	6322
0.8-0.85	2193
0.85-0.9	342
0.9-0.95	49
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9861	High Similarity	NPC230848
0.9467	High Similarity	NPC104876
0.9467	High Similarity	NPC245891
0.9384	High Similarity	NPC472841
0.9315	High Similarity	NPC312929
0.9315	High Similarity	NPC56433
0.9315	High Similarity	NPC245584
0.9315	High Similarity	NPC190648
0.9315	High Similarity	NPC118027
0.9315	High Similarity	NPC126767
0.9315	High Similarity	NPC289042
0.931	High Similarity	NPC28632
0.9257	High Similarity	NPC290954
0.9257	High Similarity	NPC255641
0.9195	High Similarity	NPC474414
0.9145	High Similarity	NPC474637
0.9139	High Similarity	NPC66508
0.9139	High Similarity	NPC226656
0.9128	High Similarity	NPC294646
0.9128	High Similarity	NPC470568
0.9128	High Similarity	NPC147735
0.911	High Similarity	NPC19896
0.9103	High Similarity	NPC182255
0.9103	High Similarity	NPC201297
0.9103	High Similarity	NPC94076
0.9073	High Similarity	NPC208806
0.9067	High Similarity	NPC470569
0.906	High Similarity	NPC329933
0.9054	High Similarity	NPC34802
0.9041	High Similarity	NPC84266
0.902	High Similarity	NPC201127
0.9007	High Similarity	NPC154683
0.9007	High Similarity	NPC40356
0.8993	High Similarity	NPC256672
0.8993	High Similarity	NPC27221
0.8993	High Similarity	NPC7025
0.898	High Similarity	NPC475201
0.898	High Similarity	NPC21599
0.898	High Similarity	NPC193703
0.8973	High Similarity	NPC49108
0.8973	High Similarity	NPC103752
0.8961	High Similarity	NPC324736
0.8947	High Similarity	NPC107109
0.894	High Similarity	NPC78505
0.894	High Similarity	NPC258249
0.8933	High Similarity	NPC158338
0.8933	High Similarity	NPC97028
0.8933	High Similarity	NPC100985
0.8933	High Similarity	NPC97029
0.8933	High Similarity	NPC65589
0.8933	High Similarity	NPC288036
0.8926	High Similarity	NPC7943
0.8926	High Similarity	NPC123202
0.8926	High Similarity	NPC22005
0.8919	High Similarity	NPC49282
0.8912	High Similarity	NPC167663
0.8904	High Similarity	NPC110810
0.8896	High Similarity	NPC178976
0.8889	High Similarity	NPC24394
0.8867	High Similarity	NPC172329
0.8867	High Similarity	NPC2569
0.8859	High Similarity	NPC163846
0.8859	High Similarity	NPC225173
0.8851	High Similarity	NPC48762
0.8844	High Similarity	NPC18714
0.8844	High Similarity	NPC232021
0.8844	High Similarity	NPC40118
0.8844	High Similarity	NPC126534
0.8839	High Similarity	NPC228654
0.8836	High Similarity	NPC472366
0.8831	High Similarity	NPC5379
0.8831	High Similarity	NPC14561
0.8831	High Similarity	NPC77807
0.8828	High Similarity	NPC23870
0.8824	High Similarity	NPC329844
0.8824	High Similarity	NPC169990
0.8824	High Similarity	NPC210942
0.8824	High Similarity	NPC214632
0.8816	High Similarity	NPC72958
0.8816	High Similarity	NPC474417
0.8816	High Similarity	NPC189773
0.8816	High Similarity	NPC232645
0.8816	High Similarity	NPC149526
0.8811	High Similarity	NPC27643
0.8808	High Similarity	NPC65775
0.8808	High Similarity	NPC10027
0.88	High Similarity	NPC58373
0.88	High Similarity	NPC125801
0.8797	High Similarity	NPC316262
0.8797	High Similarity	NPC314653
0.8792	High Similarity	NPC34482
0.8784	High Similarity	NPC297600
0.8782	High Similarity	NPC470342
0.8782	High Similarity	NPC472060
0.8782	High Similarity	NPC313368
0.8782	High Similarity	NPC472052
0.8776	High Similarity	NPC265178
0.8776	High Similarity	NPC101366
0.8774	High Similarity	NPC96342
0.8774	High Similarity	NPC199463
0.8774	High Similarity	NPC263483
0.8774	High Similarity	NPC212967
0.8774	High Similarity	NPC164110
0.8774	High Similarity	NPC246647
0.8774	High Similarity	NPC37543
0.8767	High Similarity	NPC1268
0.8767	High Similarity	NPC470407
0.8759	High Similarity	NPC290601
0.8758	High Similarity	NPC87708
0.8758	High Similarity	NPC175978
0.875	High Similarity	NPC13282
0.875	High Similarity	NPC325983
0.875	High Similarity	NPC202595
0.875	High Similarity	NPC22644
0.8742	High Similarity	NPC472056
0.8733	High Similarity	NPC470570
0.8726	High Similarity	NPC311740
0.8726	High Similarity	NPC219686
0.8725	High Similarity	NPC105213
0.8716	High Similarity	NPC26051
0.8716	High Similarity	NPC52789
0.8716	High Similarity	NPC268204
0.8716	High Similarity	NPC55832
0.871	High Similarity	NPC180924
0.8707	High Similarity	NPC109232
0.8707	High Similarity	NPC477956
0.8707	High Similarity	NPC49242
0.8707	High Similarity	NPC295384
0.8701	High Similarity	NPC93552
0.8699	High Similarity	NPC472419
0.8693	High Similarity	NPC46882
0.8693	High Similarity	NPC478148
0.8693	High Similarity	NPC132990
0.8684	High Similarity	NPC269420
0.8675	High Similarity	NPC259632
0.8675	High Similarity	NPC77598
0.8671	High Similarity	NPC164236
0.8671	High Similarity	NPC128348
0.8671	High Similarity	NPC66384
0.8671	High Similarity	NPC309717
0.8671	High Similarity	NPC189106
0.8671	High Similarity	NPC112192
0.8667	High Similarity	NPC478019
0.8667	High Similarity	NPC476055
0.8662	High Similarity	NPC84571
0.8662	High Similarity	NPC27659
0.8662	High Similarity	NPC247779
0.8662	High Similarity	NPC284495
0.8658	High Similarity	NPC310340
0.8658	High Similarity	NPC3732
0.8649	High Similarity	NPC48624
0.8649	High Similarity	NPC172250
0.8649	High Similarity	NPC253822
0.8649	High Similarity	NPC259166
0.8649	High Similarity	NPC144118
0.8649	High Similarity	NPC80962
0.8649	High Similarity	NPC326109
0.8649	High Similarity	NPC11056
0.8649	High Similarity	NPC213659
0.8649	High Similarity	NPC215311
0.8649	High Similarity	NPC219917
0.8649	High Similarity	NPC204985
0.8645	High Similarity	NPC148938
0.8639	High Similarity	NPC242994
0.8639	High Similarity	NPC278323
0.8639	High Similarity	NPC472368
0.8639	High Similarity	NPC25427
0.8639	High Similarity	NPC55162
0.8639	High Similarity	NPC12175
0.8639	High Similarity	NPC138099
0.8639	High Similarity	NPC90665
0.8639	High Similarity	NPC309154
0.8639	High Similarity	NPC279668
0.8639	High Similarity	NPC21350
0.8636	High Similarity	NPC312338
0.8636	High Similarity	NPC28103
0.8636	High Similarity	NPC149889
0.8636	High Similarity	NPC470340
0.863	High Similarity	NPC12165
0.863	High Similarity	NPC274109
0.863	High Similarity	NPC66349
0.863	High Similarity	NPC471905
0.863	High Similarity	NPC25287
0.863	High Similarity	NPC476333
0.863	High Similarity	NPC477242
0.863	High Similarity	NPC477243
0.863	High Similarity	NPC150399
0.863	High Similarity	NPC473391
0.863	High Similarity	NPC472364
0.863	High Similarity	NPC168105
0.863	High Similarity	NPC186838
0.863	High Similarity	NPC477244
0.863	High Similarity	NPC1486
0.863	High Similarity	NPC249606
0.863	High Similarity	NPC186647
0.863	High Similarity	NPC53206
0.863	High Similarity	NPC53414
0.863	High Similarity	NPC98115
0.863	High Similarity	NPC472367
0.863	High Similarity	NPC41461

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 NPC80370 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	384
0.1-0.2	1020
0.2-0.3	1478
0.3-0.4	2646
0.4-0.5	1908
0.5-0.6	1095
0.6-0.7	423
0.7-0.8	167
0.8-0.85	25
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8562	High Similarity	NPD1509	Clinical (unspecified phase)
0.8553	High Similarity	NPD6232	Discontinued
0.8552	High Similarity	NPD1607	Approved
0.8543	High Similarity	NPD4378	Clinical (unspecified phase)
0.8509	High Similarity	NPD7473	Discontinued
0.8435	Intermediate Similarity	NPD1510	Phase 2
0.8414	Intermediate Similarity	NPD1240	Approved
0.84	Intermediate Similarity	NPD3750	Approved
0.8344	Intermediate Similarity	NPD7819	Suspended
0.8261	Intermediate Similarity	NPD6959	Discontinued
0.8187	Intermediate Similarity	NPD7075	Discontinued
0.8182	Intermediate Similarity	NPD2532	Approved
0.8182	Intermediate Similarity	NPD2534	Approved
0.8182	Intermediate Similarity	NPD2533	Approved
0.8146	Intermediate Similarity	NPD1549	Phase 2
0.8146	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD3882	Suspended
0.8113	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD3226	Approved
0.8079	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD5844	Phase 1
0.8067	Intermediate Similarity	NPD3748	Approved
0.8065	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD6599	Discontinued
0.8038	Intermediate Similarity	NPD4380	Phase 2
0.8013	Intermediate Similarity	NPD1512	Approved
0.8	Intermediate Similarity	NPD7390	Discontinued
0.7963	Intermediate Similarity	NPD3749	Approved
0.795	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD1934	Approved
0.7937	Intermediate Similarity	NPD6801	Discontinued
0.7895	Intermediate Similarity	NPD6099	Approved
0.7895	Intermediate Similarity	NPD6100	Approved
0.7895	Intermediate Similarity	NPD2796	Approved
0.7895	Intermediate Similarity	NPD2935	Discontinued
0.7888	Intermediate Similarity	NPD2801	Approved
0.7885	Intermediate Similarity	NPD1511	Approved
0.7885	Intermediate Similarity	NPD6799	Approved
0.7875	Intermediate Similarity	NPD7411	Suspended
0.7857	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD2800	Approved
0.7843	Intermediate Similarity	NPD2346	Discontinued
0.7838	Intermediate Similarity	NPD4625	Phase 3
0.7829	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD1470	Approved
0.7806	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD7003	Approved
0.7791	Intermediate Similarity	NPD7768	Phase 2
0.7784	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1465	Phase 2
0.774	Intermediate Similarity	NPD1283	Approved
0.773	Intermediate Similarity	NPD3817	Phase 2
0.7727	Intermediate Similarity	NPD2344	Approved
0.7697	Intermediate Similarity	NPD6651	Approved
0.7692	Intermediate Similarity	NPD3751	Discontinued
0.7692	Intermediate Similarity	NPD1651	Approved
0.7692	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD943	Approved
0.7679	Intermediate Similarity	NPD6166	Phase 2
0.7679	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD5406	Approved
0.7662	Intermediate Similarity	NPD5404	Approved
0.7662	Intermediate Similarity	NPD5408	Approved
0.7662	Intermediate Similarity	NPD1551	Phase 2
0.7662	Intermediate Similarity	NPD5405	Approved
0.7651	Intermediate Similarity	NPD5494	Approved
0.7647	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3926	Phase 2
0.7616	Intermediate Similarity	NPD6559	Discontinued
0.7613	Intermediate Similarity	NPD1471	Phase 3
0.7605	Intermediate Similarity	NPD1247	Approved
0.7603	Intermediate Similarity	NPD3972	Approved
0.7597	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD919	Approved
0.758	Intermediate Similarity	NPD4628	Phase 3
0.756	Intermediate Similarity	NPD5711	Approved
0.756	Intermediate Similarity	NPD5710	Approved
0.755	Intermediate Similarity	NPD3764	Approved
0.755	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD1281	Approved
0.7534	Intermediate Similarity	NPD1201	Approved
0.7532	Intermediate Similarity	NPD2309	Approved
0.7531	Intermediate Similarity	NPD7458	Discontinued
0.753	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1243	Approved
0.7516	Intermediate Similarity	NPD920	Approved
0.7516	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD5402	Approved
0.75	Intermediate Similarity	NPD1876	Approved
0.7485	Intermediate Similarity	NPD3818	Discontinued
0.7484	Intermediate Similarity	NPD2799	Discontinued
0.7457	Intermediate Similarity	NPD6797	Phase 2
0.7457	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD5953	Discontinued
0.7456	Intermediate Similarity	NPD7229	Phase 3
0.7434	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD6779	Approved
0.7432	Intermediate Similarity	NPD6777	Approved
0.7432	Intermediate Similarity	NPD6780	Approved
0.7432	Intermediate Similarity	NPD6781	Approved
0.7432	Intermediate Similarity	NPD6782	Approved
0.7432	Intermediate Similarity	NPD6776	Approved
0.7432	Intermediate Similarity	NPD6778	Approved
0.7416	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD7251	Discontinued
0.741	Intermediate Similarity	NPD4288	Approved
0.7407	Intermediate Similarity	NPD5403	Approved
0.7405	Intermediate Similarity	NPD7435	Discontinued
0.7403	Intermediate Similarity	NPD230	Phase 1
0.7397	Intermediate Similarity	NPD4626	Approved
0.7394	Intermediate Similarity	NPD37	Approved
0.7391	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5401	Approved
0.7384	Intermediate Similarity	NPD7177	Discontinued
0.7375	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD4308	Phase 3
0.7371	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7808	Phase 3
0.7338	Intermediate Similarity	NPD4060	Phase 1
0.732	Intermediate Similarity	NPD2313	Discontinued
0.7315	Intermediate Similarity	NPD4749	Approved
0.7312	Intermediate Similarity	NPD7697	Approved
0.7312	Intermediate Similarity	NPD7698	Approved
0.7312	Intermediate Similarity	NPD7696	Phase 3
0.731	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD8150	Discontinued
0.7303	Intermediate Similarity	NPD4908	Phase 1
0.7299	Intermediate Similarity	NPD7074	Phase 3
0.7297	Intermediate Similarity	NPD1610	Phase 2
0.7285	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD2798	Approved
0.7278	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6234	Discontinued
0.7273	Intermediate Similarity	NPD7871	Phase 2
0.7273	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7870	Phase 2
0.7262	Intermediate Similarity	NPD4965	Approved
0.7262	Intermediate Similarity	NPD4967	Phase 2
0.7262	Intermediate Similarity	NPD4966	Approved
0.7251	Intermediate Similarity	NPD3787	Discontinued
0.7248	Intermediate Similarity	NPD1608	Approved
0.7247	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7054	Approved
0.7241	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7286	Phase 2
0.7226	Intermediate Similarity	NPD2979	Phase 3
0.7211	Intermediate Similarity	NPD8151	Discontinued
0.7208	Intermediate Similarity	NPD3268	Approved
0.7208	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD8434	Phase 2
0.72	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7472	Approved
0.7178	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD7874	Approved
0.7158	Intermediate Similarity	NPD6535	Approved
0.7158	Intermediate Similarity	NPD6534	Approved
0.7158	Intermediate Similarity	NPD7701	Phase 2
0.7152	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9545	Approved
0.7143	Intermediate Similarity	NPD1548	Phase 1
0.7135	Intermediate Similarity	NPD8312	Approved
0.7135	Intermediate Similarity	NPD8313	Approved
0.7134	Intermediate Similarity	NPD6273	Approved
0.7124	Intermediate Similarity	NPD9494	Approved
0.7117	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4307	Phase 2
0.7107	Intermediate Similarity	NPD2438	Suspended
0.7105	Intermediate Similarity	NPD1164	Approved
0.7105	Intermediate Similarity	NPD2797	Approved
0.7105	Intermediate Similarity	NPD1203	Approved
0.7099	Intermediate Similarity	NPD6190	Approved
0.7095	Intermediate Similarity	NPD5691	Approved
0.7093	Intermediate Similarity	NPD7199	Phase 2
0.7078	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD422	Phase 1
0.7047	Intermediate Similarity	NPD17	Approved
0.7047	Intermediate Similarity	NPD7801	Approved
0.7047	Intermediate Similarity	NPD2932	Approved
0.7043	Intermediate Similarity	NPD7699	Phase 2
0.7043	Intermediate Similarity	NPD7700	Phase 2
0.7033	Intermediate Similarity	NPD4287	Approved
0.7032	Intermediate Similarity	NPD3027	Phase 3
0.7024	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1613	Approved
0.7	Intermediate Similarity	NPD8320	Phase 1
0.7	Intermediate Similarity	NPD2531	Phase 2
0.7	Intermediate Similarity	NPD2296	Approved
0.7	Intermediate Similarity	NPD8319	Approved
0.6994	Remote Similarity	NPD2354	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