NPASS Compound

Structure

NPC224280 OpenBabel07101718232D 25 28 0 0 1 0 0 0 0 0999 V2000 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 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 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 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 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 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 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 0.0000 -0.0000 0.0000 C 0 0 2 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 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 23 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 9 2 0 0 0 0 6 10 2 0 0 0 0 7 11 2 0 0 0 0 7 12 1 0 0 0 0 8 13 1 0 0 0 0 8 24 1 0 0 0 0 9 10 1 0 0 0 0 9 18 1 0 0 0 0 10 24 1 0 0 0 0 11 14 1 0 0 0 0 11 25 1 0 0 0 0 12 16 2 0 0 0 0 12 22 1 0 0 0 0 13 18 1 6 0 0 0 13 25 1 0 0 0 0 14 15 2 0 0 0 0 14 17 1 0 0 0 0 15 16 1 0 0 0 0 15 19 1 0 0 0 0 16 23 1 0 0 0 0 17 18 1 0 0 0 0 17 20 2 0 0 0 0 18 21 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.09
Volume:	328.735
LogP:	2.445
LogD:	2.28
LogS:	-4.219
# Rotatable Bonds:	2
TPSA:	94.45
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.855
Synthetic Accessibility Score:	3.508
Fsp3:	0.278
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.146
MDCK Permeability:	2.0760000552400015e-05
Pgp-inhibitor:	0.115
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.258
Plasma Protein Binding (PPB):	90.10520935058594%
Volume Distribution (VD):	0.97
Pgp-substrate:	10.931108474731445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.708
CYP1A2-substrate:	0.908
CYP2C19-inhibitor:	0.801
CYP2C19-substrate:	0.842
CYP2C9-inhibitor:	0.624
CYP2C9-substrate:	0.659
CYP2D6-inhibitor:	0.212
CYP2D6-substrate:	0.442
CYP3A4-inhibitor:	0.559
CYP3A4-substrate:	0.804

ADMET: Excretion

Clearance (CL):	5.237
Half-life (T1/2):	0.366

ADMET: Toxicity

hERG Blockers:	0.155
Human Hepatotoxicity (H-HT):	0.339
Drug-inuced Liver Injury (DILI):	0.536
AMES Toxicity:	0.274
Rat Oral Acute Toxicity:	0.151
Maximum Recommended Daily Dose:	0.068
Skin Sensitization:	0.481
Carcinogencity:	0.629
Eye Corrosion:	0.003
Eye Irritation:	0.136
Respiratory Toxicity:	0.023

Download Data

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

Natural Product: NPC224280

Natural Product ID:	NPC224280
*Common Name:**	Coccineone E
IUPAC Name:	(6aR,12aS)-11,12a-dihydroxy-9,10-dimethoxy-6,6a-dihydrochromeno[3,4-b]chromen-12-one
Synonyms:	Coccineone E
Standard InCHIKey:	KDJHEZRWCNFWGE-ACJLOTCBSA-N
Standard InCHI:	InChI=1S/C18H16O7/c1-22-12-7-11-14(15(19)16(12)23-2)17(20)18(21)9-5-3-4-6-10(9)24-8-13(18)25-11/h3-7,13,19,21H,8H2,1-2H3/t13-,18+/m1/s1
SMILES:	COc1cc2c(c(c1OC)O)C(=O)[C@@]1(c3ccccc3OC[C@H]1O2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL222133
PubChem CID:	12004176
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001607] Rotenoids [CHEMONTID:0003528] Rotenones

*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
NPO33416	boerhaavia diffusa	Species	n.a.	n.a.	roots	n.a.	n.a.	PMID[16792408]
NPO33416	boerhaavia diffusa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[23914900]

☑ 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
Others	2

Activity Type	# Activity
Individual Protein	1
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1422	Individual Protein	ATP-binding cassette sub-family G member 2	Homo sapiens	Activity	=	15.0	%	PMID[529055]
NPT548	Tissue	Ileum	Cavia porcellus	Emax	=	25.2	%	PMID[529056]

☑ 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 NPC224280 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	422
0.1-0.2	1776
0.2-0.3	4469
0.3-0.4	10599
0.4-0.5	7160
0.5-0.6	3638
0.6-0.7	4908
0.7-0.8	5563
0.8-0.85	2374
0.85-0.9	1409
0.9-0.95	359
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
0.9872	High Similarity	NPC234052
0.9806	High Similarity	NPC173137
0.9745	High Similarity	NPC62261
0.9677	High Similarity	NPC152904
0.9615	High Similarity	NPC263449
0.9613	High Similarity	NPC475267
0.9613	High Similarity	NPC474836
0.9613	High Similarity	NPC162869
0.9613	High Similarity	NPC156057
0.9613	High Similarity	NPC474208
0.9613	High Similarity	NPC48208
0.9563	High Similarity	NPC152477
0.9563	High Similarity	NPC177480
0.956	High Similarity	NPC477517
0.9557	High Similarity	NPC41301
0.9554	High Similarity	NPC308992
0.9551	High Similarity	NPC55738
0.9548	High Similarity	NPC303255
0.9548	High Similarity	NPC235165
0.9548	High Similarity	NPC255106
0.95	High Similarity	NPC477154
0.95	High Similarity	NPC117854
0.95	High Similarity	NPC8965
0.95	High Similarity	NPC6588
0.949	High Similarity	NPC200746
0.949	High Similarity	NPC470183
0.9487	High Similarity	NPC472914
0.9487	High Similarity	NPC99597
0.9487	High Similarity	NPC472911
0.9487	High Similarity	NPC469584
0.9487	High Similarity	NPC210084
0.9487	High Similarity	NPC471479
0.9487	High Similarity	NPC245758
0.9487	High Similarity	NPC471515
0.9487	High Similarity	NPC472910
0.9487	High Similarity	NPC67876
0.9487	High Similarity	NPC96167
0.9487	High Similarity	NPC222814
0.9487	High Similarity	NPC472913
0.9484	High Similarity	NPC37392
0.9444	High Similarity	NPC121333
0.9441	High Similarity	NPC326877
0.9441	High Similarity	NPC242395
0.9437	High Similarity	NPC120593
0.9437	High Similarity	NPC471213
0.9434	High Similarity	NPC248638
0.9434	High Similarity	NPC236521
0.9434	High Similarity	NPC472625
0.9434	High Similarity	NPC475985
0.9434	High Similarity	NPC152659
0.943	High Similarity	NPC472632
0.943	High Similarity	NPC134783
0.943	High Similarity	NPC471210
0.9427	High Similarity	NPC476242
0.9427	High Similarity	NPC250214
0.9427	High Similarity	NPC95936
0.9423	High Similarity	NPC474638
0.9423	High Similarity	NPC49824
0.9423	High Similarity	NPC13858
0.9423	High Similarity	NPC471500
0.9423	High Similarity	NPC326037
0.9423	High Similarity	NPC320825
0.9423	High Similarity	NPC201837
0.9423	High Similarity	NPC472916
0.9419	High Similarity	NPC18727
0.9383	High Similarity	NPC74559
0.9379	High Similarity	NPC14662
0.9379	High Similarity	NPC295082
0.9375	High Similarity	NPC472450
0.9375	High Similarity	NPC58223
0.9375	High Similarity	NPC7688
0.9375	High Similarity	NPC7154
0.9375	High Similarity	NPC36916
0.9375	High Similarity	NPC293319
0.9375	High Similarity	NPC36
0.9375	High Similarity	NPC239752
0.9375	High Similarity	NPC125039
0.9375	High Similarity	NPC72787
0.9375	High Similarity	NPC275780
0.9371	High Similarity	NPC472448
0.9371	High Similarity	NPC474162
0.9371	High Similarity	NPC83922
0.9371	High Similarity	NPC25152
0.9371	High Similarity	NPC474034
0.9371	High Similarity	NPC474033
0.9371	High Similarity	NPC474150
0.9367	High Similarity	NPC118256
0.9367	High Similarity	NPC287328
0.9367	High Similarity	NPC174953
0.9367	High Similarity	NPC192686
0.9367	High Similarity	NPC282009
0.9367	High Similarity	NPC204290
0.9367	High Similarity	NPC139036
0.9367	High Similarity	NPC119209
0.9363	High Similarity	NPC470402
0.9363	High Similarity	NPC224137
0.9363	High Similarity	NPC129684
0.9363	High Similarity	NPC241904
0.9363	High Similarity	NPC27337
0.9363	High Similarity	NPC78225
0.9363	High Similarity	NPC93376
0.9363	High Similarity	NPC227192
0.9363	High Similarity	NPC203891
0.9363	High Similarity	NPC52530
0.9363	High Similarity	NPC110070
0.9363	High Similarity	NPC189179
0.9363	High Similarity	NPC300727
0.9363	High Similarity	NPC101830
0.9363	High Similarity	NPC181960
0.9363	High Similarity	NPC299520
0.9363	High Similarity	NPC75215
0.9363	High Similarity	NPC223787
0.9363	High Similarity	NPC471209
0.9359	High Similarity	NPC44079
0.9359	High Similarity	NPC26227
0.9359	High Similarity	NPC472909
0.9359	High Similarity	NPC201451
0.9359	High Similarity	NPC213622
0.9359	High Similarity	NPC2928
0.9355	High Similarity	NPC199100
0.9355	High Similarity	NPC180234
0.9355	High Similarity	NPC302950
0.9355	High Similarity	NPC120537
0.9355	High Similarity	NPC219582
0.9355	High Similarity	NPC236637
0.9329	High Similarity	NPC108202
0.9317	High Similarity	NPC170245
0.9317	High Similarity	NPC173292
0.9317	High Similarity	NPC39091
0.9317	High Similarity	NPC472449
0.9313	High Similarity	NPC273959
0.9313	High Similarity	NPC186686
0.9313	High Similarity	NPC189473
0.9313	High Similarity	NPC23298
0.9308	High Similarity	NPC61010
0.9308	High Similarity	NPC29876
0.9308	High Similarity	NPC471211
0.9308	High Similarity	NPC167678
0.9308	High Similarity	NPC474038
0.9308	High Similarity	NPC471212
0.9308	High Similarity	NPC471499
0.9308	High Similarity	NPC266314
0.9304	High Similarity	NPC18607
0.9304	High Similarity	NPC19687
0.9304	High Similarity	NPC288669
0.9304	High Similarity	NPC473990
0.9304	High Similarity	NPC176300
0.9304	High Similarity	NPC152166
0.9304	High Similarity	NPC7846
0.9304	High Similarity	NPC300943
0.9304	High Similarity	NPC191459
0.9304	High Similarity	NPC9609
0.9304	High Similarity	NPC22192
0.9304	High Similarity	NPC204854
0.9304	High Similarity	NPC115798
0.9304	High Similarity	NPC329091
0.9304	High Similarity	NPC25495
0.9304	High Similarity	NPC130894
0.9304	High Similarity	NPC261004
0.9304	High Similarity	NPC253634
0.9304	High Similarity	NPC474290
0.9304	High Similarity	NPC4481
0.9304	High Similarity	NPC105242
0.9304	High Similarity	NPC22472
0.9304	High Similarity	NPC143828
0.9304	High Similarity	NPC18772
0.9299	High Similarity	NPC195796
0.9299	High Similarity	NPC245546
0.9299	High Similarity	NPC247017
0.9299	High Similarity	NPC291878
0.9299	High Similarity	NPC191146
0.9299	High Similarity	NPC474520
0.9299	High Similarity	NPC43243
0.9299	High Similarity	NPC35038
0.9299	High Similarity	NPC278778
0.9299	High Similarity	NPC266960
0.9299	High Similarity	NPC274730
0.9299	High Similarity	NPC68093
0.9299	High Similarity	NPC250922
0.9299	High Similarity	NPC98661
0.9299	High Similarity	NPC24640
0.9299	High Similarity	NPC292107
0.9295	High Similarity	NPC69394
0.9295	High Similarity	NPC206238
0.9295	High Similarity	NPC472915
0.9295	High Similarity	NPC255350
0.9295	High Similarity	NPC145379
0.9295	High Similarity	NPC22519
0.9295	High Similarity	NPC274327
0.9295	High Similarity	NPC183878
0.9295	High Similarity	NPC292214
0.9295	High Similarity	NPC203080
0.9295	High Similarity	NPC86485
0.9295	High Similarity	NPC176775
0.9295	High Similarity	NPC88645
0.9295	High Similarity	NPC141212
0.9295	High Similarity	NPC231018
0.9295	High Similarity	NPC271779
0.9295	High Similarity	NPC160951
0.9295	High Similarity	NPC167091

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 NPC224280 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	396
0.1-0.2	955
0.2-0.3	1857
0.3-0.4	2629
0.4-0.5	1752
0.5-0.6	960
0.6-0.7	427
0.7-0.8	129
0.8-0.85	29
0.85-0.9	10
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9375	High Similarity	NPD6168	Clinical (unspecified phase)
0.9375	High Similarity	NPD6167	Clinical (unspecified phase)
0.9375	High Similarity	NPD6166	Phase 2
0.9355	High Similarity	NPD1934	Approved
0.9295	High Similarity	NPD2801	Approved
0.9172	High Similarity	NPD2393	Clinical (unspecified phase)
0.9057	High Similarity	NPD3882	Suspended
0.9006	High Similarity	NPD5494	Approved
0.8982	High Similarity	NPD4338	Clinical (unspecified phase)
0.8916	High Similarity	NPD7074	Phase 3
0.8862	High Similarity	NPD6797	Phase 2
0.8855	High Similarity	NPD7054	Approved
0.8846	High Similarity	NPD1512	Approved
0.881	High Similarity	NPD7251	Discontinued
0.8802	High Similarity	NPD7472	Approved
0.8758	High Similarity	NPD3817	Phase 2
0.8757	High Similarity	NPD7808	Phase 3
0.8718	High Similarity	NPD1511	Approved
0.8704	High Similarity	NPD4868	Clinical (unspecified phase)
0.8683	High Similarity	NPD3818	Discontinued
0.8544	High Similarity	NPD4378	Clinical (unspecified phase)
0.8537	High Similarity	NPD7075	Discontinued
0.8529	High Similarity	NPD7993	Clinical (unspecified phase)
0.8509	High Similarity	NPD4380	Phase 2
0.8466	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD5402	Approved
0.8412	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8412	Intermediate Similarity	NPD5844	Phase 1
0.8397	Intermediate Similarity	NPD1549	Phase 2
0.8354	Intermediate Similarity	NPD1465	Phase 2
0.8303	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD6959	Discontinued
0.825	Intermediate Similarity	NPD6799	Approved
0.8225	Intermediate Similarity	NPD6232	Discontinued
0.8187	Intermediate Similarity	NPD7473	Discontinued
0.8182	Intermediate Similarity	NPD6801	Discontinued
0.8171	Intermediate Similarity	NPD6599	Discontinued
0.8166	Intermediate Similarity	NPD1247	Approved
0.8153	Intermediate Similarity	NPD2796	Approved
0.8133	Intermediate Similarity	NPD7819	Suspended
0.8089	Intermediate Similarity	NPD1510	Phase 2
0.8086	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD3926	Phase 2
0.8035	Intermediate Similarity	NPD3751	Discontinued
0.8012	Intermediate Similarity	NPD7411	Suspended
0.8012	Intermediate Similarity	NPD3787	Discontinued
0.7988	Intermediate Similarity	NPD5403	Approved
0.7978	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD943	Approved
0.7949	Intermediate Similarity	NPD1240	Approved
0.7949	Intermediate Similarity	NPD1613	Approved
0.7949	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD3749	Approved
0.7866	Intermediate Similarity	NPD5401	Approved
0.7853	Intermediate Similarity	NPD6559	Discontinued
0.7848	Intermediate Similarity	NPD1607	Approved
0.7845	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD919	Approved
0.7816	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6190	Approved
0.7756	Intermediate Similarity	NPD3027	Phase 3
0.775	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD3750	Approved
0.7719	Intermediate Similarity	NPD7768	Phase 2
0.7716	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD2935	Discontinued
0.7673	Intermediate Similarity	NPD230	Phase 1
0.7669	Intermediate Similarity	NPD2800	Approved
0.766	Intermediate Similarity	NPD6776	Approved
0.766	Intermediate Similarity	NPD6782	Approved
0.766	Intermediate Similarity	NPD6781	Approved
0.766	Intermediate Similarity	NPD6778	Approved
0.766	Intermediate Similarity	NPD6780	Approved
0.766	Intermediate Similarity	NPD6777	Approved
0.766	Intermediate Similarity	NPD6779	Approved
0.7657	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD2534	Approved
0.7651	Intermediate Similarity	NPD2532	Approved
0.7651	Intermediate Similarity	NPD2533	Approved
0.763	Intermediate Similarity	NPD6234	Discontinued
0.7627	Intermediate Similarity	NPD7228	Approved
0.7622	Intermediate Similarity	NPD4628	Phase 3
0.7619	Intermediate Similarity	NPD1653	Approved
0.7593	Intermediate Similarity	NPD6099	Approved
0.7593	Intermediate Similarity	NPD6100	Approved
0.7566	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD447	Suspended
0.756	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD7685	Pre-registration
0.7543	Intermediate Similarity	NPD7199	Phase 2
0.7541	Intermediate Similarity	NPD8434	Phase 2
0.7541	Intermediate Similarity	NPD8150	Discontinued
0.7539	Intermediate Similarity	NPD7696	Phase 3
0.7539	Intermediate Similarity	NPD7697	Approved
0.7539	Intermediate Similarity	NPD7435	Discontinued
0.7539	Intermediate Similarity	NPD7698	Approved
0.7485	Intermediate Similarity	NPD1551	Phase 2
0.7484	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7701	Phase 2
0.7473	Intermediate Similarity	NPD8312	Approved
0.7473	Intermediate Similarity	NPD8313	Approved
0.7468	Intermediate Similarity	NPD4908	Phase 1
0.7455	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD37	Approved
0.7439	Intermediate Similarity	NPD2344	Approved
0.7423	Intermediate Similarity	NPD3748	Approved
0.7414	Intermediate Similarity	NPD4965	Approved
0.7414	Intermediate Similarity	NPD4967	Phase 2
0.7414	Intermediate Similarity	NPD4966	Approved
0.7409	Intermediate Similarity	NPD7871	Phase 2
0.7409	Intermediate Similarity	NPD7870	Phase 2
0.7405	Intermediate Similarity	NPD9494	Approved
0.7394	Intermediate Similarity	NPD6535	Approved
0.7394	Intermediate Similarity	NPD6534	Approved
0.7381	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7699	Phase 2
0.7368	Intermediate Similarity	NPD3226	Approved
0.7368	Intermediate Similarity	NPD7700	Phase 2
0.736	Intermediate Similarity	NPD7783	Phase 2
0.736	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD920	Approved
0.7346	Intermediate Similarity	NPD1933	Approved
0.7341	Intermediate Similarity	NPD6844	Discontinued
0.7337	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2346	Discontinued
0.7329	Intermediate Similarity	NPD6233	Phase 2
0.7322	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD2403	Approved
0.7317	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD2799	Discontinued
0.7316	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7874	Approved
0.7308	Intermediate Similarity	NPD5953	Discontinued
0.7305	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD4360	Phase 2
0.7302	Intermediate Similarity	NPD4363	Phase 3
0.7296	Intermediate Similarity	NPD2861	Phase 2
0.7293	Intermediate Similarity	NPD7286	Phase 2
0.7278	Intermediate Similarity	NPD7390	Discontinued
0.7273	Intermediate Similarity	NPD7801	Approved
0.7267	Intermediate Similarity	NPD6798	Discontinued
0.7263	Intermediate Similarity	NPD5242	Approved
0.7262	Intermediate Similarity	NPD2309	Approved
0.7261	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD8151	Discontinued
0.7254	Intermediate Similarity	NPD2493	Approved
0.7254	Intermediate Similarity	NPD2494	Approved
0.7244	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1610	Phase 2
0.7239	Intermediate Similarity	NPD6355	Discontinued
0.7235	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7549	Discontinued
0.7216	Intermediate Similarity	NPD6823	Phase 2
0.7212	Intermediate Similarity	NPD7033	Discontinued
0.7207	Intermediate Similarity	NPD5710	Approved
0.7207	Intermediate Similarity	NPD5711	Approved
0.7206	Intermediate Similarity	NPD7907	Approved
0.7195	Intermediate Similarity	NPD6651	Approved
0.7192	Intermediate Similarity	NPD4665	Approved
0.7192	Intermediate Similarity	NPD4111	Phase 1
0.7174	Intermediate Similarity	NPD7240	Approved
0.7165	Intermediate Similarity	NPD3450	Approved
0.7165	Intermediate Similarity	NPD3452	Approved
0.716	Intermediate Similarity	NPD2313	Discontinued
0.7159	Intermediate Similarity	NPD5353	Approved
0.7157	Intermediate Similarity	NPD7584	Approved
0.7143	Intermediate Similarity	NPD4583	Approved
0.7143	Intermediate Similarity	NPD4582	Approved
0.7143	Intermediate Similarity	NPD1243	Approved
0.7126	Intermediate Similarity	NPD7266	Discontinued
0.7118	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD8455	Phase 2
0.7099	Intermediate Similarity	NPD4625	Phase 3
0.7092	Intermediate Similarity	NPD4002	Approved
0.7092	Intermediate Similarity	NPD4004	Approved
0.7086	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2424	Discontinued
0.7073	Intermediate Similarity	NPD4060	Phase 1
0.7069	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1203	Approved
0.7056	Intermediate Similarity	NPD8320	Phase 1
0.7056	Intermediate Similarity	NPD8319	Approved
0.7055	Intermediate Similarity	NPD3268	Approved
0.7047	Intermediate Similarity	NPD2975	Approved
0.7047	Intermediate Similarity	NPD2973	Approved
0.7047	Intermediate Similarity	NPD2974	Approved
0.7044	Intermediate Similarity	NPD4749	Approved
0.7037	Intermediate Similarity	NPD6832	Phase 2
0.7033	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD1899	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