NPASS Compound

Structure

CID250331 OpenBabel06191716052D 25 28 0 0 0 0 0 0 0 0999 V2000 -0.8390 -2.4571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1631 -2.4202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8697 0.5019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8695 -0.5023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7111 -0.9676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7109 0.0013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8721 -1.4522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8717 0.4856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8388 -1.4529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1948 -2.4205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0329 -0.9679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0327 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1945 -1.4523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6776 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6778 -0.9686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3553 -0.9682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3551 0.0007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0002 -0.9689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8384 0.4844 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 -3.7109 -3.2593 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8657 -1.4690 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8381 1.4844 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1941 0.4850 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5164 -1.4526 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 10 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 11 2 0 0 0 0 8 12 2 0 0 0 0 9 15 2 0 0 0 0 9 18 1 0 0 0 0 10 13 1 0 0 0 0 10 21 2 0 0 0 0 11 12 1 0 0 0 0 11 13 1 0 0 0 0 12 24 1 0 0 0 0 13 16 2 0 0 0 0 14 15 1 0 0 0 0 14 17 2 0 0 0 0 14 19 1 0 0 0 0 15 25 1 0 0 0 0 16 17 1 0 0 0 0 16 25 1 0 0 0 0 17 24 1 0 0 0 0 18 20 1 0 0 0 0 18 22 2 0 0 0 0 19 20 1 0 0 0 0 19 23 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	336.1
Volume:	340.473
LogP:	2.929
LogD:	2.452
LogS:	-4.101
# Rotatable Bonds:	1
TPSA:	73.58
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.746
Synthetic Accessibility Score:	3.414
Fsp3:	0.25
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:	-4.855
MDCK Permeability:	2.373593088123016e-05
Pgp-inhibitor:	0.891
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	85.09626007080078%
Volume Distribution (VD):	1.846
Pgp-substrate:	9.10000228881836%

ADMET: Metabolism

CYP1A2-inhibitor:	0.927
CYP1A2-substrate:	0.87
CYP2C19-inhibitor:	0.902
CYP2C19-substrate:	0.466
CYP2C9-inhibitor:	0.883
CYP2C9-substrate:	0.365
CYP2D6-inhibitor:	0.227
CYP2D6-substrate:	0.124
CYP3A4-inhibitor:	0.515
CYP3A4-substrate:	0.594

ADMET: Excretion

Clearance (CL):	0.845
Half-life (T1/2):	0.083

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.868
Drug-inuced Liver Injury (DILI):	0.991
AMES Toxicity:	0.382
Rat Oral Acute Toxicity:	0.975
Maximum Recommended Daily Dose:	0.806
Skin Sensitization:	0.653
Carcinogencity:	0.852
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.654

Download Data

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

Natural Product: NPC250331

Natural Product ID:	NPC250331
*Common Name:**	Psorothamnone A
IUPAC Name:	11-acetyl-7,7,9-trimethyl-[1]benzofuro[3,2-b]chromene-6,8-dione
Synonyms:
Standard InCHIKey:	CQEHHYNZYRAVFN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H16O5/c1-9-15-14(19(23)20(3,4)18(9)22)17-16(25-15)13(10(2)21)11-7-5-6-8-12(11)24-17/h5-8H,1-4H3
SMILES:	CC(=O)C1=c2oc3=C(C)C(=O)C(C(=O)c3c2Oc2c1cccc2)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464403
PubChem CID:	10065574
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000254] Ethers [CHEMONTID:0002463] Diarylethers

*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
NPO26504	Psorothamnus junceus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11000028]
NPO26504	Psorothamnus junceus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26504	Psorothamnus junceus	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
GI50	5
IC50	1

Activity Type	# Activity
Cell Line	5
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	GI50	=	40.0	ug.mL-1	PMID[477558]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	60.0	ug.mL-1	PMID[477558]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	=	50.0	ug.mL-1	PMID[477558]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	=	20.0	ug.mL-1	PMID[477558]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	=	60.0	ug.mL-1	PMID[477558]
NPT2	Others	Unspecified		IC50	=	14.0	ug.mL-1	PMID[477558]

☑ 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 NPC250331 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	457
0.1-0.2	1844
0.2-0.3	5061
0.3-0.4	11948
0.4-0.5	6188
0.5-0.6	5698
0.6-0.7	6481
0.7-0.8	4966
0.8-0.85	52
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9928	High Similarity	NPC474261
0.8367	Intermediate Similarity	NPC265181
0.8269	Intermediate Similarity	NPC41719
0.8258	Intermediate Similarity	NPC98028
0.8205	Intermediate Similarity	NPC288534
0.8187	Intermediate Similarity	NPC264293
0.817	Intermediate Similarity	NPC310259
0.8141	Intermediate Similarity	NPC81474
0.8137	Intermediate Similarity	NPC219861
0.8129	Intermediate Similarity	NPC69752
0.8117	Intermediate Similarity	NPC117463
0.8117	Intermediate Similarity	NPC252208
0.8117	Intermediate Similarity	NPC299923
0.8113	Intermediate Similarity	NPC476930
0.8098	Intermediate Similarity	NPC472895
0.8089	Intermediate Similarity	NPC470353
0.8086	Intermediate Similarity	NPC65846
0.8077	Intermediate Similarity	NPC135303
0.8077	Intermediate Similarity	NPC259058
0.8077	Intermediate Similarity	NPC201547
0.8077	Intermediate Similarity	NPC148423
0.8075	Intermediate Similarity	NPC216092
0.8065	Intermediate Similarity	NPC192069
0.8065	Intermediate Similarity	NPC280025
0.8054	Intermediate Similarity	NPC301341
0.8054	Intermediate Similarity	NPC177262
0.8054	Intermediate Similarity	NPC61546
0.8054	Intermediate Similarity	NPC284184
0.8054	Intermediate Similarity	NPC72452
0.8052	Intermediate Similarity	NPC190572
0.8052	Intermediate Similarity	NPC281398
0.805	Intermediate Similarity	NPC470352
0.805	Intermediate Similarity	NPC470354
0.8039	Intermediate Similarity	NPC473812
0.8039	Intermediate Similarity	NPC473813
0.8039	Intermediate Similarity	NPC17262
0.8038	Intermediate Similarity	NPC88958
0.8013	Intermediate Similarity	NPC181250
0.8013	Intermediate Similarity	NPC226578
0.8012	Intermediate Similarity	NPC243509
0.8	Intermediate Similarity	NPC471285
0.8	Intermediate Similarity	NPC310206
0.7988	Intermediate Similarity	NPC210460
0.7988	Intermediate Similarity	NPC193881
0.7988	Intermediate Similarity	NPC476056
0.7988	Intermediate Similarity	NPC476273
0.7988	Intermediate Similarity	NPC323137
0.7988	Intermediate Similarity	NPC155264
0.7988	Intermediate Similarity	NPC67450
0.7987	Intermediate Similarity	NPC136278
0.7987	Intermediate Similarity	NPC472446
0.7987	Intermediate Similarity	NPC284353
0.7987	Intermediate Similarity	NPC472447
0.7987	Intermediate Similarity	NPC471590
0.7975	Intermediate Similarity	NPC472581
0.7975	Intermediate Similarity	NPC130015
0.7975	Intermediate Similarity	NPC38361
0.7974	Intermediate Similarity	NPC9966
0.7974	Intermediate Similarity	NPC117674
0.7974	Intermediate Similarity	NPC70853
0.7964	Intermediate Similarity	NPC62640
0.7962	Intermediate Similarity	NPC144010
0.7962	Intermediate Similarity	NPC177839
0.7959	Intermediate Similarity	NPC153453
0.7952	Intermediate Similarity	NPC28042
0.795	Intermediate Similarity	NPC250076
0.795	Intermediate Similarity	NPC125969
0.795	Intermediate Similarity	NPC33320
0.795	Intermediate Similarity	NPC238405
0.795	Intermediate Similarity	NPC104459
0.795	Intermediate Similarity	NPC257914
0.7949	Intermediate Similarity	NPC306788
0.7949	Intermediate Similarity	NPC261548
0.7939	Intermediate Similarity	NPC193222
0.7937	Intermediate Similarity	NPC221992
0.7937	Intermediate Similarity	NPC470625
0.7935	Intermediate Similarity	NPC178343
0.7935	Intermediate Similarity	NPC110639
0.7935	Intermediate Similarity	NPC40818
0.7935	Intermediate Similarity	NPC14958
0.7935	Intermediate Similarity	NPC5820
0.7935	Intermediate Similarity	NPC306488
0.7935	Intermediate Similarity	NPC215932
0.7935	Intermediate Similarity	NPC106461
0.7933	Intermediate Similarity	NPC161196
0.7933	Intermediate Similarity	NPC254741
0.7933	Intermediate Similarity	NPC29638
0.7929	Intermediate Similarity	NPC168050
0.7929	Intermediate Similarity	NPC77179
0.7929	Intermediate Similarity	NPC23553
0.7929	Intermediate Similarity	NPC221820
0.7927	Intermediate Similarity	NPC259007
0.7927	Intermediate Similarity	NPC204088
0.7927	Intermediate Similarity	NPC329215
0.7925	Intermediate Similarity	NPC473664
0.7925	Intermediate Similarity	NPC279930
0.7922	Intermediate Similarity	NPC24821
0.7922	Intermediate Similarity	NPC9117
0.7922	Intermediate Similarity	NPC293053
0.7922	Intermediate Similarity	NPC212932
0.7922	Intermediate Similarity	NPC11700
0.7922	Intermediate Similarity	NPC113089
0.7922	Intermediate Similarity	NPC190637
0.7917	Intermediate Similarity	NPC289244
0.7914	Intermediate Similarity	NPC302741
0.7914	Intermediate Similarity	NPC193998
0.7914	Intermediate Similarity	NPC272722
0.7911	Intermediate Similarity	NPC236769
0.7911	Intermediate Similarity	NPC471613
0.7911	Intermediate Similarity	NPC474170
0.7911	Intermediate Similarity	NPC472407
0.7911	Intermediate Similarity	NPC145830
0.7911	Intermediate Similarity	NPC474388
0.7911	Intermediate Similarity	NPC472535
0.7908	Intermediate Similarity	NPC214919
0.7908	Intermediate Similarity	NPC29536
0.7908	Intermediate Similarity	NPC124467
0.7905	Intermediate Similarity	NPC101294
0.7905	Intermediate Similarity	NPC473655
0.7901	Intermediate Similarity	NPC475107
0.7901	Intermediate Similarity	NPC43490
0.7898	Intermediate Similarity	NPC37208
0.7898	Intermediate Similarity	NPC221868
0.7892	Intermediate Similarity	NPC202470
0.7888	Intermediate Similarity	NPC473282
0.7888	Intermediate Similarity	NPC294300
0.7888	Intermediate Similarity	NPC317900
0.7888	Intermediate Similarity	NPC476404
0.7888	Intermediate Similarity	NPC104380
0.7888	Intermediate Similarity	NPC210048
0.7888	Intermediate Similarity	NPC19097
0.7888	Intermediate Similarity	NPC217602
0.7885	Intermediate Similarity	NPC205522
0.7885	Intermediate Similarity	NPC85233
0.7885	Intermediate Similarity	NPC198427
0.7879	Intermediate Similarity	NPC298071
0.7879	Intermediate Similarity	NPC475109
0.7875	Intermediate Similarity	NPC122623
0.7875	Intermediate Similarity	NPC241774
0.7875	Intermediate Similarity	NPC34725
0.7875	Intermediate Similarity	NPC233776
0.7875	Intermediate Similarity	NPC189960
0.7875	Intermediate Similarity	NPC32557
0.7875	Intermediate Similarity	NPC276059
0.7875	Intermediate Similarity	NPC471116
0.7871	Intermediate Similarity	NPC233763
0.7871	Intermediate Similarity	NPC273538
0.7871	Intermediate Similarity	NPC326500
0.7871	Intermediate Similarity	NPC216538
0.7867	Intermediate Similarity	NPC46869
0.7866	Intermediate Similarity	NPC476931
0.7866	Intermediate Similarity	NPC179464
0.7866	Intermediate Similarity	NPC132054
0.7862	Intermediate Similarity	NPC134677
0.7862	Intermediate Similarity	NPC68882
0.7857	Intermediate Similarity	NPC473042
0.7857	Intermediate Similarity	NPC313036
0.7857	Intermediate Similarity	NPC43435
0.7857	Intermediate Similarity	NPC200694
0.7857	Intermediate Similarity	NPC30550
0.7852	Intermediate Similarity	NPC292998
0.7849	Intermediate Similarity	NPC476170
0.7848	Intermediate Similarity	NPC191104
0.7848	Intermediate Similarity	NPC189270
0.7848	Intermediate Similarity	NPC476185
0.7848	Intermediate Similarity	NPC166753
0.7848	Intermediate Similarity	NPC5840
0.7848	Intermediate Similarity	NPC472406
0.7848	Intermediate Similarity	NPC321896
0.7848	Intermediate Similarity	NPC50728
0.7843	Intermediate Similarity	NPC474037
0.784	Intermediate Similarity	NPC264932
0.784	Intermediate Similarity	NPC311574
0.7838	Intermediate Similarity	NPC278556
0.7834	Intermediate Similarity	NPC272194
0.7834	Intermediate Similarity	NPC476342
0.7834	Intermediate Similarity	NPC10304
0.7834	Intermediate Similarity	NPC63256
0.7834	Intermediate Similarity	NPC266743
0.7831	Intermediate Similarity	NPC95715
0.7829	Intermediate Similarity	NPC17848
0.7829	Intermediate Similarity	NPC276905
0.7826	Intermediate Similarity	NPC178854
0.7826	Intermediate Similarity	NPC3980
0.7826	Intermediate Similarity	NPC257277
0.7826	Intermediate Similarity	NPC248299
0.7826	Intermediate Similarity	NPC19860
0.7826	Intermediate Similarity	NPC265511
0.7821	Intermediate Similarity	NPC124729
0.7821	Intermediate Similarity	NPC302408
0.7821	Intermediate Similarity	NPC283002
0.7821	Intermediate Similarity	NPC329678
0.7821	Intermediate Similarity	NPC210826
0.7818	Intermediate Similarity	NPC173149
0.7818	Intermediate Similarity	NPC179015
0.7818	Intermediate Similarity	NPC36320
0.7812	Intermediate Similarity	NPC86485
0.7812	Intermediate Similarity	NPC236223
0.7812	Intermediate Similarity	NPC270620
0.7812	Intermediate Similarity	NPC179126

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 NPC250331 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	395
0.1-0.2	965
0.2-0.3	1592
0.3-0.4	2876
0.4-0.5	1917
0.5-0.6	1018
0.6-0.7	283
0.7-0.8	103
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8367	Intermediate Similarity	NPD1471	Phase 3
0.8187	Intermediate Similarity	NPD1247	Approved
0.7975	Intermediate Similarity	NPD3926	Phase 2
0.795	Intermediate Similarity	NPD919	Approved
0.7881	Intermediate Similarity	NPD2344	Approved
0.7871	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD3882	Suspended
0.7815	Intermediate Similarity	NPD2796	Approved
0.7778	Intermediate Similarity	NPD1243	Approved
0.7764	Intermediate Similarity	NPD3817	Phase 2
0.7736	Intermediate Similarity	NPD6599	Discontinued
0.7702	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6799	Approved
0.7683	Intermediate Similarity	NPD5494	Approved
0.7677	Intermediate Similarity	NPD2309	Approved
0.7662	Intermediate Similarity	NPD2800	Approved
0.7658	Intermediate Similarity	NPD920	Approved
0.764	Intermediate Similarity	NPD6801	Discontinued
0.7622	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD3267	Approved
0.7603	Intermediate Similarity	NPD3266	Approved
0.7593	Intermediate Similarity	NPD2801	Approved
0.7584	Intermediate Similarity	NPD2313	Discontinued
0.7561	Intermediate Similarity	NPD7075	Discontinued
0.755	Intermediate Similarity	NPD1933	Approved
0.7532	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1512	Approved
0.7467	Intermediate Similarity	NPD3268	Approved
0.745	Intermediate Similarity	NPD6832	Phase 2
0.7448	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD5403	Approved
0.7432	Intermediate Similarity	NPD2798	Approved
0.7423	Intermediate Similarity	NPD1934	Approved
0.7421	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD5401	Approved
0.7403	Intermediate Similarity	NPD2799	Discontinued
0.7396	Intermediate Similarity	NPD2403	Approved
0.7381	Intermediate Similarity	NPD6808	Phase 2
0.7378	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD7411	Suspended
0.7358	Intermediate Similarity	NPD1511	Approved
0.7333	Intermediate Similarity	NPD5402	Approved
0.7333	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD447	Suspended
0.7317	Intermediate Similarity	NPD6280	Approved
0.7317	Intermediate Similarity	NPD6279	Approved
0.731	Intermediate Similarity	NPD3818	Discontinued
0.7308	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD4380	Phase 2
0.7294	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD6166	Phase 2
0.729	Intermediate Similarity	NPD1510	Phase 2
0.729	Intermediate Similarity	NPD3748	Approved
0.7279	Intermediate Similarity	NPD3972	Approved
0.7267	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1549	Phase 2
0.7255	Intermediate Similarity	NPD4307	Phase 2
0.7246	Intermediate Similarity	NPD3749	Approved
0.7239	Intermediate Similarity	NPD3226	Approved
0.7232	Intermediate Similarity	NPD8434	Phase 2
0.7215	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD2346	Discontinued
0.7197	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6585	Discontinued
0.7169	Intermediate Similarity	NPD7819	Suspended
0.7162	Intermediate Similarity	NPD9717	Approved
0.7152	Intermediate Similarity	NPD5890	Approved
0.7152	Intermediate Similarity	NPD5889	Approved
0.7143	Intermediate Similarity	NPD1240	Approved
0.7143	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1203	Approved
0.7133	Intermediate Similarity	NPD2797	Approved
0.7126	Intermediate Similarity	NPD2296	Approved
0.7117	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD7808	Phase 3
0.7097	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD2353	Approved
0.7086	Intermediate Similarity	NPD6797	Phase 2
0.7076	Intermediate Similarity	NPD6232	Discontinued
0.707	Intermediate Similarity	NPD4308	Phase 3
0.7063	Intermediate Similarity	NPD3750	Approved
0.7052	Intermediate Similarity	NPD7473	Discontinued
0.7051	Intermediate Similarity	NPD1607	Approved
0.7051	Intermediate Similarity	NPD6651	Approved
0.7045	Intermediate Similarity	NPD7251	Discontinued
0.7025	Intermediate Similarity	NPD2935	Discontinued
0.7019	Intermediate Similarity	NPD3887	Approved
0.7013	Intermediate Similarity	NPD6798	Discontinued
0.7011	Intermediate Similarity	NPD2163	Approved
0.6994	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6355	Discontinued
0.6974	Remote Similarity	NPD1019	Discontinued
0.6971	Remote Similarity	NPD7054	Approved
0.6957	Remote Similarity	NPD4628	Phase 3
0.6957	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1876	Approved
0.6949	Remote Similarity	NPD6559	Discontinued
0.6944	Remote Similarity	NPD1241	Discontinued
0.6932	Remote Similarity	NPD7472	Approved
0.6932	Remote Similarity	NPD7074	Phase 3
0.6914	Remote Similarity	NPD2354	Approved
0.6897	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD2654	Approved
0.6855	Remote Similarity	NPD7033	Discontinued
0.6852	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5049	Phase 3
0.6842	Remote Similarity	NPD3225	Approved
0.6839	Remote Similarity	NPD7095	Approved
0.6832	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD7458	Discontinued
0.6816	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD1551	Phase 2
0.6813	Remote Similarity	NPD6099	Approved
0.6813	Remote Similarity	NPD6100	Approved
0.6797	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD411	Approved
0.6788	Remote Similarity	NPD2532	Approved
0.6788	Remote Similarity	NPD4662	Approved
0.6788	Remote Similarity	NPD2534	Approved
0.6788	Remote Similarity	NPD2533	Approved
0.6788	Remote Similarity	NPD4661	Approved
0.6784	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7768	Phase 2
0.676	Remote Similarity	NPD6765	Approved
0.676	Remote Similarity	NPD6764	Approved
0.6757	Remote Similarity	NPD5536	Phase 2
0.6752	Remote Similarity	NPD6233	Phase 2
0.6743	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD17	Approved
0.6728	Remote Similarity	NPD2897	Discontinued
0.6728	Remote Similarity	NPD2424	Discontinued
0.6727	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD6959	Discontinued
0.6723	Remote Similarity	NPD3751	Discontinued
0.6709	Remote Similarity	NPD943	Approved
0.6706	Remote Similarity	NPD6844	Discontinued
0.6705	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD5953	Discontinued
0.669	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD5844	Phase 1
0.6667	Remote Similarity	NPD5761	Phase 2
0.6667	Remote Similarity	NPD5760	Phase 2
0.6646	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD8032	Phase 2
0.6632	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD6785	Approved
0.6612	Remote Similarity	NPD6784	Approved
0.6611	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD3142	Approved
0.6604	Remote Similarity	NPD3140	Approved
0.6601	Remote Similarity	NPD1608	Approved
0.6591	Remote Similarity	NPD3787	Discontinued
0.659	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD1296	Phase 2
0.6581	Remote Similarity	NPD1470	Approved
0.6577	Remote Similarity	NPD9493	Approved
0.657	Remote Similarity	NPD1465	Phase 2
0.6561	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD6273	Approved
0.6545	Remote Similarity	NPD7003	Approved
0.6541	Remote Similarity	NPD4062	Phase 3
0.6534	Remote Similarity	NPD7199	Phase 2
0.6531	Remote Similarity	NPD5535	Approved
0.6529	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD4534	Discontinued
0.6519	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD3869	Phase 3
0.6509	Remote Similarity	NPD3873	Phase 3
0.65	Remote Similarity	NPD7286	Phase 2
0.65	Remote Similarity	NPD4060	Phase 1
0.6497	Remote Similarity	NPD9494	Approved
0.6492	Remote Similarity	NPD8285	Discontinued
0.6491	Remote Similarity	NPD7028	Phase 2
0.648	Remote Similarity	NPD3446	Phase 1
0.6467	Remote Similarity	NPD405	Clinical (unspecified phase)
0.646	Remote Similarity	NPD4622	Approved
0.646	Remote Similarity	NPD4618	Approved
0.6458	Remote Similarity	NPD4107	Approved
0.6452	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD5585	Approved
0.6447	Remote Similarity	NPD1651	Approved
0.6446	Remote Similarity	NPD4110	Phase 3
0.6446	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD5978	Approved
0.6437	Remote Similarity	NPD4288	Approved
0.6437	Remote Similarity	NPD5977	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