NPASS Compound

Structure

NPC473976 OpenBabel07101718292D 29 31 0 0 1 0 0 0 0 0999 V2000 -5.7839 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6500 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1859 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4538 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4538 -0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3198 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4538 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9179 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0519 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7839 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1859 -0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9179 -0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2812 -0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7839 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 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 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 6 7 1 0 0 0 0 6 10 1 0 0 0 0 7 15 2 0 0 0 0 8 9 2 0 0 0 0 8 17 1 0 0 0 0 9 19 1 0 0 0 0 10 24 1 0 0 0 0 11 14 2 0 0 0 0 11 18 1 0 0 0 0 12 15 1 0 0 0 0 12 18 1 0 0 0 0 13 17 2 0 0 0 0 13 20 1 0 0 0 0 16 21 1 0 0 0 0 16 24 1 6 0 0 0 17 25 1 0 0 0 0 18 26 2 0 0 0 0 19 20 2 0 0 0 0 19 22 1 0 0 0 0 20 28 1 0 0 0 0 21 22 1 0 0 0 0 21 23 2 0 0 0 0 22 27 2 0 0 0 0 23 28 1 0 0 0 0 23 29 1 0 0 0 0 24 5 1 1 0 0 0 24 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	396.19
Volume:	420.85
LogP:	4.275
LogD:	3.101
LogS:	-3.896
# Rotatable Bonds:	6
TPSA:	76.74
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.661
Synthetic Accessibility Score:	4.233
Fsp3:	0.417
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.809
MDCK Permeability:	2.065142325591296e-05
Pgp-inhibitor:	0.92
Pgp-substrate:	0.12
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.09

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.035
Plasma Protein Binding (PPB):	97.02864837646484%
Volume Distribution (VD):	1.512
Pgp-substrate:	4.377667427062988%

ADMET: Metabolism

CYP1A2-inhibitor:	0.862
CYP1A2-substrate:	0.956
CYP2C19-inhibitor:	0.947
CYP2C19-substrate:	0.686
CYP2C9-inhibitor:	0.933
CYP2C9-substrate:	0.884
CYP2D6-inhibitor:	0.905
CYP2D6-substrate:	0.67
CYP3A4-inhibitor:	0.857
CYP3A4-substrate:	0.645

ADMET: Excretion

Clearance (CL):	1.428
Half-life (T1/2):	0.684

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.693
Drug-inuced Liver Injury (DILI):	0.621
AMES Toxicity:	0.039
Rat Oral Acute Toxicity:	0.379
Maximum Recommended Daily Dose:	0.938
Skin Sensitization:	0.931
Carcinogencity:	0.326
Eye Corrosion:	0.003
Eye Irritation:	0.19
Respiratory Toxicity:	0.773

Download Data

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

Natural Product: NPC473976

Natural Product ID:	NPC473976
*Common Name:**	Fukanefurochromone B
IUPAC Name:	(2R,3R)-2-[(3E)-4,8-dimethyl-6-oxonona-3,7-dienyl]-7-hydroxy-2,3-dimethyl-3H-furo[2,3-b]chromen-4-one
Synonyms:	Fukanefurochromone B
Standard InCHIKey:	OROKUKZIDYKSRX-BAFNZYHESA-N
Standard InCHI:	InChI=1S/C24H28O5/c1-14(2)11-18(26)12-15(3)7-6-10-24(5)16(4)21-22(27)19-9-8-17(25)13-20(19)28-23(21)29-24/h7-9,11,13,16,25H,6,10,12H2,1-5H3/b15-7+/t16-,24-/m1/s1
SMILES:	C/C(=CCC[C@@]1(C)Oc2c([C@H]1C)c(=O)c1c(o2)cc(cc1)O)/CC(=O)C=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL456950
PubChem CID:	11589332
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives

*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
NPO3780	Ferula fukanensis	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[15043424]
NPO3780	Ferula fukanensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043424]
NPO3780	Ferula fukanensis	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[15467238]
NPO3780	Ferula fukanensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787437]
NPO3780	Ferula fukanensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16378364]
NPO3780	Ferula fukanensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3780	Ferula fukanensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	8.9	ug.mL-1	PMID[448974]

☑ 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 NPC473976 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	382
0.1-0.2	1569
0.2-0.3	3814
0.3-0.4	8917
0.4-0.5	9777
0.5-0.6	3877
0.6-0.7	6075
0.7-0.8	5234
0.8-0.85	2460
0.85-0.9	574
0.9-0.95	7
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC131043
1.0	High Similarity	NPC313039
1.0	High Similarity	NPC198459
1.0	High Similarity	NPC109812
0.9071	High Similarity	NPC213603
0.9014	High Similarity	NPC477956
0.8944	High Similarity	NPC472368
0.8944	High Similarity	NPC309154
0.8944	High Similarity	NPC12175
0.8944	High Similarity	NPC470669
0.8944	High Similarity	NPC90665
0.8944	High Similarity	NPC55162
0.8944	High Similarity	NPC278323
0.8944	High Similarity	NPC279668
0.8944	High Similarity	NPC470668
0.8944	High Similarity	NPC21350
0.8929	High Similarity	NPC286336
0.8889	High Similarity	NPC26051
0.8889	High Similarity	NPC52789
0.8889	High Similarity	NPC268204
0.8889	High Similarity	NPC55832
0.8889	High Similarity	NPC49108
0.8873	High Similarity	NPC181124
0.8873	High Similarity	NPC7013
0.8873	High Similarity	NPC116632
0.8873	High Similarity	NPC209560
0.8873	High Similarity	NPC153979
0.8873	High Similarity	NPC294409
0.8873	High Similarity	NPC162680
0.8873	High Similarity	NPC303644
0.8873	High Similarity	NPC472419
0.8873	High Similarity	NPC317119
0.8857	High Similarity	NPC204960
0.8857	High Similarity	NPC159623
0.8857	High Similarity	NPC242294
0.8857	High Similarity	NPC263670
0.8857	High Similarity	NPC20560
0.8857	High Similarity	NPC192304
0.8857	High Similarity	NPC472365
0.8857	High Similarity	NPC294593
0.8857	High Similarity	NPC312318
0.8857	High Similarity	NPC82225
0.8857	High Similarity	NPC337373
0.8857	High Similarity	NPC144051
0.8857	High Similarity	NPC28753
0.8857	High Similarity	NPC139813
0.8857	High Similarity	NPC188646
0.8857	High Similarity	NPC56031
0.8857	High Similarity	NPC18877
0.8857	High Similarity	NPC175098
0.8836	High Similarity	NPC476055
0.8836	High Similarity	NPC311741
0.8836	High Similarity	NPC234629
0.8819	High Similarity	NPC172250
0.8819	High Similarity	NPC253822
0.8819	High Similarity	NPC477272
0.8819	High Similarity	NPC265178
0.8819	High Similarity	NPC215311
0.8819	High Similarity	NPC144118
0.8819	High Similarity	NPC80962
0.8819	High Similarity	NPC101366
0.8819	High Similarity	NPC11056
0.8819	High Similarity	NPC48624
0.8819	High Similarity	NPC213659
0.8819	High Similarity	NPC326109
0.8819	High Similarity	NPC219917
0.8819	High Similarity	NPC204985
0.8819	High Similarity	NPC259166
0.8811	High Similarity	NPC470671
0.8811	High Similarity	NPC131130
0.8811	High Similarity	NPC474504
0.8811	High Similarity	NPC470672
0.8811	High Similarity	NPC474487
0.8803	High Similarity	NPC24394
0.8803	High Similarity	NPC472364
0.8803	High Similarity	NPC249606
0.8803	High Similarity	NPC1486
0.8803	High Similarity	NPC41461
0.8803	High Similarity	NPC12165
0.8803	High Similarity	NPC168105
0.8803	High Similarity	NPC87545
0.8803	High Similarity	NPC25287
0.8803	High Similarity	NPC472367
0.8803	High Similarity	NPC150399
0.8803	High Similarity	NPC476333
0.8803	High Similarity	NPC473391
0.8803	High Similarity	NPC274109
0.8803	High Similarity	NPC477242
0.8803	High Similarity	NPC187826
0.8803	High Similarity	NPC98115
0.8803	High Similarity	NPC66349
0.8803	High Similarity	NPC186838
0.8803	High Similarity	NPC477244
0.8803	High Similarity	NPC235428
0.8803	High Similarity	NPC477243
0.8786	High Similarity	NPC129132
0.8786	High Similarity	NPC87231
0.8786	High Similarity	NPC10971
0.8786	High Similarity	NPC212631
0.8786	High Similarity	NPC257756
0.8786	High Similarity	NPC205468
0.8776	High Similarity	NPC299011
0.8776	High Similarity	NPC25844
0.8776	High Similarity	NPC477955
0.8768	High Similarity	NPC69235
0.8768	High Similarity	NPC212379
0.8759	High Similarity	NPC126534
0.8759	High Similarity	NPC469404
0.8759	High Similarity	NPC64908
0.8759	High Similarity	NPC156590
0.8759	High Similarity	NPC147688
0.8759	High Similarity	NPC232021
0.8759	High Similarity	NPC40118
0.8759	High Similarity	NPC118840
0.8759	High Similarity	NPC205006
0.875	High Similarity	NPC109232
0.875	High Similarity	NPC23257
0.875	High Similarity	NPC295384
0.875	High Similarity	NPC283429
0.875	High Similarity	NPC472366
0.8741	High Similarity	NPC228661
0.8733	High Similarity	NPC318424
0.8732	High Similarity	NPC131039
0.8732	High Similarity	NPC156092
0.8732	High Similarity	NPC234560
0.8732	High Similarity	NPC13575
0.8732	High Similarity	NPC475955
0.8732	High Similarity	NPC474726
0.8732	High Similarity	NPC39426
0.8732	High Similarity	NPC151113
0.8725	High Similarity	NPC65775
0.8725	High Similarity	NPC10027
0.8714	High Similarity	NPC164236
0.8714	High Similarity	NPC262359
0.8714	High Similarity	NPC128348
0.8714	High Similarity	NPC475008
0.8714	High Similarity	NPC186097
0.8714	High Similarity	NPC475009
0.8714	High Similarity	NPC308037
0.8714	High Similarity	NPC313618
0.8714	High Similarity	NPC27490
0.8714	High Similarity	NPC189106
0.8714	High Similarity	NPC112192
0.8714	High Similarity	NPC66384
0.8714	High Similarity	NPC64359
0.8714	High Similarity	NPC309717
0.8707	High Similarity	NPC303185
0.8707	High Similarity	NPC311144
0.8707	High Similarity	NPC328623
0.8707	High Similarity	NPC184649
0.8705	High Similarity	NPC185497
0.8699	High Similarity	NPC226636
0.8699	High Similarity	NPC202981
0.8699	High Similarity	NPC297600
0.8699	High Similarity	NPC11561
0.8699	High Similarity	NPC144499
0.8696	High Similarity	NPC80694
0.8696	High Similarity	NPC186098
0.869	High Similarity	NPC261227
0.869	High Similarity	NPC235239
0.869	High Similarity	NPC305355
0.869	High Similarity	NPC270883
0.869	High Similarity	NPC471587
0.869	High Similarity	NPC172986
0.869	High Similarity	NPC475680
0.8681	High Similarity	NPC124269
0.8671	High Similarity	NPC174999
0.8671	High Similarity	NPC13408
0.8667	High Similarity	NPC471115
0.8667	High Similarity	NPC158866
0.8667	High Similarity	NPC471984
0.8667	High Similarity	NPC29777
0.8667	High Similarity	NPC234152
0.8662	High Similarity	NPC103842
0.8662	High Similarity	NPC236974
0.8662	High Similarity	NPC144027
0.8662	High Similarity	NPC164136
0.8658	High Similarity	NPC266572
0.8658	High Similarity	NPC39195
0.8652	High Similarity	NPC25937
0.8649	High Similarity	NPC154217
0.8643	High Similarity	NPC5515
0.8643	High Similarity	NPC324482
0.8643	High Similarity	NPC270369
0.8639	High Similarity	NPC11700
0.8639	High Similarity	NPC51887
0.8639	High Similarity	NPC475705
0.8639	High Similarity	NPC117836
0.8639	High Similarity	NPC166138
0.8639	High Similarity	NPC106985
0.8639	High Similarity	NPC219915
0.8639	High Similarity	NPC113770
0.8639	High Similarity	NPC38219
0.8639	High Similarity	NPC18585
0.8639	High Similarity	NPC476178
0.8633	High Similarity	NPC60558
0.863	High Similarity	NPC470089
0.863	High Similarity	NPC250755
0.863	High Similarity	NPC282300
0.863	High Similarity	NPC103362

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 NPC473976 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	333
0.1-0.2	927
0.2-0.3	1658
0.3-0.4	2602
0.4-0.5	2027
0.5-0.6	1093
0.6-0.7	340
0.7-0.8	120
0.8-0.85	43
0.85-0.9	6
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8732	High Similarity	NPD1510	Phase 2
0.8714	High Similarity	NPD1240	Approved
0.869	High Similarity	NPD1878	Clinical (unspecified phase)
0.8592	High Similarity	NPD1607	Approved
0.8552	High Similarity	NPD970	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8299	Intermediate Similarity	NPD1549	Phase 2
0.8288	Intermediate Similarity	NPD2796	Approved
0.8286	Intermediate Similarity	NPD2798	Approved
0.8243	Intermediate Similarity	NPD2800	Approved
0.8231	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD3749	Approved
0.8188	Intermediate Similarity	NPD3750	Approved
0.8182	Intermediate Similarity	NPD4380	Phase 2
0.8148	Intermediate Similarity	NPD3818	Discontinued
0.8092	Intermediate Similarity	NPD2534	Approved
0.8092	Intermediate Similarity	NPD2533	Approved
0.8092	Intermediate Similarity	NPD2532	Approved
0.8089	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD6651	Approved
0.8038	Intermediate Similarity	NPD3882	Suspended
0.8026	Intermediate Similarity	NPD6799	Approved
0.8026	Intermediate Similarity	NPD1511	Approved
0.8025	Intermediate Similarity	NPD7819	Suspended
0.8025	Intermediate Similarity	NPD2801	Approved
0.8013	Intermediate Similarity	NPD7411	Suspended
0.8	Intermediate Similarity	NPD1243	Approved
0.7987	Intermediate Similarity	NPD2344	Approved
0.7987	Intermediate Similarity	NPD7075	Discontinued
0.7973	Intermediate Similarity	NPD2799	Discontinued
0.7949	Intermediate Similarity	NPD6599	Discontinued
0.7922	Intermediate Similarity	NPD1512	Approved
0.7919	Intermediate Similarity	NPD2935	Discontinued
0.7911	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD920	Approved
0.7866	Intermediate Similarity	NPD7473	Discontinued
0.7852	Intermediate Similarity	NPD3748	Approved
0.7848	Intermediate Similarity	NPD1934	Approved
0.7848	Intermediate Similarity	NPD6801	Discontinued
0.7823	Intermediate Similarity	NPD943	Approved
0.7812	Intermediate Similarity	NPD7768	Phase 2
0.7805	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD1551	Phase 2
0.7791	Intermediate Similarity	NPD6232	Discontinued
0.7778	Intermediate Similarity	NPD2309	Approved
0.7771	Intermediate Similarity	NPD7054	Approved
0.7756	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD7074	Phase 3
0.7725	Intermediate Similarity	NPD7472	Approved
0.7712	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD6100	Approved
0.7682	Intermediate Similarity	NPD6099	Approved
0.7679	Intermediate Similarity	NPD6797	Phase 2
0.7669	Intermediate Similarity	NPD5494	Approved
0.7647	Intermediate Similarity	NPD2654	Approved
0.7647	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD3817	Phase 2
0.7633	Intermediate Similarity	NPD6559	Discontinued
0.7633	Intermediate Similarity	NPD7251	Discontinued
0.7622	Intermediate Similarity	NPD9717	Approved
0.7588	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD7808	Phase 3
0.7586	Intermediate Similarity	NPD1203	Approved
0.7574	Intermediate Similarity	NPD5953	Discontinued
0.7568	Intermediate Similarity	NPD3268	Approved
0.7568	Intermediate Similarity	NPD2313	Discontinued
0.7568	Intermediate Similarity	NPD3764	Approved
0.7552	Intermediate Similarity	NPD422	Phase 1
0.7547	Intermediate Similarity	NPD7458	Discontinued
0.7532	Intermediate Similarity	NPD5403	Approved
0.7515	Intermediate Similarity	NPD6959	Discontinued
0.75	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9493	Approved
0.7485	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6166	Phase 2
0.7484	Intermediate Similarity	NPD4628	Phase 3
0.747	Intermediate Similarity	NPD5710	Approved
0.747	Intermediate Similarity	NPD5711	Approved
0.7466	Intermediate Similarity	NPD2797	Approved
0.7456	Intermediate Similarity	NPD7286	Phase 2
0.7452	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD3226	Approved
0.7425	Intermediate Similarity	NPD3926	Phase 2
0.7423	Intermediate Similarity	NPD5402	Approved
0.7417	Intermediate Similarity	NPD230	Phase 1
0.7405	Intermediate Similarity	NPD5401	Approved
0.7394	Intermediate Similarity	NPD919	Approved
0.7394	Intermediate Similarity	NPD9545	Approved
0.7386	Intermediate Similarity	NPD4308	Phase 3
0.7386	Intermediate Similarity	NPD7033	Discontinued
0.7379	Intermediate Similarity	NPD3972	Approved
0.7345	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD7390	Discontinued
0.7315	Intermediate Similarity	NPD6832	Phase 2
0.7315	Intermediate Similarity	NPD4908	Phase 1
0.7305	Intermediate Similarity	NPD1247	Approved
0.7303	Intermediate Similarity	NPD447	Suspended
0.7301	Intermediate Similarity	NPD37	Approved
0.729	Intermediate Similarity	NPD2346	Discontinued
0.7279	Intermediate Similarity	NPD1876	Approved
0.7278	Intermediate Similarity	NPD2403	Approved
0.726	Intermediate Similarity	NPD1608	Approved
0.7256	Intermediate Similarity	NPD1465	Phase 2
0.7232	Intermediate Similarity	NPD4287	Approved
0.723	Intermediate Similarity	NPD3267	Approved
0.723	Intermediate Similarity	NPD3266	Approved
0.723	Intermediate Similarity	NPD1470	Approved
0.723	Intermediate Similarity	NPD1164	Approved
0.7219	Intermediate Similarity	NPD411	Approved
0.7219	Intermediate Similarity	NPD1296	Phase 2
0.7219	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD2296	Approved
0.7212	Intermediate Similarity	NPD4288	Approved
0.7211	Intermediate Similarity	NPD4749	Approved
0.7202	Intermediate Similarity	NPD7199	Phase 2
0.7193	Intermediate Similarity	NPD3751	Discontinued
0.7192	Intermediate Similarity	NPD1610	Phase 2
0.719	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD5124	Phase 1
0.719	Intermediate Similarity	NPD1933	Approved
0.7186	Intermediate Similarity	NPD6234	Discontinued
0.7169	Intermediate Similarity	NPD4965	Approved
0.7169	Intermediate Similarity	NPD4967	Phase 2
0.7169	Intermediate Similarity	NPD4966	Approved
0.7159	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7003	Approved
0.7151	Intermediate Similarity	NPD5844	Phase 1
0.7133	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD4361	Phase 2
0.7126	Intermediate Similarity	NPD7685	Pre-registration
0.7124	Intermediate Similarity	NPD4307	Phase 2
0.7118	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5404	Approved
0.7115	Intermediate Similarity	NPD5406	Approved
0.7115	Intermediate Similarity	NPD5405	Approved
0.7115	Intermediate Similarity	NPD5408	Approved
0.7103	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1201	Approved
0.7072	Intermediate Similarity	NPD4360	Phase 2
0.7072	Intermediate Similarity	NPD4363	Phase 3
0.707	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD1471	Phase 3
0.7069	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD6781	Approved
0.7065	Intermediate Similarity	NPD6780	Approved
0.7065	Intermediate Similarity	NPD6778	Approved
0.7065	Intermediate Similarity	NPD6777	Approved
0.7065	Intermediate Similarity	NPD6776	Approved
0.7065	Intermediate Similarity	NPD6782	Approved
0.7065	Intermediate Similarity	NPD6779	Approved
0.7059	Intermediate Similarity	NPD3787	Discontinued
0.7055	Intermediate Similarity	NPD17	Approved
0.705	Intermediate Similarity	NPD9266	Approved
0.705	Intermediate Similarity	NPD74	Approved
0.7047	Intermediate Similarity	NPD3225	Approved
0.7045	Intermediate Similarity	NPD8312	Approved
0.7045	Intermediate Similarity	NPD8313	Approved
0.7039	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1548	Phase 1
0.7027	Intermediate Similarity	NPD9269	Phase 2
0.7021	Intermediate Similarity	NPD7584	Approved
0.702	Intermediate Similarity	NPD9494	Approved
0.7011	Intermediate Similarity	NPD1729	Discontinued
0.6986	Remote Similarity	NPD9268	Approved
0.6978	Remote Similarity	NPD9263	Approved
0.6978	Remote Similarity	NPD9267	Approved
0.6978	Remote Similarity	NPD9264	Approved
0.6978	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6355	Discontinued
0.6968	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7229	Phase 3
0.6954	Remote Similarity	NPD1019	Discontinued
0.6952	Remote Similarity	NPD7696	Phase 3
0.6952	Remote Similarity	NPD7435	Discontinued
0.6952	Remote Similarity	NPD7698	Approved
0.6952	Remote Similarity	NPD7697	Approved
0.6946	Remote Similarity	NPD5761	Phase 2
0.6946	Remote Similarity	NPD5760	Phase 2
0.6932	Remote Similarity	NPD6104	Discontinued
0.6928	Remote Similarity	NPD4625	Phase 3
0.6928	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD8434	Phase 2
0.6923	Remote Similarity	NPD1241	Discontinued
0.6915	Remote Similarity	NPD7870	Phase 2
0.6915	Remote Similarity	NPD7871	Phase 2

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