NPASS Compound

Structure

CID305261 OpenBabel06191716112D 65 68 0 0 1 0 0 0 0 0999 V2000 -1.5000 -7.7942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0000 -3.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 -6.9282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5000 -4.3301 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5000 -6.0622 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0000 -5.1962 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5000 -6.0622 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0000 -3.4641 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5000 -2.5981 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0000 -3.4641 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0000 -1.7321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5000 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5000 -4.3301 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5000 -2.5981 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5000 -4.3301 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5000 -2.5981 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5000 -4.3301 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -2.5981 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5000 -4.3301 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.0000 -5.1962 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5000 -2.5981 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0000 -1.7321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0000 -6.9282 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -6.0622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0000 -5.1962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0000 -6.9282 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -3.4641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -3.4641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -6.0622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -5.1962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -3.4641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 -5.1962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3660 -3.8301 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0000 -5.1962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6340 -4.8301 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3660 1.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6340 0.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6340 -6.5622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0000 -6.9282 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3660 -5.5622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0000 -3.4641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5000 -4.3301 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 -3.4641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 -5.1962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.4641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 -5.1962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -6.5000 -4.3301 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 0.8660 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -6.0622 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 52 1 0 0 0 0 3 62 1 0 0 0 0 4 27 2 3 0 0 0 4 28 1 0 0 0 0 5 3 1 6 0 0 0 5 13 1 0 0 0 0 5 14 1 0 0 0 0 6 2 1 1 0 0 0 6 8 1 0 0 0 0 6 53 1 0 0 0 0 7 9 1 0 0 0 0 7 24 1 0 0 0 0 7 27 1 6 0 0 0 8 9 1 0 0 0 0 8 29 1 6 0 0 0 9 30 1 1 0 0 0 10 11 1 0 0 0 0 10 15 1 0 0 0 0 10 31 1 6 0 0 0 11 25 1 0 0 0 0 11 32 1 1 0 0 0 12 16 1 0 0 0 0 12 17 1 0 0 0 0 12 33 1 1 0 0 0 13 22 1 0 0 0 0 13 55 1 1 0 0 0 14 26 1 0 0 0 0 14 60 1 1 0 0 0 15 19 1 0 0 0 0 15 56 1 1 0 0 0 16 18 1 0 0 0 0 16 57 1 6 0 0 0 17 23 1 0 0 0 0 17 61 1 6 0 0 0 18 20 1 6 0 0 0 18 54 1 0 0 0 0 19 21 1 6 0 0 0 19 58 1 0 0 0 0 20 34 2 0 0 0 0 20 35 1 0 0 0 0 21 36 2 0 0 0 0 21 37 1 0 0 0 0 22 38 1 6 0 0 0 22 59 1 0 0 0 0 23 39 1 0 0 0 0 23 54 1 0 0 0 0 24 53 1 0 0 0 0 24 56 1 6 0 0 0 25 55 1 6 0 0 0 25 58 1 0 0 0 0 26 57 1 1 0 0 0 26 59 1 0 0 0 0 40 62 1 0 0 0 0 41 62 2 0 0 0 0 42 62 2 0 0 0 0 43 63 1 0 0 0 0 44 63 2 0 0 0 0 45 63 2 0 0 0 0 46 64 1 0 0 0 0 47 64 2 0 0 0 0 48 64 2 0 0 0 0 49 65 1 0 0 0 0 50 65 2 0 0 0 0 51 65 2 0 0 0 0 52 63 1 0 0 0 0 60 64 1 0 0 0 0 61 65 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1039.04
Volume:	800.017
LogP:	-5.908
LogD:	-3.348
LogS:	2.793
# Rotatable Bonds:	19
TPSA:	555.09
# H-Bond Aceptor:	35
# H-Bond Donor:	14
# Rings:	4
# Heavy Atoms:	39

MedChem Properties

QED Drug-Likeness Score:	0.057
Synthetic Accessibility Score:	6.398
Fsp3:	0.885
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.95
MDCK Permeability:	0.0006760728429071605
Pgp-inhibitor:	0.0
Pgp-substrate:	0.798
Human Intestinal Absorption (HIA):	1.0
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.04
Plasma Protein Binding (PPB):	43.344566345214844%
Volume Distribution (VD):	0.363
Pgp-substrate:	37.83195877075195%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.003
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.01
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.018
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.012
CYP3A4-inhibitor:	0.0
CYP3A4-substrate:	0.0

ADMET: Excretion

Clearance (CL):	0.571
Half-life (T1/2):	0.638

ADMET: Toxicity

hERG Blockers:	0.572
Human Hepatotoxicity (H-HT):	0.301
Drug-inuced Liver Injury (DILI):	0.773
AMES Toxicity:	0.065
Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.445
Carcinogencity:	0.117
Eye Corrosion:	0.003
Eye Irritation:	0.025
Respiratory Toxicity:	0.994

Download Data

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

Natural Product: NPC305261

Natural Product ID:	NPC305261
*Common Name:**	Sodium Heparin
IUPAC Name:	(2S,3S,4R,5R,6R)-3-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(sulfooxymethyl)oxan-2-yl]oxy-6-[(2S,3S,4S,5R,6S)-6-[(2R,3S,4S,5R)-2-carboxy-4,6-dihydroxy-5-sulfooxyoxan-3-yl]oxy-2-hydroxy-4-(sulfomethyl)-5-sulfooxyoxan-3-yl]oxy-4,5-dihydroxyoxane-2-carboxylic acid
Synonyms:
Standard InCHIKey:	ZFGMDIBRIDKWMY-PASTXAENSA-N
Standard InCHI:	InChI=1S/C26H41NO34S4/c1-4(28)27-7-9(30)8(29)6(2-52-63(43,44)45)53-24(7)56-15-10(31)11(32)25(58-19(15)21(36)37)55-13-5(3-62(40,41)42)14(60-64(46,47)48)26(59-22(13)38)57-16-12(33)17(61-65(49,50)51)23(39)54-18(16)20(34)35/h5-19,22-26,29-33,38-39H,2-3H2,1H3,(H,27,28)(H,34,35)(H,36,37)(H,40,41,42)(H,43,44,45)(H,46,47,48)(H,49,50,51)/t5-,6+,7+,8+,9+,10+,11+,12-,13-,14+,15-,16-,17+,18+,19-,22-,23?,24+,25+,26-/m0/s1
SMILES:	CC(=N[C@H]1[C@@H](O[C@@H]2[C@H](O[C@H]([C@@H]([C@H]2O)O)O[C@@H]2[C@@H](O)O[C@@H]([C@@H]([C@H]2CS(=O)(=O)O)OS(=O)(=O)O)O[C@@H]2[C@@H](OC([C@@H]([C@H]2O)OS(=O)(=O)O)O)C(=O)O)C(=O)O)O[C@@H]([C@H]([C@@H]1O)O)COS(=O)(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL526514
PubChem CID:	22833565
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0003305] Aminosaccharides [CHEMONTID:0002276] N-acyl-alpha-hexosamines

*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
NPO9518.1	Gardenia jasminoides var. grandiflora	Varieties	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9518.1	Gardenia jasminoides var. grandiflora	Varieties	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	1
Others	14

Activity Type	# Activity
Individual Protein	1
NON-MOLECULAR	5
Others	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	>	200.0	ug.mL-1	PMID[569812]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Hepatotoxicity (moderate)	=	20.0	n.a.	PMID[569813]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Hepatotoxicity (moderate)	=	90.0	%	PMID[569813]
NPT2	Others	Unspecified		Hepatotoxicity (acute)	=	4.0	n.a.	PMID[569813]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Hepatotoxicity (acute)	=	0.0	%	PMID[569813]
NPT2	Others	Unspecified		Hepatotoxicity (cytolytic)	=	3.0	n.a.	PMID[569813]
NPT2	Others	Unspecified		Hepatotoxicity (choleostasis)	=	1.0	n.a.	PMID[569813]
NPT2	Others	Unspecified		Hepatotoxicity (severe hepatitis)	=	1.0	n.a.	PMID[569813]
NPT2	Others	Unspecified		Hepatotoxicity (chronic liver disease)	=	0.0	n.a.	PMID[569813]
NPT2	Others	Unspecified		Hepatotoxicity (cirrhosis)	=	0.0	n.a.	PMID[569813]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Hepatotoxicity (granulomatous hepatitis)	=	0.0	n.a.	PMID[569813]
NPT2	Others	Unspecified		Hepatotoxicity (association with vascular disease)	=	0.0	n.a.	PMID[569813]
NPT2	Others	Unspecified		Hepatotoxicity (steatosis)	=	0.0	n.a.	PMID[569813]
NPT2	Others	Unspecified		Hepatotoxicity (malignant tumour)	=	0.0	n.a.	PMID[569813]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Hepatotoxicity (benign tumour)	=	0.0	n.a.	PMID[569813]

☑ 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 NPC305261 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	310
0.1-0.2	5093
0.2-0.3	19107
0.3-0.4	13020
0.4-0.5	4319
0.5-0.6	775
0.6-0.7	70
0.7-0.8	2
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.75	Intermediate Similarity	NPC188453
0.75	Intermediate Similarity	NPC42320
0.6983	Remote Similarity	NPC470283
0.681	Remote Similarity	NPC208537
0.681	Remote Similarity	NPC270005
0.6552	Remote Similarity	NPC470284
0.6552	Remote Similarity	NPC292345
0.6508	Remote Similarity	NPC137453
0.6452	Remote Similarity	NPC227622
0.6396	Remote Similarity	NPC316807
0.6276	Remote Similarity	NPC200788
0.6276	Remote Similarity	NPC243680
0.619	Remote Similarity	NPC82931
0.619	Remote Similarity	NPC210729
0.619	Remote Similarity	NPC172365
0.6174	Remote Similarity	NPC475892
0.6172	Remote Similarity	NPC475918
0.6138	Remote Similarity	NPC145899
0.6107	Remote Similarity	NPC475152
0.6107	Remote Similarity	NPC475584
0.6107	Remote Similarity	NPC475394
0.6087	Remote Similarity	NPC297768
0.6087	Remote Similarity	NPC477347
0.6087	Remote Similarity	NPC475327
0.6087	Remote Similarity	NPC269318
0.6087	Remote Similarity	NPC238056
0.6087	Remote Similarity	NPC475667
0.6087	Remote Similarity	NPC475270
0.6087	Remote Similarity	NPC173328
0.6087	Remote Similarity	NPC476087
0.6087	Remote Similarity	NPC186992
0.6069	Remote Similarity	NPC75318
0.6069	Remote Similarity	NPC280941
0.6069	Remote Similarity	NPC235772
0.6014	Remote Similarity	NPC265908
0.6	Remote Similarity	NPC76999
0.5983	Remote Similarity	NPC60849
0.5983	Remote Similarity	NPC477332
0.5983	Remote Similarity	NPC472352
0.5932	Remote Similarity	NPC476523
0.5931	Remote Similarity	NPC73829
0.5931	Remote Similarity	NPC119794
0.5917	Remote Similarity	NPC470282
0.5913	Remote Similarity	NPC85759
0.5913	Remote Similarity	NPC146992
0.5913	Remote Similarity	NPC294748
0.5913	Remote Similarity	NPC477346
0.5913	Remote Similarity	NPC477344
0.5913	Remote Similarity	NPC318258
0.5913	Remote Similarity	NPC22742
0.5913	Remote Similarity	NPC158302
0.589	Remote Similarity	NPC477072
0.5882	Remote Similarity	NPC83839
0.5862	Remote Similarity	NPC475472
0.586	Remote Similarity	NPC265699
0.5833	Remote Similarity	NPC315387
0.5833	Remote Similarity	NPC316205
0.5823	Remote Similarity	NPC113620
0.5823	Remote Similarity	NPC475599
0.5823	Remote Similarity	NPC187497
0.5823	Remote Similarity	NPC174336
0.5823	Remote Similarity	NPC100612
0.5818	Remote Similarity	NPC327486
0.5818	Remote Similarity	NPC223174
0.5818	Remote Similarity	NPC327753
0.5812	Remote Similarity	NPC472205
0.5812	Remote Similarity	NPC89843
0.5812	Remote Similarity	NPC259294
0.5812	Remote Similarity	NPC183888
0.5812	Remote Similarity	NPC472201
0.5812	Remote Similarity	NPC184915
0.5812	Remote Similarity	NPC472203
0.5812	Remote Similarity	NPC115013
0.5812	Remote Similarity	NPC472202
0.5812	Remote Similarity	NPC290012
0.5812	Remote Similarity	NPC477331
0.5812	Remote Similarity	NPC119583
0.5812	Remote Similarity	NPC169345
0.5812	Remote Similarity	NPC477319
0.5812	Remote Similarity	NPC307400
0.5812	Remote Similarity	NPC126685
0.5812	Remote Similarity	NPC472204
0.5812	Remote Similarity	NPC477317
0.5812	Remote Similarity	NPC44782
0.5812	Remote Similarity	NPC477318
0.5812	Remote Similarity	NPC27289
0.5812	Remote Similarity	NPC224953
0.5812	Remote Similarity	NPC123204
0.5812	Remote Similarity	NPC143421
0.5812	Remote Similarity	NPC472200
0.58	Remote Similarity	NPC302276
0.5769	Remote Similarity	NPC221148
0.5759	Remote Similarity	NPC475527
0.5758	Remote Similarity	NPC59589
0.5727	Remote Similarity	NPC250619
0.5726	Remote Similarity	NPC267592
0.5724	Remote Similarity	NPC162910
0.5714	Remote Similarity	NPC330590
0.5703	Remote Similarity	NPC474952
0.5695	Remote Similarity	NPC180770
0.5694	Remote Similarity	NPC314282
0.5677	Remote Similarity	NPC316249
0.5669	Remote Similarity	NPC160066
0.5664	Remote Similarity	NPC314451
0.5664	Remote Similarity	NPC313333
0.5664	Remote Similarity	NPC313342
0.5664	Remote Similarity	NPC314512
0.5659	Remote Similarity	NPC225978
0.5659	Remote Similarity	NPC255175
0.5659	Remote Similarity	NPC271207
0.5659	Remote Similarity	NPC206711
0.5652	Remote Similarity	NPC477350
0.5649	Remote Similarity	NPC141669
0.5649	Remote Similarity	NPC193579
0.5649	Remote Similarity	NPC298469
0.5649	Remote Similarity	NPC69176
0.5649	Remote Similarity	NPC284625
0.5646	Remote Similarity	NPC139585
0.5643	Remote Similarity	NPC313802
0.5643	Remote Similarity	NPC67917
0.5643	Remote Similarity	NPC314268
0.5643	Remote Similarity	NPC477515
0.5636	Remote Similarity	NPC32148
0.5634	Remote Similarity	NPC94319
0.563	Remote Similarity	NPC248415
0.5613	Remote Similarity	NPC214821
0.5613	Remote Similarity	NPC298067
0.5603	Remote Similarity	NPC216883
0.5603	Remote Similarity	NPC476783
0.5603	Remote Similarity	NPC476781
0.5603	Remote Similarity	NPC476782
0.56	Remote Similarity	NPC472430

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 NPC305261 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	121
0.1-0.2	2662
0.2-0.3	4719
0.3-0.4	1299
0.4-0.5	222
0.5-0.6	94
0.6-0.7	26
0.7-0.8	3
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8378	Intermediate Similarity	NPD7140	Approved
0.8378	Intermediate Similarity	NPD7139	Approved
0.8378	Intermediate Similarity	NPD7141	Clinical (unspecified phase)
0.8273	Intermediate Similarity	NPD2255	Approved
0.7818	Intermediate Similarity	NPD1447	Phase 3
0.7818	Intermediate Similarity	NPD1446	Phase 3
0.7391	Intermediate Similarity	NPD881	Approved
0.7073	Intermediate Similarity	NPD6941	Approved
0.6723	Remote Similarity	NPD6428	Approved
0.664	Remote Similarity	NPD8307	Discontinued
0.6636	Remote Similarity	NPD7329	Approved
0.6609	Remote Similarity	NPD4759	Clinical (unspecified phase)
0.656	Remote Similarity	NPD8393	Approved
0.6552	Remote Similarity	NPD618	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD8275	Approved
0.6532	Remote Similarity	NPD8276	Approved
0.6508	Remote Similarity	NPD8140	Approved
0.6496	Remote Similarity	NPD3716	Discontinued
0.6484	Remote Similarity	NPD8087	Discontinued
0.6452	Remote Similarity	NPD8086	Approved
0.6452	Remote Similarity	NPD8139	Approved
0.6452	Remote Similarity	NPD8085	Approved
0.6452	Remote Similarity	NPD8138	Approved
0.6452	Remote Similarity	NPD8084	Approved
0.6452	Remote Similarity	NPD8083	Approved
0.6452	Remote Similarity	NPD8082	Approved
0.6418	Remote Similarity	NPD8345	Approved
0.6418	Remote Similarity	NPD8346	Approved
0.6418	Remote Similarity	NPD8347	Approved
0.6406	Remote Similarity	NPD8305	Approved
0.6406	Remote Similarity	NPD8306	Approved
0.6349	Remote Similarity	NPD8081	Approved
0.619	Remote Similarity	NPD8301	Approved
0.619	Remote Similarity	NPD8300	Approved
0.6142	Remote Similarity	NPD8045	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD619	Phase 3
0.6016	Remote Similarity	NPD8394	Approved
0.5899	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5857	Remote Similarity	NPD8080	Discontinued
0.5821	Remote Similarity	NPD2690	Discontinued
0.5818	Remote Similarity	NPD9445	Approved
0.5804	Remote Similarity	NPD3181	Approved
0.5793	Remote Similarity	NPD8391	Approved
0.5793	Remote Similarity	NPD8392	Approved
0.5793	Remote Similarity	NPD8390	Approved
0.5769	Remote Similarity	NPD1407	Approved
0.5769	Remote Similarity	NPD1450	Approved
0.5769	Remote Similarity	NPD1449	Approved
0.5725	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5377	Approved
0.5714	Remote Similarity	NPD5378	Approved
0.5714	Remote Similarity	NPD5381	Approved
0.5694	Remote Similarity	NPD8448	Approved
0.5693	Remote Similarity	NPD7915	Approved
0.5693	Remote Similarity	NPD7916	Approved
0.5682	Remote Similarity	NPD5376	Approved
0.5664	Remote Similarity	NPD8342	Approved
0.5664	Remote Similarity	NPD8340	Approved
0.5664	Remote Similarity	NPD8341	Approved
0.5664	Remote Similarity	NPD8299	Approved
0.5636	Remote Similarity	NPD896	Approved
0.5636	Remote Similarity	NPD898	Approved
0.5636	Remote Similarity	NPD897	Approved
0.5634	Remote Similarity	NPD4827	Approved
0.5634	Remote Similarity	NPD4826	Approved
0.5634	Remote Similarity	NPD4828	Approved
0.5625	Remote Similarity	NPD8451	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