NPASS Compound

Structure

NPC473964 OpenBabel07101719242D 26 28 0 0 1 0 0 0 0 0999 V2000 -0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0491 2.6750 0.0000 C 0 0 0 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 4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6831 -2.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 4.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0491 2.6750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 2 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 6 7 1 0 0 0 0 6 13 1 0 0 0 0 7 19 1 0 0 0 0 8 18 1 0 0 0 0 9 17 1 0 0 0 0 10 20 2 0 0 0 0 10 24 1 0 0 0 0 11 21 2 0 0 0 0 11 25 1 0 0 0 0 12 8 1 6 0 0 0 12 14 1 0 0 0 0 12 26 1 0 0 0 0 13 18 1 1 0 0 0 13 24 1 0 0 0 0 14 9 1 1 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 15 25 1 6 0 0 0 16 18 1 6 0 0 0 16 19 1 0 0 0 0 17 22 2 0 0 0 0 17 26 1 0 0 0 0 18 4 1 1 0 0 0 19 5 1 1 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	366.17
Volume:	362.497
LogP:	0.975
LogD:	1.323
LogS:	-2.748
# Rotatable Bonds:	4
TPSA:	99.13
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.449
Synthetic Accessibility Score:	4.626
Fsp3:	0.737
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.015
MDCK Permeability:	7.641703268745914e-05
Pgp-inhibitor:	0.895
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.315
20% Bioavailability (F20%):	0.565
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.575
Plasma Protein Binding (PPB):	32.955848693847656%
Volume Distribution (VD):	0.876
Pgp-substrate:	45.42544937133789%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.067
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.291
CYP2C9-inhibitor:	0.034
CYP2C9-substrate:	0.075
CYP2D6-inhibitor:	0.124
CYP2D6-substrate:	0.101
CYP3A4-inhibitor:	0.206
CYP3A4-substrate:	0.294

ADMET: Excretion

Clearance (CL):	2.932
Half-life (T1/2):	0.806

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.837
Drug-inuced Liver Injury (DILI):	0.855
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.608
Maximum Recommended Daily Dose:	0.042
Skin Sensitization:	0.668
Carcinogencity:	0.047
Eye Corrosion:	0.074
Eye Irritation:	0.135
Respiratory Toxicity:	0.939

Download Data

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

Natural Product: NPC473964

Natural Product ID:	NPC473964
*Common Name:**	Acetic Acid (3Ar,4S,4Ar,5R,8R,8Ar,9As)-4-Acetoxy-5-Hydroxy-5,8A-Dimethyl-3-Methylene-2-Oxo-Dodecahydro-Naphtho[2,3-B]Furan-8-Yl Ester
IUPAC Name:	[(3aR,4S,4aR,5R,8R,8aR,9aS)-4-acetyloxy-5-hydroxy-5,8a-dimethyl-3-methylidene-2-oxo-3a,4,4a,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-8-yl] acetate
Synonyms:
Standard InCHIKey:	CHXVTGFPYRYMMI-XNTGMIQRSA-N
Standard InCHI:	InChI=1S/C19H26O7/c1-9-14-12(26-17(9)22)8-18(4)13(24-10(2)20)6-7-19(5,23)16(18)15(14)25-11(3)21/h12-16,23H,1,6-8H2,2-5H3/t12-,13+,14+,15-,16-,18-,19+/m0/s1
SMILES:	CC(=O)O[C@H]1[C@H]2[C@@H](OC(=O)C2=C)C[C@@]2([C@H]1[C@](C)(O)CC[C@H]2OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL456557
PubChem CID:	44587991
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001772] Eudesmanolides, secoeudesmanolides, 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
NPO8480	Gonospermum fruticosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19053514]
NPO22963	Gonospermum gomerae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19053514]
NPO22963	Gonospermum gomerae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8480	Gonospermum fruticosum	Species	Asteraceae	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
IC50	4
Others	5

Activity Type	# Activity
Cell Line	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	13300.0	nM	PMID[545510]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	10400.0	nM	PMID[545510]
NPT926	Cell Line	SK-MEL-1	Homo sapiens	IC50	=	27900.0	nM	PMID[545510]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[545510]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	11.8	%	PMID[545510]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	39.3	%	PMID[545510]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	21.5	%	PMID[545510]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	21.8	%	PMID[545510]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	12.0	%	PMID[545510]

☑ 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 NPC473964 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	209
0.1-0.2	1412
0.2-0.3	4726
0.3-0.4	8164
0.4-0.5	12921
0.5-0.6	5835
0.6-0.7	6758
0.7-0.8	2447
0.8-0.85	152
0.85-0.9	37
0.9-0.95	27
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9889	High Similarity	NPC473963
0.9778	High Similarity	NPC93245
0.9667	High Similarity	NPC259042
0.9667	High Similarity	NPC157686
0.9556	High Similarity	NPC148000
0.9556	High Similarity	NPC469596
0.9556	High Similarity	NPC225474
0.9457	High Similarity	NPC136781
0.9438	High Similarity	NPC475776
0.9368	High Similarity	NPC61442
0.9362	High Similarity	NPC475958
0.9341	High Similarity	NPC24861
0.9255	High Similarity	NPC47024
0.9247	High Similarity	NPC474921
0.9239	High Similarity	NPC90014
0.9167	High Similarity	NPC99510
0.9149	High Similarity	NPC476806
0.9149	High Similarity	NPC476807
0.914	High Similarity	NPC284518
0.9111	High Similarity	NPC116620
0.9101	High Similarity	NPC175293
0.9032	High Similarity	NPC56369
0.8989	High Similarity	NPC9231
0.8969	High Similarity	NPC72842
0.8947	High Similarity	NPC216478
0.8936	High Similarity	NPC165528
0.8936	High Similarity	NPC228766
0.8925	High Similarity	NPC474841
0.8925	High Similarity	NPC471446
0.8925	High Similarity	NPC473434
0.8901	High Similarity	NPC194642
0.8889	High Similarity	NPC305029
0.8878	High Similarity	NPC283850
0.8866	High Similarity	NPC164551
0.8817	High Similarity	NPC147272
0.8778	High Similarity	NPC85698
0.8778	High Similarity	NPC185638
0.8763	High Similarity	NPC242666
0.8763	High Similarity	NPC308824
0.87	High Similarity	NPC284732
0.87	High Similarity	NPC78966
0.8681	High Similarity	NPC181103
0.8673	High Similarity	NPC476081
0.8646	High Similarity	NPC474395
0.8614	High Similarity	NPC37628
0.8602	High Similarity	NPC153853
0.8586	High Similarity	NPC156681
0.8571	High Similarity	NPC111292
0.8556	High Similarity	NPC97505
0.8539	High Similarity	NPC226988
0.8529	High Similarity	NPC474243
0.8485	Intermediate Similarity	NPC162973
0.8478	Intermediate Similarity	NPC470012
0.84	Intermediate Similarity	NPC120321
0.8381	Intermediate Similarity	NPC477126
0.837	Intermediate Similarity	NPC477920
0.8367	Intermediate Similarity	NPC98837
0.8367	Intermediate Similarity	NPC38296
0.8367	Intermediate Similarity	NPC89099
0.8367	Intermediate Similarity	NPC28864
0.8367	Intermediate Similarity	NPC20479
0.8367	Intermediate Similarity	NPC162459
0.8367	Intermediate Similarity	NPC38471
0.8352	Intermediate Similarity	NPC470011
0.8333	Intermediate Similarity	NPC67321
0.8333	Intermediate Similarity	NPC187435
0.8333	Intermediate Similarity	NPC302788
0.8333	Intermediate Similarity	NPC66581
0.8317	Intermediate Similarity	NPC477127
0.8316	Intermediate Similarity	NPC186363
0.8316	Intermediate Similarity	NPC233345
0.83	Intermediate Similarity	NPC170615
0.8283	Intermediate Similarity	NPC471413
0.8283	Intermediate Similarity	NPC293866
0.8283	Intermediate Similarity	NPC477656
0.8265	Intermediate Similarity	NPC111348
0.8265	Intermediate Similarity	NPC10864
0.8252	Intermediate Similarity	NPC189075
0.8252	Intermediate Similarity	NPC275539
0.8252	Intermediate Similarity	NPC255082
0.8242	Intermediate Similarity	NPC243347
0.8235	Intermediate Similarity	NPC34768
0.8229	Intermediate Similarity	NPC199543
0.8222	Intermediate Similarity	NPC209318
0.8222	Intermediate Similarity	NPC223330
0.8218	Intermediate Similarity	NPC87927
0.8211	Intermediate Similarity	NPC158488
0.8202	Intermediate Similarity	NPC263951
0.82	Intermediate Similarity	NPC46848
0.82	Intermediate Similarity	NPC471412
0.8191	Intermediate Similarity	NPC50847
0.8191	Intermediate Similarity	NPC277771
0.819	Intermediate Similarity	NPC474846
0.819	Intermediate Similarity	NPC469655
0.819	Intermediate Similarity	NPC469656
0.8182	Intermediate Similarity	NPC16911
0.8182	Intermediate Similarity	NPC473155
0.8182	Intermediate Similarity	NPC78427
0.8163	Intermediate Similarity	NPC256227
0.8163	Intermediate Similarity	NPC29410
0.8163	Intermediate Similarity	NPC200054
0.8163	Intermediate Similarity	NPC234993
0.8163	Intermediate Similarity	NPC134072
0.8155	Intermediate Similarity	NPC110496
0.8152	Intermediate Similarity	NPC219011
0.8144	Intermediate Similarity	NPC57117
0.8137	Intermediate Similarity	NPC146731
0.8125	Intermediate Similarity	NPC72845
0.8119	Intermediate Similarity	NPC275990
0.8119	Intermediate Similarity	NPC88203
0.8119	Intermediate Similarity	NPC76866
0.8119	Intermediate Similarity	NPC31058
0.8119	Intermediate Similarity	NPC304832
0.8119	Intermediate Similarity	NPC148628
0.8119	Intermediate Similarity	NPC469606
0.8119	Intermediate Similarity	NPC165250
0.8119	Intermediate Similarity	NPC246736
0.8119	Intermediate Similarity	NPC286519
0.8119	Intermediate Similarity	NPC214946
0.8119	Intermediate Similarity	NPC273005
0.8119	Intermediate Similarity	NPC58329
0.8113	Intermediate Similarity	NPC269530
0.81	Intermediate Similarity	NPC477655
0.81	Intermediate Similarity	NPC287676
0.81	Intermediate Similarity	NPC476303
0.8095	Intermediate Similarity	NPC253906
0.8081	Intermediate Similarity	NPC253586
0.8081	Intermediate Similarity	NPC70145
0.8081	Intermediate Similarity	NPC91695
0.8077	Intermediate Similarity	NPC218123
0.8077	Intermediate Similarity	NPC306265
0.8077	Intermediate Similarity	NPC112895
0.8077	Intermediate Similarity	NPC231278
0.8061	Intermediate Similarity	NPC276110
0.8061	Intermediate Similarity	NPC183012
0.8061	Intermediate Similarity	NPC98639
0.8058	Intermediate Similarity	NPC28791
0.8058	Intermediate Similarity	NPC295366
0.8058	Intermediate Similarity	NPC469607
0.8056	Intermediate Similarity	NPC270478
0.8043	Intermediate Similarity	NPC194637
0.8041	Intermediate Similarity	NPC139692
0.8041	Intermediate Similarity	NPC7349
0.8039	Intermediate Similarity	NPC36688
0.8039	Intermediate Similarity	NPC221421
0.8039	Intermediate Similarity	NPC254202
0.8037	Intermediate Similarity	NPC25909
0.8022	Intermediate Similarity	NPC475951
0.8022	Intermediate Similarity	NPC38642
0.802	Intermediate Similarity	NPC121218
0.802	Intermediate Similarity	NPC253886
0.802	Intermediate Similarity	NPC289148
0.802	Intermediate Similarity	NPC163963
0.802	Intermediate Similarity	NPC98225
0.802	Intermediate Similarity	NPC52899
0.8019	Intermediate Similarity	NPC94650
0.8	Intermediate Similarity	NPC477302
0.8	Intermediate Similarity	NPC471038
0.8	Intermediate Similarity	NPC474793
0.8	Intermediate Similarity	NPC474724
0.7981	Intermediate Similarity	NPC180744
0.7981	Intermediate Similarity	NPC143609
0.7981	Intermediate Similarity	NPC86852
0.7981	Intermediate Similarity	NPC251824
0.7981	Intermediate Similarity	NPC179380
0.798	Intermediate Similarity	NPC202833
0.798	Intermediate Similarity	NPC29952
0.7961	Intermediate Similarity	NPC296950
0.7961	Intermediate Similarity	NPC84928
0.7961	Intermediate Similarity	NPC13149
0.7961	Intermediate Similarity	NPC301787
0.7959	Intermediate Similarity	NPC224410
0.7959	Intermediate Similarity	NPC3359
0.7959	Intermediate Similarity	NPC47853
0.7959	Intermediate Similarity	NPC105490
0.7959	Intermediate Similarity	NPC475118
0.7959	Intermediate Similarity	NPC250075
0.7959	Intermediate Similarity	NPC100257
0.7944	Intermediate Similarity	NPC12046
0.7944	Intermediate Similarity	NPC472002
0.7944	Intermediate Similarity	NPC194951
0.7944	Intermediate Similarity	NPC476964
0.7941	Intermediate Similarity	NPC475038
0.7941	Intermediate Similarity	NPC109195
0.7938	Intermediate Similarity	NPC198054
0.7938	Intermediate Similarity	NPC130840
0.7938	Intermediate Similarity	NPC165180
0.7925	Intermediate Similarity	NPC472666
0.7925	Intermediate Similarity	NPC5103
0.7925	Intermediate Similarity	NPC124053
0.7925	Intermediate Similarity	NPC478209
0.7921	Intermediate Similarity	NPC470761
0.7921	Intermediate Similarity	NPC267921
0.7921	Intermediate Similarity	NPC16601
0.7921	Intermediate Similarity	NPC473219
0.7921	Intermediate Similarity	NPC108371
0.7921	Intermediate Similarity	NPC293890
0.7917	Intermediate Similarity	NPC291875
0.7917	Intermediate Similarity	NPC253618
0.7917	Intermediate Similarity	NPC206001

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 NPC473964 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	189
0.1-0.2	1830
0.2-0.3	3809
0.3-0.4	2157
0.4-0.5	672
0.5-0.6	230
0.6-0.7	209
0.7-0.8	54
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7925	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.783	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7638	Approved
0.7647	Intermediate Similarity	NPD4225	Approved
0.7642	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD8034	Phase 2
0.7576	Intermediate Similarity	NPD8035	Phase 2
0.7573	Intermediate Similarity	NPD7639	Approved
0.7573	Intermediate Similarity	NPD7640	Approved
0.7383	Intermediate Similarity	NPD6008	Approved
0.7327	Intermediate Similarity	NPD6399	Phase 3
0.7248	Intermediate Similarity	NPD6686	Approved
0.7232	Intermediate Similarity	NPD8133	Approved
0.7212	Intermediate Similarity	NPD7902	Approved
0.7193	Intermediate Similarity	NPD7115	Discovery
0.7188	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD5697	Approved
0.7143	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1694	Approved
0.7103	Intermediate Similarity	NPD7632	Discontinued
0.7091	Intermediate Similarity	NPD6881	Approved
0.7091	Intermediate Similarity	NPD6899	Approved
0.7087	Intermediate Similarity	NPD7748	Approved
0.7064	Intermediate Similarity	NPD7128	Approved
0.7064	Intermediate Similarity	NPD6402	Approved
0.7064	Intermediate Similarity	NPD5739	Approved
0.7064	Intermediate Similarity	NPD6675	Approved
0.7054	Intermediate Similarity	NPD6649	Approved
0.7054	Intermediate Similarity	NPD6650	Approved
0.7027	Intermediate Similarity	NPD6012	Approved
0.7027	Intermediate Similarity	NPD6373	Approved
0.7027	Intermediate Similarity	NPD6013	Approved
0.7027	Intermediate Similarity	NPD6372	Approved
0.7027	Intermediate Similarity	NPD6014	Approved
0.7009	Intermediate Similarity	NPD5344	Discontinued
0.7	Intermediate Similarity	NPD5701	Approved
0.6964	Remote Similarity	NPD7102	Approved
0.6964	Remote Similarity	NPD6883	Approved
0.6964	Remote Similarity	NPD7290	Approved
0.6949	Remote Similarity	NPD6921	Approved
0.6937	Remote Similarity	NPD6011	Approved
0.6937	Remote Similarity	NPD7320	Approved
0.693	Remote Similarity	NPD4632	Approved
0.6923	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7900	Approved
0.6916	Remote Similarity	NPD6648	Approved
0.6903	Remote Similarity	NPD6617	Approved
0.6903	Remote Similarity	NPD6847	Approved
0.6903	Remote Similarity	NPD6869	Approved
0.6903	Remote Similarity	NPD8130	Phase 1
0.69	Remote Similarity	NPD3618	Phase 1
0.6893	Remote Similarity	NPD7515	Phase 2
0.6864	Remote Similarity	NPD6319	Approved
0.6863	Remote Similarity	NPD1695	Approved
0.686	Remote Similarity	NPD7507	Approved
0.6857	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6882	Approved
0.6842	Remote Similarity	NPD8297	Approved
0.6838	Remote Similarity	NPD7328	Approved
0.6838	Remote Similarity	NPD7327	Approved
0.6829	Remote Similarity	NPD7319	Approved
0.6822	Remote Similarity	NPD5696	Approved
0.6789	Remote Similarity	NPD5211	Phase 2
0.678	Remote Similarity	NPD7516	Approved
0.6777	Remote Similarity	NPD7492	Approved
0.6771	Remote Similarity	NPD6118	Approved
0.6771	Remote Similarity	NPD6114	Approved
0.6771	Remote Similarity	NPD6115	Approved
0.6771	Remote Similarity	NPD6697	Approved
0.6762	Remote Similarity	NPD5282	Discontinued
0.6759	Remote Similarity	NPD5285	Approved
0.6759	Remote Similarity	NPD4696	Approved
0.6759	Remote Similarity	NPD5286	Approved
0.6752	Remote Similarity	NPD6009	Approved
0.6729	Remote Similarity	NPD6084	Phase 2
0.6729	Remote Similarity	NPD4755	Approved
0.6729	Remote Similarity	NPD6083	Phase 2
0.6726	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD6054	Approved
0.6721	Remote Similarity	NPD6616	Approved
0.6698	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5695	Phase 3
0.6696	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6053	Discontinued
0.6667	Remote Similarity	NPD6116	Phase 1
0.6667	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD7078	Approved
0.6667	Remote Similarity	NPD5983	Phase 2
0.6667	Remote Similarity	NPD3573	Approved
0.6667	Remote Similarity	NPD5141	Approved
0.6667	Remote Similarity	NPD6015	Approved
0.6667	Remote Similarity	NPD6371	Approved
0.6636	Remote Similarity	NPD4633	Approved
0.6636	Remote Similarity	NPD5224	Approved
0.6636	Remote Similarity	NPD5226	Approved
0.6636	Remote Similarity	NPD5225	Approved
0.6635	Remote Similarity	NPD6698	Approved
0.6635	Remote Similarity	NPD46	Approved
0.6634	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD7736	Approved
0.6612	Remote Similarity	NPD6370	Approved
0.6612	Remote Similarity	NPD5988	Approved
0.6609	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD4700	Approved
0.66	Remote Similarity	NPD4788	Approved
0.6583	Remote Similarity	NPD6059	Approved
0.6577	Remote Similarity	NPD5175	Approved
0.6577	Remote Similarity	NPD5174	Approved
0.6571	Remote Similarity	NPD5693	Phase 1
0.6571	Remote Similarity	NPD6079	Approved
0.6571	Remote Similarity	NPD7637	Suspended
0.6569	Remote Similarity	NPD7146	Approved
0.6569	Remote Similarity	NPD6409	Approved
0.6569	Remote Similarity	NPD5330	Approved
0.6569	Remote Similarity	NPD7334	Approved
0.6569	Remote Similarity	NPD6684	Approved
0.6569	Remote Similarity	NPD7521	Approved
0.6569	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6117	Approved
0.6557	Remote Similarity	NPD7604	Phase 2
0.6549	Remote Similarity	NPD6412	Phase 2
0.6545	Remote Similarity	NPD1700	Approved
0.6545	Remote Similarity	NPD5223	Approved
0.6538	Remote Similarity	NPD5328	Approved
0.6535	Remote Similarity	NPD4786	Approved
0.6535	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD8293	Discontinued
0.6529	Remote Similarity	NPD8335	Approved
0.6529	Remote Similarity	NPD8378	Approved
0.6529	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD8033	Approved
0.6529	Remote Similarity	NPD8380	Approved
0.6529	Remote Similarity	NPD8379	Approved
0.6529	Remote Similarity	NPD8296	Approved
0.6522	Remote Similarity	NPD4634	Approved
0.6509	Remote Similarity	NPD5779	Approved
0.6509	Remote Similarity	NPD5778	Approved
0.65	Remote Similarity	NPD7100	Approved
0.65	Remote Similarity	NPD7101	Approved
0.6481	Remote Similarity	NPD5222	Approved
0.6481	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD5221	Approved
0.6481	Remote Similarity	NPD4697	Phase 3
0.6471	Remote Similarity	NPD6317	Approved
0.6471	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6336	Discontinued
0.6449	Remote Similarity	NPD6001	Approved
0.6446	Remote Similarity	NPD8377	Approved
0.6446	Remote Similarity	NPD8294	Approved
0.6442	Remote Similarity	NPD6672	Approved
0.6442	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD6903	Approved
0.6442	Remote Similarity	NPD5737	Approved
0.6436	Remote Similarity	NPD6695	Phase 3
0.6423	Remote Similarity	NPD8328	Phase 3
0.6422	Remote Similarity	NPD5173	Approved
0.6417	Remote Similarity	NPD6313	Approved
0.6417	Remote Similarity	NPD6335	Approved
0.6417	Remote Similarity	NPD6314	Approved
0.6415	Remote Similarity	NPD6411	Approved
0.6415	Remote Similarity	NPD5281	Approved
0.6415	Remote Similarity	NPD5284	Approved
0.6393	Remote Similarity	NPD7503	Approved
0.6393	Remote Similarity	NPD8515	Approved
0.6393	Remote Similarity	NPD8517	Approved
0.6393	Remote Similarity	NPD8516	Approved
0.6393	Remote Similarity	NPD8513	Phase 3
0.6389	Remote Similarity	NPD5210	Approved
0.6389	Remote Similarity	NPD4629	Approved
0.6381	Remote Similarity	NPD4753	Phase 2
0.6373	Remote Similarity	NPD3133	Approved
0.6373	Remote Similarity	NPD3668	Phase 3
0.6373	Remote Similarity	NPD3665	Phase 1
0.6373	Remote Similarity	NPD3666	Approved
0.6354	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD4730	Approved
0.6348	Remote Similarity	NPD4729	Approved
0.6348	Remote Similarity	NPD5128	Approved
0.6325	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD5785	Approved
0.6316	Remote Similarity	NPD4768	Approved
0.6316	Remote Similarity	NPD4767	Approved
0.63	Remote Similarity	NPD7525	Registered
0.63	Remote Similarity	NPD4695	Discontinued
0.6289	Remote Similarity	NPD3702	Approved
0.6289	Remote Similarity	NPD3703	Phase 2
0.6283	Remote Similarity	NPD4754	Approved
0.626	Remote Similarity	NPD6909	Approved
0.626	Remote Similarity	NPD6908	Approved
0.625	Remote Similarity	NPD6868	Approved
0.6239	Remote Similarity	NPD5249	Phase 3
0.6239	Remote Similarity	NPD5247	Approved
0.6239	Remote Similarity	NPD5251	Approved
0.6239	Remote Similarity	NPD5248	Approved
0.6239	Remote Similarity	NPD5250	Approved
0.6226	Remote Similarity	NPD6904	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