NPASS Compound

Structure

CID226491 OpenBabel06191716022D 31 34 0 0 1 0 0 0 0 0999 V2000 6.9833 -0.8003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8022 0.9223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7631 -3.5409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 -1.3501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9942 -1.0093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4010 -0.0958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5820 -1.8183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 -3.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 -3.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2026 -1.1422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8717 -0.3991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3955 0.0088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1753 -2.7319 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1808 -2.8364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 -2.0933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5627 0.5520 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 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 17 1 0 0 0 0 2 17 1 0 0 0 0 5 26 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 11 19 1 0 0 0 0 12 26 1 0 0 0 0 13 14 1 0 0 0 0 13 25 1 0 0 0 0 14 28 1 0 0 0 0 15 23 1 0 0 0 0 16 19 1 0 0 0 0 18 3 1 1 0 0 0 18 21 1 0 0 0 0 19 29 1 6 0 0 0 20 15 1 1 0 0 0 20 22 1 0 0 0 0 20 24 1 0 0 0 0 21 25 1 1 0 0 0 22 25 1 1 0 0 0 23 27 1 6 0 0 0 23 31 1 0 0 0 0 24 26 1 0 0 0 0 24 30 2 0 0 0 0 25 4 1 1 0 0 0 26 27 1 6 0 0 0 27 16 1 1 0 0 0 27 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	434.34
Volume:	473.847
LogP:	5.111
LogD:	5.202
LogS:	-5.371
# Rotatable Bonds:	8
TPSA:	70.06
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.519
Synthetic Accessibility Score:	5.401
Fsp3:	0.963
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.701
MDCK Permeability:	3.090704558417201e-05
Pgp-inhibitor:	0.444
Pgp-substrate:	0.744
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.503
30% Bioavailability (F30%):	0.433

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.259
Plasma Protein Binding (PPB):	96.53018951416016%
Volume Distribution (VD):	1.324
Pgp-substrate:	1.6380912065505981%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.377
CYP2C19-inhibitor:	0.079
CYP2C19-substrate:	0.893
CYP2C9-inhibitor:	0.328
CYP2C9-substrate:	0.069
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.034
CYP3A4-inhibitor:	0.908
CYP3A4-substrate:	0.79

ADMET: Excretion

Clearance (CL):	13.181
Half-life (T1/2):	0.156

ADMET: Toxicity

hERG Blockers:	0.203
Human Hepatotoxicity (H-HT):	0.272
Drug-inuced Liver Injury (DILI):	0.201
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.833
Maximum Recommended Daily Dose:	0.36
Skin Sensitization:	0.415
Carcinogencity:	0.187
Eye Corrosion:	0.926
Eye Irritation:	0.718
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC226491

Natural Product ID:	NPC226491
*Common Name:**	3Beta,11Alpha-Dihydroxy-5Beta,6Beta-Epoxy-9,11-Secocholestan-9-One
IUPAC Name:	(1aR,3S,4aS,7S,8aS)-7-hydroxy-3-[(1S,2R,3R)-2-(2-hydroxyethyl)-2-methyl-3-[(2R)-6-methylheptan-2-yl]cyclopentyl]-4a-methyl-2,3,5,6,7,8-hexahydro-1aH-naphtho[4,4a-b]oxiren-4-one
Synonyms:
Standard InCHIKey:	QKTFOALELBKRRS-YBHPAICNSA-N
Standard InCHI:	InChI=1S/C27H46O4/c1-17(2)7-6-8-18(3)21-9-10-22(25(21,4)13-14-28)20-15-23-27(31-23)16-19(29)11-12-26(27,5)24(20)30/h17-23,28-29H,6-16H2,1-5H3/t18-,19+,20+,21-,22+,23-,25-,26-,27-/m1/s1
SMILES:	CC(C)CCC[C@@H](C)[C@H]1CC[C@@H]([C@@H]2C[C@@H]3[C@@]4(C[C@H](CC[C@]4(C)C2=O)O)O3)[C@]1(C)CCO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL525180
PubChem CID:	16083145
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO24310	Cespitularia hypotentaculata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398538]
NPO24310	Cespitularia hypotentaculata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16933873]
NPO22004	Cystodytes solitus	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18484775]
NPO24310	Cespitularia hypotentaculata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19061391]
NPO24805	Thorecta reticulata	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21513294]
NPO25343	Tanacetum microphyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25548	Balanophora indica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25548	Balanophora indica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25343	Tanacetum microphyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25548	Balanophora indica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5278	Acacia cyperophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11177	0ctiluca scintillans	Species	0ctilucaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24616	Ottonia vahlii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO5543	Persicaria tomentosa	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25205	Thymus borgiae	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3706	Hedypnois rhagadioloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25343	Tanacetum microphyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24310	Cespitularia hypotentaculata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24805	Thorecta reticulata	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24435	Beschorneria bracteata	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25684	Fagus dombeyi	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25631	Picris kamtschatica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25606	Aster patagonicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22004	Cystodytes solitus	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25314	Usnea ceratina	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25655	Pseudocyphellaria granulata	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23999	Rhipidothuria racowitzai	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO2404	Heterophragma quadriloculare	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6639	Flagelloscypha pilatii	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25427	Solanum vespertilio	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24482	Phyllanthus oxyphyllus	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25516	Dahlia sherffii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25452	Crucigenia apiculata	Species	Scenedesmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25548	Balanophora indica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28702	Cyclolepis genistoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23333	Michelia excelsa	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25485	Agathosma lanceolata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20428	Debregeasia salicifolia	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19210	Quercus lusitanica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25061	Lactarius glyciosmus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	1.0	ug ml-1	PMID[513634]

☑ 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 NPC226491 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	399
0.1-0.2	3342
0.2-0.3	8445
0.3-0.4	14055
0.4-0.5	6244
0.5-0.6	6242
0.6-0.7	3216
0.7-0.8	684
0.8-0.85	51
0.85-0.9	14
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477614
0.9318	High Similarity	NPC17336
0.9186	High Similarity	NPC61688
0.9111	High Similarity	NPC111187
0.9111	High Similarity	NPC190080
0.9048	High Similarity	NPC50438
0.8941	High Similarity	NPC473350
0.8824	High Similarity	NPC475689
0.8736	High Similarity	NPC263802
0.8681	High Similarity	NPC62407
0.8681	High Similarity	NPC287354
0.8667	High Similarity	NPC476189
0.8621	High Similarity	NPC474215
0.8621	High Similarity	NPC475729
0.8605	High Similarity	NPC477434
0.8602	High Similarity	NPC476294
0.8554	High Similarity	NPC475725
0.8409	Intermediate Similarity	NPC302111
0.8391	Intermediate Similarity	NPC473336
0.8391	Intermediate Similarity	NPC471044
0.8333	Intermediate Similarity	NPC24705
0.8333	Intermediate Similarity	NPC200580
0.8333	Intermediate Similarity	NPC56962
0.8333	Intermediate Similarity	NPC477440
0.8333	Intermediate Similarity	NPC477443
0.8315	Intermediate Similarity	NPC202937
0.8276	Intermediate Similarity	NPC227170
0.8256	Intermediate Similarity	NPC254123
0.8247	Intermediate Similarity	NPC34562
0.8242	Intermediate Similarity	NPC477444
0.8242	Intermediate Similarity	NPC477442
0.8242	Intermediate Similarity	NPC476296
0.8242	Intermediate Similarity	NPC477433
0.8235	Intermediate Similarity	NPC275243
0.8202	Intermediate Similarity	NPC80700
0.8202	Intermediate Similarity	NPC83242
0.8191	Intermediate Similarity	NPC477264
0.8191	Intermediate Similarity	NPC193785
0.8191	Intermediate Similarity	NPC116683
0.8172	Intermediate Similarity	NPC470424
0.8172	Intermediate Similarity	NPC477495
0.8152	Intermediate Similarity	NPC52756
0.8144	Intermediate Similarity	NPC471254
0.8132	Intermediate Similarity	NPC67653
0.8132	Intermediate Similarity	NPC471459
0.8111	Intermediate Similarity	NPC239938
0.8095	Intermediate Similarity	NPC472487
0.8095	Intermediate Similarity	NPC472486
0.809	Intermediate Similarity	NPC477445
0.809	Intermediate Similarity	NPC477205
0.8068	Intermediate Similarity	NPC327451
0.8068	Intermediate Similarity	NPC15091
0.8046	Intermediate Similarity	NPC469745
0.8043	Intermediate Similarity	NPC77756
0.8041	Intermediate Similarity	NPC46848
0.8022	Intermediate Similarity	NPC471221
0.8022	Intermediate Similarity	NPC90676
0.8	Intermediate Similarity	NPC475031
0.8	Intermediate Similarity	NPC163685
0.8	Intermediate Similarity	NPC476726
0.8	Intermediate Similarity	NPC476727
0.8	Intermediate Similarity	NPC235109
0.8	Intermediate Similarity	NPC472745
0.798	Intermediate Similarity	NPC88469
0.7978	Intermediate Similarity	NPC219535
0.7978	Intermediate Similarity	NPC319909
0.7978	Intermediate Similarity	NPC25037
0.7978	Intermediate Similarity	NPC34984
0.7978	Intermediate Similarity	NPC237938
0.7976	Intermediate Similarity	NPC21220
0.7976	Intermediate Similarity	NPC125767
0.7976	Intermediate Similarity	NPC159789
0.7961	Intermediate Similarity	NPC476964
0.7959	Intermediate Similarity	NPC275990
0.7959	Intermediate Similarity	NPC470172
0.7955	Intermediate Similarity	NPC268040
0.7955	Intermediate Similarity	NPC317066
0.7938	Intermediate Similarity	NPC94906
0.7917	Intermediate Similarity	NPC170978
0.7907	Intermediate Similarity	NPC471769
0.7895	Intermediate Similarity	NPC82633
0.7882	Intermediate Similarity	NPC474020
0.7879	Intermediate Similarity	NPC473406
0.7879	Intermediate Similarity	NPC471253
0.7872	Intermediate Similarity	NPC161035
0.7865	Intermediate Similarity	NPC292458
0.7865	Intermediate Similarity	NPC268578
0.7865	Intermediate Similarity	NPC472847
0.7865	Intermediate Similarity	NPC217559
0.7857	Intermediate Similarity	NPC178853
0.7849	Intermediate Similarity	NPC88337
0.7849	Intermediate Similarity	NPC475211
0.7841	Intermediate Similarity	NPC475743
0.7835	Intermediate Similarity	NPC98837
0.7835	Intermediate Similarity	NPC474793
0.7835	Intermediate Similarity	NPC38296
0.7835	Intermediate Similarity	NPC20479
0.7835	Intermediate Similarity	NPC472028
0.7835	Intermediate Similarity	NPC471038
0.7835	Intermediate Similarity	NPC253995
0.7835	Intermediate Similarity	NPC28864
0.7835	Intermediate Similarity	NPC162459
0.7835	Intermediate Similarity	NPC38471
0.7826	Intermediate Similarity	NPC3032
0.7826	Intermediate Similarity	NPC476379
0.7826	Intermediate Similarity	NPC473319
0.7826	Intermediate Similarity	NPC476435
0.7826	Intermediate Similarity	NPC131104
0.7816	Intermediate Similarity	NPC320144
0.7816	Intermediate Similarity	NPC80891
0.7816	Intermediate Similarity	NPC201276
0.7812	Intermediate Similarity	NPC476728
0.7802	Intermediate Similarity	NPC476717
0.7802	Intermediate Similarity	NPC472272
0.7802	Intermediate Similarity	NPC477441
0.78	Intermediate Similarity	NPC327093
0.78	Intermediate Similarity	NPC470167
0.7791	Intermediate Similarity	NPC221420
0.7791	Intermediate Similarity	NPC471151
0.7791	Intermediate Similarity	NPC476233
0.7791	Intermediate Similarity	NPC23884
0.7791	Intermediate Similarity	NPC143250
0.7789	Intermediate Similarity	NPC470423
0.7778	Intermediate Similarity	NPC304832
0.7778	Intermediate Similarity	NPC473299
0.7778	Intermediate Similarity	NPC124544
0.7778	Intermediate Similarity	NPC76866
0.7778	Intermediate Similarity	NPC246736
0.7778	Intermediate Similarity	NPC286519
0.7778	Intermediate Similarity	NPC148628
0.7778	Intermediate Similarity	NPC214946
0.7778	Intermediate Similarity	NPC88203
0.7766	Intermediate Similarity	NPC216137
0.7765	Intermediate Similarity	NPC35871
0.7765	Intermediate Similarity	NPC273366
0.7765	Intermediate Similarity	NPC68565
0.7755	Intermediate Similarity	NPC180733
0.7755	Intermediate Similarity	NPC41971
0.7755	Intermediate Similarity	NPC37047
0.7755	Intermediate Similarity	NPC293866
0.7753	Intermediate Similarity	NPC289486
0.7753	Intermediate Similarity	NPC61107
0.7738	Intermediate Similarity	NPC232112
0.7732	Intermediate Similarity	NPC253586
0.7727	Intermediate Similarity	NPC16449
0.7727	Intermediate Similarity	NPC470609
0.7727	Intermediate Similarity	NPC474714
0.7727	Intermediate Similarity	NPC477851
0.7723	Intermediate Similarity	NPC470587
0.7723	Intermediate Similarity	NPC200957
0.7723	Intermediate Similarity	NPC37600
0.7723	Intermediate Similarity	NPC295366
0.7723	Intermediate Similarity	NPC138908
0.7708	Intermediate Similarity	NPC263135
0.7708	Intermediate Similarity	NPC288906
0.7708	Intermediate Similarity	NPC305808
0.7708	Intermediate Similarity	NPC470031
0.7701	Intermediate Similarity	NPC34046
0.7701	Intermediate Similarity	NPC171426
0.7701	Intermediate Similarity	NPC324700
0.7701	Intermediate Similarity	NPC185465
0.7701	Intermediate Similarity	NPC80089
0.7701	Intermediate Similarity	NPC224802
0.77	Intermediate Similarity	NPC87927
0.77	Intermediate Similarity	NPC107385
0.7692	Intermediate Similarity	NPC473062
0.7684	Intermediate Similarity	NPC474379
0.7677	Intermediate Similarity	NPC259654
0.7677	Intermediate Similarity	NPC14634
0.7677	Intermediate Similarity	NPC298266
0.7677	Intermediate Similarity	NPC236585
0.7677	Intermediate Similarity	NPC253886
0.7677	Intermediate Similarity	NPC121218
0.7677	Intermediate Similarity	NPC289148
0.7677	Intermediate Similarity	NPC52899
0.7677	Intermediate Similarity	NPC75941
0.7677	Intermediate Similarity	NPC163963
0.7674	Intermediate Similarity	NPC475742
0.7674	Intermediate Similarity	NPC5767
0.7667	Intermediate Similarity	NPC472744
0.766	Intermediate Similarity	NPC46758
0.7653	Intermediate Similarity	NPC89099
0.7647	Intermediate Similarity	NPC201908
0.7647	Intermediate Similarity	NPC176949
0.7647	Intermediate Similarity	NPC475458
0.7647	Intermediate Similarity	NPC166993
0.7642	Intermediate Similarity	NPC470116
0.7642	Intermediate Similarity	NPC238667
0.7642	Intermediate Similarity	NPC470115
0.764	Intermediate Similarity	NPC50658
0.764	Intermediate Similarity	NPC58631
0.7629	Intermediate Similarity	NPC200054
0.7629	Intermediate Similarity	NPC329910
0.7629	Intermediate Similarity	NPC29410
0.7619	Intermediate Similarity	NPC89310
0.7619	Intermediate Similarity	NPC187471
0.7619	Intermediate Similarity	NPC252182
0.7619	Intermediate Similarity	NPC1340
0.7619	Intermediate Similarity	NPC470071
0.7619	Intermediate Similarity	NPC151018

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 NPC226491 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	433
0.1-0.2	3692
0.2-0.3	3354
0.3-0.4	969
0.4-0.5	332
0.5-0.6	205
0.6-0.7	150
0.7-0.8	15
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
0.7976	Intermediate Similarity	NPD3703	Phase 2
0.7701	Intermediate Similarity	NPD6115	Approved
0.7701	Intermediate Similarity	NPD6118	Approved
0.7701	Intermediate Similarity	NPD6114	Approved
0.7701	Intermediate Similarity	NPD6697	Approved
0.7677	Intermediate Similarity	NPD1700	Approved
0.7619	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD6116	Phase 1
0.7471	Intermediate Similarity	NPD6117	Approved
0.7381	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD5360	Phase 3
0.7262	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD4245	Approved
0.7093	Intermediate Similarity	NPD4244	Approved
0.7093	Intermediate Similarity	NPD4789	Approved
0.6977	Remote Similarity	NPD3698	Phase 2
0.6977	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD3702	Approved
0.6887	Remote Similarity	NPD6008	Approved
0.6887	Remote Similarity	NPD6402	Approved
0.6887	Remote Similarity	NPD5739	Approved
0.6887	Remote Similarity	NPD6675	Approved
0.6887	Remote Similarity	NPD7128	Approved
0.6869	Remote Similarity	NPD8034	Phase 2
0.6869	Remote Similarity	NPD8035	Phase 2
0.6863	Remote Similarity	NPD4755	Approved
0.6852	Remote Similarity	NPD6373	Approved
0.6852	Remote Similarity	NPD6372	Approved
0.6842	Remote Similarity	NPD6059	Approved
0.6842	Remote Similarity	NPD6054	Approved
0.6837	Remote Similarity	NPD5328	Approved
0.6818	Remote Similarity	NPD4758	Discontinued
0.6789	Remote Similarity	NPD4634	Approved
0.6759	Remote Similarity	NPD6881	Approved
0.6759	Remote Similarity	NPD7320	Approved
0.6759	Remote Similarity	NPD6899	Approved
0.6739	Remote Similarity	NPD3671	Phase 1
0.6739	Remote Similarity	NPD5364	Discontinued
0.6731	Remote Similarity	NPD5286	Approved
0.6731	Remote Similarity	NPD4700	Approved
0.6731	Remote Similarity	NPD4696	Approved
0.6731	Remote Similarity	NPD5285	Approved
0.6727	Remote Similarity	NPD6650	Approved
0.6727	Remote Similarity	NPD6649	Approved
0.6724	Remote Similarity	NPD6370	Approved
0.67	Remote Similarity	NPD6079	Approved
0.6696	Remote Similarity	NPD6319	Approved
0.6667	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD5701	Approved
0.6638	Remote Similarity	NPD6015	Approved
0.6638	Remote Similarity	NPD6016	Approved
0.6636	Remote Similarity	NPD7102	Approved
0.6636	Remote Similarity	NPD7290	Approved
0.6636	Remote Similarity	NPD6883	Approved
0.6634	Remote Similarity	NPD6399	Phase 3
0.6629	Remote Similarity	NPD5777	Approved
0.6629	Remote Similarity	NPD6081	Approved
0.661	Remote Similarity	NPD7492	Approved
0.6604	Remote Similarity	NPD5225	Approved
0.6604	Remote Similarity	NPD5226	Approved
0.6604	Remote Similarity	NPD5211	Phase 2
0.6604	Remote Similarity	NPD4633	Approved
0.6604	Remote Similarity	NPD5224	Approved
0.6602	Remote Similarity	NPD4697	Phase 3
0.6598	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD6928	Phase 2
0.6581	Remote Similarity	NPD5988	Approved
0.6579	Remote Similarity	NPD7115	Discovery
0.6577	Remote Similarity	NPD8130	Phase 1
0.6577	Remote Similarity	NPD6847	Approved
0.6577	Remote Similarity	NPD6869	Approved
0.6577	Remote Similarity	NPD6617	Approved
0.6555	Remote Similarity	NPD6616	Approved
0.6545	Remote Similarity	NPD6013	Approved
0.6545	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6012	Approved
0.6545	Remote Similarity	NPD6014	Approved
0.6542	Remote Similarity	NPD5175	Approved
0.6542	Remote Similarity	NPD5174	Approved
0.6531	Remote Similarity	NPD3618	Phase 1
0.6518	Remote Similarity	NPD6882	Approved
0.6518	Remote Similarity	NPD8297	Approved
0.6509	Remote Similarity	NPD5223	Approved
0.65	Remote Similarity	NPD8293	Discontinued
0.65	Remote Similarity	NPD7078	Approved
0.6496	Remote Similarity	NPD6921	Approved
0.6495	Remote Similarity	NPD4786	Approved
0.6486	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD5141	Approved
0.6471	Remote Similarity	NPD4202	Approved
0.646	Remote Similarity	NPD4632	Approved
0.6455	Remote Similarity	NPD6011	Approved
0.6446	Remote Similarity	NPD7736	Approved
0.6442	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD5221	Approved
0.6442	Remote Similarity	NPD5222	Approved
0.6437	Remote Similarity	NPD4224	Phase 2
0.6429	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD4768	Approved
0.6422	Remote Similarity	NPD4767	Approved
0.6393	Remote Similarity	NPD7319	Approved
0.6392	Remote Similarity	NPD4788	Approved
0.6389	Remote Similarity	NPD4754	Approved
0.6387	Remote Similarity	NPD7604	Phase 2
0.6383	Remote Similarity	NPD4238	Approved
0.6383	Remote Similarity	NPD4802	Phase 2
0.6381	Remote Similarity	NPD5173	Approved
0.6364	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4787	Phase 1
0.6321	Remote Similarity	NPD7638	Approved
0.6311	Remote Similarity	NPD6033	Approved
0.6306	Remote Similarity	NPD5128	Approved
0.6306	Remote Similarity	NPD4730	Approved
0.6306	Remote Similarity	NPD4729	Approved
0.6293	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD6009	Approved
0.6289	Remote Similarity	NPD3667	Approved
0.6262	Remote Similarity	NPD7639	Approved
0.6262	Remote Similarity	NPD8418	Phase 2
0.6262	Remote Similarity	NPD7640	Approved
0.625	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7525	Registered
0.6226	Remote Similarity	NPD6083	Phase 2
0.6226	Remote Similarity	NPD6084	Phase 2
0.6218	Remote Similarity	NPD5983	Phase 2
0.6216	Remote Similarity	NPD6412	Phase 2
0.6216	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6274	Approved
0.6207	Remote Similarity	NPD371	Approved
0.6195	Remote Similarity	NPD5248	Approved
0.6195	Remote Similarity	NPD5249	Phase 3
0.6195	Remote Similarity	NPD5247	Approved
0.6195	Remote Similarity	NPD5250	Approved
0.6195	Remote Similarity	NPD5251	Approved
0.6186	Remote Similarity	NPD7100	Approved
0.6186	Remote Similarity	NPD7101	Approved
0.6176	Remote Similarity	NPD4753	Phase 2
0.6174	Remote Similarity	NPD8133	Approved
0.6162	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD8171	Discontinued
0.6148	Remote Similarity	NPD7507	Approved
0.6148	Remote Similarity	NPD6336	Discontinued
0.6147	Remote Similarity	NPD7632	Discontinued
0.614	Remote Similarity	NPD5216	Approved
0.614	Remote Similarity	NPD5215	Approved
0.614	Remote Similarity	NPD5217	Approved
0.6126	Remote Similarity	NPD6920	Discontinued
0.6116	Remote Similarity	NPD8328	Phase 3
0.6102	Remote Similarity	NPD6335	Approved
0.6083	Remote Similarity	NPD6909	Approved
0.6083	Remote Similarity	NPD6908	Approved
0.6075	Remote Similarity	NPD7902	Approved
0.6068	Remote Similarity	NPD6940	Discontinued
0.6061	Remote Similarity	NPD6695	Phase 3
0.6058	Remote Similarity	NPD7637	Suspended
0.6053	Remote Similarity	NPD5169	Approved
0.6053	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD5135	Approved
0.6038	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD5210	Approved
0.6038	Remote Similarity	NPD4629	Approved
0.6036	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.602	Remote Similarity	NPD1780	Approved
0.602	Remote Similarity	NPD1779	Approved
0.6019	Remote Similarity	NPD5696	Approved
0.6017	Remote Similarity	NPD6317	Approved
0.6	Remote Similarity	NPD3665	Phase 1
0.6	Remote Similarity	NPD3666	Approved
0.6	Remote Similarity	NPD3133	Approved
0.6	Remote Similarity	NPD5127	Approved
0.5966	Remote Similarity	NPD6313	Approved
0.5966	Remote Similarity	NPD6314	Approved
0.595	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD7748	Approved
0.5943	Remote Similarity	NPD5282	Discontinued
0.5934	Remote Similarity	NPD229	Approved
0.5932	Remote Similarity	NPD6868	Approved
0.5905	Remote Similarity	NPD6411	Approved
0.5905	Remote Similarity	NPD7515	Phase 2
0.59	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.59	Remote Similarity	NPD3669	Approved
0.5888	Remote Similarity	NPD5695	Phase 3
0.5877	Remote Similarity	NPD5168	Approved
0.5849	Remote Similarity	NPD5778	Approved
0.5849	Remote Similarity	NPD5779	Approved
0.5847	Remote Similarity	NPD5167	Approved
0.5842	Remote Similarity	NPD3668	Phase 3
0.5825	Remote Similarity	NPD7524	Approved
0.5825	Remote Similarity	NPD7750	Discontinued
0.5812	Remote Similarity	NPD6053	Discontinued
0.5806	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.58	Remote Similarity	NPD4221	Approved
0.58	Remote Similarity	NPD4223	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