NPASS Compound

Structure

NPC475266 OpenBabel07101719122D 54 57 0 0 1 0 0 0 0 0999 V2000 -16.8280 -0.9590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6637 0.6386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.2622 -1.3499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.8500 -0.5409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2677 -1.2454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.8445 -0.6454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.8609 -0.3318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.4323 0.1636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8664 -0.2273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.4268 0.0591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4597 0.6862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -17.0091 0.7635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0972 4.2916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2437 4.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 1.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -17.4158 -0.1500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 0.7431 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -16.0146 0.8681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8893 3.3135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.4651 0.7908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 4.4067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6456 0.4067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.0482 4.6006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0584 1.7043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 1.6092 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.5584 2.5703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 3.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5116 -0.0933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8090 1.4013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3776 0.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2437 2.9067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.0803 1.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 3.4067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3776 1.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9135 0.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -18.4104 -0.2545 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -15.6078 1.7816 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -9.2561 5.5788 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.9757 2.9067 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.8774 -0.0183 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 4.9067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.7914 3.9315 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5759 2.5227 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5529 2.6749 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 2.9067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 -1.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5522 2.0704 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2437 -0.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3371 1.2431 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 4.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 1.9067 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 -1.7796 -0.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2437 1.9067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 8 2 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 2 0 0 0 0 10 18 2 0 0 0 0 11 20 1 0 0 0 0 12 16 2 0 0 0 0 12 18 1 0 0 0 0 13 23 1 0 0 0 0 14 21 1 0 0 0 0 14 50 1 0 0 0 0 15 22 1 0 0 0 0 15 51 1 0 0 0 0 16 36 1 0 0 0 0 17 2 1 1 0 0 0 17 25 1 0 0 0 0 17 52 1 0 0 0 0 18 37 1 0 0 0 0 19 13 1 6 0 0 0 19 26 1 0 0 0 0 19 39 1 0 0 0 0 20 24 2 0 0 0 0 20 40 1 0 0 0 0 21 27 1 0 0 0 0 21 41 1 1 0 0 0 22 28 1 0 0 0 0 22 53 1 1 0 0 0 23 38 2 0 0 0 0 23 42 1 0 0 0 0 24 26 1 0 0 0 0 24 32 1 0 0 0 0 25 29 1 0 0 0 0 25 43 1 6 0 0 0 26 44 2 0 0 0 0 27 31 1 0 0 0 0 27 45 1 6 0 0 0 28 30 1 0 0 0 0 28 46 1 1 0 0 0 29 35 1 0 0 0 0 29 47 1 1 0 0 0 30 34 1 0 0 0 0 30 48 1 6 0 0 0 31 33 1 0 0 0 0 31 54 1 1 0 0 0 32 39 1 0 0 0 0 32 49 2 0 0 0 0 33 39 1 6 0 0 0 33 50 1 0 0 0 0 34 51 1 0 0 0 0 34 54 1 6 0 0 0 35 52 1 0 0 0 0 35 53 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	802.21
Volume:	737.595
LogP:	0.004
LogD:	0.055
LogS:	-2.63
# Rotatable Bonds:	14
TPSA:	273.08
# H-Bond Aceptor:	17
# H-Bond Donor:	10
# Rings:	4
# Heavy Atoms:	19

MedChem Properties

QED Drug-Likeness Score:	0.069
Synthetic Accessibility Score:	6.084
Fsp3:	0.486
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:	-5.764
MDCK Permeability:	4.559517037705518e-06
Pgp-inhibitor:	0.113
Pgp-substrate:	0.049
Human Intestinal Absorption (HIA):	0.524
20% Bioavailability (F20%):	0.443
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.053
Plasma Protein Binding (PPB):	95.08142852783203%
Volume Distribution (VD):	0.451
Pgp-substrate:	7.497861385345459%

ADMET: Metabolism

CYP1A2-inhibitor:	0.109
CYP1A2-substrate:	0.009
CYP2C19-inhibitor:	0.15
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.043
CYP2C9-substrate:	0.837
CYP2D6-inhibitor:	0.035
CYP2D6-substrate:	0.193
CYP3A4-inhibitor:	0.381
CYP3A4-substrate:	0.045

ADMET: Excretion

Clearance (CL):	0.335
Half-life (T1/2):	0.389

ADMET: Toxicity

hERG Blockers:	0.06
Human Hepatotoxicity (H-HT):	0.52
Drug-inuced Liver Injury (DILI):	0.98
AMES Toxicity:	0.856
Rat Oral Acute Toxicity:	0.033
Maximum Recommended Daily Dose:	0.123
Skin Sensitization:	0.831
Carcinogencity:	0.846
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.73

Download Data

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

Natural Product: NPC475266

Natural Product ID:	NPC475266
*Common Name:**	Aurantoside B
IUPAC Name:	2-[(2S,4Z)-4-[(2E,4E,6E,8E,10Z,12E)-11,13-dichloro-1-hydroxytetradeca-2,4,6,8,10,12-hexaenylidene]-1-[(2R,3R,4S,5R)-3-[(2S,3S,4S,5R)-5-[(2S,3S,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]oxy-3,4-dihydroxyoxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]-3,5-dioxopyrrolidin-2-yl]acetamide
Synonyms:
Standard InCHIKey:	YZIOORMSEXDTKB-OBRNCPAPSA-N
Standard InCHI:	InChI=1S/C35H44Cl2N2O15/c1-16(36)12-18(37)10-8-6-4-3-5-7-9-11-20(40)24-26(44)19(13-23(38)42)39(32(24)49)33-31(27(45)21(41)14-50-33)54-34-30(48)28(46)22(15-51-34)53-35-29(47)25(43)17(2)52-35/h3-12,17,19,21-22,25,27-31,33-35,40-41,43,45-48H,13-15H2,1-2H3,(H2,38,42)/b4-3+,7-5+,8-6+,11-9+,16-12+,18-10-,24-20-/t17-,19+,21-,22-,25-,27+,28-,29+,30+,31-,33-,34+,35+/m1/s1
SMILES:	OC(=N)C[C@H]1C(=O)/C(=C(C=CC=CC=CC=CC=C(C=C(Cl)/C)/Cl)/O)/C(=O)N1[C@@H]1OC[C@H]([C@@H]([C@H]1O[C@@H]1OC[C@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@@H]([C@H]([C@@H]1O)O)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL502323
PubChem CID:	54730004
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0000198] Oligosaccharides

*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
NPO25388	Siliquariaspongia japonica	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10425118]
NPO25388	Siliquariaspongia japonica	n.a.	n.a.	n.a.	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
IC50	1
MIC	2
Others	2

Activity Type	# Activity
Cell Line	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	>	5.0	ug.mL-1	PMID[565973]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	0.63	ug.mL-1	PMID[565973]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	11.8	mm	PMID[565973]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	IZ	=	17.2	mm	PMID[565973]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	=	0.16	ug.mL-1	PMID[565973]

☑ 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 NPC475266 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	136
0.1-0.2	997
0.2-0.3	9260
0.3-0.4	22830
0.4-0.5	8397
0.5-0.6	1043
0.6-0.7	25
0.7-0.8	2
0.8-0.85	0
0.85-0.9	1
0.9-0.95	1
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC247776
1.0	High Similarity	NPC304299
1.0	High Similarity	NPC309450
1.0	High Similarity	NPC475278
0.9697	High Similarity	NPC71866
0.8769	High Similarity	NPC36254
0.8042	Intermediate Similarity	NPC315848
0.8042	Intermediate Similarity	NPC315210
0.6536	Remote Similarity	NPC471256
0.6531	Remote Similarity	NPC471255
0.6449	Remote Similarity	NPC201128
0.6447	Remote Similarity	NPC120335
0.6443	Remote Similarity	NPC471263
0.6443	Remote Similarity	NPC315058
0.6424	Remote Similarity	NPC313962
0.6405	Remote Similarity	NPC314361
0.6351	Remote Similarity	NPC273185
0.6333	Remote Similarity	NPC309525
0.6284	Remote Similarity	NPC315188
0.6268	Remote Similarity	NPC251122
0.6258	Remote Similarity	NPC78189
0.625	Remote Similarity	NPC316244
0.6242	Remote Similarity	NPC471262
0.6242	Remote Similarity	NPC230889
0.6214	Remote Similarity	NPC475918
0.6205	Remote Similarity	NPC315809
0.6205	Remote Similarity	NPC314050
0.62	Remote Similarity	NPC314629
0.619	Remote Similarity	NPC477398
0.6159	Remote Similarity	NPC314451
0.6159	Remote Similarity	NPC313333
0.6159	Remote Similarity	NPC313342
0.6159	Remote Similarity	NPC314512
0.6104	Remote Similarity	NPC316205
0.6104	Remote Similarity	NPC315387
0.6103	Remote Similarity	NPC8098
0.6103	Remote Similarity	NPC197294
0.6103	Remote Similarity	NPC45313
0.6103	Remote Similarity	NPC183449
0.6096	Remote Similarity	NPC103391
0.6096	Remote Similarity	NPC472536
0.6084	Remote Similarity	NPC298484
0.6071	Remote Similarity	NPC55336
0.6069	Remote Similarity	NPC314306
0.6067	Remote Similarity	NPC477462
0.6065	Remote Similarity	NPC477988
0.6053	Remote Similarity	NPC470653
0.6053	Remote Similarity	NPC470654
0.6053	Remote Similarity	NPC470650
0.6036	Remote Similarity	NPC475342
0.6023	Remote Similarity	NPC327517
0.6023	Remote Similarity	NPC319334
0.6023	Remote Similarity	NPC322372
0.6013	Remote Similarity	NPC99864
0.5987	Remote Similarity	NPC325750
0.5974	Remote Similarity	NPC314282
0.5973	Remote Similarity	NPC235625
0.5959	Remote Similarity	NPC314550
0.5959	Remote Similarity	NPC469865
0.5956	Remote Similarity	NPC256570
0.5956	Remote Similarity	NPC158445
0.5956	Remote Similarity	NPC156782
0.5956	Remote Similarity	NPC70323
0.5956	Remote Similarity	NPC157353
0.5956	Remote Similarity	NPC54961
0.5956	Remote Similarity	NPC23454
0.5956	Remote Similarity	NPC262312
0.5956	Remote Similarity	NPC282088
0.5956	Remote Similarity	NPC192066
0.5956	Remote Similarity	NPC17290
0.5956	Remote Similarity	NPC35269
0.5956	Remote Similarity	NPC3568
0.5949	Remote Similarity	NPC120420
0.5948	Remote Similarity	NPC97580
0.5948	Remote Similarity	NPC469494
0.5948	Remote Similarity	NPC204639
0.5944	Remote Similarity	NPC315426
0.5935	Remote Similarity	NPC329919
0.5935	Remote Similarity	NPC477793
0.5935	Remote Similarity	NPC470651
0.5935	Remote Similarity	NPC470655
0.5929	Remote Similarity	NPC188785
0.5924	Remote Similarity	NPC316401
0.5906	Remote Similarity	NPC6531
0.5903	Remote Similarity	NPC474099
0.5894	Remote Similarity	NPC470652
0.589	Remote Similarity	NPC476875
0.5879	Remote Similarity	NPC298067
0.5879	Remote Similarity	NPC214821
0.5878	Remote Similarity	NPC475975
0.5878	Remote Similarity	NPC272166
0.5871	Remote Similarity	NPC247902
0.5871	Remote Similarity	NPC262880
0.5855	Remote Similarity	NPC160688
0.5852	Remote Similarity	NPC209047
0.5852	Remote Similarity	NPC43074
0.5852	Remote Similarity	NPC242503
0.5852	Remote Similarity	NPC139782
0.5852	Remote Similarity	NPC74672
0.585	Remote Similarity	NPC478024
0.5845	Remote Similarity	NPC476877
0.5844	Remote Similarity	NPC469999
0.5839	Remote Similarity	NPC30196
0.5838	Remote Similarity	NPC297145
0.5838	Remote Similarity	NPC321485
0.5838	Remote Similarity	NPC197743
0.5838	Remote Similarity	NPC317377
0.5833	Remote Similarity	NPC471820
0.5833	Remote Similarity	NPC471821
0.5818	Remote Similarity	NPC193579
0.5818	Remote Similarity	NPC298469
0.5809	Remote Similarity	NPC111567
0.5809	Remote Similarity	NPC473604
0.5809	Remote Similarity	NPC475125
0.5809	Remote Similarity	NPC475603
0.5809	Remote Similarity	NPC61894
0.5809	Remote Similarity	NPC309898
0.5809	Remote Similarity	NPC186840
0.5809	Remote Similarity	NPC263545
0.5809	Remote Similarity	NPC473581
0.5809	Remote Similarity	NPC282705
0.5809	Remote Similarity	NPC182632
0.5809	Remote Similarity	NPC473950
0.5809	Remote Similarity	NPC15851
0.5808	Remote Similarity	NPC61717
0.5808	Remote Similarity	NPC244380
0.5806	Remote Similarity	NPC477987
0.5806	Remote Similarity	NPC329401
0.5801	Remote Similarity	NPC471165
0.5799	Remote Similarity	NPC2501
0.5793	Remote Similarity	NPC207820
0.5793	Remote Similarity	NPC475150
0.5789	Remote Similarity	NPC122590
0.5789	Remote Similarity	NPC473341
0.5783	Remote Similarity	NPC52748
0.5782	Remote Similarity	NPC181510
0.5782	Remote Similarity	NPC47857
0.5782	Remote Similarity	NPC168758
0.5779	Remote Similarity	NPC293550
0.5779	Remote Similarity	NPC16709
0.5779	Remote Similarity	NPC477990
0.5779	Remote Similarity	NPC50520
0.5779	Remote Similarity	NPC323168
0.5779	Remote Similarity	NPC477989
0.5779	Remote Similarity	NPC111162
0.5779	Remote Similarity	NPC315783
0.5775	Remote Similarity	NPC474244
0.5769	Remote Similarity	NPC473249
0.5767	Remote Similarity	NPC180770
0.5764	Remote Similarity	NPC476876
0.5762	Remote Similarity	NPC17581
0.5762	Remote Similarity	NPC476155
0.5759	Remote Similarity	NPC41162
0.5753	Remote Similarity	NPC473578
0.5752	Remote Similarity	NPC469515
0.5745	Remote Similarity	NPC233932
0.5743	Remote Similarity	NPC60432
0.5743	Remote Similarity	NPC1111
0.5743	Remote Similarity	NPC261750
0.574	Remote Similarity	NPC298005
0.574	Remote Similarity	NPC36463
0.5733	Remote Similarity	NPC66007
0.5733	Remote Similarity	NPC296043
0.5732	Remote Similarity	NPC173173
0.5724	Remote Similarity	NPC313802
0.5724	Remote Similarity	NPC67917
0.5724	Remote Similarity	NPC314268
0.5724	Remote Similarity	NPC477515
0.5723	Remote Similarity	NPC69176
0.5723	Remote Similarity	NPC139585
0.5723	Remote Similarity	NPC284625
0.5705	Remote Similarity	NPC313173
0.5698	Remote Similarity	NPC475599
0.5698	Remote Similarity	NPC113620
0.5698	Remote Similarity	NPC100612
0.5698	Remote Similarity	NPC187497
0.5698	Remote Similarity	NPC174336
0.5697	Remote Similarity	NPC162910
0.5695	Remote Similarity	NPC329216
0.5695	Remote Similarity	NPC65045
0.5694	Remote Similarity	NPC74035
0.5686	Remote Similarity	NPC11379
0.5683	Remote Similarity	NPC469739
0.5679	Remote Similarity	NPC472430
0.5679	Remote Similarity	NPC82129
0.5677	Remote Similarity	NPC316133
0.5677	Remote Similarity	NPC318445
0.5676	Remote Similarity	NPC29501
0.5671	Remote Similarity	NPC302276
0.5667	Remote Similarity	NPC471645
0.5664	Remote Similarity	NPC475149
0.5664	Remote Similarity	NPC471097
0.5663	Remote Similarity	NPC470886
0.5658	Remote Similarity	NPC106791
0.5658	Remote Similarity	NPC470300
0.5658	Remote Similarity	NPC201889
0.5655	Remote Similarity	NPC472433
0.5641	Remote Similarity	NPC477985
0.5641	Remote Similarity	NPC471087
0.5641	Remote Similarity	NPC326386

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 NPC475266 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	88
0.1-0.2	387
0.2-0.3	2771
0.3-0.4	4654
0.4-0.5	1114
0.5-0.6	132
0.6-0.7	4
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6159	Remote Similarity	NPD8342	Approved
0.6159	Remote Similarity	NPD8341	Approved
0.6159	Remote Similarity	NPD8340	Approved
0.6159	Remote Similarity	NPD8299	Approved
0.6081	Remote Similarity	NPD7641	Discontinued
0.6076	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6069	Remote Similarity	NPD6429	Approved
0.6069	Remote Similarity	NPD6430	Approved
0.6065	Remote Similarity	NPD8392	Approved
0.6065	Remote Similarity	NPD8391	Approved
0.6065	Remote Similarity	NPD8390	Approved
0.6013	Remote Similarity	NPD8451	Approved
0.6013	Remote Similarity	NPD8415	Approved
0.5974	Remote Similarity	NPD8448	Approved
0.5921	Remote Similarity	NPD6436	Phase 3
0.589	Remote Similarity	NPD8384	Approved
0.5878	Remote Similarity	NPD1000	Clinical (unspecified phase)
0.5852	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5845	Remote Similarity	NPD8045	Clinical (unspecified phase)
0.5845	Remote Similarity	NPD1407	Approved
0.5817	Remote Similarity	NPD7623	Phase 3
0.5817	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.58	Remote Similarity	NPD6936	Clinical (unspecified phase)
0.58	Remote Similarity	NPD6935	Phase 3
0.5779	Remote Similarity	NPD7830	Approved
0.5779	Remote Similarity	NPD7829	Approved
0.5769	Remote Similarity	NPD7747	Phase 1
0.5769	Remote Similarity	NPD7746	Phase 1
0.5733	Remote Similarity	NPD4830	Approved
0.5733	Remote Similarity	NPD4831	Approved
0.5733	Remote Similarity	NPD4832	Approved
0.5714	Remote Similarity	NPD8080	Discontinued
0.5705	Remote Similarity	NPD8273	Phase 1
0.5695	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5677	Remote Similarity	NPD7642	Approved
0.5649	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5649	Remote Similarity	NPD8444	Approved
0.5649	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.5643	Remote Similarity	NPD6428	Approved
0.5632	Remote Similarity	NPD8414	Discontinued
0.5608	Remote Similarity	NPD6421	Discontinued
0.5605	Remote Similarity	NPD4816	Clinical (unspecified phase)
0.56	Remote Similarity	NPD8417	Discontinued
0.56	Remote Similarity	NPD3731	Phase 3

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