NPASS Compound

Structure

NPC475108 OpenBabel07101719512D 28 29 0 0 1 0 0 0 0 0999 V2000 -2.5115 3.3833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1858 1.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8372 2.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1576 -0.8372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3538 2.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6410 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5795 3.9615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3486 2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8372 3.1243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1295 3.1243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6743 0.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8372 -0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3486 1.9333 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8372 1.4500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3205 2.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6743 0.9667 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.9667 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8372 -0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6743 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8372 1.4500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6743 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2872 2.2872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8372 -1.4500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6410 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1576 -0.8372 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6128 3.9615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 13 1 0 0 0 0 7 28 1 0 0 0 0 8 13 1 0 0 0 0 9 10 2 0 0 0 0 9 15 1 0 0 0 0 10 28 1 0 0 0 0 11 14 1 0 0 0 0 11 19 1 0 0 0 0 12 19 1 0 0 0 0 12 22 1 0 0 0 0 13 16 1 0 0 0 0 14 3 1 6 0 0 0 14 17 1 0 0 0 0 15 20 1 0 0 0 0 15 23 2 0 0 0 0 16 20 1 6 0 0 0 16 21 1 0 0 0 0 17 20 1 1 0 0 0 17 22 1 0 0 0 0 18 21 1 0 0 0 0 18 22 1 0 0 0 0 18 24 2 0 0 0 0 19 4 1 6 0 0 0 19 25 1 0 0 0 0 20 5 1 6 0 0 0 21 6 1 6 0 0 0 21 26 1 0 0 0 0 22 27 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	396.25
Volume:	416.787
LogP:	2.456
LogD:	2.928
LogS:	-4.136
# Rotatable Bonds:	5
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.486
Synthetic Accessibility Score:	5.436
Fsp3:	0.818
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:	-4.76
MDCK Permeability:	2.2008736777934246e-05
Pgp-inhibitor:	0.15
Pgp-substrate:	0.02
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.126

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.93
Plasma Protein Binding (PPB):	59.92632293701172%
Volume Distribution (VD):	0.501
Pgp-substrate:	37.42718505859375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.944
CYP2C19-inhibitor:	0.153
CYP2C19-substrate:	0.851
CYP2C9-inhibitor:	0.17
CYP2C9-substrate:	0.162
CYP2D6-inhibitor:	0.04
CYP2D6-substrate:	0.07
CYP3A4-inhibitor:	0.952
CYP3A4-substrate:	0.828

ADMET: Excretion

Clearance (CL):	4.011
Half-life (T1/2):	0.466

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.312
Drug-inuced Liver Injury (DILI):	0.466
AMES Toxicity:	0.096
Rat Oral Acute Toxicity:	0.746
Maximum Recommended Daily Dose:	0.029
Skin Sensitization:	0.491
Carcinogencity:	0.063
Eye Corrosion:	0.039
Eye Irritation:	0.105
Respiratory Toxicity:	0.362

Download Data

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

Natural Product: NPC475108

Natural Product ID:	NPC475108
*Common Name:**	10-Hydroxy-18-Methoxybetaenone
IUPAC Name:	(2S,3R,4R,4aR,5R,7R,8aR)-3-butan-2-yl-2,7,8a-trihydroxy-4-[(E)-3-methoxyprop-2-enoyl]-2,4,5,7-tetramethyl-4a,5,6,8-tetrahydro-3H-naphthalen-1-one
Synonyms:
Standard InCHIKey:	ONZDNBGTAVEQQN-FJXLOMMUSA-N
Standard InCHI:	InChI=1S/C22H36O6/c1-8-13(2)16-20(5,15(23)9-10-28-7)17-14(3)11-19(4,25)12-22(17,27)18(24)21(16,6)26/h9-10,13-14,16-17,25-27H,8,11-12H2,1-7H3/b10-9+/t13?,14-,16-,17-,19-,20-,21+,22-/m1/s1
SMILES:	CO/C=C/C(=O)[C@]1(C)[C@@H](C(CC)C)[C@](C)(O)C(=O)[C@@]2([C@@H]1[C@H](C)C[C@@](C2)(C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL498247
PubChem CID:	10644450
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0002088] Acyloins

*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
NPO33476	microsphaeropsis sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[10869191]
NPO33476	microsphaeropsis sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[12027766]
NPO33476	microsphaeropsis sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[32243151]
NPO33476	microsphaeropsis sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[9917295]

☑ 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	3

Activity Type	# Activity
Individual Protein	2
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6611	Individual Protein	Protein kinase C epsilon	Mus musculus	IC50	=	36000.0	nM	PMID[572994]
NPT285	Individual Protein	Epidermal growth factor receptor erbB1	Homo sapiens	IC50	=	10500.0	nM	PMID[572994]
NPT1560	Protein Complex	Cyclin-dependent kinase 4/cyclin D1	Homo sapiens	IC50	=	11500.0	nM	PMID[572994]

☑ 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 NPC475108 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	210
0.1-0.2	1661
0.2-0.3	5779
0.3-0.4	11800
0.4-0.5	12230
0.5-0.6	7191
0.6-0.7	3535
0.7-0.8	290
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8125	Intermediate Similarity	NPC474724
0.7957	Intermediate Similarity	NPC46758
0.7895	Intermediate Similarity	NPC103527
0.7835	Intermediate Similarity	NPC273269
0.7812	Intermediate Similarity	NPC476245
0.7778	Intermediate Similarity	NPC477051
0.7778	Intermediate Similarity	NPC477053
0.7778	Intermediate Similarity	NPC477052
0.7766	Intermediate Similarity	NPC474209
0.7766	Intermediate Similarity	NPC475823
0.7765	Intermediate Similarity	NPC162164
0.7765	Intermediate Similarity	NPC38426
0.7755	Intermediate Similarity	NPC477653
0.7755	Intermediate Similarity	NPC191565
0.7701	Intermediate Similarity	NPC476811
0.7701	Intermediate Similarity	NPC472746
0.77	Intermediate Similarity	NPC477054
0.7677	Intermediate Similarity	NPC55503
0.7677	Intermediate Similarity	NPC46761
0.7677	Intermediate Similarity	NPC156324
0.7642	Intermediate Similarity	NPC198539
0.764	Intermediate Similarity	NPC469637
0.7629	Intermediate Similarity	NPC272617
0.7624	Intermediate Similarity	NPC247957
0.7624	Intermediate Similarity	NPC249187
0.7609	Intermediate Similarity	NPC224345
0.7547	Intermediate Similarity	NPC90769
0.7526	Intermediate Similarity	NPC64006
0.75	Intermediate Similarity	NPC26865
0.75	Intermediate Similarity	NPC198054
0.75	Intermediate Similarity	NPC293890
0.7477	Intermediate Similarity	NPC474271
0.7476	Intermediate Similarity	NPC257353
0.7451	Intermediate Similarity	NPC320294
0.7447	Intermediate Similarity	NPC153604
0.7426	Intermediate Similarity	NPC118964
0.7419	Intermediate Similarity	NPC241512
0.7419	Intermediate Similarity	NPC477445
0.7419	Intermediate Similarity	NPC6185
0.7412	Intermediate Similarity	NPC163020
0.74	Intermediate Similarity	NPC98837
0.74	Intermediate Similarity	NPC162459
0.74	Intermediate Similarity	NPC28864
0.74	Intermediate Similarity	NPC20479
0.74	Intermediate Similarity	NPC38471
0.74	Intermediate Similarity	NPC38296
0.7396	Intermediate Similarity	NPC149761
0.7396	Intermediate Similarity	NPC470378
0.7396	Intermediate Similarity	NPC472325
0.7396	Intermediate Similarity	NPC261994
0.7386	Intermediate Similarity	NPC104806
0.7379	Intermediate Similarity	NPC72255
0.7374	Intermediate Similarity	NPC260223
0.7374	Intermediate Similarity	NPC140242
0.7374	Intermediate Similarity	NPC165616
0.7374	Intermediate Similarity	NPC219353
0.7374	Intermediate Similarity	NPC223169
0.7374	Intermediate Similarity	NPC473964
0.7364	Intermediate Similarity	NPC146786
0.7363	Intermediate Similarity	NPC473217
0.7347	Intermediate Similarity	NPC91772
0.7347	Intermediate Similarity	NPC169751
0.7347	Intermediate Similarity	NPC153775
0.7347	Intermediate Similarity	NPC245972
0.7347	Intermediate Similarity	NPC292374
0.7347	Intermediate Similarity	NPC196485
0.7347	Intermediate Similarity	NPC29247
0.7347	Intermediate Similarity	NPC261333
0.7347	Intermediate Similarity	NPC215271
0.7347	Intermediate Similarity	NPC289539
0.7347	Intermediate Similarity	NPC272635
0.7347	Intermediate Similarity	NPC23170
0.7347	Intermediate Similarity	NPC129004
0.7347	Intermediate Similarity	NPC101233
0.7347	Intermediate Similarity	NPC258674
0.7347	Intermediate Similarity	NPC104371
0.7347	Intermediate Similarity	NPC209662
0.7347	Intermediate Similarity	NPC111524
0.734	Intermediate Similarity	NPC203795
0.734	Intermediate Similarity	NPC94666
0.734	Intermediate Similarity	NPC34190
0.7333	Intermediate Similarity	NPC289702
0.7333	Intermediate Similarity	NPC208461
0.7333	Intermediate Similarity	NPC476812
0.7327	Intermediate Similarity	NPC293866
0.732	Intermediate Similarity	NPC299185
0.7312	Intermediate Similarity	NPC251170
0.7308	Intermediate Similarity	NPC85529
0.7308	Intermediate Similarity	NPC32006
0.7308	Intermediate Similarity	NPC34768
0.73	Intermediate Similarity	NPC190080
0.73	Intermediate Similarity	NPC10864
0.73	Intermediate Similarity	NPC111187
0.73	Intermediate Similarity	NPC473963
0.7283	Intermediate Similarity	NPC48362
0.7282	Intermediate Similarity	NPC239716
0.7282	Intermediate Similarity	NPC179208
0.7282	Intermediate Similarity	NPC275583
0.7282	Intermediate Similarity	NPC478057
0.7273	Intermediate Similarity	NPC157686
0.7273	Intermediate Similarity	NPC217329
0.7273	Intermediate Similarity	NPC472824
0.7273	Intermediate Similarity	NPC259042
0.7273	Intermediate Similarity	NPC98639
0.7273	Intermediate Similarity	NPC180950
0.7264	Intermediate Similarity	NPC300026
0.7264	Intermediate Similarity	NPC27814
0.7263	Intermediate Similarity	NPC259009
0.7263	Intermediate Similarity	NPC174619
0.7255	Intermediate Similarity	NPC71706
0.7255	Intermediate Similarity	NPC46848
0.7253	Intermediate Similarity	NPC476809
0.7245	Intermediate Similarity	NPC233118
0.7245	Intermediate Similarity	NPC294263
0.7245	Intermediate Similarity	NPC144739
0.7245	Intermediate Similarity	NPC181594
0.7241	Intermediate Similarity	NPC177826
0.7238	Intermediate Similarity	NPC302788
0.7238	Intermediate Similarity	NPC185
0.7238	Intermediate Similarity	NPC165873
0.7238	Intermediate Similarity	NPC179380
0.7238	Intermediate Similarity	NPC176949
0.7238	Intermediate Similarity	NPC201908
0.7234	Intermediate Similarity	NPC474680
0.7234	Intermediate Similarity	NPC471034
0.7234	Intermediate Similarity	NPC263997
0.7234	Intermediate Similarity	NPC8518
0.7234	Intermediate Similarity	NPC132228
0.7234	Intermediate Similarity	NPC190704
0.7228	Intermediate Similarity	NPC78427
0.7228	Intermediate Similarity	NPC89099
0.7228	Intermediate Similarity	NPC16911
0.7228	Intermediate Similarity	NPC109059
0.7228	Intermediate Similarity	NPC17183
0.7228	Intermediate Similarity	NPC288
0.7222	Intermediate Similarity	NPC476810
0.7222	Intermediate Similarity	NPC476808
0.7216	Intermediate Similarity	NPC263977
0.7216	Intermediate Similarity	NPC80401
0.7212	Intermediate Similarity	NPC84928
0.7212	Intermediate Similarity	NPC98603
0.72	Intermediate Similarity	NPC470387
0.72	Intermediate Similarity	NPC264979
0.72	Intermediate Similarity	NPC29410
0.72	Intermediate Similarity	NPC49371
0.72	Intermediate Similarity	NPC200054
0.72	Intermediate Similarity	NPC135548
0.72	Intermediate Similarity	NPC469545
0.72	Intermediate Similarity	NPC61369
0.72	Intermediate Similarity	NPC93245
0.72	Intermediate Similarity	NPC284518
0.72	Intermediate Similarity	NPC5532
0.7196	Intermediate Similarity	NPC100908
0.7191	Intermediate Similarity	NPC198473
0.7191	Intermediate Similarity	NPC63958
0.7188	Intermediate Similarity	NPC471791
0.7188	Intermediate Similarity	NPC292491
0.7188	Intermediate Similarity	NPC471793
0.7188	Intermediate Similarity	NPC193360
0.7188	Intermediate Similarity	NPC310752
0.7184	Intermediate Similarity	NPC476081
0.7184	Intermediate Similarity	NPC304832
0.7184	Intermediate Similarity	NPC88203
0.7184	Intermediate Similarity	NPC148628
0.7184	Intermediate Similarity	NPC275990
0.7184	Intermediate Similarity	NPC76866
0.7184	Intermediate Similarity	NPC214946
0.7184	Intermediate Similarity	NPC272472
0.7184	Intermediate Similarity	NPC246736
0.7184	Intermediate Similarity	NPC286519
0.7182	Intermediate Similarity	NPC270478
0.7174	Intermediate Similarity	NPC48673
0.7174	Intermediate Similarity	NPC20096
0.7174	Intermediate Similarity	NPC328264
0.7172	Intermediate Similarity	NPC24861
0.7172	Intermediate Similarity	NPC299100
0.7172	Intermediate Similarity	NPC148000
0.7172	Intermediate Similarity	NPC469596
0.7172	Intermediate Similarity	NPC293086
0.7172	Intermediate Similarity	NPC225474
0.7172	Intermediate Similarity	NPC47853
0.7172	Intermediate Similarity	NPC471207
0.7172	Intermediate Similarity	NPC474328
0.717	Intermediate Similarity	NPC168883
0.7158	Intermediate Similarity	NPC158393
0.7158	Intermediate Similarity	NPC73038
0.7157	Intermediate Similarity	NPC474720
0.7157	Intermediate Similarity	NPC287676
0.7157	Intermediate Similarity	NPC144956
0.7157	Intermediate Similarity	NPC477655
0.7157	Intermediate Similarity	NPC47024
0.7157	Intermediate Similarity	NPC471727
0.7157	Intermediate Similarity	NPC477656
0.7143	Intermediate Similarity	NPC252433
0.7143	Intermediate Similarity	NPC473167
0.7143	Intermediate Similarity	NPC472978
0.7143	Intermediate Similarity	NPC475708
0.7143	Intermediate Similarity	NPC279143
0.7143	Intermediate Similarity	NPC248913
0.7143	Intermediate Similarity	NPC131872

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 NPC475108 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	200
0.1-0.2	2203
0.2-0.3	4013
0.3-0.4	1863
0.4-0.5	504
0.5-0.6	186
0.6-0.7	174
0.7-0.8	7
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
0.7449	Intermediate Similarity	NPD4629	Approved
0.7449	Intermediate Similarity	NPD5210	Approved
0.7333	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD5286	Approved
0.7157	Intermediate Similarity	NPD5285	Approved
0.7157	Intermediate Similarity	NPD4696	Approved
0.7065	Intermediate Similarity	NPD4695	Discontinued
0.7059	Intermediate Similarity	NPD5696	Approved
0.703	Intermediate Similarity	NPD5221	Approved
0.703	Intermediate Similarity	NPD5222	Approved
0.703	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4788	Approved
0.7019	Intermediate Similarity	NPD5225	Approved
0.7019	Intermediate Similarity	NPD5226	Approved
0.7019	Intermediate Similarity	NPD4633	Approved
0.7019	Intermediate Similarity	NPD5224	Approved
0.7019	Intermediate Similarity	NPD5211	Phase 2
0.7009	Intermediate Similarity	NPD6899	Approved
0.7009	Intermediate Similarity	NPD6881	Approved
0.6979	Remote Similarity	NPD3618	Phase 1
0.6979	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6649	Approved
0.6972	Remote Similarity	NPD6650	Approved
0.697	Remote Similarity	NPD6079	Approved
0.6961	Remote Similarity	NPD4755	Approved
0.6961	Remote Similarity	NPD5173	Approved
0.6952	Remote Similarity	NPD5174	Approved
0.6952	Remote Similarity	NPD5175	Approved
0.6939	Remote Similarity	NPD4753	Phase 2
0.6923	Remote Similarity	NPD5223	Approved
0.6916	Remote Similarity	NPD5697	Approved
0.6887	Remote Similarity	NPD5141	Approved
0.6881	Remote Similarity	NPD4634	Approved
0.6881	Remote Similarity	NPD7102	Approved
0.6881	Remote Similarity	NPD6883	Approved
0.6881	Remote Similarity	NPD7290	Approved
0.6863	Remote Similarity	NPD4697	Phase 3
0.6832	Remote Similarity	NPD5282	Discontinued
0.6832	Remote Similarity	NPD7748	Approved
0.6827	Remote Similarity	NPD4700	Approved
0.6822	Remote Similarity	NPD6675	Approved
0.6822	Remote Similarity	NPD7128	Approved
0.6822	Remote Similarity	NPD5739	Approved
0.6822	Remote Similarity	NPD6402	Approved
0.6818	Remote Similarity	NPD6869	Approved
0.6818	Remote Similarity	NPD8130	Phase 1
0.6818	Remote Similarity	NPD6847	Approved
0.6818	Remote Similarity	NPD6617	Approved
0.68	Remote Similarity	NPD7515	Phase 2
0.6796	Remote Similarity	NPD6084	Phase 2
0.6796	Remote Similarity	NPD6083	Phase 2
0.6796	Remote Similarity	NPD7902	Approved
0.6789	Remote Similarity	NPD6373	Approved
0.6789	Remote Similarity	NPD6012	Approved
0.6789	Remote Similarity	NPD6372	Approved
0.6789	Remote Similarity	NPD6013	Approved
0.6789	Remote Similarity	NPD6014	Approved
0.6768	Remote Similarity	NPD5328	Approved
0.6757	Remote Similarity	NPD6882	Approved
0.6757	Remote Similarity	NPD8297	Approved
0.6701	Remote Similarity	NPD5329	Approved
0.6697	Remote Similarity	NPD7320	Approved
0.6697	Remote Similarity	NPD4730	Approved
0.6697	Remote Similarity	NPD4729	Approved
0.6697	Remote Similarity	NPD6011	Approved
0.6696	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD3617	Approved
0.6638	Remote Similarity	NPD6054	Approved
0.6634	Remote Similarity	NPD8034	Phase 2
0.6634	Remote Similarity	NPD8035	Phase 2
0.6633	Remote Similarity	NPD5690	Phase 2
0.6606	Remote Similarity	NPD5701	Approved
0.6602	Remote Similarity	NPD5695	Phase 3
0.66	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD4197	Approved
0.6598	Remote Similarity	NPD4786	Approved
0.6581	Remote Similarity	NPD6921	Approved
0.6577	Remote Similarity	NPD5250	Approved
0.6577	Remote Similarity	NPD5251	Approved
0.6577	Remote Similarity	NPD5247	Approved
0.6577	Remote Similarity	NPD5248	Approved
0.6577	Remote Similarity	NPD5249	Phase 3
0.6569	Remote Similarity	NPD6399	Phase 3
0.6569	Remote Similarity	NPD4202	Approved
0.6566	Remote Similarity	NPD3573	Approved
0.6562	Remote Similarity	NPD3667	Approved
0.6545	Remote Similarity	NPD5128	Approved
0.6542	Remote Similarity	NPD5091	Approved
0.6531	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD6370	Approved
0.6522	Remote Similarity	NPD3703	Phase 2
0.6522	Remote Similarity	NPD6009	Approved
0.6518	Remote Similarity	NPD5215	Approved
0.6518	Remote Similarity	NPD5216	Approved
0.6518	Remote Similarity	NPD5217	Approved
0.6514	Remote Similarity	NPD4767	Approved
0.6514	Remote Similarity	NPD4768	Approved
0.6505	Remote Similarity	NPD7900	Approved
0.6505	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5737	Approved
0.65	Remote Similarity	NPD6672	Approved
0.6496	Remote Similarity	NPD6319	Approved
0.6489	Remote Similarity	NPD6115	Approved
0.6489	Remote Similarity	NPD6697	Approved
0.6489	Remote Similarity	NPD6118	Approved
0.6489	Remote Similarity	NPD6114	Approved
0.6481	Remote Similarity	NPD4754	Approved
0.6444	Remote Similarity	NPD4789	Approved
0.6441	Remote Similarity	NPD6016	Approved
0.6441	Remote Similarity	NPD6015	Approved
0.6429	Remote Similarity	NPD3665	Phase 1
0.6429	Remote Similarity	NPD3666	Approved
0.6429	Remote Similarity	NPD5135	Approved
0.6429	Remote Similarity	NPD5169	Approved
0.6429	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3133	Approved
0.6417	Remote Similarity	NPD7492	Approved
0.6415	Remote Similarity	NPD7638	Approved
0.641	Remote Similarity	NPD7100	Approved
0.641	Remote Similarity	NPD7101	Approved
0.6404	Remote Similarity	NPD5360	Phase 3
0.6404	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD5168	Approved
0.6392	Remote Similarity	NPD4223	Phase 3
0.6392	Remote Similarity	NPD4221	Approved
0.6387	Remote Similarity	NPD5988	Approved
0.6379	Remote Similarity	NPD7115	Discovery
0.6374	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD5127	Approved
0.6364	Remote Similarity	NPD6616	Approved
0.6356	Remote Similarity	NPD6059	Approved
0.6355	Remote Similarity	NPD7639	Approved
0.6355	Remote Similarity	NPD7640	Approved
0.6333	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD7604	Phase 2
0.6333	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD6335	Approved
0.6311	Remote Similarity	NPD7078	Approved
0.6303	Remote Similarity	NPD5983	Phase 2
0.63	Remote Similarity	NPD5280	Approved
0.63	Remote Similarity	NPD4694	Approved
0.63	Remote Similarity	NPD5279	Phase 3
0.63	Remote Similarity	NPD4623	Approved
0.63	Remote Similarity	NPD4519	Discontinued
0.6293	Remote Similarity	NPD6274	Approved
0.6293	Remote Similarity	NPD6868	Approved
0.6286	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD6117	Approved
0.6275	Remote Similarity	NPD6080	Approved
0.6275	Remote Similarity	NPD6904	Approved
0.6275	Remote Similarity	NPD6673	Approved
0.6263	Remote Similarity	NPD3668	Phase 3
0.626	Remote Similarity	NPD7736	Approved
0.625	Remote Similarity	NPD7645	Phase 2
0.625	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6317	Approved
0.623	Remote Similarity	NPD6336	Discontinued
0.6226	Remote Similarity	NPD7614	Phase 1
0.6216	Remote Similarity	NPD6008	Approved
0.6211	Remote Similarity	NPD6116	Phase 1
0.6207	Remote Similarity	NPD5167	Approved
0.62	Remote Similarity	NPD1694	Approved
0.6198	Remote Similarity	NPD8328	Phase 3
0.6196	Remote Similarity	NPD6081	Approved
0.6195	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6314	Approved
0.6186	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD7525	Registered
0.6186	Remote Similarity	NPD6313	Approved
0.6167	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD6412	Phase 2
0.6161	Remote Similarity	NPD6614	Approved
0.6154	Remote Similarity	NPD5281	Approved
0.6154	Remote Similarity	NPD5284	Approved
0.6139	Remote Similarity	NPD4138	Approved
0.6139	Remote Similarity	NPD7521	Approved
0.6139	Remote Similarity	NPD5330	Approved
0.6139	Remote Similarity	NPD6098	Approved
0.6139	Remote Similarity	NPD4689	Approved
0.6139	Remote Similarity	NPD4693	Phase 3
0.6139	Remote Similarity	NPD6684	Approved
0.6139	Remote Similarity	NPD7334	Approved
0.6139	Remote Similarity	NPD7146	Approved
0.6139	Remote Similarity	NPD4690	Approved
0.6139	Remote Similarity	NPD6409	Approved
0.6139	Remote Similarity	NPD5205	Approved
0.6139	Remote Similarity	NPD4688	Approved
0.6111	Remote Similarity	NPD4225	Approved
0.6087	Remote Similarity	NPD4244	Approved
0.6087	Remote Similarity	NPD4245	Approved
0.6082	Remote Similarity	NPD4195	Approved
0.6075	Remote Similarity	NPD7732	Phase 3
0.6064	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD8293	Discontinued
0.604	Remote Similarity	NPD1696	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