NPASS Compound

Structure

NPC136095 OpenBabel07101718192D 23 25 0 0 0 0 0 0 0 0999 V2000 -4.3301 1.5000 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 1.7321 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 2.5981 3.5000 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 -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 -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 -4.3301 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 3.4641 3.0000 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 -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 -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 -5.1962 0.0000 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 4.3301 3.5000 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 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 21 1 0 0 0 0 3 5 1 0 0 0 0 3 12 2 0 0 0 0 4 6 2 0 0 0 0 4 12 1 0 0 0 0 5 13 2 0 0 0 0 6 13 1 0 0 0 0 7 8 2 0 0 0 0 7 14 1 0 0 0 0 8 15 1 0 0 0 0 9 14 2 0 0 0 0 9 17 1 0 0 0 0 10 16 2 0 0 0 0 10 22 1 0 0 0 0 11 19 2 0 0 0 0 11 23 1 0 0 0 0 12 16 1 0 0 0 0 13 21 1 0 0 0 0 14 23 1 0 0 0 0 15 17 2 0 0 0 0 15 18 1 0 0 0 0 16 18 1 0 0 0 0 17 22 1 0 0 0 0 18 20 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	310.08
Volume:	314.438
LogP:	3.248
LogD:	2.706
LogS:	-4.296
# Rotatable Bonds:	4
TPSA:	65.74
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.548
Synthetic Accessibility Score:	2.025
Fsp3:	0.111
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.717
MDCK Permeability:	4.5673787099076435e-05
Pgp-inhibitor:	0.349
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.031
30% Bioavailability (F30%):	0.923

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.215
Plasma Protein Binding (PPB):	91.41058349609375%
Volume Distribution (VD):	0.581
Pgp-substrate:	5.637465000152588%

ADMET: Metabolism

CYP1A2-inhibitor:	0.926
CYP1A2-substrate:	0.658
CYP2C19-inhibitor:	0.608
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.574
CYP2C9-substrate:	0.919
CYP2D6-inhibitor:	0.552
CYP2D6-substrate:	0.899
CYP3A4-inhibitor:	0.48
CYP3A4-substrate:	0.289

ADMET: Excretion

Clearance (CL):	1.774
Half-life (T1/2):	0.29

ADMET: Toxicity

hERG Blockers:	0.091
Human Hepatotoxicity (H-HT):	0.049
Drug-inuced Liver Injury (DILI):	0.86
AMES Toxicity:	0.676
Rat Oral Acute Toxicity:	0.371
Maximum Recommended Daily Dose:	0.561
Skin Sensitization:	0.8
Carcinogencity:	0.642
Eye Corrosion:	0.004
Eye Irritation:	0.731
Respiratory Toxicity:	0.422

Download Data

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

Natural Product: NPC136095

Natural Product ID:	NPC136095
*Common Name:**	7-O-Acetylformononetin
IUPAC Name:	[3-(4-methoxyphenyl)-4-oxochromen-7-yl] acetate
Synonyms:	7-O-Acetylformononetin
Standard InCHIKey:	GGGJVAAAUYBGSQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H14O5/c1-11(19)23-14-7-8-15-17(9-14)22-10-16(18(15)20)12-3-5-13(21-2)6-4-12/h3-10H,1-2H3
SMILES:	CC(=O)Oc1ccc2c(c1)occ(c1ccc(cc1)OC)c2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463063
PubChem CID:	908827
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002586] O-methylated isoflavonoids [CHEMONTID:0002606] 4'-O-methylated isoflavonoids [CHEMONTID:0002687] 4'-O-methylisoflavones

*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
NPO20912	Wisteria brachybotrys	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2853205]
NPO20912	Wisteria brachybotrys	Species	Fabaceae	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	10

Activity Type	# Activity
Cell Line	5
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	Inhibition	=	40.2	%	PMID[456296]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	100.0	%	PMID[456296]
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[456296]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	80.0	%	PMID[456296]
NPT2	Others	Unspecified		Activity	=	0.0	%	PMID[456296]
NPT2	Others	Unspecified		Activity	=	100.0	%	PMID[456296]
NPT2	Others	Unspecified		Activity	=	95.2	%	PMID[456296]
NPT2	Others	Unspecified		Activity	=	15.2	%	PMID[456296]

☑ 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 NPC136095 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	451
0.1-0.2	1886
0.2-0.3	4702
0.3-0.4	10740
0.4-0.5	7148
0.5-0.6	4394
0.6-0.7	6020
0.7-0.8	4742
0.8-0.85	1810
0.85-0.9	700
0.9-0.95	98
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.985	High Similarity	NPC103001
0.9627	High Similarity	NPC254741
0.9549	High Similarity	NPC292998
0.9478	High Similarity	NPC66705
0.9474	High Similarity	NPC182428
0.9416	High Similarity	NPC473209
0.9412	High Similarity	NPC253616
0.9403	High Similarity	NPC223354
0.9398	High Similarity	NPC278556
0.9398	High Similarity	NPC284424
0.9343	High Similarity	NPC36414
0.9338	High Similarity	NPC268081
0.9333	High Similarity	NPC125269
0.9328	High Similarity	NPC473655
0.9328	High Similarity	NPC101294
0.9281	High Similarity	NPC24075
0.9275	High Similarity	NPC472515
0.9265	High Similarity	NPC99854
0.9209	High Similarity	NPC474037
0.9197	High Similarity	NPC472516
0.9197	High Similarity	NPC161196
0.9155	High Similarity	NPC470322
0.9155	High Similarity	NPC154217
0.9137	High Similarity	NPC11566
0.913	High Similarity	NPC116632
0.913	High Similarity	NPC7013
0.913	High Similarity	NPC303644
0.913	High Similarity	NPC209560
0.913	High Similarity	NPC162680
0.913	High Similarity	NPC259685
0.913	High Similarity	NPC228661
0.913	High Similarity	NPC266597
0.913	High Similarity	NPC250266
0.913	High Similarity	NPC294409
0.913	High Similarity	NPC38153
0.913	High Similarity	NPC181124
0.911	High Similarity	NPC186507
0.9097	High Similarity	NPC88445
0.9097	High Similarity	NPC164299
0.9091	High Similarity	NPC218300
0.9091	High Similarity	NPC282335
0.9085	High Similarity	NPC471590
0.9085	High Similarity	NPC171656
0.9085	High Similarity	NPC179970
0.9085	High Similarity	NPC1886
0.9085	High Similarity	NPC469953
0.9085	High Similarity	NPC196137
0.9078	High Similarity	NPC202981
0.9078	High Similarity	NPC36181
0.9071	High Similarity	NPC470856
0.9071	High Similarity	NPC171094
0.9071	High Similarity	NPC472409
0.9065	High Similarity	NPC90665
0.9065	High Similarity	NPC55162
0.9065	High Similarity	NPC279668
0.9065	High Similarity	NPC278323
0.9065	High Similarity	NPC17848
0.9065	High Similarity	NPC309154
0.9065	High Similarity	NPC188947
0.9065	High Similarity	NPC124269
0.9065	High Similarity	NPC280284
0.9065	High Similarity	NPC99333
0.9065	High Similarity	NPC12175
0.9058	High Similarity	NPC231772
0.9058	High Similarity	NPC47815
0.9058	High Similarity	NPC61546
0.9058	High Similarity	NPC29353
0.9058	High Similarity	NPC124784
0.9058	High Similarity	NPC234133
0.9058	High Similarity	NPC194281
0.9058	High Similarity	NPC473887
0.9058	High Similarity	NPC72452
0.9058	High Similarity	NPC127447
0.9034	High Similarity	NPC191104
0.9034	High Similarity	NPC474735
0.903	High Similarity	NPC211120
0.9028	High Similarity	NPC266743
0.9023	High Similarity	NPC49852
0.9023	High Similarity	NPC475496
0.9023	High Similarity	NPC41721
0.9021	High Similarity	NPC181388
0.9014	High Similarity	NPC470216
0.9014	High Similarity	NPC94794
0.9014	High Similarity	NPC470296
0.9014	High Similarity	NPC112791
0.9014	High Similarity	NPC188632
0.9014	High Similarity	NPC59522
0.9014	High Similarity	NPC196459
0.9014	High Similarity	NPC87609
0.9007	High Similarity	NPC103362
0.9007	High Similarity	NPC254010
0.9007	High Similarity	NPC3188
0.9007	High Similarity	NPC110969
0.9	High Similarity	NPC78913
0.9	High Similarity	NPC265871
0.9	High Similarity	NPC274784
0.9	High Similarity	NPC329203
0.9	High Similarity	NPC262635
0.9	High Similarity	NPC310135
0.9	High Similarity	NPC225153
0.9	High Similarity	NPC20709
0.9	High Similarity	NPC150648
0.9	High Similarity	NPC18260
0.9	High Similarity	NPC295384
0.9	High Similarity	NPC261234
0.9	High Similarity	NPC222342
0.8993	High Similarity	NPC275055
0.8993	High Similarity	NPC157855
0.8993	High Similarity	NPC290291
0.8993	High Similarity	NPC188879
0.8986	High Similarity	NPC234560
0.8986	High Similarity	NPC46869
0.8986	High Similarity	NPC39426
0.8986	High Similarity	NPC474983
0.8973	High Similarity	NPC290671
0.8966	High Similarity	NPC474648
0.8966	High Similarity	NPC19238
0.8963	High Similarity	NPC228184
0.8958	High Similarity	NPC237635
0.8958	High Similarity	NPC97716
0.8958	High Similarity	NPC140120
0.8958	High Similarity	NPC104406
0.8958	High Similarity	NPC74539
0.8958	High Similarity	NPC180477
0.8958	High Similarity	NPC79469
0.8958	High Similarity	NPC304443
0.8958	High Similarity	NPC201731
0.8958	High Similarity	NPC24673
0.8955	High Similarity	NPC473907
0.8951	High Similarity	NPC469935
0.8951	High Similarity	NPC234629
0.8951	High Similarity	NPC178627
0.8951	High Similarity	NPC294365
0.8951	High Similarity	NPC184649
0.8951	High Similarity	NPC303185
0.8951	High Similarity	NPC311741
0.8944	High Similarity	NPC226636
0.8944	High Similarity	NPC147145
0.8944	High Similarity	NPC11561
0.8944	High Similarity	NPC51146
0.8944	High Similarity	NPC166858
0.8944	High Similarity	NPC313036
0.8936	High Similarity	NPC6407
0.8936	High Similarity	NPC204985
0.8936	High Similarity	NPC261227
0.8936	High Similarity	NPC215311
0.8936	High Similarity	NPC172250
0.8936	High Similarity	NPC159275
0.8936	High Similarity	NPC129853
0.8936	High Similarity	NPC213659
0.8936	High Similarity	NPC172986
0.8936	High Similarity	NPC76445
0.8936	High Similarity	NPC48624
0.8936	High Similarity	NPC259166
0.8936	High Similarity	NPC270883
0.8936	High Similarity	NPC110228
0.8936	High Similarity	NPC150522
0.8936	High Similarity	NPC101366
0.8936	High Similarity	NPC144118
0.8936	High Similarity	NPC80962
0.8936	High Similarity	NPC281207
0.8936	High Similarity	NPC269652
0.8936	High Similarity	NPC326109
0.8936	High Similarity	NPC188243
0.8936	High Similarity	NPC241100
0.8936	High Similarity	NPC284550
0.8936	High Similarity	NPC219917
0.8929	High Similarity	NPC118813
0.8929	High Similarity	NPC329225
0.8929	High Similarity	NPC201395
0.8929	High Similarity	NPC276905
0.8929	High Similarity	NPC147686
0.8929	High Similarity	NPC472460
0.8921	High Similarity	NPC240593
0.8921	High Similarity	NPC13408
0.8921	High Similarity	NPC87545
0.8921	High Similarity	NPC235428
0.8913	High Similarity	NPC172262
0.8905	High Similarity	NPC229646
0.8904	High Similarity	NPC474660
0.8904	High Similarity	NPC295036
0.8897	High Similarity	NPC183236
0.8897	High Similarity	NPC168085
0.8897	High Similarity	NPC266572
0.8897	High Similarity	NPC208303
0.8897	High Similarity	NPC6511
0.8897	High Similarity	NPC161864
0.8889	High Similarity	NPC153758
0.8889	High Similarity	NPC57470
0.8889	High Similarity	NPC299011
0.8889	High Similarity	NPC473894
0.8889	High Similarity	NPC473927
0.8881	High Similarity	NPC175504
0.8881	High Similarity	NPC164980
0.8881	High Similarity	NPC17262
0.8881	High Similarity	NPC91560
0.8881	High Similarity	NPC113089
0.8881	High Similarity	NPC68104
0.8881	High Similarity	NPC257097
0.8881	High Similarity	NPC169591

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 NPC136095 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	411
0.1-0.2	987
0.2-0.3	1635
0.3-0.4	2628
0.4-0.5	1892
0.5-0.6	1091
0.6-0.7	335
0.7-0.8	109
0.8-0.85	37
0.85-0.9	21
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9481	High Similarity	NPD2796	Approved
0.9014	High Similarity	NPD6799	Approved
0.9	High Similarity	NPD1243	Approved
0.8986	High Similarity	NPD1510	Phase 2
0.8986	High Similarity	NPD3748	Approved
0.8958	High Similarity	NPD920	Approved
0.8944	High Similarity	NPD643	Clinical (unspecified phase)
0.8929	High Similarity	NPD1549	Phase 2
0.8857	High Similarity	NPD1552	Clinical (unspecified phase)
0.8857	High Similarity	NPD1550	Clinical (unspecified phase)
0.8851	High Similarity	NPD7819	Suspended
0.8851	High Similarity	NPD7096	Clinical (unspecified phase)
0.8844	High Similarity	NPD7411	Suspended
0.8819	High Similarity	NPD642	Clinical (unspecified phase)
0.8819	High Similarity	NPD4378	Clinical (unspecified phase)
0.8784	High Similarity	NPD6801	Discontinued
0.8776	High Similarity	NPD6599	Discontinued
0.8696	High Similarity	NPD1240	Approved
0.8676	High Similarity	NPD6832	Phase 2
0.8675	High Similarity	NPD7075	Discontinued
0.8671	High Similarity	NPD3750	Approved
0.8667	High Similarity	NPD3817	Phase 2
0.8571	High Similarity	NPD1607	Approved
0.8562	High Similarity	NPD7410	Clinical (unspecified phase)
0.8562	High Similarity	NPD5401	Approved
0.8551	High Similarity	NPD6859	Clinical (unspecified phase)
0.8521	High Similarity	NPD1551	Phase 2
0.8497	Intermediate Similarity	NPD919	Approved
0.8472	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8446	Intermediate Similarity	NPD5403	Approved
0.8431	Intermediate Similarity	NPD3749	Approved
0.8431	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD1934	Approved
0.8403	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD4380	Phase 2
0.8369	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.8367	Intermediate Similarity	NPD1511	Approved
0.8366	Intermediate Similarity	NPD7768	Phase 2
0.8355	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8321	Intermediate Similarity	NPD3267	Approved
0.8321	Intermediate Similarity	NPD3266	Approved
0.8301	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8298	Intermediate Similarity	NPD4307	Phase 2
0.8296	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8286	Intermediate Similarity	NPD2313	Discontinued
0.8255	Intermediate Similarity	NPD1512	Approved
0.8235	Intermediate Similarity	NPD2801	Approved
0.8205	Intermediate Similarity	NPD5494	Approved
0.8194	Intermediate Similarity	NPD2799	Discontinued
0.8188	Intermediate Similarity	NPD1203	Approved
0.8182	Intermediate Similarity	NPD5402	Approved
0.8156	Intermediate Similarity	NPD1296	Phase 2
0.8129	Intermediate Similarity	NPD3882	Suspended
0.8129	Intermediate Similarity	NPD1019	Discontinued
0.8112	Intermediate Similarity	NPD1933	Approved
0.8102	Intermediate Similarity	NPD9717	Approved
0.8079	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8069	Intermediate Similarity	NPD4308	Phase 3
0.8041	Intermediate Similarity	NPD4628	Phase 3
0.8028	Intermediate Similarity	NPD3268	Approved
0.8014	Intermediate Similarity	NPD2935	Discontinued
0.8013	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD3818	Discontinued
0.8	Intermediate Similarity	NPD2798	Approved
0.7975	Intermediate Similarity	NPD5953	Discontinued
0.7974	Intermediate Similarity	NPD3226	Approved
0.7963	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD7033	Discontinued
0.7929	Intermediate Similarity	NPD2797	Approved
0.7925	Intermediate Similarity	NPD1247	Approved
0.7899	Intermediate Similarity	NPD422	Phase 1
0.7888	Intermediate Similarity	NPD6166	Phase 2
0.7888	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7883	Intermediate Similarity	NPD17	Approved
0.7857	Intermediate Similarity	NPD3225	Approved
0.7853	Intermediate Similarity	NPD7286	Phase 2
0.7853	Intermediate Similarity	NPD7054	Approved
0.7853	Intermediate Similarity	NPD5844	Phase 1
0.7852	Intermediate Similarity	NPD2800	Approved
0.7838	Intermediate Similarity	NPD2344	Approved
0.7838	Intermediate Similarity	NPD2346	Discontinued
0.7834	Intermediate Similarity	NPD4288	Approved
0.7829	Intermediate Similarity	NPD2533	Approved
0.7829	Intermediate Similarity	NPD2532	Approved
0.7829	Intermediate Similarity	NPD2534	Approved
0.7826	Intermediate Similarity	NPD3926	Phase 2
0.7812	Intermediate Similarity	NPD6959	Discontinued
0.7805	Intermediate Similarity	NPD7074	Phase 3
0.7805	Intermediate Similarity	NPD7472	Approved
0.7778	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD6232	Discontinued
0.7762	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7761	Intermediate Similarity	NPD1241	Discontinued
0.7758	Intermediate Similarity	NPD6797	Phase 2
0.7756	Intermediate Similarity	NPD5889	Approved
0.7756	Intermediate Similarity	NPD5890	Approved
0.7733	Intermediate Similarity	NPD2654	Approved
0.773	Intermediate Similarity	NPD7473	Discontinued
0.7714	Intermediate Similarity	NPD1608	Approved
0.7714	Intermediate Similarity	NPD3972	Approved
0.7711	Intermediate Similarity	NPD6559	Discontinued
0.7711	Intermediate Similarity	NPD7251	Discontinued
0.7665	Intermediate Similarity	NPD7808	Phase 3
0.7665	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD1465	Phase 2
0.7655	Intermediate Similarity	NPD411	Approved
0.7632	Intermediate Similarity	NPD2309	Approved
0.7632	Intermediate Similarity	NPD3887	Approved
0.7619	Intermediate Similarity	NPD5124	Phase 1
0.7619	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD447	Suspended
0.7609	Intermediate Similarity	NPD9545	Approved
0.7609	Intermediate Similarity	NPD1548	Phase 1
0.76	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD2353	Approved
0.758	Intermediate Similarity	NPD6585	Discontinued
0.7576	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD6651	Approved
0.7566	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD5535	Approved
0.7551	Intermediate Similarity	NPD943	Approved
0.7546	Intermediate Similarity	NPD6808	Phase 2
0.7545	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD6798	Discontinued
0.7518	Intermediate Similarity	NPD1610	Phase 2
0.7517	Intermediate Similarity	NPD4908	Phase 1
0.75	Intermediate Similarity	NPD230	Phase 1
0.7484	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1876	Approved
0.7483	Intermediate Similarity	NPD1471	Phase 3
0.7467	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD9493	Approved
0.7443	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD6100	Approved
0.7417	Intermediate Similarity	NPD6099	Approved
0.7415	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD3764	Approved
0.7405	Intermediate Similarity	NPD7458	Discontinued
0.7403	Intermediate Similarity	NPD2354	Approved
0.7399	Intermediate Similarity	NPD4287	Approved
0.7394	Intermediate Similarity	NPD5242	Approved
0.7386	Intermediate Similarity	NPD1652	Phase 2
0.7383	Intermediate Similarity	NPD6355	Discontinued
0.7378	Intermediate Similarity	NPD7199	Phase 2
0.7375	Intermediate Similarity	NPD6279	Approved
0.7375	Intermediate Similarity	NPD6280	Approved
0.7357	Intermediate Similarity	NPD1894	Discontinued
0.7333	Intermediate Similarity	NPD7229	Phase 3
0.7325	Intermediate Similarity	NPD6273	Approved
0.7315	Intermediate Similarity	NPD3142	Approved
0.7315	Intermediate Similarity	NPD3140	Approved
0.7308	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6971	Discontinued
0.7296	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD9697	Approved
0.7289	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6233	Phase 2
0.7246	Intermediate Similarity	NPD2403	Approved
0.7232	Intermediate Similarity	NPD4360	Phase 2
0.7232	Intermediate Similarity	NPD4363	Phase 3
0.7229	Intermediate Similarity	NPD5710	Approved
0.7229	Intermediate Similarity	NPD5711	Approved
0.7226	Intermediate Similarity	NPD7003	Approved
0.7215	Intermediate Similarity	NPD2186	Approved
0.7205	Intermediate Similarity	NPD6386	Approved
0.7205	Intermediate Similarity	NPD6385	Approved
0.7193	Intermediate Similarity	NPD6104	Discontinued
0.7192	Intermediate Similarity	NPD1164	Approved
0.7191	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD4361	Phase 2
0.719	Intermediate Similarity	NPD4476	Approved
0.719	Intermediate Similarity	NPD4477	Approved
0.7178	Intermediate Similarity	NPD5353	Approved
0.716	Intermediate Similarity	NPD6844	Discontinued
0.716	Intermediate Similarity	NPD3751	Discontinued
0.7153	Intermediate Similarity	NPD1281	Approved
0.7152	Intermediate Similarity	NPD4622	Approved
0.7152	Intermediate Similarity	NPD4618	Approved
0.7152	Intermediate Similarity	NPD4661	Approved
0.7152	Intermediate Similarity	NPD4662	Approved
0.7143	Intermediate Similarity	NPD9261	Approved
0.7134	Intermediate Similarity	NPD7440	Discontinued
0.7133	Intermediate Similarity	NPD8032	Phase 2
0.7133	Intermediate Similarity	NPD1778	Approved
0.7119	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD3134	Approved
0.7107	Intermediate Similarity	NPD5049	Phase 3
0.7103	Intermediate Similarity	NPD1481	Phase 2
0.7099	Intermediate Similarity	NPD2366	Approved
0.7089	Intermediate Similarity	NPD7390	Discontinued
0.7086	Intermediate Similarity	NPD2979	Phase 3
0.7086	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1613	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