NPASS Compound

Structure

NPC28589 OpenBabel07101718202D 28 32 0 0 1 0 0 0 0 0999 V2000 -2.5981 -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 -3.4641 0.0000 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 1.3522 1.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 1.9962 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 2.5981 -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 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7589 2.7007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7534 2.8052 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 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9345 1.0827 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 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1711 3.5097 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1602 3.7188 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 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 0.1691 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 1 3 1 0 0 0 0 1 9 2 0 0 0 0 2 4 2 0 0 0 0 2 9 1 0 0 0 0 3 10 2 0 0 0 0 4 10 1 0 0 0 0 5 11 1 0 0 0 0 5 12 2 0 0 0 0 6 13 2 0 0 0 0 6 17 1 0 0 0 0 7 14 1 0 0 0 0 7 16 1 0 0 0 0 8 15 2 0 0 0 0 8 18 1 0 0 0 0 10 22 1 0 0 0 0 11 17 2 0 0 0 0 11 19 1 0 0 0 0 12 13 1 0 0 0 0 12 23 1 0 0 0 0 13 24 1 0 0 0 0 14 20 1 0 0 0 0 14 25 2 0 0 0 0 15 20 1 0 0 0 0 15 26 1 0 0 0 0 16 9 1 1 0 0 0 16 28 1 0 0 0 0 17 27 1 0 0 0 0 18 19 2 0 0 0 0 18 27 1 0 0 0 0 19 21 1 0 0 0 0 20 21 2 0 0 0 0 21 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.07
Volume:	364.157
LogP:	4.388
LogD:	3.105
LogS:	-5.757
# Rotatable Bonds:	1
TPSA:	120.36
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.368
Synthetic Accessibility Score:	3.271
Fsp3:	0.095
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.969
MDCK Permeability:	9.068874533113558e-06
Pgp-inhibitor:	0.021
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.271
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	94.46620178222656%
Volume Distribution (VD):	0.563
Pgp-substrate:	10.350072860717773%

ADMET: Metabolism

CYP1A2-inhibitor:	0.912
CYP1A2-substrate:	0.218
CYP2C19-inhibitor:	0.557
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.748
CYP2C9-substrate:	0.919
CYP2D6-inhibitor:	0.386
CYP2D6-substrate:	0.456
CYP3A4-inhibitor:	0.34
CYP3A4-substrate:	0.116

ADMET: Excretion

Clearance (CL):	16.081
Half-life (T1/2):	0.718

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.21
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.638
Rat Oral Acute Toxicity:	0.891
Maximum Recommended Daily Dose:	0.895
Skin Sensitization:	0.952
Carcinogencity:	0.646
Eye Corrosion:	0.003
Eye Irritation:	0.933
Respiratory Toxicity:	0.345

Download Data

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

Natural Product: NPC28589

Natural Product ID:	NPC28589
*Common Name:**	Anastatin B
IUPAC Name:	(2S)-5,9,10-trihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-[1]benzofuro[2,3-h]chromen-4-one
Synonyms:
Standard InCHIKey:	ZXWMKYBQWBZFAK-INIZCTEOSA-N
Standard InCHI:	InChI=1S/C21H14O7/c22-10-3-1-9(2-4-10)16-7-14(25)20-15(26)8-18-19(21(20)28-16)11-5-12(23)13(24)6-17(11)27-18/h1-6,8,16,22-24,26H,7H2/t16-/m0/s1
SMILES:	c1cc(ccc1[C@@H]1CC(=O)c2c(cc3c(c4cc(c(cc4o3)O)O)c2O1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL9464
PubChem CID:	10407286
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002614] Furanoflavonoids and dihydrofuranoflavonoids

*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
NPO21361	Anastatica hierochuntica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12643908]
NPO21361	Anastatica hierochuntica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20189399]
NPO21361	Anastatica hierochuntica	Species	Brassicaceae	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
Individual Protein	1
Organism	4
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	<	10.4	%	PMID[487863]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	0.0	%	PMID[487862]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	28.6	%	PMID[487862]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	40.5	%	PMID[487862]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	55.0	%	PMID[487862]
NPT2	Others	Unspecified		Inhibition	=	-1.1	%	PMID[487863]
NPT2	Others	Unspecified		Inhibition	=	10.1	%	PMID[487863]
NPT2	Others	Unspecified		Inhibition	=	19.5	%	PMID[487863]
NPT2	Others	Unspecified		Inhibition	=	40.3	%	PMID[487863]
NPT27	Others	Unspecified		Inhibition	<	8.8	%	PMID[487863]

☑ 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 NPC28589 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	512
0.1-0.2	1997
0.2-0.3	4628
0.3-0.4	11213
0.4-0.5	6602
0.5-0.6	3913
0.6-0.7	5201
0.7-0.8	4991
0.8-0.85	2265
0.85-0.9	1295
0.9-0.95	78
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC248593
0.9506	High Similarity	NPC277480
0.9448	High Similarity	NPC50394
0.9444	High Similarity	NPC37183
0.9337	High Similarity	NPC310794
0.9325	High Similarity	NPC38914
0.9277	High Similarity	NPC174700
0.9212	High Similarity	NPC241820
0.9212	High Similarity	NPC247973
0.9186	High Similarity	NPC47905
0.9186	High Similarity	NPC73929
0.9186	High Similarity	NPC139683
0.9172	High Similarity	NPC475783
0.9146	High Similarity	NPC473313
0.9146	High Similarity	NPC329669
0.9146	High Similarity	NPC472278
0.9141	High Similarity	NPC188486
0.9128	High Similarity	NPC304322
0.9112	High Similarity	NPC49667
0.9112	High Similarity	NPC8127
0.9107	High Similarity	NPC261471
0.9107	High Similarity	NPC473834
0.9102	High Similarity	NPC131866
0.9096	High Similarity	NPC470704
0.9085	High Similarity	NPC84515
0.9085	High Similarity	NPC312056
0.9062	High Similarity	NPC125300
0.9053	High Similarity	NPC287243
0.9048	High Similarity	NPC230619
0.9048	High Similarity	NPC54098
0.9042	High Similarity	NPC202470
0.9036	High Similarity	NPC272560
0.9036	High Similarity	NPC320741
0.9036	High Similarity	NPC171985
0.9036	High Similarity	NPC224851
0.9018	High Similarity	NPC196879
0.9018	High Similarity	NPC16935
0.9006	High Similarity	NPC104682
0.9	High Similarity	NPC164384
0.9	High Similarity	NPC204515
0.8994	High Similarity	NPC82217
0.8994	High Similarity	NPC216842
0.8994	High Similarity	NPC476640
0.8994	High Similarity	NPC65885
0.8988	High Similarity	NPC190351
0.8988	High Similarity	NPC218533
0.8988	High Similarity	NPC78830
0.8988	High Similarity	NPC472276
0.8982	High Similarity	NPC86477
0.8976	High Similarity	NPC326520
0.8976	High Similarity	NPC472277
0.8976	High Similarity	NPC29411
0.8976	High Similarity	NPC259757
0.8976	High Similarity	NPC473286
0.8976	High Similarity	NPC291110
0.897	High Similarity	NPC81679
0.897	High Similarity	NPC476247
0.8957	High Similarity	NPC210084
0.8957	High Similarity	NPC99597
0.8951	High Similarity	NPC113906
0.8947	High Similarity	NPC265380
0.8935	High Similarity	NPC212038
0.8935	High Similarity	NPC271848
0.8935	High Similarity	NPC81332
0.8935	High Similarity	NPC262580
0.8935	High Similarity	NPC289396
0.8929	High Similarity	NPC107627
0.8929	High Similarity	NPC53252
0.8929	High Similarity	NPC288813
0.8929	High Similarity	NPC152477
0.8922	High Similarity	NPC128293
0.8922	High Similarity	NPC170245
0.8922	High Similarity	NPC173292
0.8916	High Similarity	NPC18100
0.8916	High Similarity	NPC124038
0.8916	High Similarity	NPC1755
0.8916	High Similarity	NPC133065
0.8916	High Similarity	NPC263092
0.8916	High Similarity	NPC273959
0.8916	High Similarity	NPC59295
0.8916	High Similarity	NPC39305
0.8916	High Similarity	NPC205265
0.8916	High Similarity	NPC472281
0.8916	High Similarity	NPC472581
0.8916	High Similarity	NPC1706
0.8916	High Similarity	NPC38591
0.8909	High Similarity	NPC74854
0.8909	High Similarity	NPC45124
0.8909	High Similarity	NPC30655
0.8909	High Similarity	NPC258331
0.8909	High Similarity	NPC228383
0.8909	High Similarity	NPC472275
0.8909	High Similarity	NPC142252
0.8902	High Similarity	NPC172770
0.8902	High Similarity	NPC250214
0.8902	High Similarity	NPC95936
0.8902	High Similarity	NPC185258
0.8896	High Similarity	NPC235165
0.8896	High Similarity	NPC45131
0.8896	High Similarity	NPC255106
0.8895	High Similarity	NPC324742
0.8895	High Similarity	NPC183843
0.8895	High Similarity	NPC185275
0.8889	High Similarity	NPC192083
0.8889	High Similarity	NPC1477
0.8889	High Similarity	NPC213608
0.8889	High Similarity	NPC213896
0.8882	High Similarity	NPC37606
0.8882	High Similarity	NPC117450
0.8882	High Similarity	NPC149846
0.8876	High Similarity	NPC476641
0.8876	High Similarity	NPC279209
0.8876	High Similarity	NPC102277
0.8875	High Similarity	NPC183959
0.8875	High Similarity	NPC1612
0.8869	High Similarity	NPC243877
0.8869	High Similarity	NPC260266
0.8869	High Similarity	NPC14662
0.8862	High Similarity	NPC108433
0.8862	High Similarity	NPC45449
0.8862	High Similarity	NPC39306
0.8862	High Similarity	NPC300053
0.8862	High Similarity	NPC36320
0.8855	High Similarity	NPC472448
0.8855	High Similarity	NPC83922
0.8855	High Similarity	NPC329760
0.8855	High Similarity	NPC238995
0.8855	High Similarity	NPC220912
0.8848	High Similarity	NPC476283
0.8848	High Similarity	NPC328102
0.8848	High Similarity	NPC472624
0.8844	High Similarity	NPC97523
0.8841	High Similarity	NPC474208
0.8841	High Similarity	NPC156057
0.8841	High Similarity	NPC48208
0.8841	High Similarity	NPC474836
0.8841	High Similarity	NPC162869
0.8841	High Similarity	NPC475267
0.8841	High Similarity	NPC291508
0.8841	High Similarity	NPC79053
0.8841	High Similarity	NPC262286
0.8841	High Similarity	NPC78225
0.8841	High Similarity	NPC36852
0.8841	High Similarity	NPC65504
0.8841	High Similarity	NPC471209
0.8841	High Similarity	NPC223787
0.8837	High Similarity	NPC471789
0.8834	High Similarity	NPC2928
0.8834	High Similarity	NPC321779
0.8827	High Similarity	NPC5871
0.8827	High Similarity	NPC253872
0.8827	High Similarity	NPC106976
0.8824	High Similarity	NPC257667
0.8824	High Similarity	NPC186847
0.8824	High Similarity	NPC472454
0.8824	High Similarity	NPC121333
0.882	High Similarity	NPC62042
0.8817	High Similarity	NPC242395
0.8817	High Similarity	NPC300307
0.8814	High Similarity	NPC60848
0.8812	High Similarity	NPC294852
0.8812	High Similarity	NPC321011
0.8812	High Similarity	NPC276930
0.8812	High Similarity	NPC188679
0.8812	High Similarity	NPC194856
0.881	High Similarity	NPC235610
0.8802	High Similarity	NPC109180
0.8802	High Similarity	NPC475985
0.8802	High Similarity	NPC470178
0.8802	High Similarity	NPC65846
0.8795	High Similarity	NPC304387
0.8795	High Similarity	NPC29876
0.8795	High Similarity	NPC167678
0.8795	High Similarity	NPC266314
0.8795	High Similarity	NPC32694
0.8795	High Similarity	NPC134783
0.8795	High Similarity	NPC308992
0.8793	High Similarity	NPC150977
0.8793	High Similarity	NPC228209
0.8788	High Similarity	NPC53545
0.8788	High Similarity	NPC469658
0.8788	High Similarity	NPC329091
0.8788	High Similarity	NPC472877
0.8788	High Similarity	NPC40583
0.8788	High Similarity	NPC117418
0.8788	High Similarity	NPC210459
0.8786	High Similarity	NPC476273
0.878	High Similarity	NPC137100
0.878	High Similarity	NPC195796
0.878	High Similarity	NPC472916
0.878	High Similarity	NPC68093
0.878	High Similarity	NPC208152
0.878	High Similarity	NPC191146
0.878	High Similarity	NPC278778
0.878	High Similarity	NPC472461
0.878	High Similarity	NPC138243
0.878	High Similarity	NPC201837
0.878	High Similarity	NPC142339
0.878	High Similarity	NPC78492
0.878	High Similarity	NPC291878

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 NPC28589 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	456
0.1-0.2	995
0.2-0.3	1859
0.3-0.4	2711
0.4-0.5	1722
0.5-0.6	946
0.6-0.7	300
0.7-0.8	116
0.8-0.85	30
0.85-0.9	15
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8889	High Similarity	NPD2393	Clinical (unspecified phase)
0.8735	High Similarity	NPD5494	Approved
0.8712	High Similarity	NPD1934	Approved
0.8554	High Similarity	NPD4868	Clinical (unspecified phase)
0.8545	High Similarity	NPD2801	Approved
0.8529	High Similarity	NPD6168	Clinical (unspecified phase)
0.8529	High Similarity	NPD6167	Clinical (unspecified phase)
0.8529	High Similarity	NPD6166	Phase 2
0.8503	High Similarity	NPD3749	Approved
0.8494	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD1247	Approved
0.8447	Intermediate Similarity	NPD1511	Approved
0.8443	Intermediate Similarity	NPD3882	Suspended
0.843	Intermediate Similarity	NPD3818	Discontinued
0.8382	Intermediate Similarity	NPD5844	Phase 1
0.8364	Intermediate Similarity	NPD4380	Phase 2
0.8353	Intermediate Similarity	NPD6959	Discontinued
0.8344	Intermediate Similarity	NPD1512	Approved
0.8314	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD7411	Suspended
0.825	Intermediate Similarity	NPD1549	Phase 2
0.8239	Intermediate Similarity	NPD6559	Discontinued
0.8192	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD7074	Phase 3
0.8092	Intermediate Similarity	NPD6232	Discontinued
0.807	Intermediate Similarity	NPD7075	Discontinued
0.807	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8068	Intermediate Similarity	NPD7054	Approved
0.8061	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8057	Intermediate Similarity	NPD7473	Discontinued
0.8023	Intermediate Similarity	NPD7472	Approved
0.8012	Intermediate Similarity	NPD7768	Phase 2
0.8	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7819	Suspended
0.8	Intermediate Similarity	NPD1465	Phase 2
0.7978	Intermediate Similarity	NPD6797	Phase 2
0.795	Intermediate Similarity	NPD1510	Phase 2
0.7943	Intermediate Similarity	NPD3926	Phase 2
0.7933	Intermediate Similarity	NPD7251	Discontinued
0.7923	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD919	Approved
0.7857	Intermediate Similarity	NPD920	Approved
0.7853	Intermediate Similarity	NPD2344	Approved
0.7849	Intermediate Similarity	NPD5402	Approved
0.7849	Intermediate Similarity	NPD3817	Phase 2
0.7844	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD943	Approved
0.7791	Intermediate Similarity	NPD2796	Approved
0.779	Intermediate Similarity	NPD7808	Phase 3
0.7765	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD2800	Approved
0.7733	Intermediate Similarity	NPD6801	Discontinued
0.7725	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD3751	Discontinued
0.7702	Intermediate Similarity	NPD1240	Approved
0.7665	Intermediate Similarity	NPD2309	Approved
0.7661	Intermediate Similarity	NPD3226	Approved
0.7651	Intermediate Similarity	NPD1243	Approved
0.7633	Intermediate Similarity	NPD2533	Approved
0.7633	Intermediate Similarity	NPD2534	Approved
0.7633	Intermediate Similarity	NPD2532	Approved
0.7607	Intermediate Similarity	NPD1607	Approved
0.7605	Intermediate Similarity	NPD3750	Approved
0.7593	Intermediate Similarity	NPD1613	Approved
0.7593	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD2935	Discontinued
0.7574	Intermediate Similarity	NPD6799	Approved
0.7568	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD8312	Approved
0.7554	Intermediate Similarity	NPD8313	Approved
0.7553	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD4287	Approved
0.7514	Intermediate Similarity	NPD6599	Discontinued
0.7486	Intermediate Similarity	NPD3787	Discontinued
0.7471	Intermediate Similarity	NPD7390	Discontinued
0.7461	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD5403	Approved
0.7439	Intermediate Similarity	NPD230	Phase 1
0.7433	Intermediate Similarity	NPD8434	Phase 2
0.7427	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD5401	Approved
0.7427	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD6234	Discontinued
0.741	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1551	Phase 2
0.7362	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7199	Phase 2
0.7322	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD7228	Approved
0.7321	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD2346	Discontinued
0.7312	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD3748	Approved
0.7293	Intermediate Similarity	NPD7229	Phase 3
0.7282	Intermediate Similarity	NPD6779	Approved
0.7282	Intermediate Similarity	NPD6780	Approved
0.7282	Intermediate Similarity	NPD6778	Approved
0.7282	Intermediate Similarity	NPD6776	Approved
0.7282	Intermediate Similarity	NPD6777	Approved
0.7282	Intermediate Similarity	NPD6781	Approved
0.7282	Intermediate Similarity	NPD6782	Approved
0.7256	Intermediate Similarity	NPD2313	Discontinued
0.7253	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD6190	Approved
0.725	Intermediate Similarity	NPD8151	Discontinued
0.7239	Intermediate Similarity	NPD4908	Phase 1
0.7232	Intermediate Similarity	NPD37	Approved
0.7219	Intermediate Similarity	NPD1471	Phase 3
0.7207	Intermediate Similarity	NPD4967	Phase 2
0.7207	Intermediate Similarity	NPD4965	Approved
0.7207	Intermediate Similarity	NPD4966	Approved
0.7204	Intermediate Similarity	NPD5953	Discontinued
0.7202	Intermediate Similarity	NPD2799	Discontinued
0.72	Intermediate Similarity	NPD1653	Approved
0.7198	Intermediate Similarity	NPD5710	Approved
0.7198	Intermediate Similarity	NPD5711	Approved
0.7193	Intermediate Similarity	NPD4628	Phase 3
0.7191	Intermediate Similarity	NPD8455	Phase 2
0.7189	Intermediate Similarity	NPD7286	Phase 2
0.7178	Intermediate Similarity	NPD7783	Phase 2
0.7178	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7435	Discontinued
0.7168	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5405	Approved
0.716	Intermediate Similarity	NPD5406	Approved
0.716	Intermediate Similarity	NPD5408	Approved
0.716	Intermediate Similarity	NPD5404	Approved
0.7158	Intermediate Similarity	NPD8150	Discontinued
0.7151	Intermediate Similarity	NPD2296	Approved
0.7136	Intermediate Similarity	NPD7871	Phase 2
0.7136	Intermediate Similarity	NPD7870	Phase 2
0.7128	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD447	Suspended
0.7125	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD4360	Phase 2
0.7113	Intermediate Similarity	NPD4363	Phase 3
0.7104	Intermediate Similarity	NPD6808	Phase 2
0.7095	Intermediate Similarity	NPD5760	Phase 2
0.7095	Intermediate Similarity	NPD5761	Phase 2
0.7093	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD3027	Phase 3
0.7085	Intermediate Similarity	NPD7697	Approved
0.7085	Intermediate Similarity	NPD7696	Phase 3
0.7085	Intermediate Similarity	NPD7698	Approved
0.7074	Intermediate Similarity	NPD7685	Pre-registration
0.7073	Intermediate Similarity	NPD2861	Phase 2
0.7059	Intermediate Similarity	NPD6100	Approved
0.7059	Intermediate Similarity	NPD6099	Approved
0.7048	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD3764	Approved
0.7039	Intermediate Similarity	NPD6844	Discontinued
0.7035	Intermediate Similarity	NPD6823	Phase 2
0.703	Intermediate Similarity	NPD7701	Phase 2
0.7026	Intermediate Similarity	NPD6534	Approved
0.7026	Intermediate Similarity	NPD6535	Approved
0.7019	Intermediate Similarity	NPD4665	Approved
0.7019	Intermediate Similarity	NPD1610	Phase 2
0.7019	Intermediate Similarity	NPD4111	Phase 1
0.6994	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6651	Approved
0.697	Remote Similarity	NPD9494	Approved
0.6961	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7874	Approved
0.6952	Remote Similarity	NPD7177	Discontinued
0.6952	Remote Similarity	NPD7907	Approved
0.6952	Remote Similarity	NPD2163	Approved
0.6951	Remote Similarity	NPD1203	Approved
0.6951	Remote Similarity	NPD1470	Approved
0.6944	Remote Similarity	NPD6279	Approved
0.6944	Remote Similarity	NPD6280	Approved
0.6935	Remote Similarity	NPD2403	Approved
0.6927	Remote Similarity	NPD7801	Approved
0.6923	Remote Similarity	NPD1933	Approved
0.6919	Remote Similarity	NPD7700	Phase 2
0.6919	Remote Similarity	NPD7699	Phase 2
0.6904	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD4361	Phase 2
0.6897	Remote Similarity	NPD7584	Approved
0.6895	Remote Similarity	NPD7240	Approved
0.6889	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD4625	Phase 3
0.6878	Remote Similarity	NPD1729	Discontinued
0.6872	Remote Similarity	NPD7458	Discontinued
0.6871	Remote Similarity	NPD9269	Phase 2
0.6859	Remote Similarity	NPD7549	Discontinued
0.6848	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD3268	Approved
0.6845	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1899	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