NPASS Compound

Structure

NPC475104 OpenBabel07101719512D 24 26 0 0 1 0 0 0 0 0999 V2000 -1.9319 0.5176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 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 -1.4836 2.1907 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 5.1962 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 1 11 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 7 2 0 0 0 0 4 12 1 0 0 0 0 5 6 1 0 0 0 0 5 13 2 0 0 0 0 6 14 2 0 0 0 0 7 15 1 0 0 0 0 8 12 2 0 0 0 0 8 13 1 0 0 0 0 9 16 2 0 0 0 0 9 17 1 0 0 0 0 10 11 1 0 0 0 0 10 19 1 0 0 0 0 11 20 2 0 0 0 0 12 14 1 0 0 0 0 13 23 1 0 0 0 0 14 18 1 0 0 0 0 15 18 2 0 0 0 0 15 19 1 0 0 0 0 16 18 1 0 0 0 0 16 24 1 0 0 0 0 17 19 1 0 0 0 0 17 21 2 0 0 0 0 19 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	326.12
Volume:	334.37
LogP:	1.856
LogD:	2.388
LogS:	-4.291
# Rotatable Bonds:	4
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.935
Synthetic Accessibility Score:	3.218
Fsp3:	0.263
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:	-4.88
MDCK Permeability:	2.3467931896448135e-05
Pgp-inhibitor:	0.249
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.702
30% Bioavailability (F30%):	0.023

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.451
Plasma Protein Binding (PPB):	89.84912872314453%
Volume Distribution (VD):	1.005
Pgp-substrate:	7.074398040771484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.95
CYP1A2-substrate:	0.948
CYP2C19-inhibitor:	0.804
CYP2C19-substrate:	0.899
CYP2C9-inhibitor:	0.245
CYP2C9-substrate:	0.785
CYP2D6-inhibitor:	0.469
CYP2D6-substrate:	0.878
CYP3A4-inhibitor:	0.792
CYP3A4-substrate:	0.865

ADMET: Excretion

Clearance (CL):	3.106
Half-life (T1/2):	0.183

ADMET: Toxicity

hERG Blockers:	0.061
Human Hepatotoxicity (H-HT):	0.929
Drug-inuced Liver Injury (DILI):	0.324
AMES Toxicity:	0.542
Rat Oral Acute Toxicity:	0.156
Maximum Recommended Daily Dose:	0.813
Skin Sensitization:	0.387
Carcinogencity:	0.78
Eye Corrosion:	0.003
Eye Irritation:	0.044
Respiratory Toxicity:	0.039

Download Data

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

Natural Product: NPC475104

Natural Product ID:	NPC475104
*Common Name:**	1-Hydroxy-4,7-Dimethoxy-1-(2-Oxopropyl)Phenanthren-2-One
IUPAC Name:	1-hydroxy-4,7-dimethoxy-1-(2-oxopropyl)phenanthren-2-one
Synonyms:
Standard InCHIKey:	VPXKSBCKKMQYCS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H18O5/c1-11(20)10-19(22)15-7-4-12-8-13(23-2)5-6-14(12)18(15)16(24-3)9-17(19)21/h4-9,22H,10H2,1-3H3
SMILES:	CC(=O)CC1(C2=C(C3=C(C=C2)C=C(C=C3)OC)C(=CC1=O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL498076
PubChem CID:	11645552
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[553735]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	5000.0	nM	PMID[553735]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	5000.0	nM	PMID[553735]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	5000.0	nM	PMID[553735]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	5000.0	nM	PMID[553735]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	5000.0	nM	PMID[553735]
NPT1306	Cell Line	WISH	Homo sapiens	IC50	>	5000.0	nM	PMID[553735]

☑ 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 NPC475104 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	340
0.1-0.2	1540
0.2-0.3	3301
0.3-0.4	8957
0.4-0.5	9771
0.5-0.6	3839
0.6-0.7	8979
0.7-0.8	5727
0.8-0.85	211
0.85-0.9	30
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9697	High Similarity	NPC475549
0.8963	High Similarity	NPC312560
0.8913	High Similarity	NPC6100
0.8913	High Similarity	NPC156888
0.8913	High Similarity	NPC470722
0.8913	High Similarity	NPC470721
0.8815	High Similarity	NPC470725
0.8786	High Similarity	NPC470407
0.8732	High Similarity	NPC201297
0.8723	High Similarity	NPC136649
0.8676	High Similarity	NPC27659
0.8633	High Similarity	NPC22644
0.8571	High Similarity	NPC471670
0.8552	High Similarity	NPC478019
0.8551	High Similarity	NPC183103
0.8542	High Similarity	NPC53016
0.854	High Similarity	NPC253488
0.8531	High Similarity	NPC124365
0.8521	High Similarity	NPC477408
0.8514	High Similarity	NPC58310
0.8514	High Similarity	NPC295977
0.8511	High Similarity	NPC186647
0.8511	High Similarity	NPC290601
0.85	High Similarity	NPC281513
0.85	High Similarity	NPC309056
0.85	High Similarity	NPC22222
0.8478	Intermediate Similarity	NPC205360
0.8472	Intermediate Similarity	NPC69755
0.8446	Intermediate Similarity	NPC329933
0.8446	Intermediate Similarity	NPC80370
0.8435	Intermediate Similarity	NPC58373
0.8435	Intermediate Similarity	NPC478018
0.8435	Intermediate Similarity	NPC34802
0.8421	Intermediate Similarity	NPC67197
0.8411	Intermediate Similarity	NPC3898
0.8392	Intermediate Similarity	NPC1268
0.838	Intermediate Similarity	NPC301341
0.8378	Intermediate Similarity	NPC472841
0.837	Intermediate Similarity	NPC111088
0.837	Intermediate Similarity	NPC474766
0.8367	Intermediate Similarity	NPC300540
0.8356	Intermediate Similarity	NPC477409
0.8355	Intermediate Similarity	NPC474360
0.8333	Intermediate Similarity	NPC472838
0.8333	Intermediate Similarity	NPC144283
0.8333	Intermediate Similarity	NPC306011
0.8333	Intermediate Similarity	NPC230848
0.8321	Intermediate Similarity	NPC428300
0.8312	Intermediate Similarity	NPC284495
0.8298	Intermediate Similarity	NPC27394
0.8288	Intermediate Similarity	NPC84266
0.8267	Intermediate Similarity	NPC294646
0.8252	Intermediate Similarity	NPC264022
0.8252	Intermediate Similarity	NPC284184
0.8248	Intermediate Similarity	NPC177925
0.8243	Intermediate Similarity	NPC211565
0.8243	Intermediate Similarity	NPC60389
0.8235	Intermediate Similarity	NPC75432
0.8235	Intermediate Similarity	NPC279605
0.8231	Intermediate Similarity	NPC471451
0.8231	Intermediate Similarity	NPC472836
0.8231	Intermediate Similarity	NPC471600
0.8227	Intermediate Similarity	NPC470406
0.8224	Intermediate Similarity	NPC210942
0.8224	Intermediate Similarity	NPC477691
0.8224	Intermediate Similarity	NPC169990
0.8224	Intermediate Similarity	NPC329844
0.8222	Intermediate Similarity	NPC164947
0.8219	Intermediate Similarity	NPC182255
0.8219	Intermediate Similarity	NPC94076
0.8214	Intermediate Similarity	NPC239134
0.8212	Intermediate Similarity	NPC149526
0.8212	Intermediate Similarity	NPC474417
0.8201	Intermediate Similarity	NPC206028
0.8201	Intermediate Similarity	NPC57552
0.82	Intermediate Similarity	NPC100985
0.82	Intermediate Similarity	NPC288036
0.82	Intermediate Similarity	NPC97029
0.82	Intermediate Similarity	NPC97028
0.82	Intermediate Similarity	NPC65589
0.82	Intermediate Similarity	NPC158338
0.8188	Intermediate Similarity	NPC289042
0.8188	Intermediate Similarity	NPC118027
0.8188	Intermediate Similarity	NPC126767
0.8188	Intermediate Similarity	NPC190648
0.8188	Intermediate Similarity	NPC56433
0.8188	Intermediate Similarity	NPC478163
0.8188	Intermediate Similarity	NPC245584
0.8188	Intermediate Similarity	NPC312929
0.8182	Intermediate Similarity	NPC44199
0.8182	Intermediate Similarity	NPC141934
0.817	Intermediate Similarity	NPC226656
0.817	Intermediate Similarity	NPC66508
0.8169	Intermediate Similarity	NPC1249
0.8169	Intermediate Similarity	NPC50924
0.8169	Intermediate Similarity	NPC212207
0.8163	Intermediate Similarity	NPC316691
0.8163	Intermediate Similarity	NPC163948
0.8162	Intermediate Similarity	NPC273683
0.8158	Intermediate Similarity	NPC477690
0.8158	Intermediate Similarity	NPC164912
0.8156	Intermediate Similarity	NPC474340
0.8151	Intermediate Similarity	NPC110810
0.8146	Intermediate Similarity	NPC255641
0.8146	Intermediate Similarity	NPC470568
0.8146	Intermediate Similarity	NPC147735
0.8146	Intermediate Similarity	NPC290954
0.8143	Intermediate Similarity	NPC198305
0.8141	Intermediate Similarity	NPC219686
0.8134	Intermediate Similarity	NPC103916
0.8133	Intermediate Similarity	NPC474556
0.8133	Intermediate Similarity	NPC474107
0.8133	Intermediate Similarity	NPC27221
0.8133	Intermediate Similarity	NPC256672
0.8133	Intermediate Similarity	NPC7025
0.8129	Intermediate Similarity	NPC96024
0.8129	Intermediate Similarity	NPC324736
0.8129	Intermediate Similarity	NPC228654
0.8125	Intermediate Similarity	NPC98804
0.8121	Intermediate Similarity	NPC225173
0.8121	Intermediate Similarity	NPC163846
0.8116	Intermediate Similarity	NPC474737
0.8113	Intermediate Similarity	NPC473094
0.8112	Intermediate Similarity	NPC283088
0.8108	Intermediate Similarity	NPC260152
0.8108	Intermediate Similarity	NPC91694
0.8108	Intermediate Similarity	NPC300603
0.8108	Intermediate Similarity	NPC471305
0.8105	Intermediate Similarity	NPC135522
0.8101	Intermediate Similarity	NPC26386
0.8099	Intermediate Similarity	NPC59459
0.8095	Intermediate Similarity	NPC176030
0.8095	Intermediate Similarity	NPC126534
0.8095	Intermediate Similarity	NPC141817
0.8095	Intermediate Similarity	NPC192597
0.8095	Intermediate Similarity	NPC169214
0.8095	Intermediate Similarity	NPC232021
0.8095	Intermediate Similarity	NPC40118
0.8095	Intermediate Similarity	NPC229218
0.8092	Intermediate Similarity	NPC302783
0.8092	Intermediate Similarity	NPC478148
0.8092	Intermediate Similarity	NPC473201
0.8092	Intermediate Similarity	NPC72958
0.8092	Intermediate Similarity	NPC118427
0.8092	Intermediate Similarity	NPC470569
0.8092	Intermediate Similarity	NPC232645
0.8085	Intermediate Similarity	NPC244699
0.8085	Intermediate Similarity	NPC164295
0.8085	Intermediate Similarity	NPC85342
0.8079	Intermediate Similarity	NPC269420
0.8075	Intermediate Similarity	NPC473113
0.8074	Intermediate Similarity	NPC129176
0.8067	Intermediate Similarity	NPC22005
0.8067	Intermediate Similarity	NPC123202
0.8067	Intermediate Similarity	NPC7943
0.8067	Intermediate Similarity	NPC125801
0.8065	Intermediate Similarity	NPC201127
0.8065	Intermediate Similarity	NPC474637
0.8063	Intermediate Similarity	NPC473095
0.8063	Intermediate Similarity	NPC473096
0.8058	Intermediate Similarity	NPC45537
0.8056	Intermediate Similarity	NPC232996
0.8054	Intermediate Similarity	NPC28632
0.8054	Intermediate Similarity	NPC49282
0.8054	Intermediate Similarity	NPC160777
0.8054	Intermediate Similarity	NPC73416
0.8042	Intermediate Similarity	NPC477210
0.8041	Intermediate Similarity	NPC167663
0.8041	Intermediate Similarity	NPC297600
0.8041	Intermediate Similarity	NPC66593
0.8039	Intermediate Similarity	NPC142527
0.8039	Intermediate Similarity	NPC87708
0.8039	Intermediate Similarity	NPC40356
0.8039	Intermediate Similarity	NPC3744
0.8039	Intermediate Similarity	NPC217447
0.8039	Intermediate Similarity	NPC175978
0.8039	Intermediate Similarity	NPC45934
0.8039	Intermediate Similarity	NPC154683
0.8028	Intermediate Similarity	NPC251549
0.8027	Intermediate Similarity	NPC149780
0.8027	Intermediate Similarity	NPC265178
0.8026	Intermediate Similarity	NPC227122
0.8026	Intermediate Similarity	NPC475718
0.8025	Intermediate Similarity	NPC472261
0.8014	Intermediate Similarity	NPC245395
0.8014	Intermediate Similarity	NPC223336
0.8014	Intermediate Similarity	NPC55949
0.8013	Intermediate Similarity	NPC245891
0.8013	Intermediate Similarity	NPC104876
0.8013	Intermediate Similarity	NPC172329
0.8013	Intermediate Similarity	NPC2569
0.8	Intermediate Similarity	NPC124729
0.8	Intermediate Similarity	NPC288353
0.8	Intermediate Similarity	NPC237225
0.8	Intermediate Similarity	NPC39361
0.8	Intermediate Similarity	NPC478223
0.8	Intermediate Similarity	NPC48248
0.8	Intermediate Similarity	NPC181675
0.8	Intermediate Similarity	NPC147250
0.7987	Intermediate Similarity	NPC178964

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 NPC475104 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	310
0.1-0.2	966
0.2-0.3	1281
0.3-0.4	2410
0.4-0.5	2175
0.5-0.6	1232
0.6-0.7	643
0.7-0.8	127
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8473	Intermediate Similarity	NPD1651	Approved
0.837	Intermediate Similarity	NPD1283	Approved
0.8148	Intermediate Similarity	NPD1281	Approved
0.8125	Intermediate Similarity	NPD2935	Discontinued
0.8069	Intermediate Similarity	NPD2346	Discontinued
0.8028	Intermediate Similarity	NPD2979	Phase 3
0.7961	Intermediate Similarity	NPD3226	Approved
0.7933	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD7003	Approved
0.7868	Intermediate Similarity	NPD4626	Approved
0.7862	Intermediate Similarity	NPD6232	Discontinued
0.7826	Intermediate Similarity	NPD7473	Discontinued
0.7826	Intermediate Similarity	NPD3972	Approved
0.7714	Intermediate Similarity	NPD1876	Approved
0.7688	Intermediate Similarity	NPD6959	Discontinued
0.7687	Intermediate Similarity	NPD2799	Discontinued
0.7643	Intermediate Similarity	NPD7819	Suspended
0.7635	Intermediate Similarity	NPD2531	Phase 2
0.7635	Intermediate Similarity	NPD2438	Suspended
0.7609	Intermediate Similarity	NPD2932	Approved
0.7606	Intermediate Similarity	NPD2798	Approved
0.7584	Intermediate Similarity	NPD2344	Approved
0.7584	Intermediate Similarity	NPD1471	Phase 3
0.7568	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD1607	Approved
0.7536	Intermediate Similarity	NPD5691	Approved
0.7535	Intermediate Similarity	NPD1470	Approved
0.7534	Intermediate Similarity	NPD4060	Phase 1
0.7532	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD2313	Discontinued
0.7516	Intermediate Similarity	NPD7390	Discontinued
0.75	Intermediate Similarity	NPD1201	Approved
0.75	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7458	Discontinued
0.7483	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD3019	Approved
0.7468	Intermediate Similarity	NPD2532	Approved
0.7468	Intermediate Similarity	NPD2534	Approved
0.7468	Intermediate Similarity	NPD2533	Approved
0.7451	Intermediate Similarity	NPD3300	Phase 2
0.745	Intermediate Similarity	NPD1510	Phase 2
0.7448	Intermediate Similarity	NPD7095	Approved
0.7434	Intermediate Similarity	NPD4628	Phase 3
0.7419	Intermediate Similarity	NPD6273	Approved
0.7415	Intermediate Similarity	NPD1240	Approved
0.741	Intermediate Similarity	NPD5844	Phase 1
0.74	Intermediate Similarity	NPD5404	Approved
0.74	Intermediate Similarity	NPD5408	Approved
0.74	Intermediate Similarity	NPD5406	Approved
0.74	Intermediate Similarity	NPD5405	Approved
0.7399	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD3268	Approved
0.7394	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD2309	Approved
0.7384	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD1611	Approved
0.7355	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD1241	Discontinued
0.7349	Intermediate Similarity	NPD3751	Discontinued
0.7347	Intermediate Similarity	NPD8032	Phase 2
0.7347	Intermediate Similarity	NPD6233	Phase 2
0.7342	Intermediate Similarity	NPD4380	Phase 2
0.7342	Intermediate Similarity	NPD7028	Phase 2
0.7329	Intermediate Similarity	NPD4625	Phase 3
0.7324	Intermediate Similarity	NPD1608	Approved
0.732	Intermediate Similarity	NPD3750	Approved
0.7312	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD2801	Approved
0.7308	Intermediate Similarity	NPD1512	Approved
0.7303	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD2797	Approved
0.729	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD6100	Approved
0.7285	Intermediate Similarity	NPD6099	Approved
0.7285	Intermediate Similarity	NPD4476	Approved
0.7285	Intermediate Similarity	NPD4477	Approved
0.7284	Intermediate Similarity	NPD7075	Discontinued
0.7279	Intermediate Similarity	NPD3764	Approved
0.7279	Intermediate Similarity	NPD6798	Discontinued
0.7267	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD5536	Phase 2
0.725	Intermediate Similarity	NPD1934	Approved
0.7248	Intermediate Similarity	NPD6355	Discontinued
0.7244	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4624	Approved
0.7237	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD6599	Discontinued
0.7219	Intermediate Similarity	NPD4308	Phase 3
0.7219	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD8166	Discontinued
0.7203	Intermediate Similarity	NPD1481	Phase 2
0.7194	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1549	Phase 2
0.7188	Intermediate Similarity	NPD7411	Suspended
0.7183	Intermediate Similarity	NPD3026	Approved
0.7183	Intermediate Similarity	NPD3023	Approved
0.7183	Intermediate Similarity	NPD3847	Discontinued
0.7179	Intermediate Similarity	NPD1511	Approved
0.7171	Intermediate Similarity	NPD2796	Approved
0.7168	Intermediate Similarity	NPD8434	Phase 2
0.7163	Intermediate Similarity	NPD3025	Approved
0.7163	Intermediate Similarity	NPD3024	Approved
0.716	Intermediate Similarity	NPD3817	Phase 2
0.7153	Intermediate Similarity	NPD7635	Approved
0.7153	Intermediate Similarity	NPD1669	Approved
0.7143	Intermediate Similarity	NPD6801	Discontinued
0.7134	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1535	Discovery
0.7133	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6166	Phase 2
0.7126	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7768	Phase 2
0.7117	Intermediate Similarity	NPD3882	Suspended
0.7113	Intermediate Similarity	NPD17	Approved
0.7111	Intermediate Similarity	NPD6781	Approved
0.7111	Intermediate Similarity	NPD6780	Approved
0.7111	Intermediate Similarity	NPD6778	Approved
0.7111	Intermediate Similarity	NPD6776	Approved
0.7111	Intermediate Similarity	NPD6779	Approved
0.7111	Intermediate Similarity	NPD6777	Approved
0.7111	Intermediate Similarity	NPD6782	Approved
0.711	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD3787	Discontinued
0.7105	Intermediate Similarity	NPD3748	Approved
0.7101	Intermediate Similarity	NPD5283	Phase 1
0.7091	Intermediate Similarity	NPD5494	Approved
0.7086	Intermediate Similarity	NPD4097	Suspended
0.7076	Intermediate Similarity	NPD6559	Discontinued
0.7073	Intermediate Similarity	NPD3749	Approved
0.707	Intermediate Similarity	NPD6799	Approved
0.7069	Intermediate Similarity	NPD8150	Discontinued
0.7067	Intermediate Similarity	NPD4140	Approved
0.7055	Intermediate Similarity	NPD3266	Approved
0.7055	Intermediate Similarity	NPD3267	Approved
0.7051	Intermediate Similarity	NPD2354	Approved
0.7047	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7177	Discontinued
0.7037	Intermediate Similarity	NPD37	Approved
0.7032	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD2800	Approved
0.7024	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6663	Approved
0.7	Intermediate Similarity	NPD4062	Phase 3
0.7	Intermediate Similarity	NPD6671	Approved
0.7	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7697	Approved
0.6995	Remote Similarity	NPD7698	Approved
0.6995	Remote Similarity	NPD7435	Discontinued
0.6995	Remote Similarity	NPD7696	Phase 3
0.6993	Remote Similarity	NPD7033	Discontinued
0.6986	Remote Similarity	NPD6696	Suspended
0.6981	Remote Similarity	NPD5049	Phase 3
0.698	Remote Similarity	NPD7008	Discontinued
0.698	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD1398	Phase 1
0.6974	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6651	Approved
0.6972	Remote Similarity	NPD1894	Discontinued
0.6966	Remote Similarity	NPD2232	Approved
0.6966	Remote Similarity	NPD2230	Approved
0.6966	Remote Similarity	NPD2233	Approved
0.6959	Remote Similarity	NPD2861	Phase 2
0.6959	Remote Similarity	NPD9494	Approved
0.6959	Remote Similarity	NPD5736	Approved
0.6957	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7871	Phase 2
0.6957	Remote Similarity	NPD7870	Phase 2
0.6954	Remote Similarity	NPD4307	Phase 2
0.6951	Remote Similarity	NPD5402	Approved
0.695	Remote Similarity	NPD7340	Approved
0.6944	Remote Similarity	NPD3496	Discontinued
0.6943	Remote Similarity	NPD6190	Approved
0.6943	Remote Similarity	NPD3887	Approved
0.6939	Remote Similarity	NPD1203	Approved
0.6939	Remote Similarity	NPD1164	Approved
0.6933	Remote Similarity	NPD6844	Discontinued
0.6933	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD411	Approved
0.6929	Remote Similarity	NPD5951	Approved
0.6923	Remote Similarity	NPD5585	Approved
0.6918	Remote Similarity	NPD5327	Phase 3
0.6913	Remote Similarity	NPD6832	Phase 2
0.6912	Remote Similarity	NPD2342	Discontinued
0.6909	Remote Similarity	NPD4967	Phase 2
0.6909	Remote Similarity	NPD4966	Approved
0.6909	Remote Similarity	NPD4965	Approved
0.6908	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD5535	Approved
0.6905	Remote Similarity	NPD7229	Phase 3
0.6905	Remote Similarity	NPD5710	Approved
0.6905	Remote Similarity	NPD5711	Approved
0.6903	Remote Similarity	NPD2353	Approved
0.6903	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD2355	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