NPASS Compound

Structure

CID126156 OpenBabel06191715482D 26 28 0 0 1 0 0 0 0 0999 V2000 -3.7187 -6.2744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0464 -5.3088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9481 1.5382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2611 -2.4847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9624 -1.1770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7187 -5.3088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5636 0.6683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4722 -0.8878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8825 -4.8261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5291 0.6683 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3476 -1.5231 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0928 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9616 -0.0865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7451 -1.5231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1765 -1.0279 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1311 -0.0865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0464 -1.4468 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8825 -3.8606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3795 -0.8878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9163 -1.0279 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5880 0.8288 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8317 -2.4847 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7187 -3.3778 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3208 -1.1027 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 -2.0464 -3.3778 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 9 1 0 0 0 0 5 20 1 0 0 0 0 6 9 2 0 0 0 0 7 10 1 0 0 0 0 8 12 1 0 0 0 0 8 14 1 0 0 0 0 9 18 1 0 0 0 0 10 3 1 6 0 0 0 10 16 1 0 0 0 0 11 4 1 1 0 0 0 11 15 1 0 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 12 21 1 6 0 0 0 13 7 1 1 0 0 0 13 15 1 0 0 0 0 13 25 1 0 0 0 0 14 20 1 0 0 0 0 14 22 2 0 0 0 0 15 17 1 0 0 0 0 16 20 1 0 0 0 0 17 20 1 0 0 0 0 17 26 1 0 0 0 0 18 23 2 0 0 0 0 18 26 1 0 0 0 0 19 24 2 0 0 0 0 19 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	364.19
Volume:	371.002
LogP:	1.484
LogD:	1.799
LogS:	-2.678
# Rotatable Bonds:	3
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.596
Synthetic Accessibility Score:	4.849
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.738
MDCK Permeability:	4.866762174060568e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.115
30% Bioavailability (F30%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.934
Plasma Protein Binding (PPB):	58.465858459472656%
Volume Distribution (VD):	0.719
Pgp-substrate:	30.605093002319336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.113
CYP1A2-substrate:	0.242
CYP2C19-inhibitor:	0.091
CYP2C19-substrate:	0.838
CYP2C9-inhibitor:	0.117
CYP2C9-substrate:	0.076
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.093
CYP3A4-inhibitor:	0.836
CYP3A4-substrate:	0.41

ADMET: Excretion

Clearance (CL):	10.187
Half-life (T1/2):	0.885

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.751
Drug-inuced Liver Injury (DILI):	0.5
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.564
Maximum Recommended Daily Dose:	0.019
Skin Sensitization:	0.387
Carcinogencity:	0.105
Eye Corrosion:	0.128
Eye Irritation:	0.147
Respiratory Toxicity:	0.738

Download Data

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

Natural Product: NPC126156

Natural Product ID:	NPC126156
*Common Name:**	11Alpha,13-Dihydroarnifolin
IUPAC Name:	[(1S,3aR,5R,5aS,6S,8aR,9S,9aR)-6-hydroxy-1,5,8a-trimethyl-2,8-dioxo-3a,4,5,5a,6,7,9,9a-octahydro-1H-azuleno[6,5-b]furan-9-yl] (E)-2-methylbut-2-enoate
Synonyms:	11Alpha,13-Dihydroarnifolin
Standard InCHIKey:	GLHMGBSDKSSHQL-KQCUBUPESA-N
Standard InCHI:	InChI=1S/C20H28O6/c1-6-9(2)18(23)26-17-15-11(4)19(24)25-13(15)7-10(3)16-12(21)8-14(22)20(16,17)5/h6,10-13,15-17,21H,7-8H2,1-5H3/b9-6+/t10-,11+,12+,13-,15-,16-,17+,20-/m1/s1
SMILES:	C/C=C(/C(=O)O[C@H]1[C@H]2[C@@H](C[C@H]([C@H]3[C@@]1(C)C(=O)C[C@@H]3O)C)OC(=O)[C@H]2C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509147
PubChem CID:	44559335
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones

*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
NPO5484	Arnica angustifolia	Species	Asteraceae	Eukaryota	n.a.	flower	n.a.	PMID[16644542]
NPO5484	Arnica angustifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO8104	Trocholejeunea sandvicensis	Species	Lejeuneaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5919	Phoebe cinnamomifolia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8104	Trocholejeunea sandvicensis	Species	Lejeuneaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5919	Phoebe cinnamomifolia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3832	Abuta pahni	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5148	Geranium saxatile	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7558	Primula sieboldi	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6083	Richardsonia scabra	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO2305	Naregamia alata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5320	Fleischmannia multinervis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7061	Tabernaemontana laeta	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8104	Trocholejeunea sandvicensis	Species	Lejeuneaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5484	Arnica angustifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7218	Salvia montbretii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8271	Aplophyllum tuberculatum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO1006	Ipomoea asarifolia	Species	Convolvulaceae	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	2

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[554298]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	76000.0	nM	PMID[554298]

☑ 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 NPC126156 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	282
0.1-0.2	2067
0.2-0.3	6836
0.3-0.4	13005
0.4-0.5	10378
0.5-0.6	6536
0.6-0.7	3067
0.7-0.8	438
0.8-0.85	48
0.85-0.9	33
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.957	High Similarity	NPC171759
0.914	High Similarity	NPC142529
0.914	High Similarity	NPC91771
0.9043	High Similarity	NPC213947
0.9043	High Similarity	NPC170143
0.9043	High Similarity	NPC108475
0.8936	High Similarity	NPC18019
0.8936	High Similarity	NPC24956
0.8817	High Similarity	NPC200237
0.871	High Similarity	NPC191339
0.871	High Similarity	NPC286341
0.8617	High Similarity	NPC473263
0.8617	High Similarity	NPC473234
0.8617	High Similarity	NPC473273
0.8617	High Similarity	NPC60386
0.8617	High Similarity	NPC308656
0.8617	High Similarity	NPC153590
0.8602	High Similarity	NPC54065
0.8602	High Similarity	NPC297474
0.8586	High Similarity	NPC110989
0.8571	High Similarity	NPC477950
0.8526	High Similarity	NPC473331
0.8511	High Similarity	NPC57304
0.8511	High Similarity	NPC35959
0.8511	High Similarity	NPC293001
0.8511	High Similarity	NPC171360
0.8511	High Similarity	NPC475925
0.8511	High Similarity	NPC63193
0.8511	High Similarity	NPC29821
0.8511	High Similarity	NPC133888
0.85	High Similarity	NPC203659
0.8495	Intermediate Similarity	NPC155935
0.8495	Intermediate Similarity	NPC168679
0.8495	Intermediate Similarity	NPC12872
0.8485	Intermediate Similarity	NPC225353
0.8454	Intermediate Similarity	NPC311904
0.8454	Intermediate Similarity	NPC477949
0.8404	Intermediate Similarity	NPC35809
0.8404	Intermediate Similarity	NPC19087
0.8367	Intermediate Similarity	NPC141191
0.8351	Intermediate Similarity	NPC185553
0.8316	Intermediate Similarity	NPC184063
0.8298	Intermediate Similarity	NPC38392
0.8265	Intermediate Similarity	NPC169205
0.8247	Intermediate Similarity	NPC193645
0.8247	Intermediate Similarity	NPC163228
0.8247	Intermediate Similarity	NPC48803
0.8247	Intermediate Similarity	NPC275960
0.8247	Intermediate Similarity	NPC90121
0.8235	Intermediate Similarity	NPC54737
0.8191	Intermediate Similarity	NPC217983
0.8191	Intermediate Similarity	NPC207114
0.8172	Intermediate Similarity	NPC64153
0.8172	Intermediate Similarity	NPC56593
0.8172	Intermediate Similarity	NPC238593
0.8137	Intermediate Similarity	NPC100487
0.8125	Intermediate Similarity	NPC284185
0.8105	Intermediate Similarity	NPC215556
0.81	Intermediate Similarity	NPC280963
0.8085	Intermediate Similarity	NPC201658
0.8085	Intermediate Similarity	NPC118601
0.8085	Intermediate Similarity	NPC24728
0.8081	Intermediate Similarity	NPC161493
0.8081	Intermediate Similarity	NPC471150
0.8061	Intermediate Similarity	NPC67584
0.8061	Intermediate Similarity	NPC52044
0.8061	Intermediate Similarity	NPC213698
0.8061	Intermediate Similarity	NPC476053
0.8041	Intermediate Similarity	NPC135776
0.8039	Intermediate Similarity	NPC475945
0.8039	Intermediate Similarity	NPC475871
0.8021	Intermediate Similarity	NPC216284
0.8021	Intermediate Similarity	NPC253144
0.802	Intermediate Similarity	NPC150923
0.802	Intermediate Similarity	NPC475099
0.8	Intermediate Similarity	NPC471149
0.8	Intermediate Similarity	NPC178875
0.8	Intermediate Similarity	NPC79549
0.8	Intermediate Similarity	NPC59489
0.8	Intermediate Similarity	NPC139838
0.798	Intermediate Similarity	NPC213078
0.7979	Intermediate Similarity	NPC309757
0.7979	Intermediate Similarity	NPC236692
0.7979	Intermediate Similarity	NPC304558
0.7979	Intermediate Similarity	NPC187661
0.7959	Intermediate Similarity	NPC477131
0.7959	Intermediate Similarity	NPC127019
0.7941	Intermediate Similarity	NPC474747
0.7938	Intermediate Similarity	NPC150978
0.7938	Intermediate Similarity	NPC123177
0.7938	Intermediate Similarity	NPC74103
0.7938	Intermediate Similarity	NPC221282
0.7938	Intermediate Similarity	NPC70595
0.7917	Intermediate Similarity	NPC283409
0.7917	Intermediate Similarity	NPC52198
0.7917	Intermediate Similarity	NPC117405
0.79	Intermediate Similarity	NPC474313
0.7885	Intermediate Similarity	NPC243998
0.7879	Intermediate Similarity	NPC37408
0.7879	Intermediate Similarity	NPC472873
0.7879	Intermediate Similarity	NPC170120
0.7879	Intermediate Similarity	NPC304886
0.785	Intermediate Similarity	NPC474750
0.7849	Intermediate Similarity	NPC54468
0.7843	Intermediate Similarity	NPC474742
0.7835	Intermediate Similarity	NPC71533
0.7835	Intermediate Similarity	NPC106510
0.781	Intermediate Similarity	NPC26617
0.7807	Intermediate Similarity	NPC144625
0.78	Intermediate Similarity	NPC476009
0.7798	Intermediate Similarity	NPC471380
0.7788	Intermediate Similarity	NPC474741
0.7788	Intermediate Similarity	NPC309190
0.7778	Intermediate Similarity	NPC262133
0.7778	Intermediate Similarity	NPC323008
0.7778	Intermediate Similarity	NPC90453
0.7778	Intermediate Similarity	NPC470010
0.7778	Intermediate Similarity	NPC167219
0.7778	Intermediate Similarity	NPC470013
0.7778	Intermediate Similarity	NPC198853
0.7766	Intermediate Similarity	NPC194859
0.7766	Intermediate Similarity	NPC224386
0.7757	Intermediate Similarity	NPC477103
0.7757	Intermediate Similarity	NPC257240
0.7755	Intermediate Similarity	NPC155215
0.7755	Intermediate Similarity	NPC290651
0.7755	Intermediate Similarity	NPC131209
0.7755	Intermediate Similarity	NPC133698
0.7753	Intermediate Similarity	NPC179922
0.7745	Intermediate Similarity	NPC186861
0.7745	Intermediate Similarity	NPC471381
0.7742	Intermediate Similarity	NPC246076
0.7732	Intermediate Similarity	NPC295312
0.7732	Intermediate Similarity	NPC32922
0.7714	Intermediate Similarity	NPC223450
0.7706	Intermediate Similarity	NPC209058
0.77	Intermediate Similarity	NPC469873
0.77	Intermediate Similarity	NPC475900
0.7692	Intermediate Similarity	NPC474775
0.7684	Intermediate Similarity	NPC300082
0.7684	Intermediate Similarity	NPC284534
0.7684	Intermediate Similarity	NPC204105
0.7677	Intermediate Similarity	NPC258216
0.767	Intermediate Similarity	NPC201718
0.767	Intermediate Similarity	NPC116139
0.7664	Intermediate Similarity	NPC477102
0.766	Intermediate Similarity	NPC128246
0.766	Intermediate Similarity	NPC111409
0.7658	Intermediate Similarity	NPC475305
0.7653	Intermediate Similarity	NPC37607
0.7653	Intermediate Similarity	NPC301969
0.7653	Intermediate Similarity	NPC129419
0.7647	Intermediate Similarity	NPC54843
0.7647	Intermediate Similarity	NPC221615
0.7615	Intermediate Similarity	NPC76550
0.7615	Intermediate Similarity	NPC123855
0.7604	Intermediate Similarity	NPC70422
0.7604	Intermediate Similarity	NPC470242
0.7604	Intermediate Similarity	NPC104961
0.7604	Intermediate Similarity	NPC70555
0.76	Intermediate Similarity	NPC476267
0.76	Intermediate Similarity	NPC289004
0.7596	Intermediate Similarity	NPC66110
0.7596	Intermediate Similarity	NPC86077
0.7593	Intermediate Similarity	NPC50223
0.7593	Intermediate Similarity	NPC41551
0.7589	Intermediate Similarity	NPC475372
0.7589	Intermediate Similarity	NPC161060
0.7589	Intermediate Similarity	NPC475401
0.7576	Intermediate Similarity	NPC111114
0.7576	Intermediate Similarity	NPC300312
0.7576	Intermediate Similarity	NPC261607
0.7576	Intermediate Similarity	NPC472705
0.7573	Intermediate Similarity	NPC288876
0.757	Intermediate Similarity	NPC10150
0.7568	Intermediate Similarity	NPC170692
0.7568	Intermediate Similarity	NPC255450
0.7565	Intermediate Similarity	NPC1538
0.7551	Intermediate Similarity	NPC472872
0.7551	Intermediate Similarity	NPC268298
0.7547	Intermediate Similarity	NPC179891
0.7547	Intermediate Similarity	NPC291643
0.7547	Intermediate Similarity	NPC44004
0.7545	Intermediate Similarity	NPC9848
0.7545	Intermediate Similarity	NPC106395
0.7545	Intermediate Similarity	NPC46269
0.7545	Intermediate Similarity	NPC312017
0.7542	Intermediate Similarity	NPC13071
0.7527	Intermediate Similarity	NPC293418
0.7527	Intermediate Similarity	NPC73052
0.7527	Intermediate Similarity	NPC51507
0.7527	Intermediate Similarity	NPC290508
0.7527	Intermediate Similarity	NPC6823
0.7526	Intermediate Similarity	NPC270270
0.7525	Intermediate Similarity	NPC471142
0.7525	Intermediate Similarity	NPC476487
0.7525	Intermediate Similarity	NPC476488
0.7524	Intermediate Similarity	NPC475873
0.7524	Intermediate Similarity	NPC472755
0.7523	Intermediate Similarity	NPC287311

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 NPC126156 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	354
0.1-0.2	2765
0.2-0.3	3768
0.3-0.4	1519
0.4-0.5	420
0.5-0.6	232
0.6-0.7	87
0.7-0.8	4
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8247	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7757	Intermediate Similarity	NPD6371	Approved
0.7653	Intermediate Similarity	NPD5785	Approved
0.72	Intermediate Similarity	NPD1695	Approved
0.7143	Intermediate Similarity	NPD6053	Discontinued
0.7143	Intermediate Similarity	NPD5363	Approved
0.7071	Intermediate Similarity	NPD5786	Approved
0.701	Intermediate Similarity	NPD6435	Approved
0.6923	Remote Similarity	NPD5282	Discontinued
0.69	Remote Similarity	NPD4249	Approved
0.6837	Remote Similarity	NPD4270	Approved
0.6837	Remote Similarity	NPD4269	Approved
0.6832	Remote Similarity	NPD4251	Approved
0.6832	Remote Similarity	NPD4250	Approved
0.6822	Remote Similarity	NPD7638	Approved
0.6804	Remote Similarity	NPD5368	Approved
0.68	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD7492	Approved
0.6759	Remote Similarity	NPD7640	Approved
0.6759	Remote Similarity	NPD7639	Approved
0.6757	Remote Similarity	NPD6008	Approved
0.6735	Remote Similarity	NPD5369	Approved
0.6723	Remote Similarity	NPD6054	Approved
0.6723	Remote Similarity	NPD6319	Approved
0.6721	Remote Similarity	NPD6616	Approved
0.6696	Remote Similarity	NPD5697	Approved
0.6694	Remote Similarity	NPD7319	Approved
0.6667	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD7078	Approved
0.6667	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD6015	Approved
0.6637	Remote Similarity	NPD6881	Approved
0.6637	Remote Similarity	NPD7320	Approved
0.6637	Remote Similarity	NPD6899	Approved
0.6637	Remote Similarity	NPD6686	Approved
0.6635	Remote Similarity	NPD6698	Approved
0.6635	Remote Similarity	NPD46	Approved
0.6633	Remote Similarity	NPD4252	Approved
0.6613	Remote Similarity	NPD7736	Approved
0.6612	Remote Similarity	NPD5988	Approved
0.6612	Remote Similarity	NPD6370	Approved
0.6609	Remote Similarity	NPD6650	Approved
0.6609	Remote Similarity	NPD6649	Approved
0.6607	Remote Similarity	NPD5739	Approved
0.6607	Remote Similarity	NPD6675	Approved
0.6607	Remote Similarity	NPD7128	Approved
0.6607	Remote Similarity	NPD6402	Approved
0.66	Remote Similarity	NPD5362	Discontinued
0.6585	Remote Similarity	NPD7507	Approved
0.6583	Remote Similarity	NPD6059	Approved
0.6579	Remote Similarity	NPD6013	Approved
0.6579	Remote Similarity	NPD6372	Approved
0.6579	Remote Similarity	NPD6012	Approved
0.6579	Remote Similarity	NPD6373	Approved
0.6579	Remote Similarity	NPD6014	Approved
0.6571	Remote Similarity	NPD7983	Approved
0.6549	Remote Similarity	NPD5701	Approved
0.6532	Remote Similarity	NPD8293	Discontinued
0.6522	Remote Similarity	NPD6883	Approved
0.6522	Remote Similarity	NPD7290	Approved
0.6522	Remote Similarity	NPD7102	Approved
0.6509	Remote Similarity	NPD5779	Approved
0.6509	Remote Similarity	NPD5778	Approved
0.65	Remote Similarity	NPD5209	Approved
0.6496	Remote Similarity	NPD4632	Approved
0.6491	Remote Similarity	NPD6011	Approved
0.6471	Remote Similarity	NPD7115	Discovery
0.6471	Remote Similarity	NPD1694	Approved
0.6471	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD6847	Approved
0.6466	Remote Similarity	NPD6869	Approved
0.6466	Remote Similarity	NPD6617	Approved
0.6466	Remote Similarity	NPD8130	Phase 1
0.6465	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4238	Approved
0.6429	Remote Similarity	NPD4802	Phase 2
0.6422	Remote Similarity	NPD6083	Phase 2
0.6422	Remote Similarity	NPD6084	Phase 2
0.641	Remote Similarity	NPD8297	Approved
0.641	Remote Similarity	NPD6882	Approved
0.6404	Remote Similarity	NPD6412	Phase 2
0.6389	Remote Similarity	NPD5695	Phase 3
0.6379	Remote Similarity	NPD4634	Approved
0.6372	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5696	Approved
0.6348	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD5211	Phase 2
0.6337	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6009	Approved
0.6321	Remote Similarity	NPD7838	Discovery
0.6306	Remote Similarity	NPD5286	Approved
0.6306	Remote Similarity	NPD5285	Approved
0.6306	Remote Similarity	NPD4696	Approved
0.63	Remote Similarity	NPD4819	Approved
0.63	Remote Similarity	NPD4822	Approved
0.63	Remote Similarity	NPD4820	Approved
0.63	Remote Similarity	NPD4821	Approved
0.6286	Remote Similarity	NPD6903	Approved
0.6275	Remote Similarity	NPD7154	Phase 3
0.6273	Remote Similarity	NPD4755	Approved
0.6263	Remote Similarity	NPD4271	Approved
0.6263	Remote Similarity	NPD4268	Approved
0.6262	Remote Similarity	NPD6411	Approved
0.6262	Remote Similarity	NPD7637	Suspended
0.626	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.626	Remote Similarity	NPD5983	Phase 2
0.625	Remote Similarity	NPD1700	Approved
0.625	Remote Similarity	NPD6409	Approved
0.625	Remote Similarity	NPD5330	Approved
0.625	Remote Similarity	NPD7521	Approved
0.625	Remote Similarity	NPD7146	Approved
0.625	Remote Similarity	NPD6684	Approved
0.625	Remote Similarity	NPD6274	Approved
0.625	Remote Similarity	NPD7334	Approved
0.6228	Remote Similarity	NPD5141	Approved
0.6214	Remote Similarity	NPD3666	Approved
0.6214	Remote Similarity	NPD3665	Phase 1
0.6214	Remote Similarity	NPD3133	Approved
0.6204	Remote Similarity	NPD6399	Phase 3
0.6195	Remote Similarity	NPD7632	Discontinued
0.6195	Remote Similarity	NPD5226	Approved
0.6195	Remote Similarity	NPD5225	Approved
0.6195	Remote Similarity	NPD5224	Approved
0.6195	Remote Similarity	NPD4633	Approved
0.6186	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD4700	Approved
0.616	Remote Similarity	NPD7604	Phase 2
0.614	Remote Similarity	NPD5175	Approved
0.614	Remote Similarity	NPD5174	Approved
0.6132	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD5332	Approved
0.6117	Remote Similarity	NPD5331	Approved
0.6111	Remote Similarity	NPD5281	Approved
0.6111	Remote Similarity	NPD5693	Phase 1
0.6111	Remote Similarity	NPD5284	Approved
0.6106	Remote Similarity	NPD5223	Approved
0.6098	Remote Similarity	NPD7101	Approved
0.6098	Remote Similarity	NPD7100	Approved
0.6094	Remote Similarity	NPD6033	Approved
0.6091	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD5210	Approved
0.6091	Remote Similarity	NPD4629	Approved
0.6078	Remote Similarity	NPD4790	Discontinued
0.6077	Remote Similarity	NPD7260	Phase 2
0.6075	Remote Similarity	NPD4753	Phase 2
0.6075	Remote Similarity	NPD6101	Approved
0.6075	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD6317	Approved
0.6063	Remote Similarity	NPD6336	Discontinued
0.6036	Remote Similarity	NPD7839	Suspended
0.6031	Remote Similarity	NPD6845	Suspended
0.6019	Remote Similarity	NPD5207	Approved
0.6017	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD6313	Approved
0.6016	Remote Similarity	NPD7328	Approved
0.6016	Remote Similarity	NPD7327	Approved
0.6016	Remote Similarity	NPD6314	Approved
0.6016	Remote Similarity	NPD6335	Approved
0.6	Remote Similarity	NPD8516	Approved
0.6	Remote Similarity	NPD8515	Approved
0.6	Remote Similarity	NPD8517	Approved
0.6	Remote Similarity	NPD5956	Approved
0.6	Remote Similarity	NPD3198	Approved
0.6	Remote Similarity	NPD8513	Phase 3
0.5968	Remote Similarity	NPD7516	Approved
0.5966	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD6079	Approved
0.5943	Remote Similarity	NPD3618	Phase 1
0.5943	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD4729	Approved
0.5932	Remote Similarity	NPD4730	Approved
0.5932	Remote Similarity	NPD5128	Approved
0.5929	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD5328	Approved
0.5926	Remote Similarity	NPD6334	Approved
0.5926	Remote Similarity	NPD6333	Approved
0.592	Remote Similarity	NPD8377	Approved
0.592	Remote Similarity	NPD8294	Approved
0.5917	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD4202	Approved
0.5906	Remote Similarity	NPD8328	Phase 3
0.5897	Remote Similarity	NPD4767	Approved
0.5897	Remote Similarity	NPD4768	Approved
0.5893	Remote Similarity	NPD4697	Phase 3
0.5893	Remote Similarity	NPD5222	Approved
0.5893	Remote Similarity	NPD5221	Approved
0.5893	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD8296	Approved
0.5873	Remote Similarity	NPD6908	Approved
0.5873	Remote Similarity	NPD8335	Approved
0.5873	Remote Similarity	NPD8379	Approved
0.5873	Remote Similarity	NPD6909	Approved
0.5873	Remote Similarity	NPD7503	Approved
0.5873	Remote Similarity	NPD8380	Approved
0.5873	Remote Similarity	NPD8378	Approved
0.5873	Remote Similarity	NPD8033	Approved
0.5862	Remote Similarity	NPD4754	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