NPASS Compound

Structure

NPC247146 OpenBabel07101718312D 41 44 0 0 1 0 0 0 0 0999 V2000 6.9282 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 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 6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 0.0000 C 0 0 1 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 6.9282 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7942 0.5000 0.0000 C 0 0 2 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 9.5263 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 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 6.0622 4.5000 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 4.3301 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 0.0000 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 35 1 0 0 0 0 2 36 1 0 0 0 0 3 6 2 0 0 0 0 3 11 1 0 0 0 0 4 5 2 0 0 0 0 4 12 1 0 0 0 0 5 13 1 0 0 0 0 6 14 1 0 0 0 0 7 11 2 0 0 0 0 7 16 1 0 0 0 0 8 12 2 0 0 0 0 8 15 1 0 0 0 0 9 27 1 0 0 0 0 10 28 1 0 0 0 0 11 37 1 0 0 0 0 12 38 1 0 0 0 0 13 15 2 0 0 0 0 13 37 1 0 0 0 0 14 16 2 0 0 0 0 14 39 1 0 0 0 0 15 35 1 0 0 0 0 16 36 1 0 0 0 0 17 9 1 6 0 0 0 17 19 1 0 0 0 0 17 40 1 0 0 0 0 18 10 1 1 0 0 0 18 20 1 0 0 0 0 18 41 1 0 0 0 0 19 21 1 0 0 0 0 19 29 1 1 0 0 0 20 22 1 0 0 0 0 20 30 1 6 0 0 0 21 23 1 0 0 0 0 21 31 1 6 0 0 0 22 24 1 0 0 0 0 22 32 1 1 0 0 0 23 25 1 0 0 0 0 23 33 1 1 0 0 0 24 26 1 0 0 0 0 24 34 1 6 0 0 0 25 38 1 6 0 0 0 25 40 1 0 0 0 0 26 39 1 1 0 0 0 26 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	586.19
Volume:	540.061
LogP:	-0.485
LogD:	-0.283
LogS:	-2.383
# Rotatable Bonds:	10
TPSA:	226.45
# H-Bond Aceptor:	15
# H-Bond Donor:	8
# Rings:	4
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.149
Synthetic Accessibility Score:	4.343
Fsp3:	0.538
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:	-6.559
MDCK Permeability:	7.504353561671451e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.98
Human Intestinal Absorption (HIA):	0.848
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.159
Plasma Protein Binding (PPB):	53.1911735534668%
Volume Distribution (VD):	0.451
Pgp-substrate:	15.268882751464844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.04
CYP1A2-substrate:	0.069
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.682
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.176
CYP2D6-inhibitor:	0.026
CYP2D6-substrate:	0.514
CYP3A4-inhibitor:	0.005
CYP3A4-substrate:	0.017

ADMET: Excretion

Clearance (CL):	1.349
Half-life (T1/2):	0.688

ADMET: Toxicity

hERG Blockers:	0.354
Human Hepatotoxicity (H-HT):	0.107
Drug-inuced Liver Injury (DILI):	0.049
AMES Toxicity:	0.114
Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.376
Carcinogencity:	0.52
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.022

Download Data

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

Natural Product: NPC247146

Natural Product ID:	NPC247146
*Common Name:**	Cinnacasolide C
IUPAC Name:	(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[3-methoxy-4-[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenoxy]phenoxy]oxane-3,4,5-triol
Synonyms:	Cinnacasolide C
Standard InCHIKey:	BRGMLXAIQVVQOP-PCIRLDFKSA-N
Standard InCHI:	InChI=1S/C26H34O15/c1-35-15-8-12(38-25-23(33)21(31)19(29)17(9-27)40-25)4-5-13(15)37-11-3-6-14(16(7-11)36-2)39-26-24(34)22(32)20(30)18(10-28)41-26/h3-8,17-34H,9-10H2,1-2H3/t17-,18-,19-,20-,21+,22+,23-,24-,25-,26-/m1/s1
SMILES:	COc1cc(ccc1Oc1ccc(c(c1)OC)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2048806
PubChem CID:	70694646
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic glycosides

*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
NPO31458	Cinnamomum cassia	Species	Lauraceae	Eukaryota	twigs	n.a.	n.a.	PMID[19555125]
NPO31458	Cinnamomum cassia	Species	Lauraceae	Eukaryota	twigs	n.a.	n.a.	PMID[22677314]
NPO31458	Cinnamomum cassia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31458	Cinnamomum cassia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	1
Others	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT967	Individual Protein	Xanthine dehydrogenase	Homo sapiens	Inhibition	=	28.2	%	PMID[497135]
NPT967	Individual Protein	Xanthine dehydrogenase	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[497135]

☑ 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 NPC247146 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	384
0.1-0.2	2300
0.2-0.3	8118
0.3-0.4	10936
0.4-0.5	6532
0.5-0.6	8190
0.6-0.7	4956
0.7-0.8	1178
0.8-0.85	70
0.85-0.9	15
0.9-0.95	15
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9669	High Similarity	NPC25817
0.9587	High Similarity	NPC217854
0.952	High Similarity	NPC60756
0.9512	High Similarity	NPC298845
0.9444	High Similarity	NPC287780
0.9435	High Similarity	NPC37074
0.9365	High Similarity	NPC208769
0.9355	High Similarity	NPC189589
0.9355	High Similarity	NPC469622
0.9339	High Similarity	NPC276195
0.9297	High Similarity	NPC60982
0.9194	High Similarity	NPC221090
0.9187	High Similarity	NPC152722
0.9127	High Similarity	NPC469621
0.9113	High Similarity	NPC192810
0.9091	High Similarity	NPC228907
0.9048	High Similarity	NPC171533
0.88	High Similarity	NPC57751
0.8722	High Similarity	NPC470236
0.8657	High Similarity	NPC164857
0.8548	High Similarity	NPC9248
0.8529	High Similarity	NPC98777
0.8529	High Similarity	NPC212770
0.8519	High Similarity	NPC138350
0.8519	High Similarity	NPC40664
0.8519	High Similarity	NPC197723
0.8519	High Similarity	NPC104167
0.8519	High Similarity	NPC165482
0.8519	High Similarity	NPC3293
0.8496	Intermediate Similarity	NPC162093
0.8478	Intermediate Similarity	NPC469559
0.8456	Intermediate Similarity	NPC59324
0.8456	Intermediate Similarity	NPC65530
0.8455	Intermediate Similarity	NPC142319
0.8444	Intermediate Similarity	NPC238243
0.844	Intermediate Similarity	NPC227902
0.8433	Intermediate Similarity	NPC49074
0.8425	Intermediate Similarity	NPC205850
0.8421	Intermediate Similarity	NPC473412
0.8421	Intermediate Similarity	NPC469698
0.8417	Intermediate Similarity	NPC252169
0.8413	Intermediate Similarity	NPC214289
0.8382	Intermediate Similarity	NPC242028
0.8382	Intermediate Similarity	NPC203230
0.837	Intermediate Similarity	NPC130496
0.837	Intermediate Similarity	NPC188555
0.837	Intermediate Similarity	NPC187194
0.8369	Intermediate Similarity	NPC125755
0.8345	Intermediate Similarity	NPC189115
0.8345	Intermediate Similarity	NPC475084
0.8321	Intermediate Similarity	NPC262328
0.8321	Intermediate Similarity	NPC87777
0.8298	Intermediate Similarity	NPC277867
0.8298	Intermediate Similarity	NPC475096
0.8298	Intermediate Similarity	NPC161700
0.8296	Intermediate Similarity	NPC294166
0.8296	Intermediate Similarity	NPC215833
0.8296	Intermediate Similarity	NPC115022
0.8296	Intermediate Similarity	NPC69513
0.8295	Intermediate Similarity	NPC105147
0.8295	Intermediate Similarity	NPC126216
0.8295	Intermediate Similarity	NPC228875
0.8273	Intermediate Similarity	NPC89686
0.8273	Intermediate Similarity	NPC273932
0.8273	Intermediate Similarity	NPC257095
0.8273	Intermediate Similarity	NPC469661
0.8271	Intermediate Similarity	NPC218003
0.8264	Intermediate Similarity	NPC238140
0.8254	Intermediate Similarity	NPC151617
0.8254	Intermediate Similarity	NPC76915
0.8252	Intermediate Similarity	NPC175976
0.8252	Intermediate Similarity	NPC478237
0.8235	Intermediate Similarity	NPC48863
0.8235	Intermediate Similarity	NPC13745
0.8235	Intermediate Similarity	NPC251981
0.8235	Intermediate Similarity	NPC476411
0.8227	Intermediate Similarity	NPC76176
0.8227	Intermediate Similarity	NPC138227
0.8227	Intermediate Similarity	NPC168579
0.8227	Intermediate Similarity	NPC25292
0.8227	Intermediate Similarity	NPC469313
0.8227	Intermediate Similarity	NPC473045
0.8222	Intermediate Similarity	NPC303422
0.8222	Intermediate Similarity	NPC85799
0.8222	Intermediate Similarity	NPC26080
0.8222	Intermediate Similarity	NPC299144
0.8222	Intermediate Similarity	NPC165686
0.8201	Intermediate Similarity	NPC106944
0.8195	Intermediate Similarity	NPC302378
0.8194	Intermediate Similarity	NPC55715
0.8194	Intermediate Similarity	NPC95392
0.8194	Intermediate Similarity	NPC35877
0.8188	Intermediate Similarity	NPC138738
0.8188	Intermediate Similarity	NPC470413
0.8182	Intermediate Similarity	NPC15538
0.8182	Intermediate Similarity	NPC39657
0.8182	Intermediate Similarity	NPC110677
0.8182	Intermediate Similarity	NPC473480
0.8162	Intermediate Similarity	NPC132895
0.8156	Intermediate Similarity	NPC116922
0.8156	Intermediate Similarity	NPC473044
0.8156	Intermediate Similarity	NPC37793
0.8148	Intermediate Similarity	NPC475067
0.8148	Intermediate Similarity	NPC121376
0.8148	Intermediate Similarity	NPC9912
0.8143	Intermediate Similarity	NPC108674
0.8138	Intermediate Similarity	NPC114740
0.8134	Intermediate Similarity	NPC248355
0.8125	Intermediate Similarity	NPC280945
0.8125	Intermediate Similarity	NPC270751
0.8116	Intermediate Similarity	NPC25695
0.8116	Intermediate Similarity	NPC172818
0.8112	Intermediate Similarity	NPC190714
0.8112	Intermediate Similarity	NPC99515
0.8102	Intermediate Similarity	NPC87696
0.8099	Intermediate Similarity	NPC225445
0.8099	Intermediate Similarity	NPC471063
0.8099	Intermediate Similarity	NPC177597
0.8095	Intermediate Similarity	NPC78809
0.8085	Intermediate Similarity	NPC230718
0.8085	Intermediate Similarity	NPC5262
0.8085	Intermediate Similarity	NPC84207
0.8085	Intermediate Similarity	NPC5253
0.8085	Intermediate Similarity	NPC49542
0.8085	Intermediate Similarity	NPC139976
0.8085	Intermediate Similarity	NPC128337
0.8085	Intermediate Similarity	NPC472714
0.8082	Intermediate Similarity	NPC473621
0.8074	Intermediate Similarity	NPC472024
0.8074	Intermediate Similarity	NPC80600
0.8071	Intermediate Similarity	NPC210478
0.8069	Intermediate Similarity	NPC51328
0.8069	Intermediate Similarity	NPC286235
0.8069	Intermediate Similarity	NPC55158
0.8069	Intermediate Similarity	NPC106138
0.8058	Intermediate Similarity	NPC124149
0.8058	Intermediate Similarity	NPC195196
0.8027	Intermediate Similarity	NPC476352
0.8027	Intermediate Similarity	NPC215060
0.8015	Intermediate Similarity	NPC30043
0.8015	Intermediate Similarity	NPC469613
0.8015	Intermediate Similarity	NPC469625
0.8	Intermediate Similarity	NPC248132
0.8	Intermediate Similarity	NPC93924
0.8	Intermediate Similarity	NPC96294
0.8	Intermediate Similarity	NPC130449
0.8	Intermediate Similarity	NPC270849
0.8	Intermediate Similarity	NPC166040
0.8	Intermediate Similarity	NPC26653
0.7986	Intermediate Similarity	NPC177035
0.7986	Intermediate Similarity	NPC276753
0.7986	Intermediate Similarity	NPC205796
0.7986	Intermediate Similarity	NPC52277
0.7986	Intermediate Similarity	NPC199459
0.7986	Intermediate Similarity	NPC469383
0.7986	Intermediate Similarity	NPC476865
0.7985	Intermediate Similarity	NPC140750
0.7972	Intermediate Similarity	NPC187774
0.7972	Intermediate Similarity	NPC472712
0.7972	Intermediate Similarity	NPC472713
0.7972	Intermediate Similarity	NPC473046
0.7972	Intermediate Similarity	NPC118385
0.7971	Intermediate Similarity	NPC170694
0.7971	Intermediate Similarity	NPC310854
0.7971	Intermediate Similarity	NPC107478
0.7971	Intermediate Similarity	NPC35731
0.797	Intermediate Similarity	NPC12308
0.7958	Intermediate Similarity	NPC472353
0.7958	Intermediate Similarity	NPC246947
0.7956	Intermediate Similarity	NPC470270
0.7941	Intermediate Similarity	NPC262606
0.7941	Intermediate Similarity	NPC470079
0.7941	Intermediate Similarity	NPC469612
0.7941	Intermediate Similarity	NPC469614
0.7933	Intermediate Similarity	NPC284810
0.7931	Intermediate Similarity	NPC52740
0.7929	Intermediate Similarity	NPC134260
0.7917	Intermediate Similarity	NPC476869
0.7917	Intermediate Similarity	NPC476868
0.7917	Intermediate Similarity	NPC476866
0.7917	Intermediate Similarity	NPC476864
0.791	Intermediate Similarity	NPC233559
0.7905	Intermediate Similarity	NPC302610
0.7905	Intermediate Similarity	NPC21902
0.7902	Intermediate Similarity	NPC278961
0.7902	Intermediate Similarity	NPC470950
0.7902	Intermediate Similarity	NPC113680
0.7902	Intermediate Similarity	NPC46092
0.7902	Intermediate Similarity	NPC185307
0.7899	Intermediate Similarity	NPC263064
0.7899	Intermediate Similarity	NPC25821
0.7895	Intermediate Similarity	NPC1253
0.7895	Intermediate Similarity	NPC100936
0.7891	Intermediate Similarity	NPC472709
0.7891	Intermediate Similarity	NPC472710
0.7887	Intermediate Similarity	NPC210192
0.7887	Intermediate Similarity	NPC76871
0.7883	Intermediate Similarity	NPC166168
0.7879	Intermediate Similarity	NPC476142
0.7868	Intermediate Similarity	NPC218856

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 NPC247146 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	305
0.1-0.2	996
0.2-0.3	2735
0.3-0.4	2740
0.4-0.5	1457
0.5-0.6	746
0.6-0.7	157
0.7-0.8	14
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
0.7803	Intermediate Similarity	NPD1091	Approved
0.7801	Intermediate Similarity	NPD3454	Phase 3
0.7769	Intermediate Similarity	NPD291	Approved
0.7703	Intermediate Similarity	NPD1653	Approved
0.7619	Intermediate Similarity	NPD556	Approved
0.7482	Intermediate Similarity	NPD3027	Phase 3
0.7447	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD1613	Approved
0.7438	Intermediate Similarity	NPD7054	Approved
0.741	Intermediate Similarity	NPD3537	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7472	Approved
0.7391	Intermediate Similarity	NPD7074	Phase 3
0.7379	Intermediate Similarity	NPD7266	Discontinued
0.7293	Intermediate Similarity	NPD1408	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD6674	Discontinued
0.7256	Intermediate Similarity	NPD7808	Phase 3
0.7239	Intermediate Similarity	NPD7533	Approved
0.7239	Intermediate Similarity	NPD7534	Approved
0.7195	Intermediate Similarity	NPD7251	Discontinued
0.7163	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7228	Approved
0.7152	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6797	Phase 2
0.7092	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD2982	Phase 2
0.705	Intermediate Similarity	NPD2983	Phase 2
0.7042	Intermediate Similarity	NPD4908	Phase 1
0.7025	Intermediate Similarity	NPD9365	Approved
0.7012	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD8455	Phase 2
0.6988	Remote Similarity	NPD7240	Approved
0.6978	Remote Similarity	NPD2981	Phase 2
0.6957	Remote Similarity	NPD7199	Phase 2
0.6951	Remote Similarity	NPD3818	Discontinued
0.6944	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD37	Approved
0.6918	Remote Similarity	NPD4966	Approved
0.6918	Remote Similarity	NPD4965	Approved
0.6918	Remote Similarity	NPD4967	Phase 2
0.6908	Remote Similarity	NPD5058	Phase 3
0.6861	Remote Similarity	NPD1548	Phase 1
0.6855	Remote Similarity	NPD9296	Approved
0.6853	Remote Similarity	NPD3018	Phase 2
0.6835	Remote Similarity	NPD3384	Approved
0.6835	Remote Similarity	NPD3383	Approved
0.6835	Remote Similarity	NPD3382	Approved
0.6832	Remote Similarity	NPD6234	Discontinued
0.6831	Remote Similarity	NPD3827	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6166	Phase 2
0.6829	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD1652	Phase 2
0.6812	Remote Similarity	NPD1357	Approved
0.6794	Remote Similarity	NPD290	Approved
0.6791	Remote Similarity	NPD7843	Approved
0.6786	Remote Similarity	NPD1610	Phase 2
0.6786	Remote Similarity	NPD3705	Approved
0.6781	Remote Similarity	NPD6233	Phase 2
0.6768	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.673	Remote Similarity	NPD1934	Approved
0.6718	Remote Similarity	NPD968	Approved
0.6711	Remote Similarity	NPD4536	Approved
0.6711	Remote Similarity	NPD7097	Phase 1
0.6711	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD4538	Approved
0.6708	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD3787	Discontinued
0.6707	Remote Similarity	NPD5844	Phase 1
0.6689	Remote Similarity	NPD521	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD2801	Approved
0.6667	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9552	Approved
0.6646	Remote Similarity	NPD5402	Approved
0.6646	Remote Similarity	NPD3817	Phase 2
0.6642	Remote Similarity	NPD191	Approved
0.6642	Remote Similarity	NPD7157	Approved
0.6624	Remote Similarity	NPD5403	Approved
0.6621	Remote Similarity	NPD5266	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD2861	Phase 2
0.6617	Remote Similarity	NPD2684	Approved
0.6603	Remote Similarity	NPD5401	Approved
0.6599	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD7685	Pre-registration
0.6588	Remote Similarity	NPD6559	Discontinued
0.6585	Remote Similarity	NPD5494	Approved
0.6585	Remote Similarity	NPD9295	Approved
0.6584	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD5124	Phase 1
0.6577	Remote Similarity	NPD1933	Approved
0.6571	Remote Similarity	NPD1797	Approved
0.6571	Remote Similarity	NPD1798	Approved
0.6556	Remote Similarity	NPD5588	Approved
0.6556	Remote Similarity	NPD5960	Phase 3
0.6543	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4625	Phase 3
0.6525	Remote Similarity	NPD5125	Phase 3
0.6525	Remote Similarity	NPD5126	Approved
0.6519	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4678	Approved
0.65	Remote Similarity	NPD4380	Phase 2
0.65	Remote Similarity	NPD4675	Approved
0.6494	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD7075	Discontinued
0.6458	Remote Similarity	NPD4749	Approved
0.6457	Remote Similarity	NPD6841	Approved
0.6457	Remote Similarity	NPD6843	Phase 3
0.6457	Remote Similarity	NPD6842	Approved
0.645	Remote Similarity	NPD3751	Discontinued
0.6439	Remote Similarity	NPD9501	Approved
0.6438	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD7212	Phase 2
0.6433	Remote Similarity	NPD7213	Phase 3
0.6429	Remote Similarity	NPD1102	Approved
0.6429	Remote Similarity	NPD1103	Approved
0.6414	Remote Similarity	NPD8651	Approved
0.6409	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6516	Phase 2
0.6408	Remote Similarity	NPD5846	Approved
0.6403	Remote Similarity	NPD6671	Approved
0.6397	Remote Similarity	NPD2673	Approved
0.6397	Remote Similarity	NPD2671	Approved
0.6395	Remote Similarity	NPD2250	Discontinued
0.6392	Remote Similarity	NPD7447	Phase 1
0.6377	Remote Similarity	NPD5283	Phase 1
0.6376	Remote Similarity	NPD6798	Discontinued
0.6371	Remote Similarity	NPD9094	Approved
0.6364	Remote Similarity	NPD3540	Phase 1
0.6359	Remote Similarity	NPD7680	Approved
0.6358	Remote Similarity	NPD7549	Discontinued
0.6358	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.634	Remote Similarity	NPD7033	Discontinued
0.6338	Remote Similarity	NPD6382	Discontinued
0.6329	Remote Similarity	NPD6799	Approved
0.6327	Remote Similarity	NPD1469	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD8313	Approved
0.6322	Remote Similarity	NPD8312	Approved
0.6319	Remote Similarity	NPD422	Phase 1
0.6319	Remote Similarity	NPD6801	Discontinued
0.6306	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD6190	Approved
0.6303	Remote Similarity	NPD3882	Suspended
0.6301	Remote Similarity	NPD3225	Approved
0.6299	Remote Similarity	NPD3539	Phase 1
0.6287	Remote Similarity	NPD5677	Discontinued
0.6282	Remote Similarity	NPD5177	Phase 3
0.628	Remote Similarity	NPD1465	Phase 2
0.628	Remote Similarity	NPD2977	Approved
0.628	Remote Similarity	NPD2978	Approved
0.6275	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD6362	Approved
0.6258	Remote Similarity	NPD7411	Suspended
0.6258	Remote Similarity	NPD5762	Approved
0.6258	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD5763	Approved
0.6258	Remote Similarity	NPD1375	Discontinued
0.6257	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4340	Discontinued
0.625	Remote Similarity	NPD6355	Discontinued
0.6243	Remote Similarity	NPD7007	Discovery
0.6242	Remote Similarity	NPD4535	Phase 3
0.6242	Remote Similarity	NPD4628	Phase 3
0.6242	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD4005	Discontinued
0.6233	Remote Similarity	NPD3685	Discontinued
0.6232	Remote Similarity	NPD228	Approved
0.6226	Remote Similarity	NPD1774	Approved
0.6226	Remote Similarity	NPD1511	Approved
0.6226	Remote Similarity	NPD4357	Discontinued
0.6225	Remote Similarity	NPD4062	Phase 3
0.6225	Remote Similarity	NPD3530	Approved
0.6225	Remote Similarity	NPD3531	Approved
0.6225	Remote Similarity	NPD3532	Approved
0.6218	Remote Similarity	NPD1549	Phase 2
0.6216	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD5647	Approved
0.6209	Remote Similarity	NPD2223	Approved
0.6209	Remote Similarity	NPD6653	Approved
0.6209	Remote Similarity	NPD2224	Approved
0.6203	Remote Similarity	NPD2677	Approved
0.62	Remote Similarity	NPD3180	Approved
0.62	Remote Similarity	NPD7095	Approved
0.62	Remote Similarity	NPD3179	Approved
0.6197	Remote Similarity	NPD5536	Phase 2
0.6188	Remote Similarity	NPD4123	Phase 3
0.6188	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6187	Remote Similarity	NPD5535	Approved
0.6184	Remote Similarity	NPD1558	Phase 1
0.6182	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD7819	Suspended
0.6178	Remote Similarity	NPD4236	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