NPASS Compound

Structure

NPC470670 OpenBabel07101718182D 26 27 0 0 1 0 0 0 0 0999 V2000 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3660 -3.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8660 -2.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 0.3660 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 -2.3660 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3660 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -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 -3.8660 -2.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 3 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 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 0.0000 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 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 12 1 0 0 0 0 3 12 1 0 0 0 0 4 13 1 0 0 0 0 6 13 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 12 2 0 0 0 0 9 21 1 0 0 0 0 10 14 1 0 0 0 0 10 17 1 0 0 0 0 11 15 2 0 0 0 0 11 16 1 0 0 0 0 13 19 1 0 0 0 0 14 15 1 0 0 0 0 14 20 2 0 0 0 0 15 22 1 0 0 0 0 16 18 2 0 0 0 0 16 23 1 0 0 0 0 17 21 1 6 0 0 0 17 24 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 19 25 2 0 0 0 0 20 26 1 0 0 0 0 21 5 1 6 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.21
Volume:	385.428
LogP:	4.905
LogD:	3.791
LogS:	-3.36
# Rotatable Bonds:	6
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.523
Synthetic Accessibility Score:	4.195
Fsp3:	0.571
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.709
MDCK Permeability:	1.7422818928025663e-05
Pgp-inhibitor:	0.644
Pgp-substrate:	0.347
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.895
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.223
Plasma Protein Binding (PPB):	99.14900970458984%
Volume Distribution (VD):	1.063
Pgp-substrate:	2.5331060886383057%

ADMET: Metabolism

CYP1A2-inhibitor:	0.888
CYP1A2-substrate:	0.566
CYP2C19-inhibitor:	0.299
CYP2C19-substrate:	0.379
CYP2C9-inhibitor:	0.603
CYP2C9-substrate:	0.842
CYP2D6-inhibitor:	0.853
CYP2D6-substrate:	0.219
CYP3A4-inhibitor:	0.528
CYP3A4-substrate:	0.281

ADMET: Excretion

Clearance (CL):	12.766
Half-life (T1/2):	0.172

ADMET: Toxicity

hERG Blockers:	0.069
Human Hepatotoxicity (H-HT):	0.545
Drug-inuced Liver Injury (DILI):	0.506
AMES Toxicity:	0.041
Rat Oral Acute Toxicity:	0.942
Maximum Recommended Daily Dose:	0.849
Skin Sensitization:	0.699
Carcinogencity:	0.151
Eye Corrosion:	0.003
Eye Irritation:	0.386
Respiratory Toxicity:	0.852

Download Data

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

Natural Product: NPC470670

Natural Product ID:	NPC470670
*Common Name:**	Empetrikarinol B
IUPAC Name:	2-methyl-1-[(2R,3S)-3,5,7-trihydroxy-2-methyl-2-(4-methylpent-3-enyl)-3,4-dihydrochromen-8-yl]butan-1-one
Synonyms:	Empetrikarinol B
Standard InCHIKey:	OOUQAKUAWXZBEN-PTPQSVRFSA-N
Standard InCHI:	InChI=1S/C21H30O5/c1-6-13(4)19(25)18-16(23)11-15(22)14-10-17(24)21(5,26-20(14)18)9-7-8-12(2)3/h8,11,13,17,22-24H,6-7,9-10H2,1-5H3/t13?,17-,21+/m0/s1
SMILES:	CCC(C)C(=O)c1c(cc(c2C[C@@H]([C@@](C)(CCC=C(C)C)Oc12)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2152494
PubChem CID:	71458439
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000350] Butyrophenones

*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
NPO33078	hypericum empetrifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23030826]
NPO30921	Hypericum roeperianum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24930002]
NPO30921	Hypericum roeperianum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26358281]
NPO40851	Garcinia dauphinensis	Species	Clusiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30354100]
NPO30921	Hypericum roeperianum	Species	Hypericaceae	Eukaryota	n.a.	root	n.a.	PMID[8862040]

☑ 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
EC50	1
IC50	2
MIC	3
Others	5

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT25	Cell Line	MT4	Homo sapiens	CC50	=	45000.0	nM	PMID[491801]
NPT306	Cell Line	PC-3	Homo sapiens	GI	<	20.0	%	PMID[491801]
NPT139	Cell Line	HT-29	Homo sapiens	GI	=	20.0	%	PMID[491801]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	10000.0	nM	PMID[491802]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	18400.0	nM	PMID[491800]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	1.0	ug.mL-1	PMID[491801]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	>	45000.0	nM	PMID[491801]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	1.0	ug.mL-1	PMID[491801]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	>	1.0	ug.mL-1	PMID[491801]
NPT530	Organism	Caenorhabditis elegans	Caenorhabditis elegans	Activity	=	0.7	%	PMID[491801]

☑ 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 NPC470670 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	365
0.1-0.2	1359
0.2-0.3	3569
0.3-0.4	8320
0.4-0.5	10260
0.5-0.6	3816
0.6-0.7	5402
0.7-0.8	5872
0.8-0.85	2288
0.85-0.9	1067
0.9-0.95	355
0.95-1	24

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473133
1.0	High Similarity	NPC47388
0.9858	High Similarity	NPC91902
0.9786	High Similarity	NPC18886
0.972	High Similarity	NPC307052
0.972	High Similarity	NPC139966
0.9718	High Similarity	NPC85773
0.965	High Similarity	NPC10097
0.9648	High Similarity	NPC474302
0.9586	High Similarity	NPC474021
0.9586	High Similarity	NPC472422
0.9586	High Similarity	NPC471677
0.9586	High Similarity	NPC471676
0.9586	High Similarity	NPC474023
0.9586	High Similarity	NPC244577
0.9586	High Similarity	NPC472420
0.9586	High Similarity	NPC263384
0.958	High Similarity	NPC202494
0.9521	High Similarity	NPC217149
0.9521	High Similarity	NPC475790
0.9521	High Similarity	NPC216035
0.9521	High Similarity	NPC256141
0.9459	High Similarity	NPC10754
0.9459	High Similarity	NPC215917
0.9459	High Similarity	NPC20530
0.9456	High Similarity	NPC469405
0.9456	High Similarity	NPC223701
0.9456	High Similarity	NPC7989
0.9456	High Similarity	NPC472583
0.9452	High Similarity	NPC254412
0.9452	High Similarity	NPC474772
0.9452	High Similarity	NPC472423
0.9452	High Similarity	NPC262038
0.9452	High Similarity	NPC472636
0.9452	High Similarity	NPC262039
0.9452	High Similarity	NPC474744
0.9452	High Similarity	NPC278476
0.9452	High Similarity	NPC319910
0.9448	High Similarity	NPC472628
0.9444	High Similarity	NPC472627
0.9441	High Similarity	NPC470890
0.9441	High Similarity	NPC297788
0.9437	High Similarity	NPC276565
0.9429	High Similarity	NPC470671
0.9429	High Similarity	NPC474504
0.9429	High Similarity	NPC470672
0.9429	High Similarity	NPC474487
0.9392	High Similarity	NPC259710
0.9392	High Similarity	NPC217706
0.9392	High Similarity	NPC48579
0.9392	High Similarity	NPC304207
0.9392	High Similarity	NPC207809
0.9392	High Similarity	NPC477958
0.9388	High Similarity	NPC171651
0.9388	High Similarity	NPC473996
0.9388	High Similarity	NPC150123
0.9388	High Similarity	NPC244583
0.9388	High Similarity	NPC243171
0.9388	High Similarity	NPC138288
0.9388	High Similarity	NPC161881
0.9388	High Similarity	NPC56232
0.9388	High Similarity	NPC10807
0.9388	High Similarity	NPC35567
0.9384	High Similarity	NPC105136
0.9384	High Similarity	NPC180351
0.9384	High Similarity	NPC472421
0.9375	High Similarity	NPC316769
0.9375	High Similarity	NPC472629
0.9366	High Similarity	NPC74397
0.9362	High Similarity	NPC471697
0.9362	High Similarity	NPC139554
0.9329	High Similarity	NPC164427
0.9324	High Similarity	NPC293286
0.9324	High Similarity	NPC180301
0.9324	High Similarity	NPC248793
0.932	High Similarity	NPC472580
0.932	High Similarity	NPC209846
0.932	High Similarity	NPC328740
0.932	High Similarity	NPC190217
0.932	High Similarity	NPC289774
0.932	High Similarity	NPC477897
0.932	High Similarity	NPC471675
0.9315	High Similarity	NPC89442
0.9306	High Similarity	NPC131568
0.9306	High Similarity	NPC224714
0.9306	High Similarity	NPC131579
0.9306	High Similarity	NPC87486
0.9306	High Similarity	NPC124780
0.9301	High Similarity	NPC130206
0.9296	High Similarity	NPC477272
0.9291	High Similarity	NPC131130
0.9286	High Similarity	NPC156910
0.9286	High Similarity	NPC470397
0.9262	High Similarity	NPC470605
0.9262	High Similarity	NPC304745
0.9262	High Similarity	NPC111341
0.9262	High Similarity	NPC470604
0.9262	High Similarity	NPC470681
0.9262	High Similarity	NPC470603
0.9257	High Similarity	NPC285623
0.9257	High Similarity	NPC477957
0.9257	High Similarity	NPC31627
0.9257	High Similarity	NPC210597
0.9257	High Similarity	NPC327269
0.9257	High Similarity	NPC476238
0.9252	High Similarity	NPC470908
0.9252	High Similarity	NPC106025
0.9252	High Similarity	NPC477240
0.9252	High Similarity	NPC214454
0.9241	High Similarity	NPC127059
0.9241	High Similarity	NPC24136
0.9241	High Similarity	NPC285630
0.9241	High Similarity	NPC290133
0.9241	High Similarity	NPC187282
0.9236	High Similarity	NPC125894
0.9236	High Similarity	NPC255133
0.9236	High Similarity	NPC112749
0.9236	High Similarity	NPC478086
0.9236	High Similarity	NPC107177
0.9236	High Similarity	NPC242100
0.9236	High Similarity	NPC77794
0.9236	High Similarity	NPC214166
0.9236	High Similarity	NPC85162
0.9236	High Similarity	NPC223812
0.9236	High Similarity	NPC81697
0.9236	High Similarity	NPC278249
0.9236	High Similarity	NPC316816
0.9231	High Similarity	NPC17170
0.9231	High Similarity	NPC96408
0.9231	High Similarity	NPC166689
0.9231	High Similarity	NPC279650
0.9231	High Similarity	NPC258630
0.9231	High Similarity	NPC156190
0.9231	High Similarity	NPC171870
0.9225	High Similarity	NPC23257
0.9214	High Similarity	NPC84699
0.9205	High Similarity	NPC470607
0.9205	High Similarity	NPC473990
0.92	High Similarity	NPC208152
0.92	High Similarity	NPC78492
0.9195	High Similarity	NPC311579
0.9195	High Similarity	NPC109594
0.9195	High Similarity	NPC78021
0.9195	High Similarity	NPC326592
0.9195	High Similarity	NPC268950
0.9195	High Similarity	NPC211158
0.9195	High Similarity	NPC112701
0.9195	High Similarity	NPC108706
0.9195	High Similarity	NPC87304
0.9195	High Similarity	NPC244250
0.9195	High Similarity	NPC236756
0.9195	High Similarity	NPC20907
0.9195	High Similarity	NPC74924
0.9195	High Similarity	NPC268193
0.9195	High Similarity	NPC209760
0.9195	High Similarity	NPC100134
0.9189	High Similarity	NPC473131
0.9189	High Similarity	NPC470675
0.9184	High Similarity	NPC473016
0.9184	High Similarity	NPC5173
0.9178	High Similarity	NPC222298
0.9178	High Similarity	NPC51070
0.9178	High Similarity	NPC14875
0.9178	High Similarity	NPC122828
0.9178	High Similarity	NPC296998
0.9178	High Similarity	NPC176869
0.9178	High Similarity	NPC211466
0.9178	High Similarity	NPC40086
0.9178	High Similarity	NPC3779
0.9178	High Similarity	NPC476182
0.9178	High Similarity	NPC308200
0.9178	High Similarity	NPC44721
0.9178	High Similarity	NPC472918
0.9178	High Similarity	NPC473077
0.9172	High Similarity	NPC294365
0.9172	High Similarity	NPC271288
0.9172	High Similarity	NPC473013
0.9172	High Similarity	NPC473015
0.9172	High Similarity	NPC235217
0.9172	High Similarity	NPC473014
0.9172	High Similarity	NPC209040
0.9167	High Similarity	NPC220998
0.9167	High Similarity	NPC166482
0.9167	High Similarity	NPC32739
0.9167	High Similarity	NPC37496
0.9167	High Similarity	NPC265040
0.9167	High Similarity	NPC10937
0.9167	High Similarity	NPC228504
0.9167	High Similarity	NPC227579
0.9167	High Similarity	NPC64915
0.9167	High Similarity	NPC223500
0.9167	High Similarity	NPC296917
0.9167	High Similarity	NPC66515
0.9167	High Similarity	NPC324436
0.9167	High Similarity	NPC324134
0.9167	High Similarity	NPC182852
0.9167	High Similarity	NPC161506
0.9167	High Similarity	NPC107572
0.9167	High Similarity	NPC78
0.9167	High Similarity	NPC76338

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 NPC470670 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	325
0.1-0.2	868
0.2-0.3	1865
0.3-0.4	2535
0.4-0.5	1853
0.5-0.6	1066
0.6-0.7	447
0.7-0.8	151
0.8-0.85	28
0.85-0.9	12
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9122	High Similarity	NPD4380	Phase 2
0.9067	High Similarity	NPD2393	Clinical (unspecified phase)
0.8912	High Similarity	NPD4378	Clinical (unspecified phase)
0.8889	High Similarity	NPD7075	Discontinued
0.8874	High Similarity	NPD1934	Approved
0.8819	High Similarity	NPD1550	Clinical (unspecified phase)
0.8819	High Similarity	NPD1552	Clinical (unspecified phase)
0.8816	High Similarity	NPD7096	Clinical (unspecified phase)
0.8766	High Similarity	NPD4381	Clinical (unspecified phase)
0.8759	High Similarity	NPD1549	Phase 2
0.8758	High Similarity	NPD8443	Clinical (unspecified phase)
0.8627	High Similarity	NPD6801	Discontinued
0.8625	High Similarity	NPD7804	Clinical (unspecified phase)
0.8553	High Similarity	NPD6168	Clinical (unspecified phase)
0.8553	High Similarity	NPD6167	Clinical (unspecified phase)
0.8553	High Similarity	NPD6166	Phase 2
0.8533	High Similarity	NPD7410	Clinical (unspecified phase)
0.8493	Intermediate Similarity	NPD2796	Approved
0.8467	Intermediate Similarity	NPD6799	Approved
0.8452	Intermediate Similarity	NPD2801	Approved
0.8446	Intermediate Similarity	NPD2800	Approved
0.8442	Intermediate Similarity	NPD7411	Suspended
0.8425	Intermediate Similarity	NPD1510	Phase 2
0.8403	Intermediate Similarity	NPD1240	Approved
0.8365	Intermediate Similarity	NPD6959	Discontinued
0.8344	Intermediate Similarity	NPD3882	Suspended
0.8344	Intermediate Similarity	NPD7074	Phase 3
0.8344	Intermediate Similarity	NPD1511	Approved
0.8333	Intermediate Similarity	NPD7819	Suspended
0.8302	Intermediate Similarity	NPD5494	Approved
0.8288	Intermediate Similarity	NPD6651	Approved
0.8288	Intermediate Similarity	NPD1607	Approved
0.8282	Intermediate Similarity	NPD7054	Approved
0.8258	Intermediate Similarity	NPD6599	Discontinued
0.8255	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD6559	Discontinued
0.8235	Intermediate Similarity	NPD1512	Approved
0.8232	Intermediate Similarity	NPD7472	Approved
0.8228	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD3818	Discontinued
0.8182	Intermediate Similarity	NPD6797	Phase 2
0.817	Intermediate Similarity	NPD2532	Approved
0.817	Intermediate Similarity	NPD2534	Approved
0.817	Intermediate Similarity	NPD2533	Approved
0.8165	Intermediate Similarity	NPD3817	Phase 2
0.8133	Intermediate Similarity	NPD7251	Discontinued
0.8098	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD7808	Phase 3
0.8065	Intermediate Similarity	NPD5403	Approved
0.8026	Intermediate Similarity	NPD4628	Phase 3
0.8	Intermediate Similarity	NPD7768	Phase 2
0.7976	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD1243	Approved
0.7961	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD5844	Phase 1
0.7949	Intermediate Similarity	NPD920	Approved
0.7939	Intermediate Similarity	NPD7473	Discontinued
0.7937	Intermediate Similarity	NPD5402	Approved
0.7935	Intermediate Similarity	NPD5401	Approved
0.7908	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD2424	Discontinued
0.7891	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD2935	Discontinued
0.7881	Intermediate Similarity	NPD1551	Phase 2
0.7881	Intermediate Similarity	NPD6100	Approved
0.7881	Intermediate Similarity	NPD6099	Approved
0.787	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD6232	Discontinued
0.7857	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD5124	Phase 1
0.784	Intermediate Similarity	NPD3749	Approved
0.7821	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD2799	Discontinued
0.7806	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD3750	Approved
0.7792	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD5953	Discontinued
0.7738	Intermediate Similarity	NPD7286	Phase 2
0.7727	Intermediate Similarity	NPD4360	Phase 2
0.7727	Intermediate Similarity	NPD4363	Phase 3
0.7697	Intermediate Similarity	NPD1247	Approved
0.7683	Intermediate Similarity	NPD919	Approved
0.7667	Intermediate Similarity	NPD1613	Approved
0.7667	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD5710	Approved
0.7651	Intermediate Similarity	NPD5711	Approved
0.7635	Intermediate Similarity	NPD4908	Phase 1
0.7616	Intermediate Similarity	NPD230	Phase 1
0.7614	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD2344	Approved
0.7582	Intermediate Similarity	NPD7033	Discontinued
0.756	Intermediate Similarity	NPD2403	Approved
0.7554	Intermediate Similarity	NPD7584	Approved
0.755	Intermediate Similarity	NPD943	Approved
0.7546	Intermediate Similarity	NPD1465	Phase 2
0.7542	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD2313	Discontinued
0.7531	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1610	Phase 2
0.7514	Intermediate Similarity	NPD8313	Approved
0.7514	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD2654	Approved
0.75	Intermediate Similarity	NPD1652	Phase 2
0.7471	Intermediate Similarity	NPD3751	Discontinued
0.7468	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD3748	Approved
0.7467	Intermediate Similarity	NPD3027	Phase 3
0.7466	Intermediate Similarity	NPD9717	Approved
0.745	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD3787	Discontinued
0.7432	Intermediate Similarity	NPD1203	Approved
0.7421	Intermediate Similarity	NPD7390	Discontinued
0.7415	Intermediate Similarity	NPD4749	Approved
0.7407	Intermediate Similarity	NPD3226	Approved
0.7405	Intermediate Similarity	NPD2309	Approved
0.74	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD6832	Phase 2
0.7397	Intermediate Similarity	NPD422	Phase 1
0.7396	Intermediate Similarity	NPD3926	Phase 2
0.7389	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD4361	Phase 2
0.7386	Intermediate Similarity	NPD447	Suspended
0.7386	Intermediate Similarity	NPD8434	Phase 2
0.7386	Intermediate Similarity	NPD6355	Discontinued
0.7375	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD6005	Phase 3
0.7372	Intermediate Similarity	NPD6004	Phase 3
0.7372	Intermediate Similarity	NPD6002	Phase 3
0.7372	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD2346	Discontinued
0.7372	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD3823	Discontinued
0.7333	Intermediate Similarity	NPD8455	Phase 2
0.7322	Intermediate Similarity	NPD6777	Approved
0.7322	Intermediate Similarity	NPD6776	Approved
0.7322	Intermediate Similarity	NPD6780	Approved
0.7322	Intermediate Similarity	NPD6781	Approved
0.7322	Intermediate Similarity	NPD6778	Approved
0.7322	Intermediate Similarity	NPD6779	Approved
0.7322	Intermediate Similarity	NPD6782	Approved
0.7303	Intermediate Similarity	NPD3268	Approved
0.7303	Intermediate Similarity	NPD6798	Discontinued
0.7301	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7458	Discontinued
0.7288	Intermediate Similarity	NPD8150	Discontinued
0.7283	Intermediate Similarity	NPD1729	Discontinued
0.7279	Intermediate Similarity	NPD1091	Approved
0.7278	Intermediate Similarity	NPD7199	Phase 2
0.7273	Intermediate Similarity	NPD37	Approved
0.7267	Intermediate Similarity	NPD2798	Approved
0.7267	Intermediate Similarity	NPD4661	Approved
0.7267	Intermediate Similarity	NPD4662	Approved
0.7262	Intermediate Similarity	NPD6234	Discontinued
0.7246	Intermediate Similarity	NPD4967	Phase 2
0.7246	Intermediate Similarity	NPD4966	Approved
0.7246	Intermediate Similarity	NPD4965	Approved
0.7244	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1548	Phase 1
0.7241	Intermediate Similarity	NPD9545	Approved
0.7239	Intermediate Similarity	NPD1653	Approved
0.7237	Intermediate Similarity	NPD4625	Phase 3
0.7229	Intermediate Similarity	NPD5760	Phase 2
0.7229	Intermediate Similarity	NPD5761	Phase 2
0.7228	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD4060	Phase 1
0.7204	Intermediate Similarity	NPD7435	Discontinued
0.72	Intermediate Similarity	NPD6104	Discontinued
0.72	Intermediate Similarity	NPD2797	Approved
0.7196	Intermediate Similarity	NPD8151	Discontinued
0.7186	Intermediate Similarity	NPD5353	Approved
0.7178	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7228	Approved
0.7161	Intermediate Similarity	NPD1933	Approved
0.7161	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1019	Discontinued
0.7152	Intermediate Similarity	NPD5647	Approved
0.7152	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6233	Phase 2
0.7143	Intermediate Similarity	NPD7585	Approved
0.7135	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7229	Phase 3
0.7134	Intermediate Similarity	NPD4308	Phase 3
0.7133	Intermediate Similarity	NPD1241	Discontinued
0.7133	Intermediate Similarity	NPD8651	Approved
0.712	Intermediate Similarity	NPD7783	Phase 2
0.712	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD5049	Phase 3
0.7114	Intermediate Similarity	NPD1608	Approved
0.7112	Intermediate Similarity	NPD7696	Phase 3
0.7112	Intermediate Similarity	NPD7697	Approved
0.7112	Intermediate Similarity	NPD7698	Approved
0.7111	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD9494	Approved
0.7105	Intermediate Similarity	NPD2861	Phase 2
0.7103	Intermediate Similarity	NPD9493	Approved
0.7093	Intermediate Similarity	NPD7184	Clinical (unspecified phase)

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