NPASS Compound

Structure

NPC475549 OpenBabel07101718282D 23 25 0 0 1 0 0 0 0 0999 V2000 1.4836 2.1907 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 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 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 0.2588 0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2247 1.2247 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 -4.3301 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 0.5000 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 0.0000 -1.0000 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 0.0000 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.9319 0.5176 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 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 0.7934 -0.6088 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 1 10 1 0 0 0 0 2 23 1 0 0 0 0 3 6 2 0 0 0 0 3 11 1 0 0 0 0 4 5 1 0 0 0 0 4 12 2 0 0 0 0 5 13 2 0 0 0 0 6 14 1 0 0 0 0 7 11 2 0 0 0 0 7 12 1 0 0 0 0 8 15 2 0 0 0 0 8 16 1 0 0 0 0 9 10 1 0 0 0 0 9 18 1 0 0 0 0 10 19 2 0 0 0 0 11 13 1 0 0 0 0 12 20 1 0 0 0 0 13 17 1 0 0 0 0 14 17 2 0 0 0 0 14 18 1 0 0 0 0 15 17 1 0 0 0 0 15 23 1 0 0 0 0 16 18 1 0 0 0 0 16 21 2 0 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	312.1
Volume:	317.074
LogP:	1.411
LogD:	2.091
LogS:	-3.244
# Rotatable Bonds:	3
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.908
Synthetic Accessibility Score:	3.356
Fsp3:	0.222
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.924
MDCK Permeability:	2.2234960852074437e-05
Pgp-inhibitor:	0.019
Pgp-substrate:	0.049
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.161
Plasma Protein Binding (PPB):	85.97504425048828%
Volume Distribution (VD):	0.877
Pgp-substrate:	9.03958797454834%

ADMET: Metabolism

CYP1A2-inhibitor:	0.962
CYP1A2-substrate:	0.937
CYP2C19-inhibitor:	0.523
CYP2C19-substrate:	0.743
CYP2C9-inhibitor:	0.191
CYP2C9-substrate:	0.849
CYP2D6-inhibitor:	0.485
CYP2D6-substrate:	0.513
CYP3A4-inhibitor:	0.662
CYP3A4-substrate:	0.698

ADMET: Excretion

Clearance (CL):	3.061
Half-life (T1/2):	0.4

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.882
Drug-inuced Liver Injury (DILI):	0.291
AMES Toxicity:	0.325
Rat Oral Acute Toxicity:	0.162
Maximum Recommended Daily Dose:	0.846
Skin Sensitization:	0.481
Carcinogencity:	0.689
Eye Corrosion:	0.003
Eye Irritation:	0.05
Respiratory Toxicity:	0.098

Download Data

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

Natural Product: NPC475549

Natural Product ID:	NPC475549
*Common Name:**	1,7-Dihydroxy-4-Methoxy-1-(2-Oxopropyl)Phenanthren-2-One
IUPAC Name:	1,7-dihydroxy-4-methoxy-1-(2-oxopropyl)phenanthren-2-one
Synonyms:
Standard InCHIKey:	SWSOAHKDNLMNLA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H16O5/c1-10(19)9-18(22)14-6-3-11-7-12(20)4-5-13(11)17(14)15(23-2)8-16(18)21/h3-8,20,22H,9H2,1-2H3
SMILES:	COC1=CC(=O)C(c2c1c1ccc(cc1cc2)O)(O)CC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL507982
PubChem CID:	11716581
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001194] Oxosteroids [CHEMONTID:0003060] 16-oxosteroids

*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
NPO1756	Cremastra appendiculata	Species	Orchidaceae	Eukaryota	n.a.	bulb	n.a.	PMID[14994197]
NPO1756	Cremastra appendiculata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844951]
NPO1756	Cremastra appendiculata	Species	Orchidaceae	Eukaryota	tubers	n.a.	n.a.	PMID[16792409]
NPO1756	Cremastra appendiculata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1756	Cremastra appendiculata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1756	Cremastra appendiculata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1756	Cremastra appendiculata	Species	Orchidaceae	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
IC50	7

Activity Type	# Activity
Cell Line	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	5000.0	nM	PMID[546206]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	5000.0	nM	PMID[546206]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	5000.0	nM	PMID[546206]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	5000.0	nM	PMID[546206]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	5000.0	nM	PMID[546206]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	5000.0	nM	PMID[546206]
NPT1306	Cell Line	WISH	Homo sapiens	IC50	>	5000.0	nM	PMID[546206]

☑ 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 NPC475549 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	329
0.1-0.2	1520
0.2-0.3	3171
0.3-0.4	8565
0.4-0.5	10325
0.5-0.6	4314
0.6-0.7	9207
0.7-0.8	4999
0.8-0.85	246
0.85-0.9	18
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9697	High Similarity	NPC475104
0.8947	High Similarity	NPC27659
0.8806	High Similarity	NPC253488
0.8676	High Similarity	NPC312560
0.8636	High Similarity	NPC474766
0.8633	High Similarity	NPC470721
0.8633	High Similarity	NPC156888
0.8633	High Similarity	NPC470722
0.8633	High Similarity	NPC6100
0.8623	High Similarity	NPC309056
0.8592	High Similarity	NPC201297
0.8529	High Similarity	NPC470725
0.8511	High Similarity	NPC470407
0.85	High Similarity	NPC264022
0.8485	Intermediate Similarity	NPC164947
0.8451	Intermediate Similarity	NPC136649
0.8421	Intermediate Similarity	NPC273683
0.8417	Intermediate Similarity	NPC50924
0.8414	Intermediate Similarity	NPC478019
0.8394	Intermediate Similarity	NPC198305
0.8392	Intermediate Similarity	NPC110810
0.8392	Intermediate Similarity	NPC124365
0.8382	Intermediate Similarity	NPC96024
0.8378	Intermediate Similarity	NPC295977
0.8378	Intermediate Similarity	NPC58310
0.8357	Intermediate Similarity	NPC22222
0.8357	Intermediate Similarity	NPC281513
0.8357	Intermediate Similarity	NPC22644
0.8357	Intermediate Similarity	NPC283088
0.8345	Intermediate Similarity	NPC59459
0.8333	Intermediate Similarity	NPC85342
0.8333	Intermediate Similarity	NPC244699
0.8333	Intermediate Similarity	NPC69755
0.8311	Intermediate Similarity	NPC80370
0.8311	Intermediate Similarity	NPC329933
0.8299	Intermediate Similarity	NPC34802
0.8299	Intermediate Similarity	NPC58373
0.8298	Intermediate Similarity	NPC471670
0.8289	Intermediate Similarity	NPC67197
0.8286	Intermediate Similarity	NPC212207
0.8276	Intermediate Similarity	NPC66593
0.8276	Intermediate Similarity	NPC53016
0.8273	Intermediate Similarity	NPC183103
0.8261	Intermediate Similarity	NPC55949
0.8252	Intermediate Similarity	NPC1268
0.8252	Intermediate Similarity	NPC477408
0.8248	Intermediate Similarity	NPC237225
0.8248	Intermediate Similarity	NPC48248
0.8239	Intermediate Similarity	NPC290601
0.8239	Intermediate Similarity	NPC186647
0.8235	Intermediate Similarity	NPC15837
0.8231	Intermediate Similarity	NPC300540
0.8231	Intermediate Similarity	NPC147250
0.8224	Intermediate Similarity	NPC474360
0.8222	Intermediate Similarity	NPC164014
0.8222	Intermediate Similarity	NPC199273
0.8219	Intermediate Similarity	NPC29932
0.8219	Intermediate Similarity	NPC193703
0.8219	Intermediate Similarity	NPC21599
0.8219	Intermediate Similarity	NPC477409
0.8214	Intermediate Similarity	NPC263817
0.8214	Intermediate Similarity	NPC171968
0.8214	Intermediate Similarity	NPC53896
0.8214	Intermediate Similarity	NPC52407
0.8209	Intermediate Similarity	NPC176208
0.8201	Intermediate Similarity	NPC205360
0.82	Intermediate Similarity	NPC144283
0.82	Intermediate Similarity	NPC306011
0.82	Intermediate Similarity	NPC230848
0.82	Intermediate Similarity	NPC472838
0.8194	Intermediate Similarity	NPC168471
0.8188	Intermediate Similarity	NPC34414
0.8188	Intermediate Similarity	NPC146647
0.8188	Intermediate Similarity	NPC276238
0.8188	Intermediate Similarity	NPC171460
0.8188	Intermediate Similarity	NPC278928
0.8182	Intermediate Similarity	NPC284495
0.8176	Intermediate Similarity	NPC478018
0.8169	Intermediate Similarity	NPC474311
0.8169	Intermediate Similarity	NPC155211
0.8163	Intermediate Similarity	NPC34482
0.8163	Intermediate Similarity	NPC474630
0.8162	Intermediate Similarity	NPC123506
0.8158	Intermediate Similarity	NPC66029
0.8158	Intermediate Similarity	NPC3898
0.8156	Intermediate Similarity	NPC27394
0.8151	Intermediate Similarity	NPC476473
0.8151	Intermediate Similarity	NPC84266
0.8148	Intermediate Similarity	NPC135062
0.8143	Intermediate Similarity	NPC165612
0.8143	Intermediate Similarity	NPC309430
0.8134	Intermediate Similarity	NPC154696
0.8133	Intermediate Similarity	NPC294646
0.8133	Intermediate Similarity	NPC205766
0.8129	Intermediate Similarity	NPC199253
0.8129	Intermediate Similarity	NPC136588
0.8121	Intermediate Similarity	NPC472841
0.8112	Intermediate Similarity	NPC305060
0.8112	Intermediate Similarity	NPC245923
0.8112	Intermediate Similarity	NPC53001
0.8112	Intermediate Similarity	NPC301341
0.8108	Intermediate Similarity	NPC136878
0.8108	Intermediate Similarity	NPC60389
0.8108	Intermediate Similarity	NPC211565
0.8108	Intermediate Similarity	NPC470570
0.8105	Intermediate Similarity	NPC279605
0.8102	Intermediate Similarity	NPC254492
0.8102	Intermediate Similarity	NPC51037
0.8102	Intermediate Similarity	NPC306765
0.8102	Intermediate Similarity	NPC71610
0.8099	Intermediate Similarity	NPC80035
0.8095	Intermediate Similarity	NPC48762
0.8095	Intermediate Similarity	NPC471600
0.8092	Intermediate Similarity	NPC210942
0.8092	Intermediate Similarity	NPC477691
0.8092	Intermediate Similarity	NPC169990
0.8092	Intermediate Similarity	NPC329844
0.8088	Intermediate Similarity	NPC111088
0.8088	Intermediate Similarity	NPC310540
0.8085	Intermediate Similarity	NPC314048
0.8085	Intermediate Similarity	NPC225051
0.8082	Intermediate Similarity	NPC94076
0.8082	Intermediate Similarity	NPC182255
0.8082	Intermediate Similarity	NPC474300
0.8079	Intermediate Similarity	NPC474417
0.8079	Intermediate Similarity	NPC477276
0.8079	Intermediate Similarity	NPC149526
0.8074	Intermediate Similarity	NPC91478
0.8071	Intermediate Similarity	NPC205992
0.8071	Intermediate Similarity	NPC72669
0.8071	Intermediate Similarity	NPC474517
0.8067	Intermediate Similarity	NPC100985
0.8067	Intermediate Similarity	NPC97029
0.8067	Intermediate Similarity	NPC97028
0.8067	Intermediate Similarity	NPC65589
0.8067	Intermediate Similarity	NPC158338
0.8067	Intermediate Similarity	NPC288036
0.806	Intermediate Similarity	NPC259703
0.806	Intermediate Similarity	NPC32322
0.8058	Intermediate Similarity	NPC99731
0.8058	Intermediate Similarity	NPC206028
0.8056	Intermediate Similarity	NPC87723
0.8056	Intermediate Similarity	NPC13715
0.8056	Intermediate Similarity	NPC173980
0.8054	Intermediate Similarity	NPC190648
0.8054	Intermediate Similarity	NPC118027
0.8054	Intermediate Similarity	NPC312929
0.8054	Intermediate Similarity	NPC126767
0.8054	Intermediate Similarity	NPC289042
0.8054	Intermediate Similarity	NPC245584
0.8054	Intermediate Similarity	NPC119767
0.8054	Intermediate Similarity	NPC56433
0.8052	Intermediate Similarity	NPC44199
0.8043	Intermediate Similarity	NPC428300
0.8043	Intermediate Similarity	NPC471530
0.8043	Intermediate Similarity	NPC72667
0.8042	Intermediate Similarity	NPC474813
0.8042	Intermediate Similarity	NPC272268
0.8042	Intermediate Similarity	NPC141934
0.8041	Intermediate Similarity	NPC478160
0.8039	Intermediate Similarity	NPC318270
0.8039	Intermediate Similarity	NPC66508
0.8039	Intermediate Similarity	NPC226656
0.8028	Intermediate Similarity	NPC12070
0.8028	Intermediate Similarity	NPC202225
0.8027	Intermediate Similarity	NPC143898
0.8027	Intermediate Similarity	NPC478164
0.8027	Intermediate Similarity	NPC316691
0.8027	Intermediate Similarity	NPC163948
0.8026	Intermediate Similarity	NPC477690
0.8026	Intermediate Similarity	NPC164912
0.8014	Intermediate Similarity	NPC283292
0.8014	Intermediate Similarity	NPC70622
0.8014	Intermediate Similarity	NPC187843
0.8014	Intermediate Similarity	NPC58685
0.8014	Intermediate Similarity	NPC477406
0.8013	Intermediate Similarity	NPC255641
0.8013	Intermediate Similarity	NPC470568
0.8013	Intermediate Similarity	NPC147735
0.8013	Intermediate Similarity	NPC219686
0.8013	Intermediate Similarity	NPC290954
0.8	Intermediate Similarity	NPC324736
0.8	Intermediate Similarity	NPC228654
0.8	Intermediate Similarity	NPC120545
0.8	Intermediate Similarity	NPC7025
0.8	Intermediate Similarity	NPC242994
0.8	Intermediate Similarity	NPC138099
0.8	Intermediate Similarity	NPC108129
0.8	Intermediate Similarity	NPC27221
0.8	Intermediate Similarity	NPC474556
0.8	Intermediate Similarity	NPC256672
0.7987	Intermediate Similarity	NPC225173
0.7987	Intermediate Similarity	NPC163846
0.7987	Intermediate Similarity	NPC473094
0.7986	Intermediate Similarity	NPC119542
0.7986	Intermediate Similarity	NPC284184
0.7986	Intermediate Similarity	NPC118366
0.7986	Intermediate Similarity	NPC98804
0.7986	Intermediate Similarity	NPC282923
0.7986	Intermediate Similarity	NPC469930

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 NPC475549 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	302
0.1-0.2	961
0.2-0.3	1264
0.3-0.4	2456
0.4-0.5	2238
0.5-0.6	1231
0.6-0.7	595
0.7-0.8	101
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8182	Intermediate Similarity	NPD1651	Approved
0.8088	Intermediate Similarity	NPD1283	Approved
0.7986	Intermediate Similarity	NPD2935	Discontinued
0.7868	Intermediate Similarity	NPD1281	Approved
0.7852	Intermediate Similarity	NPD2932	Approved
0.7808	Intermediate Similarity	NPD2346	Discontinued
0.78	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD1470	Approved
0.7762	Intermediate Similarity	NPD2979	Phase 3
0.7737	Intermediate Similarity	NPD1201	Approved
0.7736	Intermediate Similarity	NPD6232	Discontinued
0.7733	Intermediate Similarity	NPD7390	Discontinued
0.7721	Intermediate Similarity	NPD3019	Approved
0.7712	Intermediate Similarity	NPD3226	Approved
0.7702	Intermediate Similarity	NPD7473	Discontinued
0.7667	Intermediate Similarity	NPD3300	Phase 2
0.7651	Intermediate Similarity	NPD7003	Approved
0.7619	Intermediate Similarity	NPD5404	Approved
0.7619	Intermediate Similarity	NPD5408	Approved
0.7619	Intermediate Similarity	NPD5405	Approved
0.7619	Intermediate Similarity	NPD5406	Approved
0.7591	Intermediate Similarity	NPD4626	Approved
0.7562	Intermediate Similarity	NPD6959	Discontinued
0.7554	Intermediate Similarity	NPD3972	Approved
0.75	Intermediate Similarity	NPD3764	Approved
0.7451	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD2344	Approved
0.7447	Intermediate Similarity	NPD1876	Approved
0.7432	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD2799	Discontinued
0.7426	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD8166	Discontinued
0.7415	Intermediate Similarity	NPD1607	Approved
0.7405	Intermediate Similarity	NPD7819	Suspended
0.7405	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD4060	Phase 1
0.7388	Intermediate Similarity	NPD7635	Approved
0.7383	Intermediate Similarity	NPD2438	Suspended
0.7383	Intermediate Similarity	NPD2531	Phase 2
0.7376	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD2798	Approved
0.7338	Intermediate Similarity	NPD2532	Approved
0.7338	Intermediate Similarity	NPD2534	Approved
0.7338	Intermediate Similarity	NPD2533	Approved
0.7338	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1471	Phase 3
0.7315	Intermediate Similarity	NPD1510	Phase 2
0.7286	Intermediate Similarity	NPD3023	Approved
0.7286	Intermediate Similarity	NPD3026	Approved
0.7283	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1240	Approved
0.7267	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD3025	Approved
0.7266	Intermediate Similarity	NPD3024	Approved
0.7266	Intermediate Similarity	NPD5691	Approved
0.7261	Intermediate Similarity	NPD7458	Discontinued
0.7261	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD2313	Discontinued
0.7255	Intermediate Similarity	NPD2309	Approved
0.7254	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD8150	Discontinued
0.7237	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4380	Phase 2
0.7211	Intermediate Similarity	NPD6663	Approved
0.7192	Intermediate Similarity	NPD7095	Approved
0.7192	Intermediate Similarity	NPD4625	Phase 3
0.719	Intermediate Similarity	NPD4628	Phase 3
0.719	Intermediate Similarity	NPD3750	Approved
0.7188	Intermediate Similarity	NPD2801	Approved
0.7186	Intermediate Similarity	NPD5844	Phase 1
0.7179	Intermediate Similarity	NPD6273	Approved
0.7179	Intermediate Similarity	NPD1512	Approved
0.7172	Intermediate Similarity	NPD5736	Approved
0.7171	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7075	Discontinued
0.7153	Intermediate Similarity	NPD1164	Approved
0.7152	Intermediate Similarity	NPD6100	Approved
0.7152	Intermediate Similarity	NPD6099	Approved
0.7143	Intermediate Similarity	NPD2342	Discontinued
0.7143	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3268	Approved
0.7143	Intermediate Similarity	NPD6190	Approved
0.7126	Intermediate Similarity	NPD3751	Discontinued
0.7125	Intermediate Similarity	NPD1934	Approved
0.7113	Intermediate Similarity	NPD1611	Approved
0.7107	Intermediate Similarity	NPD7028	Phase 2
0.7105	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6233	Phase 2
0.7095	Intermediate Similarity	NPD8032	Phase 2
0.7081	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD1241	Discontinued
0.7078	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD7008	Discontinued
0.7075	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1608	Approved
0.7063	Intermediate Similarity	NPD1481	Phase 2
0.7059	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1549	Phase 2
0.7051	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD1511	Approved
0.7039	Intermediate Similarity	NPD4477	Approved
0.7039	Intermediate Similarity	NPD4476	Approved
0.7034	Intermediate Similarity	NPD2797	Approved
0.7029	Intermediate Similarity	NPD5951	Approved
0.7027	Intermediate Similarity	NPD6798	Discontinued
0.7021	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6535	Approved
0.7006	Intermediate Similarity	NPD6166	Phase 2
0.7006	Intermediate Similarity	NPD6534	Approved
0.7	Intermediate Similarity	NPD6780	Approved
0.7	Intermediate Similarity	NPD6599	Discontinued
0.7	Intermediate Similarity	NPD6777	Approved
0.7	Intermediate Similarity	NPD6778	Approved
0.7	Intermediate Similarity	NPD3020	Approved
0.7	Intermediate Similarity	NPD6782	Approved
0.7	Intermediate Similarity	NPD5536	Phase 2
0.7	Intermediate Similarity	NPD6779	Approved
0.7	Intermediate Similarity	NPD6355	Discontinued
0.7	Intermediate Similarity	NPD6776	Approved
0.7	Intermediate Similarity	NPD6781	Approved
0.6994	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD3882	Suspended
0.6994	Remote Similarity	NPD7768	Phase 2
0.6993	Remote Similarity	NPD1535	Discovery
0.6993	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD4624	Approved
0.6974	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4308	Phase 3
0.6972	Remote Similarity	NPD2286	Discontinued
0.6959	Remote Similarity	NPD6559	Discontinued
0.6957	Remote Similarity	NPD7411	Suspended
0.6954	Remote Similarity	NPD8434	Phase 2
0.6951	Remote Similarity	NPD3749	Approved
0.695	Remote Similarity	NPD9545	Approved
0.695	Remote Similarity	NPD3091	Approved
0.6933	Remote Similarity	NPD943	Approved
0.6933	Remote Similarity	NPD3817	Phase 2
0.6929	Remote Similarity	NPD9493	Approved
0.6928	Remote Similarity	NPD2796	Approved
0.6923	Remote Similarity	NPD3847	Discontinued
0.6914	Remote Similarity	NPD6801	Discontinued
0.6912	Remote Similarity	NPD3022	Approved
0.6912	Remote Similarity	NPD3021	Approved
0.6905	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD2800	Approved
0.6899	Remote Similarity	NPD2859	Approved
0.6899	Remote Similarity	NPD2860	Approved
0.6899	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1669	Approved
0.6889	Remote Similarity	NPD7699	Phase 2
0.6889	Remote Similarity	NPD7700	Phase 2
0.6886	Remote Similarity	NPD3787	Discontinued
0.6885	Remote Similarity	NPD7435	Discontinued
0.6885	Remote Similarity	NPD7697	Approved
0.6885	Remote Similarity	NPD7696	Phase 3
0.6885	Remote Similarity	NPD7698	Approved
0.6882	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7236	Approved
0.6875	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5494	Approved
0.6863	Remote Similarity	NPD3748	Approved
0.6857	Remote Similarity	NPD6671	Approved
0.6853	Remote Similarity	NPD17	Approved
0.6853	Remote Similarity	NPD4059	Approved
0.6853	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD6696	Suspended
0.6848	Remote Similarity	NPD7871	Phase 2
0.6848	Remote Similarity	NPD7870	Phase 2
0.6842	Remote Similarity	NPD4097	Suspended
0.6842	Remote Similarity	NPD6651	Approved
0.6835	Remote Similarity	NPD1398	Phase 1
0.6835	Remote Similarity	NPD6799	Approved
0.6835	Remote Similarity	NPD5283	Phase 1
0.6824	Remote Similarity	NPD9494	Approved
0.6824	Remote Similarity	NPD2861	Phase 2
0.6824	Remote Similarity	NPD7177	Discontinued
0.6822	Remote Similarity	NPD2934	Approved
0.6822	Remote Similarity	NPD2933	Approved
0.6821	Remote Similarity	NPD4140	Approved
0.6815	Remote Similarity	NPD2354	Approved
0.681	Remote Similarity	NPD37	Approved
0.6809	Remote Similarity	NPD7340	Approved
0.6803	Remote Similarity	NPD1203	Approved
0.6803	Remote Similarity	NPD3094	Phase 2
0.6803	Remote Similarity	NPD3267	Approved
0.6803	Remote Similarity	NPD3266	Approved
0.68	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD497	Approved
0.6786	Remote Similarity	NPD5711	Approved
0.6786	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5710	Approved
0.6782	Remote Similarity	NPD8313	Approved
0.6782	Remote Similarity	NPD8312	Approved
0.6782	Remote Similarity	NPD3534	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