NPASS Compound

Structure

CID44530 OpenBabel06191715382D 22 25 0 0 1 0 0 0 0 0999 V2000 -0.8341 -2.4092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -2.8908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1731 0.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1730 -1.4460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5040 0.4816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8343 0.4817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3382 -0.0002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8342 -1.4458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3382 -0.9642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8346 -2.4090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0074 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0073 -0.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6691 -0.9641 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8345 -1.4456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0001 -0.9640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6691 -0.0001 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7100 -2.9143 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8734 0.4996 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8733 -1.4643 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7097 -0.9401 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6692 0.9999 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 2 2 0 0 0 0 1 8 1 0 0 0 0 2 10 1 0 0 0 0 3 7 2 0 0 0 0 3 11 1 0 0 0 0 4 9 2 0 0 0 0 4 12 1 0 0 0 0 5 7 1 0 0 0 0 5 16 1 0 0 0 0 6 16 1 0 0 0 0 6 22 1 0 0 0 0 7 9 1 0 0 0 0 8 13 1 0 0 0 0 8 15 2 0 0 0 0 9 13 1 0 0 0 0 10 14 2 0 0 0 0 10 17 1 0 0 0 0 11 12 2 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 16 1 1 0 0 0 14 15 1 0 0 0 0 14 20 1 0 0 0 0 15 22 1 0 0 0 0 16 21 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.08
Volume:	287.989
LogP:	1.369
LogD:	0.742
LogS:	-3.443
# Rotatable Bonds:	0
TPSA:	110.38
# H-Bond Aceptor:	6
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.469
Synthetic Accessibility Score:	3.858
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.004
MDCK Permeability:	7.665265911782626e-06
Pgp-inhibitor:	0.01
Pgp-substrate:	0.983
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	94.32929229736328%
Volume Distribution (VD):	0.547
Pgp-substrate:	9.195595741271973%

ADMET: Metabolism

CYP1A2-inhibitor:	0.364
CYP1A2-substrate:	0.537
CYP2C19-inhibitor:	0.038
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.357
CYP2C9-substrate:	0.57
CYP2D6-inhibitor:	0.057
CYP2D6-substrate:	0.242
CYP3A4-inhibitor:	0.437
CYP3A4-substrate:	0.245

ADMET: Excretion

Clearance (CL):	16.94
Half-life (T1/2):	0.788

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.098
Drug-inuced Liver Injury (DILI):	0.364
AMES Toxicity:	0.699
Rat Oral Acute Toxicity:	0.214
Maximum Recommended Daily Dose:	0.929
Skin Sensitization:	0.911
Carcinogencity:	0.12
Eye Corrosion:	0.003
Eye Irritation:	0.896
Respiratory Toxicity:	0.214

Download Data

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

Natural Product: NPC44530

Natural Product ID:	NPC44530
*Common Name:**	Hematoxylin
IUPAC Name:	(6aS,11bR)-7,11b-dihydro-6H-indeno[2,1-c]chromene-3,4,6a,9,10-pentol
Synonyms:	Hematoxylin
Standard InCHIKey:	WZUVPPKBWHMQCE-XJKSGUPXSA-N
Standard InCHI:	InChI=1S/C16H14O6/c17-10-2-1-8-13-9-4-12(19)11(18)3-7(9)5-16(13,21)6-22-15(8)14(10)20/h1-4,13,17-21H,5-6H2/t13-,16+/m0/s1
SMILES:	Oc1cc2C[C@@]3([C@H](c2cc1O)c1ccc(c(c1OC3)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL477197
PubChem CID:	442514
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans

*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
NPO32846	heamatoxylon campechianum	Species	n.a.	n.a.	stems	XiShuangBanNa, Yunnan Province, China	2005-Sep	PMID[18610999]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	heartwood	n.a.	PMID[19420770]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	heartwood	n.a.	PMID[21800859]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800859]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[23127886]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23234407]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	seeds	Nanning, Guangxi Province, China	2013-APR	PMID[26398312]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	18
Others	20
Potency	16

Activity Type	# Activity
Cell Line	1
Individual Protein	34
Organism	8
Others	5
Protein-Protein Interaction	1
SINGLE PROTEIN	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT36	Individual Protein	Tyrosine-protein kinase SRC	Homo sapiens	Inhibition	=	95.4	%	PMID[461269]
NPT1478	Individual Protein	Vascular endothelial growth factor receptor 2	Homo sapiens	Inhibition	=	99.5	%	PMID[461269]
NPT1479	Individual Protein	Stem cell growth factor receptor	Homo sapiens	Inhibition	=	97.2	%	PMID[461269]
NPT285	Individual Protein	Epidermal growth factor receptor erbB1	Homo sapiens	Inhibition	=	92.4	%	PMID[461269]
NPT1480	Individual Protein	Fibroblast growth factor receptor 1	Homo sapiens	Inhibition	=	100.0	%	PMID[461269]
NPT1481	Individual Protein	Fibroblast growth factor receptor 2	Homo sapiens	Inhibition	=	73.6	%	PMID[461269]
NPT1337	Individual Protein	Hepatocyte growth factor receptor	Homo sapiens	Inhibition	=	100.0	%	PMID[461269]
NPT36	Individual Protein	Tyrosine-protein kinase SRC	Homo sapiens	IC50	=	440.0	nM	PMID[461269]
NPT1337	Individual Protein	Hepatocyte growth factor receptor	Homo sapiens	IC50	=	400.0	nM	PMID[461269]
NPT1480	Individual Protein	Fibroblast growth factor receptor 1	Homo sapiens	IC50	=	320.0	nM	PMID[461269]
NPT286	Individual Protein	Receptor protein-tyrosine kinase erbB-2	Homo sapiens	IC50	=	960.0	nM	PMID[461269]
NPT1478	Individual Protein	Vascular endothelial growth factor receptor 2	Homo sapiens	IC50	=	2100.0	nM	PMID[461269]
NPT301	Individual Protein	Vascular endothelial growth factor receptor 1	Homo sapiens	IC50	=	2900.0	nM	PMID[461269]
NPT285	Individual Protein	Epidermal growth factor receptor erbB1	Homo sapiens	IC50	=	3400.0	nM	PMID[461269]
NPT1479	Individual Protein	Stem cell growth factor receptor	Homo sapiens	IC50	=	2700.0	nM	PMID[461269]
NPT2941	Individual Protein	Ephrin type-B receptor 2	Homo sapiens	IC50	>	10000.0	nM	PMID[461269]
NPT286	Individual Protein	Receptor protein-tyrosine kinase erbB-2	Homo sapiens	Inhibition	=	97.6	%	PMID[461269]
NPT301	Individual Protein	Vascular endothelial growth factor receptor 1	Homo sapiens	Inhibition	=	79.6	%	PMID[461269]
NPT2941	Individual Protein	Ephrin type-B receptor 2	Homo sapiens	Inhibition	=	44.3	%	PMID[461269]
NPT47	Individual Protein	ATP-dependent DNA helicase Q1	Homo sapiens	Potency	=	12589.3	nM	PMID[461270]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	14125.4	nM	PMID[461270]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	=	1584.9	nM	PMID[461270]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	12589.3	nM	PMID[461270]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	14125.4	nM	PMID[461270]
NPT53	Individual Protein	4'-phosphopantetheinyl transferase ffp	Bacillus subtilis	Potency	=	31622.8	nM	PMID[461270]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	15848.9	nM	PMID[461270]
NPT55	Individual Protein	Putative fructose-1,6-bisphosphate aldolase	Giardia intestinalis	Potency	=	14091.9	nM	PMID[461270]
NPT282	Individual Protein	MAP kinase ERK2	Homo sapiens	Potency	=	39810.7	nM	PMID[461270]
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	11220.2	nM	PMID[461270]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[461270]
NPT47	Individual Protein	ATP-dependent DNA helicase Q1	Homo sapiens	Potency	n.a.	1778.3	nM	PMID[461270]
NPT112	Cell Line	MOLT-4	Homo sapiens	CC50	=	40000.0	nM	PMID[461271]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	3162.3	nM	PMID[461270]
NPT2	Others	Unspecified		IC50	=	5000.0	nM	PMID[461269]
NPT2	Others	Unspecified		Inhibition	=	93.6	%	PMID[461269]
NPT533	Protein-Protein Interaction	Runt-related transcription factor 1/Core-binding factor subunit beta	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[461270]
NPT2	Others	Unspecified		Potency	n.a.	11220.2	nM	PMID[461270]
NPT2	Others	Unspecified		IC50	=	1300.0	nM	PMID[461271]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	>	1.0	nM	PMID[461271]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	<	1000.0	nM	PMID[461271]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	100000.0	nM	PMID[461271]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	88.87	%	PMID[461272]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	91.69	%	PMID[461272]
NPT2	Others	Unspecified		Potency	n.a.	5623.4	nM	PMID[461270]
NPT23878	SINGLE PROTEIN	Translin-associated protein X	Homo sapiens	Inhibition	=	63.0	%	PMID[461273]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-7.34	%	PMID[461274]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	97.04	%	PMID[461275]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	IC50	=	220.0	nM	PMID[461275]
NPT22753	SINGLE PROTEIN	Replicase polyprotein 1ab	Middle East respiratory syndrome-related coronavirus (isolate UnitedKingdom/H123990006/2012) (Betacoronavirus England 1) (Humancoronavirus EMC)	IC50	>	10000.0	nM	PMID[461275]
NPT22753	SINGLE PROTEIN	Replicase polyprotein 1ab	Middle East respiratory syndrome-related coronavirus (isolate UnitedKingdom/H123990006/2012) (Betacoronavirus England 1) (Humancoronavirus EMC)	Inhibition	=	5.0	%	PMID[461275]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-0.12	%	PMID[461276]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[461277]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[461277]

☑ 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 NPC44530 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	520
0.1-0.2	1779
0.2-0.3	4578
0.3-0.4	12281
0.4-0.5	5850
0.5-0.6	4337
0.6-0.7	7530
0.7-0.8	4543
0.8-0.85	811
0.85-0.9	400
0.9-0.95	59
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC277951
1.0	High Similarity	NPC317237
0.9926	High Similarity	NPC135767
0.9926	High Similarity	NPC155392
0.9926	High Similarity	NPC274721
0.9855	High Similarity	NPC211758
0.9855	High Similarity	NPC87794
0.9559	High Similarity	NPC94994
0.9209	High Similarity	NPC232164
0.9209	High Similarity	NPC473739
0.9209	High Similarity	NPC236306
0.9203	High Similarity	NPC265433
0.9203	High Similarity	NPC248727
0.9203	High Similarity	NPC162659
0.9203	High Similarity	NPC270456
0.9143	High Similarity	NPC184797
0.9143	High Similarity	NPC309124
0.9071	High Similarity	NPC25966
0.9071	High Similarity	NPC319647
0.9071	High Similarity	NPC70682
0.9071	High Similarity	NPC127218
0.9071	High Similarity	NPC245207
0.9071	High Similarity	NPC260741
0.9065	High Similarity	NPC230734
0.9065	High Similarity	NPC234952
0.9065	High Similarity	NPC227503
0.9065	High Similarity	NPC269091
0.9065	High Similarity	NPC474639
0.9065	High Similarity	NPC302701
0.9058	High Similarity	NPC317380
0.9051	High Similarity	NPC86655
0.9051	High Similarity	NPC202762
0.9021	High Similarity	NPC473108
0.9014	High Similarity	NPC107161
0.9014	High Similarity	NPC204347
0.9014	High Similarity	NPC475891
0.9014	High Similarity	NPC2613
0.9014	High Similarity	NPC59841
0.9	High Similarity	NPC276490
0.8993	High Similarity	NPC94750
0.8993	High Similarity	NPC121812
0.8993	High Similarity	NPC112939
0.8993	High Similarity	NPC151224
0.8993	High Similarity	NPC164787
0.8993	High Similarity	NPC112246
0.8993	High Similarity	NPC474206
0.8993	High Similarity	NPC470356
0.8944	High Similarity	NPC471389
0.8944	High Similarity	NPC35216
0.8944	High Similarity	NPC247291
0.8936	High Similarity	NPC32630
0.8929	High Similarity	NPC173660
0.8929	High Similarity	NPC306441
0.8929	High Similarity	NPC16435
0.8913	High Similarity	NPC126029
0.8913	High Similarity	NPC261619
0.8913	High Similarity	NPC61477
0.8913	High Similarity	NPC219876
0.8913	High Similarity	NPC15658
0.8913	High Similarity	NPC78770
0.8913	High Similarity	NPC127624
0.8913	High Similarity	NPC185604
0.8905	High Similarity	NPC91291
0.8897	High Similarity	NPC233980
0.8897	High Similarity	NPC226331
0.8897	High Similarity	NPC46274
0.8889	High Similarity	NPC45257
0.8889	High Similarity	NPC50250
0.8889	High Similarity	NPC469795
0.8889	High Similarity	NPC93323
0.8889	High Similarity	NPC280092
0.8889	High Similarity	NPC12641
0.8873	High Similarity	NPC259519
0.8873	High Similarity	NPC254759
0.8873	High Similarity	NPC160283
0.8873	High Similarity	NPC27495
0.8865	High Similarity	NPC474282
0.8865	High Similarity	NPC103976
0.8865	High Similarity	NPC211549
0.8865	High Similarity	NPC102904
0.8865	High Similarity	NPC107551
0.8865	High Similarity	NPC176051
0.8865	High Similarity	NPC326797
0.8857	High Similarity	NPC260898
0.8857	High Similarity	NPC234333
0.8857	High Similarity	NPC61946
0.8857	High Similarity	NPC47398
0.8857	High Similarity	NPC195022
0.8849	High Similarity	NPC168059
0.8849	High Similarity	NPC11060
0.8849	High Similarity	NPC229442
0.8841	High Similarity	NPC42760
0.8841	High Similarity	NPC220825
0.8841	High Similarity	NPC268266
0.8841	High Similarity	NPC268342
0.8836	High Similarity	NPC16269
0.8836	High Similarity	NPC474397
0.8836	High Similarity	NPC21776
0.8824	High Similarity	NPC250432
0.8824	High Similarity	NPC5447
0.8819	High Similarity	NPC85264
0.8819	High Similarity	NPC47633
0.8819	High Similarity	NPC163508
0.8819	High Similarity	NPC81638
0.8819	High Similarity	NPC173203
0.8819	High Similarity	NPC102044
0.8811	High Similarity	NPC178054
0.8811	High Similarity	NPC263261
0.8811	High Similarity	NPC87725
0.8811	High Similarity	NPC265075
0.8803	High Similarity	NPC184613
0.8803	High Similarity	NPC471388
0.8803	High Similarity	NPC292882
0.8792	High Similarity	NPC160196
0.8786	High Similarity	NPC478085
0.8786	High Similarity	NPC106215
0.8776	High Similarity	NPC329836
0.8776	High Similarity	NPC473876
0.8768	High Similarity	NPC126836
0.8759	High Similarity	NPC304894
0.8759	High Similarity	NPC15659
0.8759	High Similarity	NPC63879
0.875	High Similarity	NPC277784
0.8741	High Similarity	NPC198038
0.8723	High Similarity	NPC473413
0.8723	High Similarity	NPC55239
0.8723	High Similarity	NPC180602
0.8723	High Similarity	NPC214853
0.8723	High Similarity	NPC313081
0.8723	High Similarity	NPC240279
0.8714	High Similarity	NPC158331
0.8714	High Similarity	NPC263064
0.8714	High Similarity	NPC475840
0.8707	High Similarity	NPC101376
0.8705	High Similarity	NPC469907
0.8699	High Similarity	NPC469557
0.8699	High Similarity	NPC307466
0.869	High Similarity	NPC477616
0.869	High Similarity	NPC474104
0.869	High Similarity	NPC469630
0.8681	High Similarity	NPC311530
0.8681	High Similarity	NPC71046
0.8675	High Similarity	NPC80918
0.8675	High Similarity	NPC188578
0.8671	High Similarity	NPC471183
0.8671	High Similarity	NPC6300
0.8671	High Similarity	NPC292487
0.8671	High Similarity	NPC114171
0.8671	High Similarity	NPC230124
0.8662	High Similarity	NPC143139
0.8662	High Similarity	NPC133025
0.8662	High Similarity	NPC472334
0.8662	High Similarity	NPC202846
0.8662	High Similarity	NPC472336
0.8662	High Similarity	NPC470802
0.8652	High Similarity	NPC160697
0.8652	High Similarity	NPC289258
0.8652	High Similarity	NPC287745
0.8652	High Similarity	NPC170694
0.8652	High Similarity	NPC276026
0.8652	High Similarity	NPC555
0.8652	High Similarity	NPC209199
0.8652	High Similarity	NPC206737
0.8652	High Similarity	NPC188378
0.8652	High Similarity	NPC7515
0.8652	High Similarity	NPC469659
0.8652	High Similarity	NPC56764
0.8649	High Similarity	NPC166584
0.8649	High Similarity	NPC301961
0.8643	High Similarity	NPC6451
0.8643	High Similarity	NPC175067
0.8643	High Similarity	NPC470752
0.8643	High Similarity	NPC253105
0.8643	High Similarity	NPC201587
0.8643	High Similarity	NPC204215
0.8639	High Similarity	NPC324492
0.8639	High Similarity	NPC260397
0.8639	High Similarity	NPC317053
0.8639	High Similarity	NPC112251
0.8639	High Similarity	NPC226540
0.863	High Similarity	NPC473845
0.8621	High Similarity	NPC470917
0.8611	High Similarity	NPC234568
0.8611	High Similarity	NPC291101
0.8611	High Similarity	NPC22317
0.8611	High Similarity	NPC109240
0.8611	High Similarity	NPC266197
0.8601	High Similarity	NPC156948
0.8601	High Similarity	NPC3072
0.8601	High Similarity	NPC46277
0.8601	High Similarity	NPC477938
0.8601	High Similarity	NPC301765
0.8601	High Similarity	NPC86605
0.8601	High Similarity	NPC35550
0.86	High Similarity	NPC2745
0.8592	High Similarity	NPC108198
0.8592	High Similarity	NPC10314
0.8592	High Similarity	NPC99572
0.8592	High Similarity	NPC69029
0.8592	High Similarity	NPC200557

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 NPC44530 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	434
0.1-0.2	928
0.2-0.3	1947
0.3-0.4	2751
0.4-0.5	1522
0.5-0.6	888
0.6-0.7	573
0.7-0.8	96
0.8-0.85	8
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8913	High Similarity	NPD1613	Approved
0.8913	High Similarity	NPD1612	Clinical (unspecified phase)
0.8897	High Similarity	NPD1529	Clinical (unspecified phase)
0.8824	High Similarity	NPD1530	Clinical (unspecified phase)
0.8429	Intermediate Similarity	NPD3027	Phase 3
0.8382	Intermediate Similarity	NPD1610	Phase 2
0.8286	Intermediate Similarity	NPD2861	Phase 2
0.8227	Intermediate Similarity	NPD4908	Phase 1
0.8112	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8042	Intermediate Similarity	NPD4625	Phase 3
0.8013	Intermediate Similarity	NPD1934	Approved
0.8	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7199	Phase 2
0.8	Intermediate Similarity	NPD3620	Phase 2
0.7956	Intermediate Similarity	NPD1548	Phase 1
0.7901	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD4749	Approved
0.7764	Intermediate Similarity	NPD6234	Discontinued
0.7763	Intermediate Similarity	NPD3892	Phase 2
0.774	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD5762	Approved
0.7682	Intermediate Similarity	NPD5763	Approved
0.7643	Intermediate Similarity	NPD1653	Approved
0.764	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD4060	Phase 1
0.7625	Intermediate Similarity	NPD1465	Phase 2
0.7625	Intermediate Similarity	NPD2801	Approved
0.7613	Intermediate Similarity	NPD1511	Approved
0.7584	Intermediate Similarity	NPD5735	Approved
0.7582	Intermediate Similarity	NPD6674	Discontinued
0.7582	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD37	Approved
0.7545	Intermediate Similarity	NPD7228	Approved
0.7534	Intermediate Similarity	NPD3018	Phase 2
0.7531	Intermediate Similarity	NPD4966	Approved
0.7531	Intermediate Similarity	NPD3882	Suspended
0.7531	Intermediate Similarity	NPD4965	Approved
0.7531	Intermediate Similarity	NPD4967	Phase 2
0.753	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD6166	Phase 2
0.753	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1512	Approved
0.7464	Intermediate Similarity	NPD5283	Phase 1
0.7451	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD228	Approved
0.744	Intermediate Similarity	NPD3818	Discontinued
0.7417	Intermediate Similarity	NPD6353	Approved
0.7396	Intermediate Similarity	NPD5844	Phase 1
0.7386	Intermediate Similarity	NPD6099	Approved
0.7386	Intermediate Similarity	NPD6100	Approved
0.7379	Intermediate Similarity	NPD2983	Phase 2
0.7379	Intermediate Similarity	NPD5327	Phase 3
0.7379	Intermediate Similarity	NPD2982	Phase 2
0.7361	Intermediate Similarity	NPD3705	Approved
0.7353	Intermediate Similarity	NPD7074	Phase 3
0.7347	Intermediate Similarity	NPD4624	Approved
0.731	Intermediate Similarity	NPD2981	Phase 2
0.7308	Intermediate Similarity	NPD3750	Approved
0.7296	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7054	Approved
0.7289	Intermediate Similarity	NPD5494	Approved
0.7285	Intermediate Similarity	NPD1558	Phase 1
0.7285	Intermediate Similarity	NPD4140	Approved
0.7283	Intermediate Similarity	NPD4577	Approved
0.7283	Intermediate Similarity	NPD4578	Approved
0.7279	Intermediate Similarity	NPD3094	Phase 2
0.726	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD4663	Approved
0.7256	Intermediate Similarity	NPD3817	Phase 2
0.7251	Intermediate Similarity	NPD7472	Approved
0.7241	Intermediate Similarity	NPD8054	Approved
0.7241	Intermediate Similarity	NPD1091	Approved
0.7241	Intermediate Similarity	NPD8053	Approved
0.7237	Intermediate Similarity	NPD3657	Discovery
0.7234	Intermediate Similarity	NPD6671	Approved
0.723	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7549	Discontinued
0.7202	Intermediate Similarity	NPD6232	Discontinued
0.72	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7313	Approved
0.7184	Intermediate Similarity	NPD7312	Approved
0.7184	Intermediate Similarity	NPD7311	Approved
0.7184	Intermediate Similarity	NPD7310	Approved
0.7179	Intermediate Similarity	NPD1549	Phase 2
0.7176	Intermediate Similarity	NPD7473	Discontinued
0.7174	Intermediate Similarity	NPD3021	Approved
0.7174	Intermediate Similarity	NPD3022	Approved
0.7168	Intermediate Similarity	NPD7685	Pre-registration
0.716	Intermediate Similarity	NPD4005	Discontinued
0.7152	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7309	Approved
0.7126	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD7447	Phase 1
0.7124	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD5124	Phase 1
0.7124	Intermediate Similarity	NPD6355	Discontinued
0.7123	Intermediate Similarity	NPD3092	Approved
0.7123	Intermediate Similarity	NPD422	Phase 1
0.7119	Intermediate Similarity	NPD7906	Approved
0.7118	Intermediate Similarity	NPD2489	Approved
0.7118	Intermediate Similarity	NPD27	Approved
0.7117	Intermediate Similarity	NPD4678	Approved
0.7117	Intermediate Similarity	NPD4675	Approved
0.7117	Intermediate Similarity	NPD4380	Phase 2
0.711	Intermediate Similarity	NPD6797	Phase 2
0.711	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD3787	Discontinued
0.7097	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5588	Approved
0.7097	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD8651	Approved
0.7095	Intermediate Similarity	NPD6696	Suspended
0.7091	Intermediate Similarity	NPD7819	Suspended
0.7089	Intermediate Similarity	NPD6331	Phase 2
0.7089	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7466	Approved
0.7078	Intermediate Similarity	NPD6653	Approved
0.7069	Intermediate Similarity	NPD7251	Discontinued
0.7069	Intermediate Similarity	NPD7240	Approved
0.7066	Intermediate Similarity	NPD7833	Phase 2
0.7066	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD7831	Phase 2
0.7066	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7212	Phase 2
0.7063	Intermediate Similarity	NPD7213	Phase 3
0.7059	Intermediate Similarity	NPD2970	Approved
0.7059	Intermediate Similarity	NPD2969	Approved
0.7044	Intermediate Similarity	NPD2677	Approved
0.7041	Intermediate Similarity	NPD8127	Discontinued
0.7035	Intermediate Similarity	NPD3751	Discontinued
0.7032	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD4536	Approved
0.7032	Intermediate Similarity	NPD4538	Approved
0.7029	Intermediate Similarity	NPD7808	Phase 3
0.7025	Intermediate Similarity	NPD1652	Phase 2
0.7025	Intermediate Similarity	NPD5177	Phase 3
0.7019	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1375	Discontinued
0.7006	Intermediate Similarity	NPD7266	Discontinued
0.7006	Intermediate Similarity	NPD3540	Phase 1
0.7	Intermediate Similarity	NPD7229	Phase 3
0.7	Intermediate Similarity	NPD5058	Phase 3
0.7	Intermediate Similarity	NPD3051	Approved
0.6993	Remote Similarity	NPD7157	Approved
0.6988	Remote Similarity	NPD5929	Approved
0.6987	Remote Similarity	NPD3748	Approved
0.6987	Remote Similarity	NPD1510	Phase 2
0.6987	Remote Similarity	NPD5960	Phase 3
0.6981	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4110	Phase 3
0.6978	Remote Similarity	NPD2684	Approved
0.6975	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7095	Approved
0.6968	Remote Similarity	NPD2157	Approved
0.6966	Remote Similarity	NPD3091	Approved
0.6964	Remote Similarity	NPD7075	Discontinued
0.6964	Remote Similarity	NPD3749	Approved
0.6962	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD968	Approved
0.6951	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD2238	Phase 2
0.6946	Remote Similarity	NPD2560	Approved
0.6946	Remote Similarity	NPD2563	Approved
0.6946	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD3539	Phase 1
0.6941	Remote Similarity	NPD6959	Discontinued
0.6914	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7028	Phase 2
0.6906	Remote Similarity	NPD290	Approved
0.6901	Remote Similarity	NPD7843	Approved
0.6901	Remote Similarity	NPD6071	Discontinued
0.6899	Remote Similarity	NPD6004	Phase 3
0.6899	Remote Similarity	NPD6005	Phase 3
0.6899	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6002	Phase 3
0.6897	Remote Similarity	NPD8156	Discontinued
0.6894	Remote Similarity	NPD7124	Phase 2
0.6887	Remote Similarity	NPD6584	Phase 3
0.6886	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7033	Discontinued
0.6875	Remote Similarity	NPD6559	Discontinued
0.6871	Remote Similarity	NPD6516	Phase 2
0.6871	Remote Similarity	NPD4059	Approved
0.6871	Remote Similarity	NPD5846	Approved
0.6867	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD4055	Discovery
0.6859	Remote Similarity	NPD4097	Suspended
0.6855	Remote Similarity	NPD7037	Approved
0.6855	Remote Similarity	NPD2424	Discontinued

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