NPASS Compound

Structure

NPC470675 OpenBabel07101718182D 26 28 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 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 2.8660 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 -2.5000 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 1.7321 -0.0000 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 -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 2 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 2 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 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 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 3.4641 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 11 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 6 11 1 0 0 0 0 7 8 1 0 0 0 0 7 16 1 0 0 0 0 8 21 1 0 0 0 0 9 12 1 0 0 0 0 9 15 1 0 0 0 0 10 13 2 0 0 0 0 10 14 1 0 0 0 0 11 18 1 0 0 0 0 12 13 1 0 0 0 0 12 19 2 0 0 0 0 13 22 1 0 0 0 0 14 17 2 0 0 0 0 14 23 1 0 0 0 0 15 20 1 0 0 0 0 15 21 1 6 0 0 0 16 20 1 0 0 0 0 16 24 1 6 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 18 25 2 0 0 0 0 19 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:	379.508
LogP:	4.148
LogD:	3.373
LogS:	-3.91
# Rotatable Bonds:	3
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.712
Synthetic Accessibility Score:	4.201
Fsp3:	0.667
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:	-4.752
MDCK Permeability:	1.4083427231526002e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.633
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.482
Plasma Protein Binding (PPB):	97.44691467285156%
Volume Distribution (VD):	0.7
Pgp-substrate:	2.3034250736236572%

ADMET: Metabolism

CYP1A2-inhibitor:	0.709
CYP1A2-substrate:	0.75
CYP2C19-inhibitor:	0.341
CYP2C19-substrate:	0.486
CYP2C9-inhibitor:	0.675
CYP2C9-substrate:	0.894
CYP2D6-inhibitor:	0.799
CYP2D6-substrate:	0.399
CYP3A4-inhibitor:	0.391
CYP3A4-substrate:	0.471

ADMET: Excretion

Clearance (CL):	5.622
Half-life (T1/2):	0.193

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.275
Drug-inuced Liver Injury (DILI):	0.256
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.679
Maximum Recommended Daily Dose:	0.941
Skin Sensitization:	0.596
Carcinogencity:	0.02
Eye Corrosion:	0.003
Eye Irritation:	0.81
Respiratory Toxicity:	0.884

Download Data

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

Natural Product: NPC470675

Natural Product ID:	NPC470675
*Common Name:**	Empetriferdinol
IUPAC Name:	1-[(7R,8aR,10aR)-1,3,7-trihydroxy-8,8,10a-trimethyl-6,7,8a,9-tetrahydro-5H-xanthen-4-yl]-2-methylbutan-1-one
Synonyms:	Empetriferdinol
Standard InCHIKey:	CQKLJJCVXBOQJX-WLLLBLRDSA-N
Standard InCHI:	InChI=1S/C21H30O5/c1-6-11(2)18(25)17-14(23)10-13(22)12-9-15-20(3,4)16(24)7-8-21(15,5)26-19(12)17/h10-11,15-16,22-24H,6-9H2,1-5H3/t11?,15-,16-,21-/m1/s1
SMILES:	CCC(C(=O)c1c(O)cc(c2c1O[C@]1(C)CC[C@H](C([C@H]1C2)(C)C)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2152499
PubChem CID:	71453068
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes

*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]

☑ 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

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	29200.0	nM	PMID[475889]

☑ 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 NPC470675 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	379
0.1-0.2	1462
0.2-0.3	3058
0.3-0.4	7475
0.4-0.5	10915
0.5-0.6	4558
0.6-0.7	5501
0.7-0.8	6177
0.8-0.85	2274
0.85-0.9	853
0.9-0.95	39
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473131
0.9583	High Similarity	NPC470673
0.9583	High Similarity	NPC117716
0.9583	High Similarity	NPC470674
0.9342	High Similarity	NPC472617
0.9338	High Similarity	NPC164427
0.9324	High Similarity	NPC471114
0.932	High Similarity	NPC10990
0.932	High Similarity	NPC300988
0.9315	High Similarity	NPC470890
0.9281	High Similarity	NPC472618
0.9276	High Similarity	NPC196448
0.9252	High Similarity	NPC24136
0.9252	High Similarity	NPC473135
0.9252	High Similarity	NPC473132
0.9252	High Similarity	NPC472629
0.9252	High Similarity	NPC290133
0.9252	High Similarity	NPC187282
0.9252	High Similarity	NPC470676
0.92	High Similarity	NPC305965
0.9195	High Similarity	NPC473016
0.9189	High Similarity	NPC47388
0.9189	High Similarity	NPC473133
0.9189	High Similarity	NPC308200
0.9189	High Similarity	NPC470670
0.9184	High Similarity	NPC131568
0.9184	High Similarity	NPC271288
0.9184	High Similarity	NPC224714
0.9184	High Similarity	NPC131579
0.9184	High Similarity	NPC87486
0.9184	High Similarity	NPC124780
0.915	High Similarity	NPC272196
0.9139	High Similarity	NPC87708
0.9139	High Similarity	NPC474843
0.9133	High Similarity	NPC321896
0.9133	High Similarity	NPC37348
0.9133	High Similarity	NPC476185
0.9133	High Similarity	NPC472633
0.9133	High Similarity	NPC29777
0.9133	High Similarity	NPC471115
0.9128	High Similarity	NPC39195
0.9128	High Similarity	NPC145467
0.9122	High Similarity	NPC285630
0.9122	High Similarity	NPC127059
0.9122	High Similarity	NPC477955
0.9116	High Similarity	NPC316816
0.9116	High Similarity	NPC125894
0.9116	High Similarity	NPC223812
0.9116	High Similarity	NPC107177
0.9116	High Similarity	NPC214166
0.9116	High Similarity	NPC85162
0.9116	High Similarity	NPC278249
0.9116	High Similarity	NPC478086
0.9116	High Similarity	NPC77794
0.9116	High Similarity	NPC81697
0.911	High Similarity	NPC279650
0.911	High Similarity	NPC258630
0.911	High Similarity	NPC17170
0.911	High Similarity	NPC166689
0.911	High Similarity	NPC96408
0.911	High Similarity	NPC156190
0.9073	High Similarity	NPC474023
0.9073	High Similarity	NPC72958
0.9073	High Similarity	NPC474021
0.9073	High Similarity	NPC472422
0.9073	High Similarity	NPC263384
0.9073	High Similarity	NPC471677
0.9073	High Similarity	NPC244577
0.9073	High Similarity	NPC471676
0.9073	High Similarity	NPC472420
0.9073	High Similarity	NPC232645
0.9067	High Similarity	NPC307052
0.9067	High Similarity	NPC139966
0.9067	High Similarity	NPC5173
0.906	High Similarity	NPC473077
0.906	High Similarity	NPC85773
0.906	High Similarity	NPC296998
0.906	High Similarity	NPC472627
0.906	High Similarity	NPC91902
0.9054	High Similarity	NPC473013
0.9054	High Similarity	NPC473014
0.9054	High Similarity	NPC311144
0.9054	High Similarity	NPC209040
0.9054	High Similarity	NPC235217
0.9054	High Similarity	NPC473015
0.9048	High Similarity	NPC296917
0.9048	High Similarity	NPC324436
0.9048	High Similarity	NPC194432
0.9048	High Similarity	NPC37496
0.9048	High Similarity	NPC66515
0.9048	High Similarity	NPC166482
0.9048	High Similarity	NPC328164
0.9048	High Similarity	NPC167624
0.9048	High Similarity	NPC182852
0.9048	High Similarity	NPC306829
0.9048	High Similarity	NPC228504
0.9048	High Similarity	NPC227579
0.9048	High Similarity	NPC125855
0.9048	High Similarity	NPC324134
0.9048	High Similarity	NPC40833
0.9048	High Similarity	NPC64915
0.9048	High Similarity	NPC166934
0.9048	High Similarity	NPC73028
0.9048	High Similarity	NPC161506
0.9048	High Similarity	NPC1089
0.9048	High Similarity	NPC148757
0.9048	High Similarity	NPC107572
0.9048	High Similarity	NPC220998
0.9048	High Similarity	NPC76338
0.9048	High Similarity	NPC78
0.9048	High Similarity	NPC32739
0.9048	High Similarity	NPC76372
0.9048	High Similarity	NPC10937
0.9048	High Similarity	NPC265040
0.9048	High Similarity	NPC223500
0.9048	High Similarity	NPC177354
0.9041	High Similarity	NPC477272
0.9038	High Similarity	NPC473022
0.9034	High Similarity	NPC474487
0.9034	High Similarity	NPC470672
0.9034	High Similarity	NPC474504
0.9034	High Similarity	NPC470671
0.902	High Similarity	NPC471116
0.902	High Similarity	NPC175192
0.9013	High Similarity	NPC216035
0.9013	High Similarity	NPC217149
0.9013	High Similarity	NPC475790
0.9007	High Similarity	NPC202595
0.9007	High Similarity	NPC61258
0.9007	High Similarity	NPC227122
0.9	High Similarity	NPC470460
0.9	High Similarity	NPC10097
0.8993	High Similarity	NPC214774
0.8993	High Similarity	NPC88964
0.8993	High Similarity	NPC312973
0.8993	High Similarity	NPC301276
0.8993	High Similarity	NPC474302
0.8993	High Similarity	NPC246948
0.8993	High Similarity	NPC176229
0.8993	High Similarity	NPC267375
0.8993	High Similarity	NPC54577
0.8993	High Similarity	NPC83357
0.8993	High Similarity	NPC195621
0.8993	High Similarity	NPC470647
0.8993	High Similarity	NPC67805
0.8993	High Similarity	NPC299011
0.8993	High Similarity	NPC142405
0.8993	High Similarity	NPC20488
0.8993	High Similarity	NPC475052
0.8993	High Similarity	NPC111786
0.8986	High Similarity	NPC185276
0.8986	High Similarity	NPC143896
0.8986	High Similarity	NPC310130
0.8986	High Similarity	NPC166138
0.8986	High Similarity	NPC149026
0.8986	High Similarity	NPC91560
0.8986	High Similarity	NPC150408
0.8986	High Similarity	NPC18585
0.8986	High Similarity	NPC75049
0.8986	High Similarity	NPC164980
0.8986	High Similarity	NPC11700
0.8986	High Similarity	NPC39329
0.8986	High Similarity	NPC106985
0.8986	High Similarity	NPC169591
0.8986	High Similarity	NPC68104
0.8986	High Similarity	NPC221432
0.8986	High Similarity	NPC257097
0.8986	High Similarity	NPC175504
0.8986	High Similarity	NPC18886
0.8986	High Similarity	NPC113770
0.8981	High Similarity	NPC476295
0.8981	High Similarity	NPC100849
0.898	High Similarity	NPC110038
0.898	High Similarity	NPC248372
0.898	High Similarity	NPC213322
0.898	High Similarity	NPC324386
0.898	High Similarity	NPC4743
0.898	High Similarity	NPC312391
0.8973	High Similarity	NPC139554
0.8973	High Similarity	NPC140890
0.8968	High Similarity	NPC186113
0.8961	High Similarity	NPC20530
0.8961	High Similarity	NPC4547
0.8961	High Similarity	NPC215917
0.8961	High Similarity	NPC10754
0.8954	High Similarity	NPC469405
0.8954	High Similarity	NPC74924
0.8954	High Similarity	NPC95842
0.8954	High Similarity	NPC178964
0.8954	High Similarity	NPC135522
0.8954	High Similarity	NPC223701
0.8954	High Similarity	NPC472583
0.8954	High Similarity	NPC280530
0.8954	High Similarity	NPC7989
0.8947	High Similarity	NPC472636
0.8947	High Similarity	NPC254412
0.8947	High Similarity	NPC207346
0.8947	High Similarity	NPC46564
0.8947	High Similarity	NPC319910
0.8947	High Similarity	NPC149526

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 NPC470675 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	326
0.1-0.2	913
0.2-0.3	1736
0.3-0.4	2551
0.4-0.5	1984
0.5-0.6	1026
0.6-0.7	433
0.7-0.8	149
0.8-0.85	26
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8831	High Similarity	NPD2393	Clinical (unspecified phase)
0.88	High Similarity	NPD4378	Clinical (unspecified phase)
0.8774	High Similarity	NPD8443	Clinical (unspecified phase)
0.8734	High Similarity	NPD6959	Discontinued
0.8707	High Similarity	NPD1550	Clinical (unspecified phase)
0.8707	High Similarity	NPD1552	Clinical (unspecified phase)
0.8649	High Similarity	NPD1549	Phase 2
0.8636	High Similarity	NPD4380	Phase 2
0.8591	High Similarity	NPD2800	Approved
0.859	High Similarity	NPD7819	Suspended
0.8526	High Similarity	NPD1934	Approved
0.8431	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD7075	Discontinued
0.8389	Intermediate Similarity	NPD2796	Approved
0.8389	Intermediate Similarity	NPD6100	Approved
0.8389	Intermediate Similarity	NPD6099	Approved
0.8354	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD7411	Suspended
0.8323	Intermediate Similarity	NPD5494	Approved
0.8322	Intermediate Similarity	NPD1510	Phase 2
0.8313	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8311	Intermediate Similarity	NPD6651	Approved
0.8291	Intermediate Similarity	NPD6801	Discontinued
0.8278	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD2801	Approved
0.8232	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD6166	Phase 2
0.8232	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD2533	Approved
0.8194	Intermediate Similarity	NPD2532	Approved
0.8194	Intermediate Similarity	NPD2534	Approved
0.8193	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD1240	Approved
0.8129	Intermediate Similarity	NPD1511	Approved
0.8121	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD5844	Phase 1
0.8067	Intermediate Similarity	NPD1607	Approved
0.8052	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD6599	Discontinued
0.8036	Intermediate Similarity	NPD7074	Phase 3
0.8025	Intermediate Similarity	NPD7768	Phase 2
0.8025	Intermediate Similarity	NPD1512	Approved
0.7976	Intermediate Similarity	NPD7054	Approved
0.7975	Intermediate Similarity	NPD3749	Approved
0.7964	Intermediate Similarity	NPD7473	Discontinued
0.7941	Intermediate Similarity	NPD6559	Discontinued
0.7935	Intermediate Similarity	NPD3750	Approved
0.7929	Intermediate Similarity	NPD7472	Approved
0.7917	Intermediate Similarity	NPD3818	Discontinued
0.7914	Intermediate Similarity	NPD3882	Suspended
0.7914	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD2935	Discontinued
0.7898	Intermediate Similarity	NPD6799	Approved
0.7895	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD6232	Discontinued
0.7882	Intermediate Similarity	NPD6797	Phase 2
0.7871	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD3817	Phase 2
0.7836	Intermediate Similarity	NPD7251	Discontinued
0.7821	Intermediate Similarity	NPD4628	Phase 3
0.78	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7808	Phase 3
0.7791	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD4360	Phase 2
0.7753	Intermediate Similarity	NPD4363	Phase 3
0.775	Intermediate Similarity	NPD920	Approved
0.7744	Intermediate Similarity	NPD5402	Approved
0.7736	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD2799	Discontinued
0.7683	Intermediate Similarity	NPD5761	Phase 2
0.7683	Intermediate Similarity	NPD5760	Phase 2
0.7682	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD5710	Approved
0.7679	Intermediate Similarity	NPD5711	Approved
0.7677	Intermediate Similarity	NPD1551	Phase 2
0.7673	Intermediate Similarity	NPD7390	Discontinued
0.7667	Intermediate Similarity	NPD4908	Phase 1
0.7661	Intermediate Similarity	NPD7286	Phase 2
0.7654	Intermediate Similarity	NPD3226	Approved
0.7647	Intermediate Similarity	NPD5124	Phase 1
0.7647	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD1243	Approved
0.764	Intermediate Similarity	NPD5403	Approved
0.764	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD2346	Discontinued
0.7614	Intermediate Similarity	NPD8434	Phase 2
0.7613	Intermediate Similarity	NPD3748	Approved
0.7595	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD1465	Phase 2
0.7572	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD5953	Discontinued
0.7551	Intermediate Similarity	NPD1610	Phase 2
0.7546	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5401	Approved
0.7516	Intermediate Similarity	NPD2344	Approved
0.7516	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4625	Phase 3
0.75	Intermediate Similarity	NPD7033	Discontinued
0.75	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3751	Discontinued
0.7471	Intermediate Similarity	NPD3787	Discontinued
0.7455	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD2313	Discontinued
0.745	Intermediate Similarity	NPD4749	Approved
0.7443	Intermediate Similarity	NPD8313	Approved
0.7443	Intermediate Similarity	NPD8312	Approved
0.7432	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD4361	Phase 2
0.7412	Intermediate Similarity	NPD1247	Approved
0.7368	Intermediate Similarity	NPD7229	Phase 3
0.7368	Intermediate Similarity	NPD2861	Phase 2
0.7362	Intermediate Similarity	NPD6273	Approved
0.7355	Intermediate Similarity	NPD1613	Approved
0.7355	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD6778	Approved
0.7351	Intermediate Similarity	NPD6776	Approved
0.7351	Intermediate Similarity	NPD6779	Approved
0.7351	Intermediate Similarity	NPD6782	Approved
0.7351	Intermediate Similarity	NPD6781	Approved
0.7351	Intermediate Similarity	NPD6777	Approved
0.7351	Intermediate Similarity	NPD6780	Approved
0.7338	Intermediate Similarity	NPD3268	Approved
0.7333	Intermediate Similarity	NPD7458	Discontinued
0.7329	Intermediate Similarity	NPD2309	Approved
0.7318	Intermediate Similarity	NPD8150	Discontinued
0.7305	Intermediate Similarity	NPD37	Approved
0.7303	Intermediate Similarity	NPD2798	Approved
0.7303	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD919	Approved
0.7283	Intermediate Similarity	NPD2403	Approved
0.7278	Intermediate Similarity	NPD4967	Phase 2
0.7278	Intermediate Similarity	NPD4965	Approved
0.7278	Intermediate Similarity	NPD4966	Approved
0.7267	Intermediate Similarity	NPD7003	Approved
0.7258	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD2424	Discontinued
0.7244	Intermediate Similarity	NPD943	Approved
0.7237	Intermediate Similarity	NPD2797	Approved
0.7237	Intermediate Similarity	NPD1203	Approved
0.7234	Intermediate Similarity	NPD7697	Approved
0.7234	Intermediate Similarity	NPD7698	Approved
0.7234	Intermediate Similarity	NPD7435	Discontinued
0.7234	Intermediate Similarity	NPD7696	Phase 3
0.7232	Intermediate Similarity	NPD6104	Discontinued
0.7226	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD3926	Phase 2
0.7211	Intermediate Similarity	NPD7584	Approved
0.7209	Intermediate Similarity	NPD7199	Phase 2
0.7208	Intermediate Similarity	NPD6832	Phase 2
0.7205	Intermediate Similarity	NPD2654	Approved
0.7202	Intermediate Similarity	NPD6844	Discontinued
0.7197	Intermediate Similarity	NPD230	Phase 1
0.7196	Intermediate Similarity	NPD7871	Phase 2
0.7196	Intermediate Similarity	NPD7870	Phase 2
0.7193	Intermediate Similarity	NPD6234	Discontinued
0.7193	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6002	Phase 3
0.7188	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6005	Phase 3
0.7188	Intermediate Similarity	NPD6004	Phase 3
0.7171	Intermediate Similarity	NPD6696	Suspended
0.7167	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1548	Phase 1
0.7152	Intermediate Similarity	NPD9717	Approved
0.7152	Intermediate Similarity	NPD1608	Approved
0.7152	Intermediate Similarity	NPD3972	Approved
0.715	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7783	Phase 2
0.7143	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD8151	Discontinued
0.7119	Intermediate Similarity	NPD1729	Discontinued
0.7102	Intermediate Similarity	NPD7228	Approved
0.7099	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD6823	Phase 2
0.7089	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1201	Approved
0.7086	Intermediate Similarity	NPD422	Phase 1
0.7083	Intermediate Similarity	NPD7701	Phase 2
0.7081	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6535	Approved
0.7081	Intermediate Similarity	NPD6534	Approved
0.7063	Intermediate Similarity	NPD4308	Phase 3
0.7063	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7801	Approved
0.7059	Intermediate Similarity	NPD8455	Phase 2
0.7051	Intermediate Similarity	NPD3027	Phase 3
0.7049	Intermediate Similarity	NPD4287	Approved
0.7039	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD4060	Phase 1
0.7019	Intermediate Similarity	NPD5405	Approved
0.7019	Intermediate Similarity	NPD5404	Approved
0.7019	Intermediate Similarity	NPD5406	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