NPASS Compound

Structure

CID118027 OpenBabel06191715472D 22 24 0 0 0 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 3.4641 -3.0000 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 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -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 -0.8660 -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 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 0.8660 -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 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 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 0.0000 -3.0000 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 3.4641 -2.0000 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 1 8 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 8 2 0 0 0 0 4 10 1 0 0 0 0 5 8 1 0 0 0 0 5 13 2 0 0 0 0 6 9 2 0 0 0 0 6 11 1 0 0 0 0 7 9 1 0 0 0 0 7 12 2 0 0 0 0 9 21 1 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 11 14 2 0 0 0 0 11 16 1 0 0 0 0 12 14 1 0 0 0 0 12 18 1 0 0 0 0 13 15 1 0 0 0 0 13 22 1 0 0 0 0 14 17 1 0 0 0 0 15 17 1 0 0 0 0 16 19 2 0 0 0 0 17 20 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.08
Volume:	299.778
LogP:	3.839
LogD:	3.063
LogS:	-6.024
# Rotatable Bonds:	2
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.787
Synthetic Accessibility Score:	2.233
Fsp3:	0.176
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.925
MDCK Permeability:	2.9602133508888073e-05
Pgp-inhibitor:	0.103
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.913

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.107
Plasma Protein Binding (PPB):	95.61964416503906%
Volume Distribution (VD):	0.482
Pgp-substrate:	2.0382235050201416%

ADMET: Metabolism

CYP1A2-inhibitor:	0.94
CYP1A2-substrate:	0.924
CYP2C19-inhibitor:	0.376
CYP2C19-substrate:	0.158
CYP2C9-inhibitor:	0.593
CYP2C9-substrate:	0.815
CYP2D6-inhibitor:	0.29
CYP2D6-substrate:	0.604
CYP3A4-inhibitor:	0.721
CYP3A4-substrate:	0.237

ADMET: Excretion

Clearance (CL):	9.472
Half-life (T1/2):	0.137

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.097
Drug-inuced Liver Injury (DILI):	0.919
AMES Toxicity:	0.831
Rat Oral Acute Toxicity:	0.246
Maximum Recommended Daily Dose:	0.915
Skin Sensitization:	0.118
Carcinogencity:	0.467
Eye Corrosion:	0.004
Eye Irritation:	0.955
Respiratory Toxicity:	0.183

Download Data

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

Natural Product: NPC118027

Natural Product ID:	NPC118027
*Common Name:**	3,8-Di-O-Methylemodin
IUPAC Name:	1-hydroxy-3,8-dimethoxy-6-methylanthracene-9,10-dione
Synonyms:
Standard InCHIKey:	UPIWKOZOBCLHSX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14O5/c1-8-4-10-15(13(5-8)22-3)17(20)14-11(16(10)19)6-9(21-2)7-12(14)18/h4-7,18H,1-3H3
SMILES:	Cc1cc2c(c(c1)OC)C(=O)c1c(cc(cc1O)OC)C2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL445726
PubChem CID:	626899
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones

*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
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	root	n.a.	PMID[16564530]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19245240]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29359942]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[31944695]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	Roots; Tubers	n.a.	n.a.	PMID[7714535]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	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
Others	6

Activity Type	# Activity
Cell Line	1
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[488939]
NPT2	Others	Unspecified		Activity	=	0.0	%	PMID[488939]
NPT2	Others	Unspecified		Activity	=	21.3	%	PMID[488939]
NPT2	Others	Unspecified		Activity	=	45.3	%	PMID[488939]
NPT2	Others	Unspecified		Activity	=	91.8	%	PMID[488939]
NPT2	Others	Unspecified		logIC50	=	2.43	n.a.	PMID[488939]

☑ 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 NPC118027 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	408
0.1-0.2	1767
0.2-0.3	4069
0.3-0.4	10241
0.4-0.5	8027
0.5-0.6	3620
0.6-0.7	5406
0.7-0.8	5385
0.8-0.85	2574
0.85-0.9	995
0.9-0.95	174
0.95-1	31

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC126767
1.0	High Similarity	NPC245584
1.0	High Similarity	NPC289042
1.0	High Similarity	NPC56433
1.0	High Similarity	NPC312929
1.0	High Similarity	NPC190648
0.979	High Similarity	NPC147735
0.979	High Similarity	NPC255641
0.979	High Similarity	NPC470568
0.979	High Similarity	NPC290954
0.979	High Similarity	NPC294646
0.9786	High Similarity	NPC19896
0.9722	High Similarity	NPC470569
0.9655	High Similarity	NPC154683
0.9655	High Similarity	NPC40356
0.9589	High Similarity	NPC107109
0.9589	High Similarity	NPC208806
0.958	High Similarity	NPC34802
0.9574	High Similarity	NPC167663
0.9524	High Similarity	NPC226656
0.9524	High Similarity	NPC66508
0.9507	High Similarity	NPC21599
0.9507	High Similarity	NPC48762
0.9507	High Similarity	NPC193703
0.9504	High Similarity	NPC94076
0.9504	High Similarity	NPC182255
0.9459	High Similarity	NPC14561
0.9459	High Similarity	NPC77807
0.9459	High Similarity	NPC5379
0.9456	High Similarity	NPC214632
0.9448	High Similarity	NPC329933
0.9441	High Similarity	NPC34482
0.9441	High Similarity	NPC49282
0.9437	High Similarity	NPC84266
0.9396	High Similarity	NPC199463
0.9396	High Similarity	NPC37543
0.9396	High Similarity	NPC178976
0.9379	High Similarity	NPC256672
0.9379	High Similarity	NPC2569
0.9379	High Similarity	NPC7025
0.9379	High Similarity	NPC27221
0.9379	High Similarity	NPC472056
0.9379	High Similarity	NPC172329
0.9375	High Similarity	NPC470570
0.9366	High Similarity	NPC49108
0.9333	High Similarity	NPC324736
0.932	High Similarity	NPC474417
0.932	High Similarity	NPC478148
0.932	High Similarity	NPC149526
0.9315	High Similarity	NPC158338
0.9315	High Similarity	NPC100985
0.9315	High Similarity	NPC97028
0.9315	High Similarity	NPC65589
0.9315	High Similarity	NPC288036
0.9315	High Similarity	NPC80370
0.9315	High Similarity	NPC97029
0.931	High Similarity	NPC22005
0.931	High Similarity	NPC7943
0.931	High Similarity	NPC123202
0.9306	High Similarity	NPC28632
0.9291	High Similarity	NPC1268
0.9286	High Similarity	NPC471905
0.9272	High Similarity	NPC84571
0.9272	High Similarity	NPC472052
0.9272	High Similarity	NPC470342
0.9272	High Similarity	NPC472060
0.9267	High Similarity	NPC263483
0.9252	High Similarity	NPC202595
0.9241	High Similarity	NPC163846
0.9241	High Similarity	NPC225173
0.9236	High Similarity	NPC475201
0.9225	High Similarity	NPC472366
0.9214	High Similarity	NPC254847
0.9211	High Similarity	NPC311740
0.9195	High Similarity	NPC329844
0.9195	High Similarity	NPC93552
0.9189	High Similarity	NPC230848
0.9189	High Similarity	NPC258249
0.9189	High Similarity	NPC232645
0.9189	High Similarity	NPC72958
0.9184	High Similarity	NPC65775
0.9184	High Similarity	NPC10027
0.9178	High Similarity	NPC125801
0.9172	High Similarity	NPC478019
0.9167	High Similarity	NPC310340
0.9161	High Similarity	NPC253822
0.9161	High Similarity	NPC305845
0.9161	High Similarity	NPC101366
0.9161	High Similarity	NPC204045
0.9155	High Similarity	NPC138099
0.9155	High Similarity	NPC242994
0.9149	High Similarity	NPC53414
0.9149	High Similarity	NPC53206
0.9139	High Similarity	NPC201127
0.9139	High Similarity	NPC474637
0.9128	High Similarity	NPC312338
0.9128	High Similarity	NPC149889
0.9128	High Similarity	NPC87708
0.9128	High Similarity	NPC175978
0.9122	High Similarity	NPC474660
0.9122	High Similarity	NPC325983
0.911	High Similarity	NPC300540
0.9097	High Similarity	NPC268204
0.9097	High Similarity	NPC40118
0.9097	High Similarity	NPC55832
0.9097	High Similarity	NPC26051
0.9097	High Similarity	NPC232021
0.9097	High Similarity	NPC52789
0.9097	High Similarity	NPC135524
0.9097	High Similarity	NPC126534
0.9091	High Similarity	NPC109232
0.9091	High Similarity	NPC477956
0.9091	High Similarity	NPC295384
0.9091	High Similarity	NPC165172
0.9091	High Similarity	NPC181560
0.9091	High Similarity	NPC169452
0.9085	High Similarity	NPC472419
0.9078	High Similarity	NPC141934
0.9073	High Similarity	NPC180924
0.9073	High Similarity	NPC146211
0.9067	High Similarity	NPC210942
0.9067	High Similarity	NPC169990
0.906	High Similarity	NPC302783
0.906	High Similarity	NPC132990
0.906	High Similarity	NPC473201
0.906	High Similarity	NPC46882
0.9054	High Similarity	NPC233267
0.9054	High Similarity	NPC291049
0.9041	High Similarity	NPC476055
0.9034	High Similarity	NPC297600
0.9028	High Similarity	NPC259166
0.9028	High Similarity	NPC246638
0.9028	High Similarity	NPC48624
0.9028	High Similarity	NPC172250
0.9028	High Similarity	NPC124365
0.9028	High Similarity	NPC144118
0.9028	High Similarity	NPC215311
0.9028	High Similarity	NPC204985
0.9028	High Similarity	NPC213659
0.9028	High Similarity	NPC265178
0.9028	High Similarity	NPC80962
0.9028	High Similarity	NPC219917
0.9028	High Similarity	NPC326109
0.9028	High Similarity	NPC11056
0.9028	High Similarity	NPC275734
0.9021	High Similarity	NPC55162
0.9021	High Similarity	NPC472368
0.9021	High Similarity	NPC90665
0.9021	High Similarity	NPC279668
0.9021	High Similarity	NPC21350
0.9021	High Similarity	NPC278323
0.9021	High Similarity	NPC143438
0.9021	High Similarity	NPC190457
0.9021	High Similarity	NPC309154
0.9021	High Similarity	NPC251681
0.9021	High Similarity	NPC12175
0.9021	High Similarity	NPC243528
0.902	High Similarity	NPC470810
0.9014	High Similarity	NPC98115
0.9014	High Similarity	NPC477244
0.9014	High Similarity	NPC168105
0.9014	High Similarity	NPC477242
0.9014	High Similarity	NPC41461
0.9014	High Similarity	NPC477243
0.9014	High Similarity	NPC25287
0.9014	High Similarity	NPC66349
0.9014	High Similarity	NPC249606
0.9014	High Similarity	NPC274109
0.9014	High Similarity	NPC1486
0.9014	High Similarity	NPC476333
0.9014	High Similarity	NPC193792
0.9014	High Similarity	NPC186838
0.9014	High Similarity	NPC473391
0.9014	High Similarity	NPC12165
0.9014	High Similarity	NPC472364
0.9014	High Similarity	NPC472367
0.9014	High Similarity	NPC150399
0.9013	High Similarity	NPC246647
0.9013	High Similarity	NPC96342
0.9013	High Similarity	NPC164110
0.9013	High Similarity	NPC212967
0.9	High Similarity	NPC470338
0.9	High Similarity	NPC470337
0.9	High Similarity	NPC470340
0.9	High Similarity	NPC51824
0.9	High Similarity	NPC180944
0.9	High Similarity	NPC267205
0.9	High Similarity	NPC113608
0.9	High Similarity	NPC268992
0.8993	High Similarity	NPC470107
0.8993	High Similarity	NPC295036
0.8993	High Similarity	NPC473466
0.8993	High Similarity	NPC280295
0.8993	High Similarity	NPC227122
0.8993	High Similarity	NPC205766
0.8993	High Similarity	NPC119929
0.8986	High Similarity	NPC472841
0.8986	High Similarity	NPC105415
0.898	High Similarity	NPC196114
0.898	High Similarity	NPC25844

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 NPC118027 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	376
0.1-0.2	1027
0.2-0.3	1540
0.3-0.4	2678
0.4-0.5	1859
0.5-0.6	1080
0.6-0.7	383
0.7-0.8	162
0.8-0.85	30
0.85-0.9	14
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9214	High Similarity	NPD1509	Clinical (unspecified phase)
0.8936	High Similarity	NPD1607	Approved
0.8903	High Similarity	NPD6232	Discontinued
0.8854	High Similarity	NPD7473	Discontinued
0.8811	High Similarity	NPD1510	Phase 2
0.8794	High Similarity	NPD1240	Approved
0.8718	High Similarity	NPD6959	Discontinued
0.8693	High Similarity	NPD7819	Suspended
0.8658	High Similarity	NPD4378	Clinical (unspecified phase)
0.8658	High Similarity	NPD2532	Approved
0.8658	High Similarity	NPD2533	Approved
0.8658	High Similarity	NPD2534	Approved
0.863	High Similarity	NPD970	Clinical (unspecified phase)
0.8553	High Similarity	NPD3226	Approved
0.8533	High Similarity	NPD7410	Clinical (unspecified phase)
0.8503	High Similarity	NPD1549	Phase 2
0.8467	Intermediate Similarity	NPD7390	Discontinued
0.8452	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8435	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8435	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD4380	Phase 2
0.8323	Intermediate Similarity	NPD7411	Suspended
0.8298	Intermediate Similarity	NPD1470	Approved
0.8291	Intermediate Similarity	NPD3749	Approved
0.8269	Intermediate Similarity	NPD1934	Approved
0.8267	Intermediate Similarity	NPD3750	Approved
0.8243	Intermediate Similarity	NPD2796	Approved
0.8243	Intermediate Similarity	NPD2935	Discontinued
0.8224	Intermediate Similarity	NPD1511	Approved
0.8217	Intermediate Similarity	NPD2801	Approved
0.82	Intermediate Similarity	NPD2800	Approved
0.8188	Intermediate Similarity	NPD2346	Discontinued
0.8176	Intermediate Similarity	NPD7075	Discontinued
0.8117	Intermediate Similarity	NPD1512	Approved
0.8113	Intermediate Similarity	NPD7768	Phase 2
0.8113	Intermediate Similarity	NPD3882	Suspended
0.8101	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD5844	Phase 1
0.8041	Intermediate Similarity	NPD6651	Approved
0.8027	Intermediate Similarity	NPD943	Approved
0.8026	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD6599	Discontinued
0.8014	Intermediate Similarity	NPD1201	Approved
0.8	Intermediate Similarity	NPD6099	Approved
0.8	Intermediate Similarity	NPD5408	Approved
0.8	Intermediate Similarity	NPD5405	Approved
0.8	Intermediate Similarity	NPD5404	Approved
0.8	Intermediate Similarity	NPD1551	Phase 2
0.8	Intermediate Similarity	NPD6100	Approved
0.8	Intermediate Similarity	NPD5406	Approved
0.7975	Intermediate Similarity	NPD5710	Approved
0.7975	Intermediate Similarity	NPD5711	Approved
0.7963	Intermediate Similarity	NPD5494	Approved
0.7961	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD2344	Approved
0.7933	Intermediate Similarity	NPD3748	Approved
0.7925	Intermediate Similarity	NPD6801	Discontinued
0.7919	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD6166	Phase 2
0.7879	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD6799	Approved
0.7843	Intermediate Similarity	NPD1243	Approved
0.784	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD2799	Discontinued
0.7811	Intermediate Similarity	NPD6559	Discontinued
0.7792	Intermediate Similarity	NPD7003	Approved
0.7792	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD3818	Discontinued
0.7764	Intermediate Similarity	NPD1465	Phase 2
0.7751	Intermediate Similarity	NPD5953	Discontinued
0.7742	Intermediate Similarity	NPD2309	Approved
0.7722	Intermediate Similarity	NPD920	Approved
0.7716	Intermediate Similarity	NPD3817	Phase 2
0.7703	Intermediate Similarity	NPD4625	Phase 3
0.7697	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD2313	Discontinued
0.7651	Intermediate Similarity	NPD3764	Approved
0.7633	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD7458	Discontinued
0.7625	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD2798	Approved
0.7611	Intermediate Similarity	NPD6776	Approved
0.7611	Intermediate Similarity	NPD6781	Approved
0.7611	Intermediate Similarity	NPD6779	Approved
0.7611	Intermediate Similarity	NPD6780	Approved
0.7611	Intermediate Similarity	NPD6778	Approved
0.7611	Intermediate Similarity	NPD6777	Approved
0.7611	Intermediate Similarity	NPD6782	Approved
0.761	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD3926	Phase 2
0.7603	Intermediate Similarity	NPD1283	Approved
0.76	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD1471	Phase 3
0.7595	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD37	Approved
0.7588	Intermediate Similarity	NPD7074	Phase 3
0.7586	Intermediate Similarity	NPD3972	Approved
0.758	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD8151	Discontinued
0.7564	Intermediate Similarity	NPD4628	Phase 3
0.7558	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD1651	Approved
0.7533	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7054	Approved
0.7529	Intermediate Similarity	NPD7286	Phase 2
0.7514	Intermediate Similarity	NPD8313	Approved
0.7514	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD5402	Approved
0.75	Intermediate Similarity	NPD230	Phase 1
0.7486	Intermediate Similarity	NPD7697	Approved
0.7486	Intermediate Similarity	NPD7698	Approved
0.7486	Intermediate Similarity	NPD7696	Phase 3
0.7486	Intermediate Similarity	NPD7435	Discontinued
0.7485	Intermediate Similarity	NPD1247	Approved
0.7485	Intermediate Similarity	NPD7472	Approved
0.7483	Intermediate Similarity	NPD1876	Approved
0.7471	Intermediate Similarity	NPD3751	Discontinued
0.747	Intermediate Similarity	NPD919	Approved
0.747	Intermediate Similarity	NPD6234	Discontinued
0.7465	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD4967	Phase 2
0.7455	Intermediate Similarity	NPD4966	Approved
0.7455	Intermediate Similarity	NPD4965	Approved
0.7446	Intermediate Similarity	NPD7870	Phase 2
0.7446	Intermediate Similarity	NPD7871	Phase 2
0.7442	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD6797	Phase 2
0.744	Intermediate Similarity	NPD7229	Phase 3
0.7432	Intermediate Similarity	NPD1203	Approved
0.7418	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD4908	Phase 1
0.7399	Intermediate Similarity	NPD7251	Discontinued
0.7397	Intermediate Similarity	NPD1281	Approved
0.7391	Intermediate Similarity	NPD5403	Approved
0.7389	Intermediate Similarity	NPD2654	Approved
0.7386	Intermediate Similarity	NPD8150	Discontinued
0.7379	Intermediate Similarity	NPD4626	Approved
0.7375	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD5401	Approved
0.7368	Intermediate Similarity	NPD7177	Discontinued
0.7356	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7808	Phase 3
0.7355	Intermediate Similarity	NPD4308	Phase 3
0.7333	Intermediate Similarity	NPD6534	Approved
0.7333	Intermediate Similarity	NPD6535	Approved
0.7326	Intermediate Similarity	NPD7701	Phase 2
0.7315	Intermediate Similarity	NPD1164	Approved
0.7303	Intermediate Similarity	NPD411	Approved
0.7303	Intermediate Similarity	NPD4287	Approved
0.7297	Intermediate Similarity	NPD4749	Approved
0.7289	Intermediate Similarity	NPD4288	Approved
0.7279	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1610	Phase 2
0.7267	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD7874	Approved
0.7243	Intermediate Similarity	NPD6823	Phase 2
0.723	Intermediate Similarity	NPD9717	Approved
0.723	Intermediate Similarity	NPD1608	Approved
0.7222	Intermediate Similarity	NPD6273	Approved
0.7222	Intermediate Similarity	NPD9493	Approved
0.7213	Intermediate Similarity	NPD7699	Phase 2
0.7213	Intermediate Similarity	NPD7700	Phase 2
0.7211	Intermediate Similarity	NPD7801	Approved
0.7205	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD3268	Approved
0.7186	Intermediate Similarity	NPD2296	Approved
0.7181	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7199	Phase 2
0.7171	Intermediate Similarity	NPD6832	Phase 2
0.7168	Intermediate Similarity	NPD7228	Approved
0.7168	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD447	Suspended
0.7152	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4360	Phase 2
0.7143	Intermediate Similarity	NPD4363	Phase 3
0.7135	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD3787	Discontinued
0.7126	Intermediate Similarity	NPD5760	Phase 2
0.7126	Intermediate Similarity	NPD5761	Phase 2
0.7123	Intermediate Similarity	NPD1548	Phase 1
0.7123	Intermediate Similarity	NPD9545	Approved
0.7105	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD9494	Approved
0.7104	Intermediate Similarity	NPD4361	Phase 2
0.7104	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4307	Phase 2
0.7097	Intermediate Similarity	NPD2979	Phase 3
0.7095	Intermediate Similarity	NPD8434	Phase 2
0.7093	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD6214	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