NPASS Compound

Structure

CID181838 OpenBabel06191715562D 38 40 0 0 1 0 0 0 0 0999 V2000 -3.7253 -4.2876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8608 -5.8505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9103 -3.1304 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1671 -2.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3118 -1.4476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3359 -0.8124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5037 -1.4696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7446 0.8637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5924 -3.5708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6720 -2.2804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5037 0.5277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5378 0.7865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9576 -0.5968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4360 -4.5585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9811 -3.2315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5260 -3.2125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6939 -2.0725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0240 -0.2385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9053 -1.5955 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5561 -0.4710 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9932 -0.0522 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5024 -4.9169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9592 -3.4394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6824 -2.2248 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3849 -1.1215 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3947 -1.0156 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8731 -5.6940 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6701 -2.3812 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5928 -0.1433 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2464 -4.5984 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6225 -0.8293 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9394 -1.8543 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 4.2682 -4.3905 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 9 15 2 0 0 0 0 9 17 1 0 0 0 0 10 16 2 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 13 19 1 0 0 0 0 13 21 1 0 0 0 0 14 20 1 0 0 0 0 14 22 1 0 0 0 0 15 25 1 0 0 0 0 16 26 1 0 0 0 0 17 27 1 0 0 0 0 18 28 1 0 0 0 0 19 29 1 0 0 0 0 20 30 1 0 0 0 0 21 27 1 1 0 0 0 21 36 1 0 0 0 0 22 28 1 1 0 0 0 22 37 1 0 0 0 0 23 11 1 1 0 0 0 23 29 1 0 0 0 0 23 35 1 0 0 0 0 24 12 1 6 0 0 0 24 30 1 0 0 0 0 24 35 1 0 0 0 0 25 31 1 0 0 0 0 26 38 1 0 0 0 0 27 5 1 6 0 0 0 27 32 1 0 0 0 0 28 6 1 1 0 0 0 28 33 1 0 0 0 0 29 7 1 6 0 0 0 29 36 1 0 0 0 0 30 8 1 6 0 0 0 30 37 1 0 0 0 0 34 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	540.37
Volume:	566.816
LogP:	3.494
LogD:	2.698
LogS:	-4.468
# Rotatable Bonds:	11
TPSA:	117.84
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.167
Synthetic Accessibility Score:	5.566
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
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:	-4.751
MDCK Permeability:	1.7888167349155992e-05
Pgp-inhibitor:	0.861
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.352
20% Bioavailability (F20%):	0.718
30% Bioavailability (F30%):	0.061

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.031
Plasma Protein Binding (PPB):	91.27730560302734%
Volume Distribution (VD):	0.575
Pgp-substrate:	7.924720764160156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.103
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.703
CYP2C9-inhibitor:	0.026
CYP2C9-substrate:	0.097
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.151
CYP3A4-inhibitor:	0.331
CYP3A4-substrate:	0.259

ADMET: Excretion

Clearance (CL):	2.529
Half-life (T1/2):	0.658

ADMET: Toxicity

hERG Blockers:	0.086
Human Hepatotoxicity (H-HT):	0.893
Drug-inuced Liver Injury (DILI):	0.079
AMES Toxicity:	0.185
Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.536
Skin Sensitization:	0.929
Carcinogencity:	0.337
Eye Corrosion:	0.01
Eye Irritation:	0.127
Respiratory Toxicity:	0.096

Download Data

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

Natural Product: NPC181838

Natural Product ID:	NPC181838
*Common Name:**	(E,6R)-6-[(2R,5S)-5-[(2R,5R)-5-[(2S,5R)-5-[(E,2R)-6-Hydroperoxy-2-Hydroxy-6-Methylhept-4-En-2-Yl]-2-Methyloxolan-2-Yl]Oxolan-2-Yl]-5-Methyloxolan-2-Yl]-2-Methylhept-3-Ene-2,6-Diol
IUPAC Name:	(E,6R)-6-[(2R,5S)-5-[(2R,5R)-5-[(2S,5R)-5-[(E,2R)-6-hydroperoxy-2-hydroxy-6-methylhept-4-en-2-yl]-2-methyloxolan-2-yl]oxolan-2-yl]-5-methyloxolan-2-yl]-2-methylhept-3-ene-2,6-diol
Synonyms:
Standard InCHIKey:	QLFRXAKUUDRERJ-QICCULDKSA-N
Standard InCHI:	InChI=1S/C30H52O8/c1-25(2,31)15-9-17-27(5,32)21-13-19-29(7,36-21)23-11-12-24(35-23)30(8)20-14-22(37-30)28(6,33)18-10-16-26(3,4)38-34/h9-10,15-16,21-24,31-34H,11-14,17-20H2,1-8H3/b15-9+,16-10+/t21-,22-,23-,24-,27-,28-,29+,30+/m1/s1
SMILES:	CC(C)(/C=C/C[C@](C)([C@H]1CC[C@@](C)([C@H]2CC[C@H]([C@]3(C)CC[C@H]([C@@](C)(C/C=C/C(C)(C)OO)O)O3)O2)O1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454715
PubChem CID:	44585468
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12828478]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	Roots	n.a.	n.a.	PMID[14575431]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[15520511]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[15620254]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[1624939]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17027268]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	root	n.a.	PMID[1800638]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	roots	n.a.	n.a.	PMID[19299148]
NPO11530	Heterosigma akashiwo	Species	Chattonellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19659728]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19715321]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919052]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19931461]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23403897]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24467387]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	roots	n.a.	n.a.	PMID[25066952]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25905468]
NPO5401	Monanchora unguiculata	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28368118]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29667820]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO893	Helichrysum sutherlandii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13494	Prosopis kuntzei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13798	Cheilanthes marantae	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3924	Penicillium alutaceum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22888	Lophiostoma vaginatispora	Species	Lophiostomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11530	Heterosigma akashiwo	Species	Chattonellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12890	Ophryosporus charua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8640	Nemuaron humboldtii	Species	Atherospermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9024	Aralidium pinnatifidum	Species	Torricelliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8820	Lophocereus marginatus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13604	Dermocybe cardinalis	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12577	Pinus glauca	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8220	Russula sardonia	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1418	Boletinus paluster	Species	Gyrodontaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12988	Blainvillea latifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13692	Leontice kiangnanensis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2084	Acinetobacter calcoaceticus	Species	Moraxellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO6626	Pteris spinulosa	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20318	Acinetobacter baumannii	Species	Moraxellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5401	Monanchora unguiculata	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12026	Papaver radicatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11072	Geigeria schinzii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2505	Pachycereus pringlei	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20383	Stenocereus thurberi	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6014	Goniothalamus undulatus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9375	Medium grandiflorum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO14280	Helichrysum angustifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3576	Bersama swinnyi	Species	Melianthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO893	Helichrysum sutherlandii	Species	Asteraceae	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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	5.3	ug.mL-1	PMID[473071]

☑ 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 NPC181838 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	190
0.1-0.2	1632
0.2-0.3	6730
0.3-0.4	18052
0.4-0.5	10434
0.5-0.6	5032
0.6-0.7	603
0.7-0.8	20
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC137345
0.8904	High Similarity	NPC306085
0.8378	Intermediate Similarity	NPC16964
0.8125	Intermediate Similarity	NPC476701
0.7895	Intermediate Similarity	NPC472947
0.7875	Intermediate Similarity	NPC476703
0.7838	Intermediate Similarity	NPC250836
0.7778	Intermediate Similarity	NPC3852
0.7662	Intermediate Similarity	NPC74722
0.7662	Intermediate Similarity	NPC304690
0.7632	Intermediate Similarity	NPC73603
0.7564	Intermediate Similarity	NPC129630
0.7532	Intermediate Similarity	NPC305698
0.7531	Intermediate Similarity	NPC236228
0.7531	Intermediate Similarity	NPC256720
0.7412	Intermediate Similarity	NPC477390
0.7412	Intermediate Similarity	NPC477385
0.7407	Intermediate Similarity	NPC12696
0.7403	Intermediate Similarity	NPC259299
0.7375	Intermediate Similarity	NPC476709
0.7356	Intermediate Similarity	NPC298595
0.7333	Intermediate Similarity	NPC478003
0.7333	Intermediate Similarity	NPC478004
0.7333	Intermediate Similarity	NPC158388
0.7317	Intermediate Similarity	NPC170148
0.7303	Intermediate Similarity	NPC231784
0.7253	Intermediate Similarity	NPC472468
0.7209	Intermediate Similarity	NPC472465
0.7179	Intermediate Similarity	NPC82337
0.7159	Intermediate Similarity	NPC471494
0.7143	Intermediate Similarity	NPC68119
0.7143	Intermediate Similarity	NPC477089
0.7143	Intermediate Similarity	NPC13823
0.7143	Intermediate Similarity	NPC474761
0.7143	Intermediate Similarity	NPC476004
0.7143	Intermediate Similarity	NPC177668
0.7143	Intermediate Similarity	NPC473722
0.7143	Intermediate Similarity	NPC472466
0.7111	Intermediate Similarity	NPC476708
0.7108	Intermediate Similarity	NPC268111
0.7108	Intermediate Similarity	NPC329626
0.7097	Intermediate Similarity	NPC472467
0.7079	Intermediate Similarity	NPC311163
0.7079	Intermediate Similarity	NPC477387
0.7079	Intermediate Similarity	NPC477389
0.7073	Intermediate Similarity	NPC471525
0.7073	Intermediate Similarity	NPC190859
0.7051	Intermediate Similarity	NPC267027
0.7045	Intermediate Similarity	NPC186155
0.7045	Intermediate Similarity	NPC160517
0.7045	Intermediate Similarity	NPC78673
0.7033	Intermediate Similarity	NPC115607
0.7033	Intermediate Similarity	NPC97103
0.7033	Intermediate Similarity	NPC133450
0.7027	Intermediate Similarity	NPC152438
0.7027	Intermediate Similarity	NPC41180
0.7024	Intermediate Similarity	NPC477426
0.7024	Intermediate Similarity	NPC477427
0.7024	Intermediate Similarity	NPC477425
0.7024	Intermediate Similarity	NPC474826
0.7024	Intermediate Similarity	NPC40049
0.7024	Intermediate Similarity	NPC84360
0.7021	Intermediate Similarity	NPC36954
0.7	Intermediate Similarity	NPC179659
0.7	Intermediate Similarity	NPC477388
0.7	Intermediate Similarity	NPC477386
0.6989	Remote Similarity	NPC476300
0.6989	Remote Similarity	NPC81419
0.6989	Remote Similarity	NPC179746
0.6988	Remote Similarity	NPC36479
0.6977	Remote Similarity	NPC472948
0.6962	Remote Similarity	NPC163290
0.6957	Remote Similarity	NPC51004
0.6951	Remote Similarity	NPC477085
0.6933	Remote Similarity	NPC122239
0.6932	Remote Similarity	NPC471340
0.6915	Remote Similarity	NPC14322
0.6915	Remote Similarity	NPC256368
0.6905	Remote Similarity	NPC293223
0.6889	Remote Similarity	NPC247826
0.6889	Remote Similarity	NPC61527
0.6882	Remote Similarity	NPC12172
0.6882	Remote Similarity	NPC208886
0.6882	Remote Similarity	NPC208839
0.6882	Remote Similarity	NPC30515
0.6875	Remote Similarity	NPC272961
0.686	Remote Similarity	NPC471537
0.686	Remote Similarity	NPC86971
0.686	Remote Similarity	NPC72755
0.686	Remote Similarity	NPC233295
0.686	Remote Similarity	NPC476367
0.6848	Remote Similarity	NPC249408
0.6848	Remote Similarity	NPC473564
0.6848	Remote Similarity	NPC104129
0.6848	Remote Similarity	NPC307411
0.6837	Remote Similarity	NPC9878
0.6835	Remote Similarity	NPC311736
0.6829	Remote Similarity	NPC477087
0.6829	Remote Similarity	NPC477086
0.6813	Remote Similarity	NPC476948
0.6813	Remote Similarity	NPC160138
0.6809	Remote Similarity	NPC475912
0.6804	Remote Similarity	NPC475068
0.6804	Remote Similarity	NPC187268
0.679	Remote Similarity	NPC239373
0.679	Remote Similarity	NPC329989
0.6782	Remote Similarity	NPC76054
0.6782	Remote Similarity	NPC474592
0.6778	Remote Similarity	NPC11804
0.6778	Remote Similarity	NPC475206
0.6774	Remote Similarity	NPC3952
0.6774	Remote Similarity	NPC191323
0.6774	Remote Similarity	NPC313670
0.6771	Remote Similarity	NPC476315
0.6768	Remote Similarity	NPC86077
0.6765	Remote Similarity	NPC473069
0.6744	Remote Similarity	NPC475980
0.6742	Remote Similarity	NPC250315
0.6742	Remote Similarity	NPC231601
0.6742	Remote Similarity	NPC49208
0.6739	Remote Similarity	NPC309656
0.6739	Remote Similarity	NPC228415
0.6739	Remote Similarity	NPC87189
0.6737	Remote Similarity	NPC81386
0.6737	Remote Similarity	NPC474035
0.6709	Remote Similarity	NPC308844
0.6707	Remote Similarity	NPC4299
0.6705	Remote Similarity	NPC184208
0.6705	Remote Similarity	NPC246621
0.6705	Remote Similarity	NPC77003
0.6705	Remote Similarity	NPC471661
0.6705	Remote Similarity	NPC474894
0.6705	Remote Similarity	NPC8538
0.6705	Remote Similarity	NPC315731
0.6703	Remote Similarity	NPC476217
0.6703	Remote Similarity	NPC25703
0.6703	Remote Similarity	NPC282815
0.6703	Remote Similarity	NPC219652
0.6703	Remote Similarity	NPC473840
0.6702	Remote Similarity	NPC476705
0.6702	Remote Similarity	NPC184463
0.6701	Remote Similarity	NPC471490
0.6701	Remote Similarity	NPC2666
0.6667	Remote Similarity	NPC93794
0.6667	Remote Similarity	NPC475963
0.6667	Remote Similarity	NPC83702
0.6667	Remote Similarity	NPC91067
0.6667	Remote Similarity	NPC270013
0.6667	Remote Similarity	NPC471492
0.6667	Remote Similarity	NPC473504
0.6667	Remote Similarity	NPC42598
0.6667	Remote Similarity	NPC180725
0.6667	Remote Similarity	NPC20621
0.6667	Remote Similarity	NPC473508
0.6667	Remote Similarity	NPC477917
0.6667	Remote Similarity	NPC14961
0.6667	Remote Similarity	NPC318963
0.6667	Remote Similarity	NPC151176
0.6667	Remote Similarity	NPC92974
0.6667	Remote Similarity	NPC107476
0.6667	Remote Similarity	NPC52012
0.6667	Remote Similarity	NPC3464
0.6667	Remote Similarity	NPC224532
0.6667	Remote Similarity	NPC291260
0.6667	Remote Similarity	NPC40066
0.6667	Remote Similarity	NPC474280
0.6667	Remote Similarity	NPC139712
0.6667	Remote Similarity	NPC81778
0.6634	Remote Similarity	NPC220964
0.6634	Remote Similarity	NPC475676
0.6633	Remote Similarity	NPC203627
0.663	Remote Similarity	NPC316629
0.663	Remote Similarity	NPC258068
0.663	Remote Similarity	NPC476583
0.663	Remote Similarity	NPC20533
0.6629	Remote Similarity	NPC103171
0.6629	Remote Similarity	NPC474252
0.6628	Remote Similarity	NPC476439
0.6628	Remote Similarity	NPC471454
0.6628	Remote Similarity	NPC474278
0.6627	Remote Similarity	NPC477084
0.6623	Remote Similarity	NPC226872
0.6623	Remote Similarity	NPC158368
0.6623	Remote Similarity	NPC154908
0.6623	Remote Similarity	NPC258788
0.6623	Remote Similarity	NPC252851
0.6623	Remote Similarity	NPC469694
0.6622	Remote Similarity	NPC227135
0.6622	Remote Similarity	NPC281590
0.6598	Remote Similarity	NPC472995
0.6598	Remote Similarity	NPC210717
0.6598	Remote Similarity	NPC103165
0.6598	Remote Similarity	NPC279621
0.6598	Remote Similarity	NPC473333
0.6596	Remote Similarity	NPC239517
0.6596	Remote Similarity	NPC477866
0.6596	Remote Similarity	NPC477865
0.6596	Remote Similarity	NPC473448
0.6593	Remote Similarity	NPC292809
0.6593	Remote Similarity	NPC290731

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 NPC181838 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	2291
0.2-0.3	4208
0.3-0.4	1929
0.4-0.5	442
0.5-0.6	97
0.6-0.7	16
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
0.6813	Remote Similarity	NPD7524	Approved
0.6774	Remote Similarity	NPD7838	Discovery
0.6702	Remote Similarity	NPD7983	Approved
0.663	Remote Similarity	NPD4250	Approved
0.663	Remote Similarity	NPD4251	Approved
0.6556	Remote Similarity	NPD6695	Phase 3
0.6522	Remote Similarity	NPD4249	Approved
0.6484	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD46	Approved
0.6421	Remote Similarity	NPD6698	Approved
0.6346	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD5344	Discontinued
0.63	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD7750	Discontinued
0.6262	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD6930	Phase 2
0.6222	Remote Similarity	NPD4820	Approved
0.6222	Remote Similarity	NPD4822	Approved
0.6222	Remote Similarity	NPD4821	Approved
0.6222	Remote Similarity	NPD6931	Approved
0.6222	Remote Similarity	NPD4819	Approved
0.6222	Remote Similarity	NPD7332	Phase 2
0.6222	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD7514	Phase 3
0.6196	Remote Similarity	NPD5362	Discontinued
0.6196	Remote Similarity	NPD7154	Phase 3
0.6154	Remote Similarity	NPD4790	Discontinued
0.6136	Remote Similarity	NPD6933	Approved
0.6111	Remote Similarity	NPD6929	Approved
0.6078	Remote Similarity	NPD6648	Approved
0.6061	Remote Similarity	NPD5282	Discontinued
0.6022	Remote Similarity	NPD5331	Approved
0.6022	Remote Similarity	NPD5332	Approved
0.602	Remote Similarity	NPD7087	Discontinued
0.6	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7145	Approved
0.6	Remote Similarity	NPD4271	Approved
0.6	Remote Similarity	NPD4268	Approved
0.5978	Remote Similarity	NPD6902	Approved
0.5977	Remote Similarity	NPD4732	Discontinued
0.596	Remote Similarity	NPD5779	Approved
0.596	Remote Similarity	NPD5778	Approved
0.5926	Remote Similarity	NPD368	Approved
0.5914	Remote Similarity	NPD4270	Approved
0.5914	Remote Similarity	NPD4269	Approved
0.5909	Remote Similarity	NPD6924	Approved
0.5909	Remote Similarity	NPD6926	Approved
0.5895	Remote Similarity	NPD6893	Approved
0.5889	Remote Similarity	NPD6932	Approved
0.5889	Remote Similarity	NPD6925	Approved
0.5889	Remote Similarity	NPD5776	Phase 2
0.5872	Remote Similarity	NPD6371	Approved
0.5859	Remote Similarity	NPD7637	Suspended
0.5851	Remote Similarity	NPD6110	Phase 1
0.5843	Remote Similarity	NPD8264	Approved
0.5833	Remote Similarity	NPD5786	Approved
0.5825	Remote Similarity	NPD4225	Approved
0.5824	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD6898	Phase 1
0.5806	Remote Similarity	NPD5369	Approved
0.5784	Remote Similarity	NPD7839	Suspended
0.5784	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD342	Phase 1
0.5758	Remote Similarity	NPD3168	Discontinued
0.5758	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.575	Remote Similarity	NPD585	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD5363	Approved
0.5729	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD4252	Approved
0.5688	Remote Similarity	NPD6686	Approved
0.5648	Remote Similarity	NPD6640	Phase 3
0.5641	Remote Similarity	NPD8517	Approved
0.5641	Remote Similarity	NPD8513	Phase 3
0.5641	Remote Similarity	NPD8515	Approved
0.5641	Remote Similarity	NPD8516	Approved
0.5625	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD7639	Approved
0.5619	Remote Similarity	NPD7640	Approved
0.561	Remote Similarity	NPD1145	Discontinued
0.56	Remote Similarity	NPD5785	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