NPASS Compound

Structure

CID156432 OpenBabel06191715522D 32 36 0 0 1 0 0 0 0 0999 V2000 7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -1.8660 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 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 6.0622 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 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 6.9282 -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 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 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 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 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 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 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 7.7942 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 2 0 0 0 0 2 10 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 5 6 2 0 0 0 0 5 11 1 0 0 0 0 6 25 1 0 0 0 0 7 12 1 0 0 0 0 7 13 1 0 0 0 0 8 14 2 0 0 0 0 8 16 1 0 0 0 0 9 15 2 0 0 0 0 9 17 1 0 0 0 0 11 17 2 0 0 0 0 11 23 1 0 0 0 0 12 10 1 6 0 0 0 12 18 1 0 0 0 0 13 21 1 0 0 0 0 13 24 2 0 0 0 0 14 19 1 0 0 0 0 14 26 1 0 0 0 0 15 20 1 0 0 0 0 15 27 1 0 0 0 0 16 22 2 0 0 0 0 16 28 1 0 0 0 0 17 32 1 0 0 0 0 18 19 2 0 0 0 0 18 22 1 0 0 0 0 19 24 1 0 0 0 0 20 21 1 0 0 0 0 20 23 2 0 0 0 0 21 29 2 0 0 0 0 22 30 1 0 0 0 0 23 31 1 0 0 0 0 24 31 1 0 0 0 0 25 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	434.14
Volume:	433.341
LogP:	5.033
LogD:	2.891
LogS:	-4.566
# Rotatable Bonds:	1
TPSA:	117.2
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.237
Synthetic Accessibility Score:	3.741
Fsp3:	0.28
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.069
MDCK Permeability:	2.0807374312425964e-05
Pgp-inhibitor:	0.165
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.4
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.03

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	88.18463897705078%
Volume Distribution (VD):	0.854
Pgp-substrate:	12.106054306030273%

ADMET: Metabolism

CYP1A2-inhibitor:	0.571
CYP1A2-substrate:	0.622
CYP2C19-inhibitor:	0.117
CYP2C19-substrate:	0.07
CYP2C9-inhibitor:	0.746
CYP2C9-substrate:	0.658
CYP2D6-inhibitor:	0.068
CYP2D6-substrate:	0.138
CYP3A4-inhibitor:	0.085
CYP3A4-substrate:	0.062

ADMET: Excretion

Clearance (CL):	1.679
Half-life (T1/2):	0.322

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.582
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.542
Rat Oral Acute Toxicity:	0.15
Maximum Recommended Daily Dose:	0.938
Skin Sensitization:	0.856
Carcinogencity:	0.783
Eye Corrosion:	0.003
Eye Irritation:	0.299
Respiratory Toxicity:	0.314

Download Data

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

Natural Product: NPC156432

Natural Product ID:	NPC156432
*Common Name:**	Artobiloxanthone
IUPAC Name:	n.a.
Synonyms:	Artobiloxanthone
Standard InCHIKey:	ZIYAGIMFLYOZDS-GFCCVEGCSA-N
Standard InCHI:	InChI=1S/C25H22O7/c1-10(2)12-7-13-21(29)20-15(27)9-17-11(5-6-25(3,4)32-17)23(20)31-24(13)19-14(26)8-16(28)22(30)18(12)19/h5-6,8-9,12,26-28,30H,1,7H2,2-4H3/t12-/m1/s1
SMILES:	CC(=C)[C@H]1Cc2c(c3c1c(O)c(O)cc3O)oc1c(c2=O)c(O)cc2c1C=CC(O2)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1099162
PubChem CID:	46887866
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones [CHEMONTID:0003521] Pyranoxanthones

*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
NPO33150	Artocarpus communis	Species	Moraceae	Eukaryota	heartwood	n.a.	n.a.	PMID[16643064]
NPO32569	artocarpus rigida	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20384315]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[21954959]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	roots	Whitessence Srl, Viterbo, Italy	2005-OCT	PMID[21954959]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[23497864]
NPO33150	Artocarpus communis	Species	Moraceae	Eukaryota	roots	Khon Kaen, Thailand	2009-DEC	PMID[25537111]
NPO33150	Artocarpus communis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26178912]
NPO32569	artocarpus rigida	Species	Moraceae	Eukaryota	Stems	n.a.	n.a.	PMID[29227656]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	LanZhou, GanSu, China	early autumn (from August to the beginning of September	PMID[32545196]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	DingXi, GanSu, China	early autumn (from August to the beginning of September	PMID[32545196]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	60 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	10 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	70 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	20 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	80 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	30 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	90 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	Maturation	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	40 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	50 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	60 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	70 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	80 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	90 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	Maturation	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	10 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	20 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	30 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	40 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	50 days after pollination	PMID[33131958]
NPO12131	Salvia calycina	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15554	Eucalyptus amplifolia	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14309	Desmodium tortuosum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14430	Grateloupia carnosa	Species	Halymeniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7819.1	Epichloe festucae var. lolii	Varieties	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14058	Papaver pavoninum	Species	Papaveraceae	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
ED50	1
IC50	2
Others	1

Activity Type	# Activity
Cell Line	2
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	IC50	=	2300.0	nM	PMID[573890]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	10.0	nM	PMID[573890]
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	32.0	%	PMID[573891]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC50	=	3700.0	nM	PMID[573890]

☑ 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 NPC156432 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	467
0.1-0.2	1871
0.2-0.3	4225
0.3-0.4	10612
0.4-0.5	7589
0.5-0.6	3678
0.6-0.7	5224
0.7-0.8	5211
0.8-0.85	2406
0.85-0.9	1160
0.9-0.95	220
0.95-1	34

Similarity Score	Similarity Level	Natural Product ID
0.981	High Similarity	NPC476637
0.9748	High Similarity	NPC101107
0.9686	High Similarity	NPC475805
0.9679	High Similarity	NPC278427
0.9557	High Similarity	NPC207690
0.9548	High Similarity	NPC276444
0.95	High Similarity	NPC126204
0.9494	High Similarity	NPC329760
0.9487	High Similarity	NPC218871
0.9487	High Similarity	NPC476630
0.9437	High Similarity	NPC472449
0.9437	High Similarity	NPC37870
0.9434	High Similarity	NPC189473
0.9434	High Similarity	NPC23298
0.9427	High Similarity	NPC197856
0.9419	High Similarity	NPC170492
0.9375	High Similarity	NPC472450
0.9375	High Similarity	NPC239752
0.9375	High Similarity	NPC275780
0.9371	High Similarity	NPC194427
0.9371	High Similarity	NPC206605
0.9367	High Similarity	NPC476280
0.9317	High Similarity	NPC39091
0.9313	High Similarity	NPC12461
0.9308	High Similarity	NPC198829
0.9308	High Similarity	NPC259456
0.9304	High Similarity	NPC46736
0.9299	High Similarity	NPC471985
0.9299	High Similarity	NPC142339
0.9255	High Similarity	NPC303174
0.925	High Similarity	NPC25152
0.925	High Similarity	NPC229632
0.9245	High Similarity	NPC235018
0.9245	High Similarity	NPC45146
0.9245	High Similarity	NPC297212
0.9245	High Similarity	NPC139036
0.9245	High Similarity	NPC471973
0.9245	High Similarity	NPC204290
0.9245	High Similarity	NPC80375
0.9245	High Similarity	NPC119224
0.9241	High Similarity	NPC236796
0.9241	High Similarity	NPC273843
0.9241	High Similarity	NPC237418
0.9236	High Similarity	NPC166054
0.9236	High Similarity	NPC55662
0.9231	High Similarity	NPC249570
0.9226	High Similarity	NPC88804
0.9226	High Similarity	NPC3825
0.9202	High Similarity	NPC188079
0.9198	High Similarity	NPC272502
0.9198	High Similarity	NPC43319
0.9193	High Similarity	NPC152659
0.9193	High Similarity	NPC270837
0.9193	High Similarity	NPC248638
0.9193	High Similarity	NPC186686
0.9193	High Similarity	NPC146134
0.9193	High Similarity	NPC236521
0.9187	High Similarity	NPC32694
0.9187	High Similarity	NPC167678
0.9187	High Similarity	NPC61010
0.9187	High Similarity	NPC29876
0.9182	High Similarity	NPC280680
0.9182	High Similarity	NPC100123
0.9182	High Similarity	NPC469658
0.9182	High Similarity	NPC474290
0.9177	High Similarity	NPC282307
0.9177	High Similarity	NPC170026
0.9177	High Similarity	NPC475799
0.9177	High Similarity	NPC13779
0.9172	High Similarity	NPC178964
0.9172	High Similarity	NPC280530
0.9172	High Similarity	NPC95842
0.9172	High Similarity	NPC476631
0.9172	High Similarity	NPC89474
0.9167	High Similarity	NPC154345
0.9141	High Similarity	NPC476306
0.9141	High Similarity	NPC218226
0.9136	High Similarity	NPC259757
0.913	High Similarity	NPC472448
0.913	High Similarity	NPC470694
0.913	High Similarity	NPC78332
0.913	High Similarity	NPC294965
0.913	High Similarity	NPC261470
0.913	High Similarity	NPC474150
0.913	High Similarity	NPC83922
0.913	High Similarity	NPC474162
0.9125	High Similarity	NPC228785
0.9125	High Similarity	NPC476980
0.9125	High Similarity	NPC320359
0.9125	High Similarity	NPC56085
0.9125	High Similarity	NPC14353
0.9125	High Similarity	NPC200746
0.9119	High Similarity	NPC136674
0.9108	High Similarity	NPC63187
0.9108	High Similarity	NPC37684
0.9108	High Similarity	NPC157784
0.9085	High Similarity	NPC300307
0.908	High Similarity	NPC120593
0.9074	High Similarity	NPC303460
0.9074	High Similarity	NPC306321
0.9074	High Similarity	NPC236132
0.9074	High Similarity	NPC220313
0.9074	High Similarity	NPC476295
0.9068	High Similarity	NPC40037
0.9068	High Similarity	NPC472275
0.9068	High Similarity	NPC278052
0.9068	High Similarity	NPC66288
0.9068	High Similarity	NPC40491
0.9062	High Similarity	NPC172770
0.9062	High Similarity	NPC185258
0.9062	High Similarity	NPC85121
0.9062	High Similarity	NPC184755
0.9062	High Similarity	NPC210459
0.9062	High Similarity	NPC476242
0.9062	High Similarity	NPC74178
0.9057	High Similarity	NPC274730
0.9057	High Similarity	NPC191146
0.9057	High Similarity	NPC3980
0.9057	High Similarity	NPC24640
0.9057	High Similarity	NPC68093
0.9045	High Similarity	NPC59162
0.9045	High Similarity	NPC304295
0.9045	High Similarity	NPC205046
0.9045	High Similarity	NPC202157
0.9042	High Similarity	NPC216307
0.9024	High Similarity	NPC478060
0.9024	High Similarity	NPC471975
0.9024	High Similarity	NPC470374
0.9024	High Similarity	NPC478059
0.9024	High Similarity	NPC117854
0.9024	High Similarity	NPC6588
0.9024	High Similarity	NPC477154
0.9024	High Similarity	NPC470377
0.9018	High Similarity	NPC293319
0.9018	High Similarity	NPC50960
0.9018	High Similarity	NPC85057
0.9018	High Similarity	NPC130920
0.9012	High Similarity	NPC52204
0.9006	High Similarity	NPC119209
0.9006	High Similarity	NPC474960
0.9006	High Similarity	NPC321399
0.9006	High Similarity	NPC28241
0.9006	High Similarity	NPC192686
0.9006	High Similarity	NPC36217
0.9006	High Similarity	NPC118256
0.9	High Similarity	NPC165977
0.9	High Similarity	NPC217677
0.9	High Similarity	NPC78225
0.9	High Similarity	NPC471209
0.9	High Similarity	NPC241904
0.9	High Similarity	NPC474681
0.9	High Similarity	NPC300727
0.9	High Similarity	NPC218313
0.9	High Similarity	NPC476981
0.9	High Similarity	NPC79053
0.8994	High Similarity	NPC133392
0.8994	High Similarity	NPC472280
0.8994	High Similarity	NPC113906
0.8994	High Similarity	NPC56786
0.8994	High Similarity	NPC67396
0.8994	High Similarity	NPC234255
0.8994	High Similarity	NPC80534
0.8987	High Similarity	NPC471982
0.8987	High Similarity	NPC237994
0.8982	High Similarity	NPC227906
0.8981	High Similarity	NPC227122
0.8981	High Similarity	NPC184136
0.8976	High Similarity	NPC4200
0.8963	High Similarity	NPC170245
0.8957	High Similarity	NPC7483
0.8951	High Similarity	NPC474038
0.8951	High Similarity	NPC258331
0.8951	High Similarity	NPC474187
0.8951	High Similarity	NPC266314
0.8951	High Similarity	NPC234644
0.8951	High Similarity	NPC472906
0.8944	High Similarity	NPC329091
0.8944	High Similarity	NPC235448
0.8944	High Similarity	NPC204879
0.8938	High Similarity	NPC133970
0.8938	High Similarity	NPC138243
0.8938	High Similarity	NPC472907
0.8938	High Similarity	NPC472455
0.8938	High Similarity	NPC474167
0.8938	High Similarity	NPC470762
0.8938	High Similarity	NPC6633
0.8938	High Similarity	NPC5322
0.8938	High Similarity	NPC153512
0.8931	High Similarity	NPC472905
0.8931	High Similarity	NPC74924
0.8931	High Similarity	NPC274327
0.8931	High Similarity	NPC145379
0.8931	High Similarity	NPC329844
0.8931	High Similarity	NPC255350
0.8931	High Similarity	NPC160951
0.8931	High Similarity	NPC93552
0.8931	High Similarity	NPC176775
0.8931	High Similarity	NPC192083
0.8931	High Similarity	NPC231018
0.8931	High Similarity	NPC47781

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 NPC156432 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	415
0.1-0.2	1010
0.2-0.3	1724
0.3-0.4	2722
0.4-0.5	1804
0.5-0.6	923
0.6-0.7	381
0.7-0.8	131
0.8-0.85	29
0.85-0.9	11
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8931	High Similarity	NPD2393	Clinical (unspecified phase)
0.8931	High Similarity	NPD2801	Approved
0.8839	High Similarity	NPD1511	Approved
0.8726	High Similarity	NPD1512	Approved
0.8634	High Similarity	NPD1934	Approved
0.8544	High Similarity	NPD4378	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD6166	Phase 2
0.8452	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD5494	Approved
0.8428	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8402	Intermediate Similarity	NPD7473	Discontinued
0.8383	Intermediate Similarity	NPD6959	Discontinued
0.8333	Intermediate Similarity	NPD6232	Discontinued
0.8304	Intermediate Similarity	NPD7054	Approved
0.8304	Intermediate Similarity	NPD5844	Phase 1
0.8282	Intermediate Similarity	NPD4380	Phase 2
0.8256	Intermediate Similarity	NPD7074	Phase 3
0.8256	Intermediate Similarity	NPD7472	Approved
0.8253	Intermediate Similarity	NPD3882	Suspended
0.8242	Intermediate Similarity	NPD7819	Suspended
0.8208	Intermediate Similarity	NPD6797	Phase 2
0.8193	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD3817	Phase 2
0.8176	Intermediate Similarity	NPD3750	Approved
0.8161	Intermediate Similarity	NPD7251	Discontinued
0.814	Intermediate Similarity	NPD3818	Discontinued
0.8114	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD1465	Phase 2
0.8011	Intermediate Similarity	NPD7808	Phase 3
0.7989	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD7075	Discontinued
0.7987	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1510	Phase 2
0.7944	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD1549	Phase 2
0.7925	Intermediate Similarity	NPD2796	Approved
0.7917	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD7390	Discontinued
0.7904	Intermediate Similarity	NPD7411	Suspended
0.7888	Intermediate Similarity	NPD2800	Approved
0.7882	Intermediate Similarity	NPD3749	Approved
0.787	Intermediate Similarity	NPD5402	Approved
0.7866	Intermediate Similarity	NPD2532	Approved
0.7866	Intermediate Similarity	NPD2534	Approved
0.7866	Intermediate Similarity	NPD2533	Approved
0.7862	Intermediate Similarity	NPD3748	Approved
0.7857	Intermediate Similarity	NPD6801	Discontinued
0.7848	Intermediate Similarity	NPD1607	Approved
0.7834	Intermediate Similarity	NPD943	Approved
0.7834	Intermediate Similarity	NPD1240	Approved
0.7816	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD6100	Approved
0.7812	Intermediate Similarity	NPD6099	Approved
0.7812	Intermediate Similarity	NPD2935	Discontinued
0.7784	Intermediate Similarity	NPD3226	Approved
0.776	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD1247	Approved
0.7738	Intermediate Similarity	NPD6599	Discontinued
0.7719	Intermediate Similarity	NPD7768	Phase 2
0.7697	Intermediate Similarity	NPD6799	Approved
0.7697	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD2346	Discontinued
0.7654	Intermediate Similarity	NPD6559	Discontinued
0.764	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD3751	Discontinued
0.7622	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD5403	Approved
0.7545	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD8150	Discontinued
0.7532	Intermediate Similarity	NPD4625	Phase 3
0.7531	Intermediate Similarity	NPD2799	Discontinued
0.7529	Intermediate Similarity	NPD6234	Discontinued
0.7529	Intermediate Similarity	NPD919	Approved
0.7516	Intermediate Similarity	NPD6651	Approved
0.7516	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3787	Discontinued
0.7486	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD6778	Approved
0.7474	Intermediate Similarity	NPD6779	Approved
0.7474	Intermediate Similarity	NPD6781	Approved
0.7474	Intermediate Similarity	NPD6780	Approved
0.7474	Intermediate Similarity	NPD6782	Approved
0.7474	Intermediate Similarity	NPD6777	Approved
0.7474	Intermediate Similarity	NPD6776	Approved
0.7473	Intermediate Similarity	NPD8312	Approved
0.7473	Intermediate Similarity	NPD8313	Approved
0.7458	Intermediate Similarity	NPD3926	Phase 2
0.7455	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD1243	Approved
0.7443	Intermediate Similarity	NPD7199	Phase 2
0.744	Intermediate Similarity	NPD5401	Approved
0.743	Intermediate Similarity	NPD7228	Approved
0.7425	Intermediate Similarity	NPD3300	Phase 2
0.7391	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1613	Approved
0.7382	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD1551	Phase 2
0.7375	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD2313	Discontinued
0.736	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7435	Discontinued
0.7353	Intermediate Similarity	NPD920	Approved
0.7351	Intermediate Similarity	NPD8434	Phase 2
0.7346	Intermediate Similarity	NPD230	Phase 1
0.7341	Intermediate Similarity	NPD37	Approved
0.7333	Intermediate Similarity	NPD2344	Approved
0.7314	Intermediate Similarity	NPD4965	Approved
0.7314	Intermediate Similarity	NPD4966	Approved
0.7314	Intermediate Similarity	NPD4967	Phase 2
0.7305	Intermediate Similarity	NPD4628	Phase 3
0.7303	Intermediate Similarity	NPD5710	Approved
0.7303	Intermediate Similarity	NPD5711	Approved
0.7302	Intermediate Similarity	NPD4360	Phase 2
0.7302	Intermediate Similarity	NPD4363	Phase 3
0.7273	Intermediate Similarity	NPD5406	Approved
0.7273	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5405	Approved
0.7273	Intermediate Similarity	NPD5408	Approved
0.7273	Intermediate Similarity	NPD5404	Approved
0.7273	Intermediate Similarity	NPD7783	Phase 2
0.7268	Intermediate Similarity	NPD7697	Approved
0.7268	Intermediate Similarity	NPD7698	Approved
0.7268	Intermediate Similarity	NPD7696	Phase 3
0.7267	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3268	Approved
0.7267	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD4749	Approved
0.7257	Intermediate Similarity	NPD4288	Approved
0.7251	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4908	Phase 1
0.7244	Intermediate Similarity	NPD1201	Approved
0.7239	Intermediate Similarity	NPD447	Suspended
0.7235	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD2798	Approved
0.7231	Intermediate Similarity	NPD7871	Phase 2
0.7231	Intermediate Similarity	NPD7870	Phase 2
0.7219	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD6823	Phase 2
0.7213	Intermediate Similarity	NPD5953	Discontinued
0.7211	Intermediate Similarity	NPD6535	Approved
0.7211	Intermediate Similarity	NPD6534	Approved
0.7208	Intermediate Similarity	NPD7701	Phase 2
0.7207	Intermediate Similarity	NPD7229	Phase 3
0.7205	Intermediate Similarity	NPD3027	Phase 3
0.7202	Intermediate Similarity	NPD7003	Approved
0.7202	Intermediate Similarity	NPD8166	Discontinued
0.7198	Intermediate Similarity	NPD7286	Phase 2
0.7186	Intermediate Similarity	NPD7801	Approved
0.7172	Intermediate Similarity	NPD8151	Discontinued
0.717	Intermediate Similarity	NPD2797	Approved
0.717	Intermediate Similarity	NPD1470	Approved
0.7168	Intermediate Similarity	NPD7458	Discontinued
0.716	Intermediate Similarity	NPD2309	Approved
0.7136	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7874	Approved
0.7135	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5124	Phase 1
0.711	Intermediate Similarity	NPD1653	Approved
0.7108	Intermediate Similarity	NPD4308	Phase 3
0.7101	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD7700	Phase 2
0.7098	Intermediate Similarity	NPD7699	Phase 2
0.7089	Intermediate Similarity	NPD1608	Approved
0.7083	Intermediate Similarity	NPD4361	Phase 2
0.7083	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7685	Pre-registration
0.7076	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD4060	Phase 1
0.7063	Intermediate Similarity	NPD1203	Approved
0.7059	Intermediate Similarity	NPD6190	Approved
0.7055	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD7549	Discontinued
0.7033	Intermediate Similarity	NPD2403	Approved
0.7025	Intermediate Similarity	NPD1610	Phase 2
0.7024	Intermediate Similarity	NPD1471	Phase 3
0.7006	Intermediate Similarity	NPD7033	Discontinued
0.7	Intermediate Similarity	NPD4287	Approved
0.7	Intermediate Similarity	NPD3225	Approved
0.6994	Remote Similarity	NPD6273	Approved
0.6989	Remote Similarity	NPD7240	Approved
0.6985	Remote Similarity	NPD7584	Approved
0.6975	Remote Similarity	NPD2861	Phase 2
0.6957	Remote Similarity	NPD3266	Approved
0.6957	Remote Similarity	NPD3267	Approved
0.6957	Remote Similarity	NPD7177	Discontinued
0.6951	Remote Similarity	NPD3764	Approved
0.6949	Remote Similarity	NPD6844	Discontinued
0.6942	Remote Similarity	NPD4665	Approved
0.6942	Remote Similarity	NPD4111	Phase 1
0.6941	Remote Similarity	NPD5698	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