NPASS Compound

Structure

CID192083 OpenBabel06191715572D 23 25 0 0 1 0 0 0 0 0999 V2000 -3.4641 -2.0000 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 1.7321 1.0000 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 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 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 -1.7321 0.0000 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 3.4641 1.0000 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 -0.0000 -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 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 -2.5981 -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 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 -0.0000 -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 -3.0000 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 7 1 0 0 0 0 2 8 1 0 0 0 0 3 4 2 0 0 0 0 3 9 1 0 0 0 0 4 10 1 0 0 0 0 5 9 2 0 0 0 0 5 11 1 0 0 0 0 6 12 1 0 0 0 0 6 13 1 0 0 0 0 7 15 2 0 0 0 0 7 16 1 0 0 0 0 8 15 1 0 0 0 0 8 17 2 0 0 0 0 9 13 1 0 0 0 0 10 11 2 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 12 14 1 0 0 0 0 12 20 2 0 0 0 0 13 23 1 0 0 0 0 14 16 2 0 0 0 0 14 17 1 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.09
Volume:	311.205
LogP:	3.098
LogD:	2.027
LogS:	-3.583
# Rotatable Bonds:	1
TPSA:	107.22
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.603
Synthetic Accessibility Score:	3.183
Fsp3:	0.235
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.087
MDCK Permeability:	9.350313121103682e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.059
30% Bioavailability (F30%):	0.153

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	98.31542205810547%
Volume Distribution (VD):	0.364
Pgp-substrate:	2.831609010696411%

ADMET: Metabolism

CYP1A2-inhibitor:	0.252
CYP1A2-substrate:	0.756
CYP2C19-inhibitor:	0.227
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.786
CYP2C9-substrate:	0.672
CYP2D6-inhibitor:	0.264
CYP2D6-substrate:	0.222
CYP3A4-inhibitor:	0.215
CYP3A4-substrate:	0.216

ADMET: Excretion

Clearance (CL):	14.844
Half-life (T1/2):	0.806

ADMET: Toxicity

hERG Blockers:	0.092
Human Hepatotoxicity (H-HT):	0.127
Drug-inuced Liver Injury (DILI):	0.901
AMES Toxicity:	0.051
Rat Oral Acute Toxicity:	0.654
Maximum Recommended Daily Dose:	0.779
Skin Sensitization:	0.958
Carcinogencity:	0.388
Eye Corrosion:	0.003
Eye Irritation:	0.922
Respiratory Toxicity:	0.225

Download Data

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

Natural Product: NPC192083

Natural Product ID:	NPC192083
*Common Name:**	Cyrtominetin
IUPAC Name:	2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6,8-dimethyl-2,3-dihydrochromen-4-one
Synonyms:	Cyrtominetin
Standard InCHIKey:	AESMRHCYHARBLU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H16O6/c1-7-15(21)8(2)17-14(16(7)22)12(20)6-13(23-17)9-3-4-10(18)11(19)5-9/h3-5,13,18-19,21-22H,6H2,1-2H3
SMILES:	Cc1c(c(C)c2c(C(=O)CC(c3ccc(c(c3)O)O)O2)c1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1224646
PubChem CID:	125309
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0001632] Flavanones

*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
NPO7155	Cypripedium calceolus	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29301	Cyrtomium fortunei	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17283	Rhizoma dryopteris crassirhizomae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO7155	Cypripedium calceolus	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29301	Cyrtomium fortunei	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7155	Cypripedium calceolus	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7155	Cypripedium calceolus	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29301	Cyrtomium fortunei	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
EC50	1
IC50	1
Others	4

Activity Type	# Activity
Cell Line	5
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	-4.85	%	PMID[558501]
NPT547	Cell Line	BGC-823	Homo sapiens	Activity	=	-19.81	%	PMID[558501]
NPT181	Cell Line	Bel-7402	Homo sapiens	Activity	=	-7.68	%	PMID[558501]
NPT91	Cell Line	KB	Homo sapiens	Activity	=	45.3	%	PMID[558501]
NPT737	Cell Line	HUVEC	Homo sapiens	EC50	>	20000.0	nM	PMID[558501]
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[558501]

☑ 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 NPC192083 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	398
0.1-0.2	1616
0.2-0.3	4145
0.3-0.4	10158
0.4-0.5	7878
0.5-0.6	3316
0.6-0.7	4692
0.7-0.8	5396
0.8-0.85	2621
0.85-0.9	1825
0.9-0.95	554
0.95-1	98

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC213896
0.9932	High Similarity	NPC106976
0.9932	High Similarity	NPC321779
0.9865	High Similarity	NPC278778
0.9865	High Similarity	NPC195796
0.9865	High Similarity	NPC291878
0.9865	High Similarity	NPC35038
0.9864	High Similarity	NPC74924
0.9864	High Similarity	NPC298692
0.9799	High Similarity	NPC472598
0.9799	High Similarity	NPC27337
0.9799	High Similarity	NPC291508
0.9799	High Similarity	NPC471209
0.9799	High Similarity	NPC474055
0.9797	High Similarity	NPC477503
0.9797	High Similarity	NPC45849
0.9797	High Similarity	NPC200761
0.9797	High Similarity	NPC470327
0.9733	High Similarity	NPC22192
0.9733	High Similarity	NPC210459
0.9732	High Similarity	NPC470328
0.9732	High Similarity	NPC209614
0.9732	High Similarity	NPC472626
0.973	High Similarity	NPC18727
0.9669	High Similarity	NPC472624
0.9669	High Similarity	NPC192686
0.9669	High Similarity	NPC287328
0.9669	High Similarity	NPC118256
0.9669	High Similarity	NPC282009
0.9669	High Similarity	NPC321399
0.9669	High Similarity	NPC36217
0.9669	High Similarity	NPC119209
0.9667	High Similarity	NPC223787
0.9664	High Similarity	NPC226025
0.9664	High Similarity	NPC67396
0.9662	High Similarity	NPC219582
0.9662	High Similarity	NPC302950
0.9662	High Similarity	NPC236637
0.966	High Similarity	NPC3825
0.966	High Similarity	NPC88804
0.9658	High Similarity	NPC294852
0.9658	High Similarity	NPC321011
0.9658	High Similarity	NPC188679
0.9605	High Similarity	NPC26326
0.9605	High Similarity	NPC472632
0.9605	High Similarity	NPC142252
0.9605	High Similarity	NPC471499
0.9605	High Similarity	NPC471210
0.9605	High Similarity	NPC472634
0.9605	High Similarity	NPC474038
0.9603	High Similarity	NPC117418
0.9603	High Similarity	NPC95936
0.9603	High Similarity	NPC250214
0.9603	High Similarity	NPC53545
0.9603	High Similarity	NPC85121
0.96	High Similarity	NPC24640
0.96	High Similarity	NPC471500
0.9592	High Similarity	NPC1612
0.9592	High Similarity	NPC183959
0.9542	High Similarity	NPC474033
0.9542	High Similarity	NPC472635
0.9542	High Similarity	NPC474034
0.9542	High Similarity	NPC201800
0.9542	High Similarity	NPC476247
0.9539	High Similarity	NPC476283
0.9539	High Similarity	NPC472630
0.9539	High Similarity	NPC470326
0.9539	High Similarity	NPC472631
0.9539	High Similarity	NPC328102
0.9539	High Similarity	NPC475784
0.9539	High Similarity	NPC174953
0.9536	High Similarity	NPC471479
0.9536	High Similarity	NPC473272
0.9536	High Similarity	NPC78225
0.9536	High Similarity	NPC156057
0.9536	High Similarity	NPC162869
0.9536	High Similarity	NPC474836
0.9536	High Similarity	NPC48208
0.9536	High Similarity	NPC475267
0.9536	High Similarity	NPC474208
0.9536	High Similarity	NPC471515
0.9536	High Similarity	NPC284820
0.9533	High Similarity	NPC113906
0.9533	High Similarity	NPC133392
0.9533	High Similarity	NPC117992
0.9533	High Similarity	NPC57674
0.9533	High Similarity	NPC168247
0.9533	High Similarity	NPC152951
0.9533	High Similarity	NPC230149
0.953	High Similarity	NPC63187
0.953	High Similarity	NPC323626
0.953	High Similarity	NPC157784
0.953	High Similarity	NPC324233
0.953	High Similarity	NPC37684
0.953	High Similarity	NPC472912
0.953	High Similarity	NPC471982
0.9527	High Similarity	NPC338131
0.9524	High Similarity	NPC3036
0.9521	High Similarity	NPC187282
0.9521	High Similarity	NPC24136
0.9521	High Similarity	NPC290133
0.9481	High Similarity	NPC124038
0.9481	High Similarity	NPC472625
0.9481	High Similarity	NPC186686
0.9477	High Similarity	NPC471212
0.9477	High Similarity	NPC266314
0.9477	High Similarity	NPC134783
0.9477	High Similarity	NPC471211
0.9477	High Similarity	NPC289771
0.9474	High Similarity	NPC473990
0.9474	High Similarity	NPC469658
0.947	High Similarity	NPC170026
0.947	High Similarity	NPC326037
0.947	High Similarity	NPC13858
0.947	High Similarity	NPC235165
0.947	High Similarity	NPC68093
0.947	High Similarity	NPC320825
0.947	High Similarity	NPC255106
0.947	High Similarity	NPC282307
0.947	High Similarity	NPC191146
0.9467	High Similarity	NPC70433
0.9467	High Similarity	NPC49402
0.9467	High Similarity	NPC33051
0.9467	High Similarity	NPC227337
0.9467	High Similarity	NPC170492
0.9467	High Similarity	NPC273462
0.9463	High Similarity	NPC304295
0.9463	High Similarity	NPC154345
0.9463	High Similarity	NPC204515
0.9463	High Similarity	NPC205046
0.9463	High Similarity	NPC59162
0.9459	High Similarity	NPC171916
0.9459	High Similarity	NPC38545
0.9459	High Similarity	NPC105512
0.9456	High Similarity	NPC108406
0.9456	High Similarity	NPC95864
0.9419	High Similarity	NPC472277
0.9419	High Similarity	NPC108433
0.9419	High Similarity	NPC293319
0.9419	High Similarity	NPC62261
0.9419	High Similarity	NPC300053
0.9416	High Similarity	NPC194427
0.9416	High Similarity	NPC474162
0.9416	High Similarity	NPC474150
0.9416	High Similarity	NPC211107
0.9412	High Similarity	NPC299436
0.9412	High Similarity	NPC470183
0.9408	High Similarity	NPC299520
0.9408	High Similarity	NPC129684
0.9408	High Similarity	NPC52889
0.9408	High Similarity	NPC472911
0.9408	High Similarity	NPC245758
0.9408	High Similarity	NPC36852
0.9408	High Similarity	NPC210084
0.9408	High Similarity	NPC52530
0.9408	High Similarity	NPC472910
0.9408	High Similarity	NPC67876
0.9408	High Similarity	NPC222814
0.9408	High Similarity	NPC262286
0.9408	High Similarity	NPC472913
0.9408	High Similarity	NPC472914
0.9408	High Similarity	NPC99597
0.9408	High Similarity	NPC96167
0.9404	High Similarity	NPC37392
0.9404	High Similarity	NPC256925
0.9404	High Similarity	NPC234255
0.94	High Similarity	NPC36835
0.94	High Similarity	NPC260491
0.94	High Similarity	NPC477231
0.94	High Similarity	NPC260979
0.94	High Similarity	NPC61506
0.94	High Similarity	NPC257648
0.94	High Similarity	NPC240476
0.94	High Similarity	NPC246162
0.94	High Similarity	NPC249570
0.94	High Similarity	NPC9743
0.9396	High Similarity	NPC472633
0.9396	High Similarity	NPC62042
0.9392	High Similarity	NPC203077
0.9392	High Similarity	NPC238279
0.9392	High Similarity	NPC476342
0.9392	High Similarity	NPC166036
0.9392	High Similarity	NPC119059
0.9388	High Similarity	NPC472629
0.9359	High Similarity	NPC471213
0.9359	High Similarity	NPC43319
0.9355	High Similarity	NPC472281
0.9355	High Similarity	NPC472278
0.9355	High Similarity	NPC205265
0.9355	High Similarity	NPC329669
0.9355	High Similarity	NPC473313
0.9355	High Similarity	NPC18100
0.9355	High Similarity	NPC476295
0.9351	High Similarity	NPC198829
0.9351	High Similarity	NPC187354
0.9351	High Similarity	NPC32694
0.9351	High Similarity	NPC112418
0.9351	High Similarity	NPC158188
0.9351	High Similarity	NPC472275
0.9346	High Similarity	NPC184755

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 NPC192083 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	362
0.1-0.2	940
0.2-0.3	1709
0.3-0.4	2610
0.4-0.5	1779
0.5-0.6	1033
0.6-0.7	520
0.7-0.8	134
0.8-0.85	37
0.85-0.9	19
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD2393	Clinical (unspecified phase)
0.9662	High Similarity	NPD1934	Approved
0.9252	High Similarity	NPD1511	Approved
0.9211	High Similarity	NPD2801	Approved
0.9172	High Similarity	NPD6166	Phase 2
0.9172	High Similarity	NPD6168	Clinical (unspecified phase)
0.9172	High Similarity	NPD6167	Clinical (unspecified phase)
0.9128	High Similarity	NPD1512	Approved
0.906	High Similarity	NPD4378	Clinical (unspecified phase)
0.9013	High Similarity	NPD4380	Phase 2
0.8973	High Similarity	NPD1550	Clinical (unspecified phase)
0.8973	High Similarity	NPD1552	Clinical (unspecified phase)
0.8968	High Similarity	NPD3882	Suspended
0.8944	High Similarity	NPD7074	Phase 3
0.8912	High Similarity	NPD1549	Phase 2
0.891	High Similarity	NPD7075	Discontinued
0.8882	High Similarity	NPD7054	Approved
0.8846	High Similarity	NPD4868	Clinical (unspecified phase)
0.8839	High Similarity	NPD7096	Clinical (unspecified phase)
0.8827	High Similarity	NPD7472	Approved
0.882	High Similarity	NPD3818	Discontinued
0.8797	High Similarity	NPD5494	Approved
0.8782	High Similarity	NPD3817	Phase 2
0.8782	High Similarity	NPD8443	Clinical (unspecified phase)
0.8773	High Similarity	NPD6797	Phase 2
0.872	High Similarity	NPD7251	Discontinued
0.8718	High Similarity	NPD7819	Suspended
0.8671	High Similarity	NPD4381	Clinical (unspecified phase)
0.8649	High Similarity	NPD2796	Approved
0.8625	High Similarity	NPD6959	Discontinued
0.859	High Similarity	NPD7411	Suspended
0.8581	High Similarity	NPD1510	Phase 2
0.8562	High Similarity	NPD7410	Clinical (unspecified phase)
0.8554	High Similarity	NPD4338	Clinical (unspecified phase)
0.8554	High Similarity	NPD7808	Phase 3
0.8537	High Similarity	NPD7804	Clinical (unspecified phase)
0.8535	High Similarity	NPD6801	Discontinued
0.8457	Intermediate Similarity	NPD6232	Discontinued
0.8435	Intermediate Similarity	NPD1240	Approved
0.8424	Intermediate Similarity	NPD5844	Phase 1
0.8415	Intermediate Similarity	NPD7473	Discontinued
0.8383	Intermediate Similarity	NPD6559	Discontinued
0.8377	Intermediate Similarity	NPD6799	Approved
0.8323	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD1607	Approved
0.8311	Intermediate Similarity	NPD943	Approved
0.8311	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8311	Intermediate Similarity	NPD1613	Approved
0.8242	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD6599	Discontinued
0.8163	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD2935	Discontinued
0.8148	Intermediate Similarity	NPD7768	Phase 2
0.8137	Intermediate Similarity	NPD1465	Phase 2
0.8117	Intermediate Similarity	NPD2800	Approved
0.8117	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD2532	Approved
0.8089	Intermediate Similarity	NPD2533	Approved
0.8089	Intermediate Similarity	NPD2534	Approved
0.8086	Intermediate Similarity	NPD5402	Approved
0.8061	Intermediate Similarity	NPD1247	Approved
0.8052	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD919	Approved
0.8013	Intermediate Similarity	NPD230	Phase 1
0.7987	Intermediate Similarity	NPD5403	Approved
0.7987	Intermediate Similarity	NPD3027	Phase 3
0.7949	Intermediate Similarity	NPD3750	Approved
0.7933	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD1551	Phase 2
0.7879	Intermediate Similarity	NPD3749	Approved
0.7875	Intermediate Similarity	NPD920	Approved
0.7862	Intermediate Similarity	NPD5401	Approved
0.7857	Intermediate Similarity	NPD3926	Phase 2
0.7843	Intermediate Similarity	NPD6651	Approved
0.7834	Intermediate Similarity	NPD4628	Phase 3
0.7815	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD6100	Approved
0.7806	Intermediate Similarity	NPD6099	Approved
0.7803	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD5953	Discontinued
0.7778	Intermediate Similarity	NPD3226	Approved
0.7778	Intermediate Similarity	NPD7286	Phase 2
0.7771	Intermediate Similarity	NPD1243	Approved
0.7764	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD2346	Discontinued
0.775	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7747	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD2799	Discontinued
0.774	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD6234	Discontinued
0.7697	Intermediate Similarity	NPD2313	Discontinued
0.7688	Intermediate Similarity	NPD7390	Discontinued
0.7687	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD4908	Phase 1
0.7667	Intermediate Similarity	NPD4360	Phase 2
0.7667	Intermediate Similarity	NPD4363	Phase 3
0.7662	Intermediate Similarity	NPD447	Suspended
0.7654	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD2344	Approved
0.7633	Intermediate Similarity	NPD7199	Phase 2
0.7628	Intermediate Similarity	NPD3748	Approved
0.7616	Intermediate Similarity	NPD3751	Discontinued
0.761	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD1653	Approved
0.7588	Intermediate Similarity	NPD5711	Approved
0.7588	Intermediate Similarity	NPD5710	Approved
0.7588	Intermediate Similarity	NPD3787	Discontinued
0.7578	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD1610	Phase 2
0.7562	Intermediate Similarity	NPD6190	Approved
0.7557	Intermediate Similarity	NPD8312	Approved
0.7557	Intermediate Similarity	NPD8313	Approved
0.7548	Intermediate Similarity	NPD1933	Approved
0.7544	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD37	Approved
0.7516	Intermediate Similarity	NPD7033	Discontinued
0.7516	Intermediate Similarity	NPD4625	Phase 3
0.7514	Intermediate Similarity	NPD7228	Approved
0.75	Intermediate Similarity	NPD9494	Approved
0.75	Intermediate Similarity	NPD4966	Approved
0.75	Intermediate Similarity	NPD4967	Phase 2
0.75	Intermediate Similarity	NPD4965	Approved
0.7486	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1203	Approved
0.7467	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2309	Approved
0.7451	Intermediate Similarity	NPD6832	Phase 2
0.7436	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD5124	Phase 1
0.7436	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD1548	Phase 1
0.7407	Intermediate Similarity	NPD7584	Approved
0.7386	Intermediate Similarity	NPD2861	Phase 2
0.7384	Intermediate Similarity	NPD7229	Phase 3
0.7375	Intermediate Similarity	NPD2424	Discontinued
0.7366	Intermediate Similarity	NPD6777	Approved
0.7366	Intermediate Similarity	NPD6780	Approved
0.7366	Intermediate Similarity	NPD6776	Approved
0.7366	Intermediate Similarity	NPD6778	Approved
0.7366	Intermediate Similarity	NPD6779	Approved
0.7366	Intermediate Similarity	NPD6781	Approved
0.7366	Intermediate Similarity	NPD6782	Approved
0.7355	Intermediate Similarity	NPD3268	Approved
0.7355	Intermediate Similarity	NPD6798	Discontinued
0.7345	Intermediate Similarity	NPD7685	Pre-registration
0.7337	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD4361	Phase 2
0.7333	Intermediate Similarity	NPD8434	Phase 2
0.7333	Intermediate Similarity	NPD8150	Discontinued
0.733	Intermediate Similarity	NPD8151	Discontinued
0.7329	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6844	Discontinued
0.732	Intermediate Similarity	NPD2798	Approved
0.7285	Intermediate Similarity	NPD9269	Phase 2
0.7285	Intermediate Similarity	NPD9717	Approved
0.7285	Intermediate Similarity	NPD1608	Approved
0.7278	Intermediate Similarity	NPD8455	Phase 2
0.7261	Intermediate Similarity	NPD4060	Phase 1
0.7255	Intermediate Similarity	NPD2797	Approved
0.7249	Intermediate Similarity	NPD7435	Discontinued
0.7246	Intermediate Similarity	NPD7458	Discontinued
0.7244	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5242	Approved
0.7237	Intermediate Similarity	NPD4749	Approved
0.7235	Intermediate Similarity	NPD5353	Approved
0.7232	Intermediate Similarity	NPD1729	Discontinued
0.7222	Intermediate Similarity	NPD2654	Approved
0.7222	Intermediate Similarity	NPD1652	Phase 2
0.7219	Intermediate Similarity	NPD422	Phase 1
0.7219	Intermediate Similarity	NPD1201	Approved
0.7215	Intermediate Similarity	NPD6355	Discontinued
0.7205	Intermediate Similarity	NPD7266	Discontinued
0.7197	Intermediate Similarity	NPD6233	Phase 2
0.7191	Intermediate Similarity	NPD3823	Discontinued
0.7188	Intermediate Similarity	NPD4308	Phase 3
0.7165	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD7783	Phase 2
0.7158	Intermediate Similarity	NPD7698	Approved
0.7158	Intermediate Similarity	NPD7697	Approved
0.7158	Intermediate Similarity	NPD7696	Phase 3
0.7143	Intermediate Similarity	NPD5406	Approved
0.7143	Intermediate Similarity	NPD5408	Approved
0.7143	Intermediate Similarity	NPD5405	Approved
0.7143	Intermediate Similarity	NPD1470	Approved
0.7143	Intermediate Similarity	NPD5404	Approved
0.7134	Intermediate Similarity	NPD411	Approved
0.712	Intermediate Similarity	NPD7871	Phase 2
0.712	Intermediate Similarity	NPD7870	Phase 2
0.7108	Intermediate Similarity	NPD4662	Approved
0.7108	Intermediate Similarity	NPD4661	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