NPASS Compound

Structure

NPC208389 OpenBabel07101719132D 26 28 0 0 1 0 0 0 0 0999 V2000 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 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 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 -2.4945 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 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 -2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 -1.0933 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 3.5000 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 -0.8660 0.5000 0.0000 C 0 0 1 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 0.0000 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 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 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1808 -1.8364 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 14 1 0 0 0 0 2 15 1 0 0 0 0 3 21 1 0 0 0 0 4 21 1 0 0 0 0 6 10 1 0 0 0 0 6 11 1 0 0 0 0 7 8 2 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 12 2 0 0 0 0 9 16 1 0 0 0 0 10 21 1 0 0 0 0 11 22 1 0 0 0 0 12 25 1 0 0 0 0 13 16 2 0 0 0 0 13 25 1 0 0 0 0 14 17 1 0 0 0 0 14 19 2 0 0 0 0 15 23 2 0 0 0 0 15 26 1 0 0 0 0 17 22 1 1 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 18 24 2 0 0 0 0 19 26 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 1 0 0 0 22 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	410.23
Volume:	417.021
LogP:	2.254
LogD:	1.36
LogS:	-3.934
# Rotatable Bonds:	3
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.467
Synthetic Accessibility Score:	4.901
Fsp3:	0.818
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:	-4.986
MDCK Permeability:	2.528308868932072e-05
Pgp-inhibitor:	0.986
Pgp-substrate:	0.941
Human Intestinal Absorption (HIA):	0.836
20% Bioavailability (F20%):	0.411
30% Bioavailability (F30%):	0.093

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.706
Plasma Protein Binding (PPB):	47.515480041503906%
Volume Distribution (VD):	0.396
Pgp-substrate:	59.46152114868164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.378
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.771
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.027
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.083
CYP3A4-inhibitor:	0.56
CYP3A4-substrate:	0.455

ADMET: Excretion

Clearance (CL):	5.592
Half-life (T1/2):	0.835

ADMET: Toxicity

hERG Blockers:	0.067
Human Hepatotoxicity (H-HT):	0.289
Drug-inuced Liver Injury (DILI):	0.199
AMES Toxicity:	0.22
Rat Oral Acute Toxicity:	0.976
Maximum Recommended Daily Dose:	0.971
Skin Sensitization:	0.438
Carcinogencity:	0.922
Eye Corrosion:	0.043
Eye Irritation:	0.035
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC208389

Natural Product ID:	NPC208389
*Common Name:**	7-Acetoxy Hedychenone
IUPAC Name:	[(4R,4aR,8aS)-4-[(E)-2-(furan-3-yl)ethenyl]-3,4a,8,8-tetramethyl-1-oxo-5,6,7,8a-tetrahydro-4H-naphthalen-2-yl] acetate
Synonyms:	7-Acetoxy Hedychenone
Standard InCHIKey:	ZZMOWNDJRNFDCJ-IIIKCKGOSA-N
Standard InCHI:	InChI=1S/C22H28O4/c1-14-17(8-7-16-9-12-25-13-16)22(5)11-6-10-21(3,4)20(22)18(24)19(14)26-15(2)23/h7-9,12-13,17,20H,6,10-11H2,1-5H3/b8-7+/t17-,20-,22+/m0/s1
SMILES:	CC(=O)OC1=C(C)[C@H](/C=C/c2cocc2)[C@@]2([C@@H](C1=O)C(C)(C)CCC2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL466124
PubChem CID:	44574536
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

*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
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[19027298]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19332371]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19782567]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23422227]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Inhibition	=	25.7	%	PMID[501258]

☑ 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 NPC208389 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	260
0.1-0.2	1430
0.2-0.3	3152
0.3-0.4	6947
0.4-0.5	12682
0.5-0.6	11807
0.6-0.7	5699
0.7-0.8	629
0.8-0.85	64
0.85-0.9	22
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9435	High Similarity	NPC26532
0.9355	High Similarity	NPC246392
0.9091	High Similarity	NPC87466
0.9048	High Similarity	NPC290955
0.8828	High Similarity	NPC279877
0.8806	High Similarity	NPC474722
0.874	High Similarity	NPC179354
0.873	High Similarity	NPC16922
0.8702	High Similarity	NPC471817
0.8682	High Similarity	NPC112706
0.8682	High Similarity	NPC207294
0.8657	High Similarity	NPC307401
0.8636	High Similarity	NPC470740
0.8615	High Similarity	NPC59502
0.8605	High Similarity	NPC83178
0.8582	High Similarity	NPC146872
0.8529	High Similarity	NPC202260
0.8527	High Similarity	NPC74612
0.8527	High Similarity	NPC138139
0.8527	High Similarity	NPC46536
0.8485	Intermediate Similarity	NPC298190
0.848	Intermediate Similarity	NPC243704
0.8467	Intermediate Similarity	NPC148374
0.845	Intermediate Similarity	NPC473885
0.845	Intermediate Similarity	NPC471074
0.8425	Intermediate Similarity	NPC97566
0.8397	Intermediate Similarity	NPC477966
0.8397	Intermediate Similarity	NPC477123
0.8385	Intermediate Similarity	NPC23086
0.8382	Intermediate Similarity	NPC310830
0.8372	Intermediate Similarity	NPC65735
0.8372	Intermediate Similarity	NPC188377
0.837	Intermediate Similarity	NPC92941
0.8361	Intermediate Similarity	NPC277525
0.8358	Intermediate Similarity	NPC293253
0.8346	Intermediate Similarity	NPC89133
0.8333	Intermediate Similarity	NPC56197
0.8321	Intermediate Similarity	NPC220094
0.8321	Intermediate Similarity	NPC476943
0.8321	Intermediate Similarity	NPC236532
0.8308	Intermediate Similarity	NPC300098
0.8308	Intermediate Similarity	NPC290193
0.8284	Intermediate Similarity	NPC473982
0.8276	Intermediate Similarity	NPC246164
0.8261	Intermediate Similarity	NPC90953
0.8258	Intermediate Similarity	NPC476917
0.8258	Intermediate Similarity	NPC327527
0.8258	Intermediate Similarity	NPC477039
0.8258	Intermediate Similarity	NPC477040
0.8248	Intermediate Similarity	NPC215109
0.8248	Intermediate Similarity	NPC470742
0.8248	Intermediate Similarity	NPC170604
0.8248	Intermediate Similarity	NPC42400
0.824	Intermediate Similarity	NPC150895
0.8239	Intermediate Similarity	NPC262198
0.8222	Intermediate Similarity	NPC471006
0.8217	Intermediate Similarity	NPC36255
0.8217	Intermediate Similarity	NPC317217
0.8214	Intermediate Similarity	NPC473152
0.8209	Intermediate Similarity	NPC61788
0.8182	Intermediate Similarity	NPC71821
0.8169	Intermediate Similarity	NPC56731
0.8168	Intermediate Similarity	NPC230979
0.8138	Intermediate Similarity	NPC46551
0.8134	Intermediate Similarity	NPC476925
0.8125	Intermediate Similarity	NPC473969
0.812	Intermediate Similarity	NPC329707
0.8112	Intermediate Similarity	NPC233763
0.8102	Intermediate Similarity	NPC158525
0.8099	Intermediate Similarity	NPC142113
0.8099	Intermediate Similarity	NPC199044
0.8099	Intermediate Similarity	NPC238843
0.8092	Intermediate Similarity	NPC243269
0.8092	Intermediate Similarity	NPC477965
0.8092	Intermediate Similarity	NPC83115
0.8092	Intermediate Similarity	NPC178382
0.8092	Intermediate Similarity	NPC130275
0.8092	Intermediate Similarity	NPC477038
0.8088	Intermediate Similarity	NPC218838
0.8082	Intermediate Similarity	NPC240214
0.8077	Intermediate Similarity	NPC477967
0.8071	Intermediate Similarity	NPC90296
0.806	Intermediate Similarity	NPC198904
0.8042	Intermediate Similarity	NPC114513
0.8042	Intermediate Similarity	NPC290038
0.8042	Intermediate Similarity	NPC245522
0.803	Intermediate Similarity	NPC474829
0.8028	Intermediate Similarity	NPC267632
0.8015	Intermediate Similarity	NPC471995
0.8014	Intermediate Similarity	NPC212257
0.8014	Intermediate Similarity	NPC228842
0.8	Intermediate Similarity	NPC93666
0.7986	Intermediate Similarity	NPC471292
0.7973	Intermediate Similarity	NPC471863
0.7969	Intermediate Similarity	NPC131801
0.7969	Intermediate Similarity	NPC217180
0.7969	Intermediate Similarity	NPC312525
0.7969	Intermediate Similarity	NPC212918
0.7959	Intermediate Similarity	NPC272590
0.7958	Intermediate Similarity	NPC263337
0.7958	Intermediate Similarity	NPC121158
0.7955	Intermediate Similarity	NPC118853
0.7953	Intermediate Similarity	NPC205523
0.7945	Intermediate Similarity	NPC95526
0.7931	Intermediate Similarity	NPC471174
0.7931	Intermediate Similarity	NPC224418
0.7931	Intermediate Similarity	NPC10088
0.7929	Intermediate Similarity	NPC177262
0.7926	Intermediate Similarity	NPC120836
0.7926	Intermediate Similarity	NPC223063
0.7919	Intermediate Similarity	NPC25351
0.7917	Intermediate Similarity	NPC34056
0.7914	Intermediate Similarity	NPC46896
0.791	Intermediate Similarity	NPC95567
0.791	Intermediate Similarity	NPC319140
0.791	Intermediate Similarity	NPC474830
0.7905	Intermediate Similarity	NPC121615
0.7905	Intermediate Similarity	NPC294511
0.7902	Intermediate Similarity	NPC243577
0.7902	Intermediate Similarity	NPC223415
0.7902	Intermediate Similarity	NPC470741
0.7891	Intermediate Similarity	NPC472298
0.7881	Intermediate Similarity	NPC473368
0.7868	Intermediate Similarity	NPC21460
0.7867	Intermediate Similarity	NPC209364
0.7867	Intermediate Similarity	NPC60973
0.7862	Intermediate Similarity	NPC346
0.7862	Intermediate Similarity	NPC276676
0.7862	Intermediate Similarity	NPC478166
0.7862	Intermediate Similarity	NPC62799
0.7847	Intermediate Similarity	NPC476944
0.7847	Intermediate Similarity	NPC251865
0.7847	Intermediate Similarity	NPC86935
0.7843	Intermediate Similarity	NPC14499
0.7843	Intermediate Similarity	NPC476035
0.7843	Intermediate Similarity	NPC475039
0.7842	Intermediate Similarity	NPC476947
0.7829	Intermediate Similarity	NPC144745
0.7829	Intermediate Similarity	NPC227660
0.7829	Intermediate Similarity	NPC208906
0.7823	Intermediate Similarity	NPC234494
0.7823	Intermediate Similarity	NPC471001
0.7817	Intermediate Similarity	NPC201370
0.7817	Intermediate Similarity	NPC473983
0.7815	Intermediate Similarity	NPC286722
0.7815	Intermediate Similarity	NPC472283
0.7808	Intermediate Similarity	NPC250228
0.7808	Intermediate Similarity	NPC216755
0.7806	Intermediate Similarity	NPC473766
0.7806	Intermediate Similarity	NPC473753
0.7801	Intermediate Similarity	NPC472376
0.78	Intermediate Similarity	NPC75310
0.78	Intermediate Similarity	NPC281258
0.7793	Intermediate Similarity	NPC247221
0.7792	Intermediate Similarity	NPC261184
0.777	Intermediate Similarity	NPC470997
0.777	Intermediate Similarity	NPC5180
0.777	Intermediate Similarity	NPC469335
0.777	Intermediate Similarity	NPC159927
0.7763	Intermediate Similarity	NPC477403
0.7763	Intermediate Similarity	NPC475295
0.7763	Intermediate Similarity	NPC473473
0.7762	Intermediate Similarity	NPC20500
0.7761	Intermediate Similarity	NPC71274
0.7761	Intermediate Similarity	NPC75557
0.7755	Intermediate Similarity	NPC19747
0.7755	Intermediate Similarity	NPC476942
0.7755	Intermediate Similarity	NPC476941
0.7755	Intermediate Similarity	NPC243165
0.7754	Intermediate Similarity	NPC470976
0.7754	Intermediate Similarity	NPC196979
0.7754	Intermediate Similarity	NPC470977
0.7752	Intermediate Similarity	NPC79202
0.7752	Intermediate Similarity	NPC59035
0.7748	Intermediate Similarity	NPC263265
0.7748	Intermediate Similarity	NPC104736
0.7748	Intermediate Similarity	NPC107646
0.7748	Intermediate Similarity	NPC41880
0.7744	Intermediate Similarity	NPC272899
0.7742	Intermediate Similarity	NPC475779
0.7733	Intermediate Similarity	NPC44606
0.7733	Intermediate Similarity	NPC10429
0.7724	Intermediate Similarity	NPC84479
0.7721	Intermediate Similarity	NPC474438
0.7721	Intermediate Similarity	NPC474279
0.7718	Intermediate Similarity	NPC291150
0.7718	Intermediate Similarity	NPC116717
0.7718	Intermediate Similarity	NPC144010
0.7714	Intermediate Similarity	NPC209858
0.771	Intermediate Similarity	NPC137710
0.7708	Intermediate Similarity	NPC52412
0.7707	Intermediate Similarity	NPC302392
0.7704	Intermediate Similarity	NPC329694
0.7704	Intermediate Similarity	NPC474260
0.7704	Intermediate Similarity	NPC329922
0.7704	Intermediate Similarity	NPC81912
0.7703	Intermediate Similarity	NPC211625
0.7703	Intermediate Similarity	NPC192069
0.7698	Intermediate Similarity	NPC474426
0.7698	Intermediate Similarity	NPC474407

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 NPC208389 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	248
0.1-0.2	1030
0.2-0.3	1786
0.3-0.4	2747
0.4-0.5	2062
0.5-0.6	1041
0.6-0.7	226
0.7-0.8	10
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
0.7746	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1471	Phase 3
0.7407	Intermediate Similarity	NPD6764	Approved
0.7407	Intermediate Similarity	NPD6765	Approved
0.7372	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6273	Approved
0.7254	Intermediate Similarity	NPD8032	Phase 2
0.7252	Intermediate Similarity	NPD1241	Discontinued
0.7241	Intermediate Similarity	NPD2799	Discontinued
0.723	Intermediate Similarity	NPD4628	Phase 3
0.7229	Intermediate Similarity	NPD6784	Approved
0.7229	Intermediate Similarity	NPD6785	Approved
0.7226	Intermediate Similarity	NPD3972	Approved
0.7194	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD8434	Phase 2
0.7163	Intermediate Similarity	NPD6832	Phase 2
0.7153	Intermediate Similarity	NPD6355	Discontinued
0.7143	Intermediate Similarity	NPD6599	Discontinued
0.7132	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD1876	Approved
0.707	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD3887	Approved
0.7059	Intermediate Similarity	NPD920	Approved
0.7059	Intermediate Similarity	NPD5585	Approved
0.7044	Intermediate Similarity	NPD919	Approved
0.7027	Intermediate Similarity	NPD2346	Discontinued
0.7023	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD3748	Approved
0.7006	Intermediate Similarity	NPD5761	Phase 2
0.7006	Intermediate Similarity	NPD5760	Phase 2
0.7	Intermediate Similarity	NPD7003	Approved
0.6966	Remote Similarity	NPD4307	Phase 2
0.6966	Remote Similarity	NPD2979	Phase 3
0.695	Remote Similarity	NPD3266	Approved
0.695	Remote Similarity	NPD3267	Approved
0.6944	Remote Similarity	NPD2313	Discontinued
0.6933	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD2353	Approved
0.6906	Remote Similarity	NPD1281	Approved
0.6906	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD2798	Approved
0.6887	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD17	Approved
0.6875	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6799	Approved
0.6859	Remote Similarity	NPD7458	Discontinued
0.6859	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD2797	Approved
0.6828	Remote Similarity	NPD3268	Approved
0.6828	Remote Similarity	NPD6798	Discontinued
0.6821	Remote Similarity	NPD1243	Approved
0.6812	Remote Similarity	NPD5691	Approved
0.6809	Remote Similarity	NPD4359	Approved
0.6803	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.68	Remote Similarity	NPD2344	Approved
0.6797	Remote Similarity	NPD7236	Approved
0.6792	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD1019	Discontinued
0.6779	Remote Similarity	NPD4308	Phase 3
0.6776	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD3750	Approved
0.6776	Remote Similarity	NPD4110	Phase 3
0.6761	Remote Similarity	NPD1283	Approved
0.6759	Remote Similarity	NPD7095	Approved
0.6755	Remote Similarity	NPD4534	Discontinued
0.6755	Remote Similarity	NPD2897	Discontinued
0.6742	Remote Similarity	NPD2182	Approved
0.6738	Remote Similarity	NPD1608	Approved
0.6738	Remote Similarity	NPD9717	Approved
0.6735	Remote Similarity	NPD4060	Phase 1
0.6735	Remote Similarity	NPD4140	Approved
0.6733	Remote Similarity	NPD2531	Phase 2
0.6733	Remote Similarity	NPD2438	Suspended
0.6733	Remote Similarity	NPD1551	Phase 2
0.6732	Remote Similarity	NPD2354	Approved
0.6718	Remote Similarity	NPD3134	Approved
0.6691	Remote Similarity	NPD1651	Approved
0.6691	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD5763	Approved
0.6689	Remote Similarity	NPD5762	Approved
0.6687	Remote Similarity	NPD7819	Suspended
0.6667	Remote Similarity	NPD6287	Discontinued
0.6667	Remote Similarity	NPD5049	Phase 3
0.6667	Remote Similarity	NPD4062	Phase 3
0.6667	Remote Similarity	NPD6233	Phase 2
0.6667	Remote Similarity	NPD8166	Discontinued
0.6667	Remote Similarity	NPD7075	Discontinued
0.6648	Remote Similarity	NPD4107	Approved
0.6647	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1247	Approved
0.6646	Remote Similarity	NPD3226	Approved
0.6645	Remote Similarity	NPD5958	Discontinued
0.6643	Remote Similarity	NPD1778	Approved
0.6625	Remote Similarity	NPD6801	Discontinued
0.6624	Remote Similarity	NPD5403	Approved
0.6624	Remote Similarity	NPD3873	Phase 3
0.6624	Remote Similarity	NPD3869	Phase 3
0.6623	Remote Similarity	NPD2935	Discontinued
0.6623	Remote Similarity	NPD4477	Approved
0.6623	Remote Similarity	NPD4476	Approved
0.6623	Remote Similarity	NPD2309	Approved
0.6623	Remote Similarity	NPD2796	Approved
0.6622	Remote Similarity	NPD3142	Approved
0.6622	Remote Similarity	NPD3140	Approved
0.6606	Remote Similarity	NPD6808	Phase 2
0.6603	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD5401	Approved
0.6599	Remote Similarity	NPD3764	Approved
0.6597	Remote Similarity	NPD1203	Approved
0.6596	Remote Similarity	NPD3496	Discontinued
0.6596	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD7239	Suspended
0.6579	Remote Similarity	NPD6002	Phase 3
0.6579	Remote Similarity	NPD6004	Phase 3
0.6579	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6005	Phase 3
0.6579	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD4622	Approved
0.6577	Remote Similarity	NPD4618	Approved
0.6577	Remote Similarity	NPD1933	Approved
0.6573	Remote Similarity	NPD5327	Phase 3
0.6567	Remote Similarity	NPD2067	Discontinued
0.6554	Remote Similarity	NPD4870	Approved
0.6552	Remote Similarity	NPD5647	Approved
0.6545	Remote Similarity	NPD8127	Discontinued
0.6544	Remote Similarity	NPD5535	Approved
0.6541	Remote Similarity	NPD1358	Approved
0.6525	Remote Similarity	NPD4626	Approved
0.6522	Remote Similarity	NPD6279	Approved
0.6522	Remote Similarity	NPD6280	Approved
0.6519	Remote Similarity	NPD4482	Phase 3
0.65	Remote Similarity	NPD7028	Phase 2
0.65	Remote Similarity	NPD1894	Discontinued
0.6497	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD6559	Discontinued
0.649	Remote Similarity	NPD5688	Approved
0.649	Remote Similarity	NPD5689	Approved
0.6486	Remote Similarity	NPD411	Approved
0.6463	Remote Similarity	NPD3749	Approved
0.6463	Remote Similarity	NPD2614	Approved
0.646	Remote Similarity	NPD7411	Suspended
0.646	Remote Similarity	NPD6873	Phase 2
0.6442	Remote Similarity	NPD5402	Approved
0.6442	Remote Similarity	NPD3817	Phase 2
0.6439	Remote Similarity	NPD164	Approved
0.6434	Remote Similarity	NPD1611	Approved
0.6419	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD7008	Discontinued
0.6415	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6403	Remote Similarity	NPD7157	Approved
0.6402	Remote Similarity	NPD3882	Suspended
0.6402	Remote Similarity	NPD7768	Phase 2
0.6392	Remote Similarity	NPD2532	Approved
0.6392	Remote Similarity	NPD2534	Approved
0.6392	Remote Similarity	NPD2533	Approved
0.6391	Remote Similarity	NPD9697	Approved
0.6387	Remote Similarity	NPD2800	Approved
0.6386	Remote Similarity	NPD5494	Approved
0.6385	Remote Similarity	NPD1238	Approved
0.6383	Remote Similarity	NPD9545	Approved
0.6376	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD957	Approved
0.637	Remote Similarity	NPD6362	Approved
0.6369	Remote Similarity	NPD3926	Phase 2
0.6369	Remote Similarity	NPD7440	Discontinued
0.6358	Remote Similarity	NPD5890	Approved
0.6358	Remote Similarity	NPD447	Suspended
0.6358	Remote Similarity	NPD5889	Approved
0.6346	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD3025	Approved
0.6338	Remote Similarity	NPD3024	Approved
0.6333	Remote Similarity	NPD6663	Approved
0.6331	Remote Similarity	NPD2629	Approved
0.6331	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD5951	Approved
0.6327	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6653	Approved
0.6312	Remote Similarity	NPD9092	Discovery
0.6304	Remote Similarity	NPD6858	Approved
0.6304	Remote Similarity	NPD7094	Approved
0.6303	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD7057	Phase 3
0.6303	Remote Similarity	NPD7058	Phase 2
0.6299	Remote Similarity	NPD6100	Approved
0.6299	Remote Similarity	NPD6099	Approved
0.6294	Remote Similarity	NPD2932	Approved
0.6289	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD4198	Discontinued
0.6284	Remote Similarity	NPD5736	Approved
0.6276	Remote Similarity	NPD1481	Phase 2
0.6267	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD987	Approved
0.6258	Remote Similarity	NPD958	Approved
0.6258	Remote Similarity	NPD6677	Suspended

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