NPASS Compound

Structure

CID279877 OpenBabel06191716082D 23 25 0 0 1 0 0 0 0 0999 V2000 0.8327 -1.4423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9789 -0.3519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4597 0.4808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8327 1.4423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6654 1.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6087 0.4310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2847 0.7873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4982 1.4423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8327 1.4423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9288 -0.2489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0911 0.2636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8327 -1.4423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8820 -0.7155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5375 0.1822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6654 -0.9615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6654 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4982 0.4808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8327 0.4808 0.0000 C 0 0 2 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 -2.4982 -1.4423 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1255 0.9533 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8423 -0.6652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 4 19 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 6 15 1 0 0 0 0 7 11 2 0 0 0 0 7 15 1 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 23 1 0 0 0 0 12 14 2 0 0 0 0 12 16 1 0 0 0 0 13 15 2 0 0 0 0 13 23 1 0 0 0 0 14 20 1 0 0 0 0 16 17 1 0 0 0 0 16 21 2 0 0 0 0 17 18 1 0 0 0 0 17 19 1 1 0 0 0 19 20 1 6 0 0 0 20 22 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.19
Volume:	341.995
LogP:	3.86
LogD:	3.766
LogS:	-4.941
# Rotatable Bonds:	2
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.881
Synthetic Accessibility Score:	4.421
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.685
MDCK Permeability:	3.05427129205782e-05
Pgp-inhibitor:	0.186
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.874
Plasma Protein Binding (PPB):	94.5825424194336%
Volume Distribution (VD):	1.764
Pgp-substrate:	5.776139736175537%

ADMET: Metabolism

CYP1A2-inhibitor:	0.669
CYP1A2-substrate:	0.73
CYP2C19-inhibitor:	0.797
CYP2C19-substrate:	0.736
CYP2C9-inhibitor:	0.797
CYP2C9-substrate:	0.074
CYP2D6-inhibitor:	0.095
CYP2D6-substrate:	0.057
CYP3A4-inhibitor:	0.712
CYP3A4-substrate:	0.762

ADMET: Excretion

Clearance (CL):	9.143
Half-life (T1/2):	0.072

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.345
Drug-inuced Liver Injury (DILI):	0.106
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.907
Maximum Recommended Daily Dose:	0.759
Skin Sensitization:	0.181
Carcinogencity:	0.922
Eye Corrosion:	0.039
Eye Irritation:	0.554
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC279877

Natural Product ID:	NPC279877
*Common Name:**	9-Hydroxy-15,16-Epoxy-7,11,13(16)14-Labdatetraen-6-One
IUPAC Name:	(4R,4aS,8aS)-4-[(E)-2-(furan-3-yl)ethenyl]-4-hydroxy-3,4a,8,8-tetramethyl-5,6,7,8a-tetrahydronaphthalen-1-one
Synonyms:
Standard InCHIKey:	USWFVTHYLJICBA-DYBKDBSWSA-N
Standard InCHI:	InChI=1S/C20H26O3/c1-14-12-16(21)17-18(2,3)8-5-9-19(17,4)20(14,22)10-6-15-7-11-23-13-15/h6-7,10-13,17,22H,5,8-9H2,1-4H3/b10-6+/t17-,19-,20+/m0/s1
SMILES:	O=C1C=C(C)[C@]([C@@]2([C@@H]1C(C)(C)CCC2)C)(O)/C=C/c1cocc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL459718
PubChem CID:	44569353
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
IC50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1161	Cell Line	CHO	Cricetulus griseus	IC50	=	15.68	ug.mL-1	PMID[547749]
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	=	24.02	ug.mL-1	PMID[547749]
NPT762	Cell Line	A-431	Homo sapiens	IC50	=	26.09	ug.mL-1	PMID[547749]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	30.94	ug.mL-1	PMID[547749]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	41.21	ug.mL-1	PMID[547749]

☑ 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 NPC279877 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	229
0.1-0.2	1271
0.2-0.3	2805
0.3-0.4	6598
0.4-0.5	12367
0.5-0.6	11177
0.6-0.7	7533
0.7-0.8	632
0.8-0.85	62
0.85-0.9	18
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.959	High Similarity	NPC290955
0.9431	High Similarity	NPC246392
0.9355	High Similarity	NPC26532
0.9167	High Similarity	NPC87466
0.8889	High Similarity	NPC23086
0.8828	High Similarity	NPC208389
0.881	High Similarity	NPC300098
0.881	High Similarity	NPC290193
0.875	High Similarity	NPC207294
0.875	High Similarity	NPC112706
0.8692	High Similarity	NPC61788
0.8682	High Similarity	NPC59502
0.8605	High Similarity	NPC329707
0.8593	High Similarity	NPC202260
0.8593	High Similarity	NPC474722
0.8583	High Similarity	NPC118853
0.8571	High Similarity	NPC477967
0.8571	High Similarity	NPC158525
0.8561	High Similarity	NPC218838
0.8548	High Similarity	NPC243704
0.854	High Similarity	NPC263337
0.8527	High Similarity	NPC83178
0.8507	High Similarity	NPC46896
0.8485	Intermediate Similarity	NPC473982
0.845	Intermediate Similarity	NPC46536
0.845	Intermediate Similarity	NPC138139
0.8444	Intermediate Similarity	NPC307401
0.8433	Intermediate Similarity	NPC476947
0.843	Intermediate Similarity	NPC277525
0.8394	Intermediate Similarity	NPC148374
0.8382	Intermediate Similarity	NPC472376
0.8372	Intermediate Similarity	NPC473885
0.8372	Intermediate Similarity	NPC471074
0.8346	Intermediate Similarity	NPC97566
0.8321	Intermediate Similarity	NPC477123
0.8321	Intermediate Similarity	NPC477966
0.8321	Intermediate Similarity	NPC90953
0.8284	Intermediate Similarity	NPC471006
0.8273	Intermediate Similarity	NPC52412
0.8217	Intermediate Similarity	NPC16922
0.8214	Intermediate Similarity	NPC243577
0.8214	Intermediate Similarity	NPC476946
0.8182	Intermediate Similarity	NPC477039
0.8182	Intermediate Similarity	NPC477040
0.8175	Intermediate Similarity	NPC215109
0.8175	Intermediate Similarity	NPC170604
0.8169	Intermediate Similarity	NPC346
0.816	Intermediate Similarity	NPC150895
0.8154	Intermediate Similarity	NPC178382
0.8154	Intermediate Similarity	NPC477038
0.8154	Intermediate Similarity	NPC65735
0.8154	Intermediate Similarity	NPC243269
0.8154	Intermediate Similarity	NPC477965
0.8154	Intermediate Similarity	NPC188377
0.8148	Intermediate Similarity	NPC470740
0.8143	Intermediate Similarity	NPC475519
0.814	Intermediate Similarity	NPC317217
0.8134	Intermediate Similarity	NPC298190
0.8134	Intermediate Similarity	NPC89133
0.8129	Intermediate Similarity	NPC67003
0.8129	Intermediate Similarity	NPC90296
0.8125	Intermediate Similarity	NPC470998
0.8116	Intermediate Similarity	NPC471996
0.8102	Intermediate Similarity	NPC146872
0.8099	Intermediate Similarity	NPC185456
0.8092	Intermediate Similarity	NPC179354
0.8088	Intermediate Similarity	NPC106247
0.8082	Intermediate Similarity	NPC246164
0.8077	Intermediate Similarity	NPC272899
0.8074	Intermediate Similarity	NPC471995
0.8071	Intermediate Similarity	NPC205765
0.8069	Intermediate Similarity	NPC228842
0.8069	Intermediate Similarity	NPC212257
0.806	Intermediate Similarity	NPC476925
0.8056	Intermediate Similarity	NPC93666
0.8045	Intermediate Similarity	NPC476917
0.8045	Intermediate Similarity	NPC327527
0.803	Intermediate Similarity	NPC74612
0.8028	Intermediate Similarity	NPC251865
0.8016	Intermediate Similarity	NPC205523
0.8015	Intermediate Similarity	NPC130275
0.8015	Intermediate Similarity	NPC293253
0.8014	Intermediate Similarity	NPC121158
0.8	Intermediate Similarity	NPC201370
0.8	Intermediate Similarity	NPC473983
0.8	Intermediate Similarity	NPC477645
0.7986	Intermediate Similarity	NPC130976
0.7986	Intermediate Similarity	NPC302987
0.7958	Intermediate Similarity	NPC267632
0.7955	Intermediate Similarity	NPC303010
0.7941	Intermediate Similarity	NPC471817
0.7919	Intermediate Similarity	NPC41880
0.7919	Intermediate Similarity	NPC104736
0.7914	Intermediate Similarity	NPC310830
0.7914	Intermediate Similarity	NPC473268
0.7902	Intermediate Similarity	NPC476944
0.7902	Intermediate Similarity	NPC158871
0.7899	Intermediate Similarity	NPC265793
0.7899	Intermediate Similarity	NPC92941
0.7891	Intermediate Similarity	NPC208906
0.7891	Intermediate Similarity	NPC217180
0.7891	Intermediate Similarity	NPC212918
0.7891	Intermediate Similarity	NPC144745
0.7891	Intermediate Similarity	NPC312525
0.7877	Intermediate Similarity	NPC211625
0.7877	Intermediate Similarity	NPC234494
0.7872	Intermediate Similarity	NPC473681
0.7872	Intermediate Similarity	NPC218204
0.7872	Intermediate Similarity	NPC56197
0.7872	Intermediate Similarity	NPC61157
0.7867	Intermediate Similarity	NPC304692
0.7862	Intermediate Similarity	NPC250228
0.7862	Intermediate Similarity	NPC471174
0.7857	Intermediate Similarity	NPC236532
0.7857	Intermediate Similarity	NPC476943
0.7857	Intermediate Similarity	NPC220094
0.7847	Intermediate Similarity	NPC56731
0.7847	Intermediate Similarity	NPC5676
0.7838	Intermediate Similarity	NPC294511
0.7838	Intermediate Similarity	NPC121615
0.7838	Intermediate Similarity	NPC33938
0.7832	Intermediate Similarity	NPC64568
0.7829	Intermediate Similarity	NPC187547
0.7829	Intermediate Similarity	NPC21831
0.7823	Intermediate Similarity	NPC196846
0.7823	Intermediate Similarity	NPC470997
0.7812	Intermediate Similarity	NPC79202
0.7812	Intermediate Similarity	NPC59035
0.7801	Intermediate Similarity	NPC233707
0.7793	Intermediate Similarity	NPC97904
0.7793	Intermediate Similarity	NPC233763
0.7786	Intermediate Similarity	NPC470742
0.7786	Intermediate Similarity	NPC278832
0.7786	Intermediate Similarity	NPC64157
0.7786	Intermediate Similarity	NPC42400
0.7785	Intermediate Similarity	NPC30222
0.7785	Intermediate Similarity	NPC44606
0.7785	Intermediate Similarity	NPC114880
0.7778	Intermediate Similarity	NPC238843
0.7778	Intermediate Similarity	NPC474279
0.7778	Intermediate Similarity	NPC474438
0.7778	Intermediate Similarity	NPC199044
0.777	Intermediate Similarity	NPC272590
0.777	Intermediate Similarity	NPC209858
0.7769	Intermediate Similarity	NPC137710
0.7763	Intermediate Similarity	NPC287559
0.7762	Intermediate Similarity	NPC473152
0.7748	Intermediate Similarity	NPC81405
0.7748	Intermediate Similarity	NPC194499
0.7748	Intermediate Similarity	NPC195954
0.7748	Intermediate Similarity	NPC7059
0.7748	Intermediate Similarity	NPC88007
0.7748	Intermediate Similarity	NPC470118
0.7746	Intermediate Similarity	NPC18904
0.774	Intermediate Similarity	NPC216755
0.774	Intermediate Similarity	NPC71821
0.774	Intermediate Similarity	NPC255414
0.7734	Intermediate Similarity	NPC28054
0.7733	Intermediate Similarity	NPC35000
0.7733	Intermediate Similarity	NPC264943
0.773	Intermediate Similarity	NPC177262
0.7727	Intermediate Similarity	NPC263870
0.7727	Intermediate Similarity	NPC36255
0.7727	Intermediate Similarity	NPC471549
0.7727	Intermediate Similarity	NPC473379
0.7724	Intermediate Similarity	NPC290038
0.7724	Intermediate Similarity	NPC247221
0.7721	Intermediate Similarity	NPC223063
0.7721	Intermediate Similarity	NPC120836
0.7718	Intermediate Similarity	NPC75906
0.7718	Intermediate Similarity	NPC470996
0.7718	Intermediate Similarity	NPC145830
0.7712	Intermediate Similarity	NPC18986
0.7712	Intermediate Similarity	NPC68848
0.7697	Intermediate Similarity	NPC474611
0.7697	Intermediate Similarity	NPC116639
0.7697	Intermediate Similarity	NPC472823
0.7697	Intermediate Similarity	NPC140952
0.7697	Intermediate Similarity	NPC477403
0.7687	Intermediate Similarity	NPC474829
0.7687	Intermediate Similarity	NPC75557
0.7687	Intermediate Similarity	NPC71274
0.7687	Intermediate Similarity	NPC476942
0.7687	Intermediate Similarity	NPC476941
0.768	Intermediate Similarity	NPC177331
0.7674	Intermediate Similarity	NPC45536
0.7671	Intermediate Similarity	NPC470999
0.7671	Intermediate Similarity	NPC471292
0.7667	Intermediate Similarity	NPC178932
0.7667	Intermediate Similarity	NPC282445
0.7667	Intermediate Similarity	NPC57998
0.7662	Intermediate Similarity	NPC88841
0.7662	Intermediate Similarity	NPC285567
0.7662	Intermediate Similarity	NPC283209
0.7662	Intermediate Similarity	NPC288602
0.766	Intermediate Similarity	NPC186626
0.766	Intermediate Similarity	NPC4764
0.7655	Intermediate Similarity	NPC142113
0.7652	Intermediate Similarity	NPC79557
0.7651	Intermediate Similarity	NPC472787

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 NPC279877 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	229
0.1-0.2	938
0.2-0.3	1743
0.3-0.4	2689
0.4-0.5	2172
0.5-0.6	1122
0.6-0.7	248
0.7-0.8	9
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
0.7929	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD5760	Phase 2
0.7616	Intermediate Similarity	NPD5761	Phase 2
0.7431	Intermediate Similarity	NPD2344	Approved
0.7308	Intermediate Similarity	NPD1241	Discontinued
0.7292	Intermediate Similarity	NPD2799	Discontinued
0.7279	Intermediate Similarity	NPD3972	Approved
0.7267	Intermediate Similarity	NPD6273	Approved
0.723	Intermediate Similarity	NPD2309	Approved
0.7229	Intermediate Similarity	NPD8434	Phase 2
0.7192	Intermediate Similarity	NPD1471	Phase 3
0.7185	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD4628	Phase 3
0.7162	Intermediate Similarity	NPD7003	Approved
0.7134	Intermediate Similarity	NPD6764	Approved
0.7134	Intermediate Similarity	NPD6765	Approved
0.7122	Intermediate Similarity	NPD2797	Approved
0.7115	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD2346	Discontinued
0.7071	Intermediate Similarity	NPD2798	Approved
0.705	Intermediate Similarity	NPD1876	Approved
0.7047	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD3268	Approved
0.6993	Remote Similarity	NPD2313	Discontinued
0.6964	Remote Similarity	NPD6785	Approved
0.6964	Remote Similarity	NPD6784	Approved
0.6939	Remote Similarity	NPD4308	Phase 3
0.6906	Remote Similarity	NPD9717	Approved
0.6903	Remote Similarity	NPD7458	Discontinued
0.6903	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6099	Approved
0.6892	Remote Similarity	NPD6100	Approved
0.6867	Remote Similarity	NPD2800	Approved
0.6853	Remote Similarity	NPD6832	Phase 2
0.6828	Remote Similarity	NPD8032	Phase 2
0.6821	Remote Similarity	NPD3750	Approved
0.6818	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD3226	Approved
0.6779	Remote Similarity	NPD1551	Phase 2
0.6774	Remote Similarity	NPD920	Approved
0.677	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD1203	Approved
0.6761	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD3764	Approved
0.6753	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6599	Discontinued
0.6735	Remote Similarity	NPD6355	Discontinued
0.6732	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD5647	Approved
0.6708	Remote Similarity	NPD3749	Approved
0.6691	Remote Similarity	NPD2932	Approved
0.6691	Remote Similarity	NPD1778	Approved
0.669	Remote Similarity	NPD1283	Approved
0.6689	Remote Similarity	NPD1607	Approved
0.6689	Remote Similarity	NPD1549	Phase 2
0.6687	Remote Similarity	NPD2296	Approved
0.6667	Remote Similarity	NPD1608	Approved
0.6667	Remote Similarity	NPD2796	Approved
0.6667	Remote Similarity	NPD3140	Approved
0.6667	Remote Similarity	NPD3142	Approved
0.6667	Remote Similarity	NPD6280	Approved
0.6667	Remote Similarity	NPD4140	Approved
0.6667	Remote Similarity	NPD4477	Approved
0.6667	Remote Similarity	NPD4476	Approved
0.6667	Remote Similarity	NPD2935	Discontinued
0.6667	Remote Similarity	NPD6279	Approved
0.6667	Remote Similarity	NPD4307	Phase 2
0.6667	Remote Similarity	NPD1240	Approved
0.6667	Remote Similarity	NPD9494	Approved
0.6667	Remote Similarity	NPD7577	Discontinued
0.6646	Remote Similarity	NPD7028	Phase 2
0.6645	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD3267	Approved
0.6643	Remote Similarity	NPD3266	Approved
0.6627	Remote Similarity	NPD6559	Discontinued
0.6625	Remote Similarity	NPD7819	Suspended
0.6623	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD6002	Phase 3
0.6623	Remote Similarity	NPD6005	Phase 3
0.6623	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD6004	Phase 3
0.6623	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD1651	Approved
0.6619	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD5585	Approved
0.6604	Remote Similarity	NPD7411	Suspended
0.6601	Remote Similarity	NPD8166	Discontinued
0.6601	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD4110	Phase 3
0.66	Remote Similarity	NPD3748	Approved
0.6584	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD2649	Approved
0.6582	Remote Similarity	NPD2651	Approved
0.6579	Remote Similarity	NPD2424	Discontinued
0.6573	Remote Similarity	NPD6696	Suspended
0.6571	Remote Similarity	NPD3019	Approved
0.6571	Remote Similarity	NPD4626	Approved
0.6566	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD3873	Phase 3
0.6561	Remote Similarity	NPD3869	Phase 3
0.6547	Remote Similarity	NPD1894	Discontinued
0.6547	Remote Similarity	NPD9545	Approved
0.6543	Remote Similarity	NPD3882	Suspended
0.6541	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD4662	Approved
0.6538	Remote Similarity	NPD4661	Approved
0.6538	Remote Similarity	NPD2532	Approved
0.6538	Remote Similarity	NPD2533	Approved
0.6538	Remote Similarity	NPD2534	Approved
0.6536	Remote Similarity	NPD1243	Approved
0.6531	Remote Similarity	NPD6798	Discontinued
0.6531	Remote Similarity	NPD411	Approved
0.6525	Remote Similarity	NPD3496	Discontinued
0.6522	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD9493	Approved
0.6516	Remote Similarity	NPD7236	Approved
0.651	Remote Similarity	NPD4622	Approved
0.651	Remote Similarity	NPD4618	Approved
0.651	Remote Similarity	NPD447	Suspended
0.6503	Remote Similarity	NPD5327	Phase 3
0.65	Remote Similarity	NPD5691	Approved
0.6497	Remote Similarity	NPD5049	Phase 3
0.6494	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.649	Remote Similarity	NPD1510	Phase 2
0.649	Remote Similarity	NPD7033	Discontinued
0.6485	Remote Similarity	NPD8127	Discontinued
0.6483	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD1019	Discontinued
0.6479	Remote Similarity	NPD1281	Approved
0.6475	Remote Similarity	NPD9092	Discovery
0.6474	Remote Similarity	NPD6799	Approved
0.6467	Remote Similarity	NPD6651	Approved
0.6467	Remote Similarity	NPD6353	Approved
0.6463	Remote Similarity	NPD7008	Discontinued
0.6454	Remote Similarity	NPD17	Approved
0.6452	Remote Similarity	NPD3887	Approved
0.6452	Remote Similarity	NPD2354	Approved
0.6449	Remote Similarity	NPD6671	Approved
0.6449	Remote Similarity	NPD7157	Approved
0.6443	Remote Similarity	NPD4060	Phase 1
0.6443	Remote Similarity	NPD2979	Phase 3
0.6442	Remote Similarity	NPD7768	Phase 2
0.6433	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD5688	Approved
0.6424	Remote Similarity	NPD7097	Phase 1
0.6424	Remote Similarity	NPD5494	Approved
0.6424	Remote Similarity	NPD5689	Approved
0.642	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.642	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD2182	Approved
0.6418	Remote Similarity	NPD2684	Approved
0.6414	Remote Similarity	NPD1470	Approved
0.641	Remote Similarity	NPD7440	Discontinued
0.6402	Remote Similarity	NPD7075	Discontinued
0.64	Remote Similarity	NPD5735	Approved
0.64	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD3134	Approved
0.6391	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD4359	Approved
0.6389	Remote Similarity	NPD4749	Approved
0.6386	Remote Similarity	NPD1247	Approved
0.6377	Remote Similarity	NPD5951	Approved
0.6377	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD6663	Approved
0.637	Remote Similarity	NPD4624	Approved
0.637	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4534	Discontinued
0.6364	Remote Similarity	NPD919	Approved
0.6364	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD1201	Approved
0.6358	Remote Similarity	NPD6844	Discontinued
0.6358	Remote Similarity	NPD6801	Discontinued
0.6353	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD5403	Approved
0.6351	Remote Similarity	NPD7095	Approved
0.6347	Remote Similarity	NPD6808	Phase 2
0.6341	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD3057	Approved
0.6335	Remote Similarity	NPD4380	Phase 2
0.6331	Remote Similarity	NPD3446	Phase 1
0.6327	Remote Similarity	NPD5736	Approved
0.6324	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD1481	Phase 2
0.6312	Remote Similarity	NPD7239	Suspended
0.6301	Remote Similarity	NPD6362	Approved
0.6299	Remote Similarity	NPD2353	Approved
0.6299	Remote Similarity	NPD5763	Approved
0.6299	Remote Similarity	NPD5762	Approved
0.6299	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD7177	Discontinued

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